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What I Wish I’d Known Before … Striking Out On My Own in Health IT Marketing/PR

I wish I had started freelancing sooner, especially in healthcare. It is so rewarding working in a field where the products or services you’re marketing can make a positive impact on someone’s health.

Don’t! The debacle of health insurance makes this an exercise in major frustration and heartache and massive risk. You can buy “insurance,” but since its not really insurance but rather a Costco membership to buy (maybe) at lower cost, you are left holding the bag and it just takes once medical issue and you are f$%#ed. Thinking about getting LTD insurance – good luck since you can only get coverage for whatever your current income is, and as you strike out, that will be low and maybe non-existent, so your previously viable LTD is nigh on useless Getting back in likely proves even harder once you discover your mistake. Suck it up and accept the crappy work environment and be grateful you have health insurance.

I started my own healthcare IT-specific product marketing business eight years ago, after 25 years in corporate product marketing in healthcare. Here is what I have learned:

  • Building a business takes three times longer than one expects.
  • In general, people have their own concept of product marketing, which (incorrectly) tends to revolve around advertising and sales sheet creation.
  • Everybody thinks they’re a marketer!
  • Business leaders don’t understand that marketing efforts take 6-10 months to have an impact. They expect an immediate impact on their sales.
  • Most healthcare IT business leaders are technical and believe that marketing is unnecessary. They frequently believe “if I build it, they will come,” which is never true.
  • Many healthcare IT business leaders under estimate the importance of collaborative reference sites and their role in marketing.

I did the solo thing for 20-plus years and it was great, yet came with a lot of headaches. Before leaving your current job, I have the following suggestions:

  • Assess your core competencies, focus on what you do best, then identify companies that need your services.
  • Survey colleagues to determine the fees you will charge. Simultaneously, create an initial business plan outlining how many hours you have to bill per month to pay yourself and pay for your business expenses (don’t forget to calculate taxes).
  • Line up a client or two and have them sign a simple contract committing to a minimum monthly fee for your services. Sample contracts are online for free or a minimal fee. Then, quit your current job.
  • At minimum, set up a sole proprietorship with your state. Preferably, set up an LLC or S corp to get some legal protection. All of this can be done online without paying someone to do it for you.
  • Set up company bank account. If you have some cash, you can self fund yourself for a while and place it into the account (essentially making a personal loan to your new business). The account will add accountability and tracking for your business expenses, which are deductible.
  • Determine office needs — what you have, what you need to purchase, including computers, phones, software, internet access, etc.
  • Set up website (free or low cost), and create your social media presence.
  • If you’ll need health insurance, get quotes to determine premium costs.
  • Evaluate other types of insurance you’ll need, e.g., workers comp, home office insurance policy rider, liability, errors and omissions, etc. Many large companies require contractors to have a $1 million liability policy and $1 million errors and omissions policy.
  • Consult with a CPA to learn what is deductible and how often you’ll have to file taxes (usually quarterly, at first), and what software they’ll want you to use to track everything (QuickBooks, Peachtree, etc.).

Most importantly, ask yourself: Will all of this be fun, or an even larger hassle than your current job? And, will you have a security net for situations when clients pay slowly or not at all?

I didn’t have all of these items in place when I quit my job and went solo, and things still worked out for me. I had a wonderful experience, and wouldn’t trade it for anything. After two decades of running a business, I decided that I wanted something different and took on a role at an amazing company. No regrets so far.

Lastly, Google is your friend. Search for lists and tutorials on starting your own business. Literally everything you need to know is out there if you search for it.

I wish you the best!

What I Wish I’d Known Before … Taking Time Off for Doing Something That Turned Out to Be Motivating, Enriching, or Transformative

I wish I’d known that it was something I shouldn’t have been afraid to do sooner. I was always worried that it would be an issue with my employer. Even though I had to burn several years worth of accumulated vacation, it was well worth it.

I tripped into an amazing pseudo-volunteer experience in Spain after taking some time off between jobs, and I think your readers would love looking into it if they have even a week to immerse in another world. The organization Diverbo is an English immersion program for Spanish-speaking professionals looking to further their English. “Volunteers” (native English speakers from all over the world) join the participants for a week at a resort where everyone is prohibited from speaking Spanish, and we spend meals and activities conversing, interacting, developing relationships, and learning about each other, all in the spirit of helping the Spaniards advance their language skills in support of career growth. It was a blast and free for volunteers (English speakers), aside from the cost of getting to in Madrid (transport to the resort, lodging, and meals were all covered by the program). Hoping I can go back soon.

Work isn’t everything.

Everyone else that didn’t have the experience didn’t understand. And I didn’t know how to manage the feeling of frustration that they didn’t get how great the experience was when I tried to explain. Reinserting myself into routine took awhile, but the lessons learned were lifelong and I’d do it again.

That taking more than the standard one business week off for a vacation offers much more opportunity and rejuvenation. I was able to spend 6 weeks in Europe (combined all my time off after a large project- thanks to my boss) and spent a minimum of two weeks off for several years. Most coworkers thought they couldn’t or the office couldn’t survive without them. Not true.

Time off – regardless of what you do – is itself motivating, enriching, and transformative. It isn’t so much about what you do rather, about your attitude while doing it. Time away from work is time well spent; for you, your employer, everyone.

To make sure that there is some type of follow-up plan in place to keep a proportion of the positive momentum going forward once you get back to “reality.”

That you have to make time to grasp opportunities and sometimes planning too far in advance limits special trips. About 15 years ago, we planned to go to Yellowstone because Uncle Tom lived in a big house close to the park. Never made it and Uncle Tom has moved so can’t stay at his place but could still visit. Had an opportunity to visit a special place given to me in January. Pushed my family to do this — one daughter in medical school and the other just starting PA school. Glad we did the trip as that person no longer works in the special place and if we had not taken the opportunity it would be gone.

What I Wish I’d Known Before … Turning 40

That perception is nine-tenths of reality.

In the work context, learn how to spot an incompetent and/or malicious boss faster and get out quicker instead of trying to hold on because I liked the company. Job hop sooner, avoid the suffering, and find the good team. Regarding personal spending, committing to a higher level of savings to make retirement possible five years earlier. (Age 60, likely to work past 65)

That I’d be divorced the year I turned 40 because (in part) I traveled too much for my job.

I wish I’d understood more the importance of good body mechanics and specific techniques to maintain optimum physical health. It’s so easy to think you’re going to be able to do everything you do in your 20s and 30s but much of your bad habits won’t ‘tell their tales’ until after your in your 50s and 60s. Moral of the story: Never underestimate the importance of taking your body in for it’s regular maintenance and tune-ups!

I’m playing catch up now and often wonder how much better shape I could be in.

That I wouldn’t feel that much older! And that listening to coworkers moan about turning 25 would be extra hilarious.

Two things: the impact that a career can have on a family. A co-worker helped me with this one when I considered returning to school to get a bachelors degree with kids nine and 10 years old. She said, “Why do you want to go back to school? Because if you think you will get paid more, that may not be the case” AND how important it is to grasp opportunities as the “right” time will never come. An executive took me to lunch at the nicest place in town and offered me a position in management. I declined, stating that I was not ready, but maybe in six months. Well, the six months never came and the executive was one of the most successful in the company. Lesson learned, especially since we were both female.

I wish I had known before I was 40 that as a female salesperson, I didn’t have to, nor should I have to, put up with sexist behavior like having the sales team go out for drinks at a strip club after team meetings. Luckily much of that B.S. has become acknowledged as inappropriate, but before I was 40, I thought I had to blend in. No more blending, boys!

That turning 50 and 60 are a heck of a lot harder. Just a number and not a milestone!

That job hunting is exponentially harder. Despite claims to the contrary, ageism exists.

Life not only gets busier, but goes by quicker. Work to live and don’t live to work.

Trusting yourself that you can start a business and learn to be productive and likely successful long before you turn 40.

That your 40s are awesome if you let them be.

Quality of life makes a BIG impact on your business. Stress can ruin you from the inside out. Do not let your business ruin your health. Incorporating meditation, exercise, and getting adequate rest to reduce stress levels will improve working smarter. And incorporating meditation, exercise, and rest gives you time for a fresh perspective. Sometimes it’s best to not respond immediately!

That before I knew it, I would be 60.

Save, save, save. And all of the little pains.

Examples of a Boss Doing Something Heartfelt or Supportive

The owner discovered that one of the employees could not afford the additional cost of their honeymoon, and the newlyweds were planning to just stay home. The owner paid for a little getaway for the couple, including the food and the hotel suite.

Any time we had a collection at work (flowers for someone who lost a family member, baby shower for a co-worker, etc.), we would always end up with more than we thought we’d get. Turns out the boss at that time would find it how much had been given, then double it out if his pocket. He did it very quietly, not wanting attention. I airways looked at him differently after that.

Working extensively with HR to ensure that a co-worker with a new cancer diagnosis would be able to continue working while going through chemo

Years ago, we had an admin for our company who had to take a second job to support her family (single mom). Our CEO heard about it, and gave her enough of a raise so that she would not have to work all the time to make ends meet.

Our CEO at the time set up an employee fund to other employees to contribute too for a fellow employee that lost his entire home to a fire.

I think the best examples are the small, every day examples that assist a staff member to navigate their career in a way that supports their needs, whether that is offering new challenges that are right up their alley, supporting them as they seek work/life balance, or getting employee input as they craft plans for the organization. That is what I feel I have always had where I work (MEDITECH), and I can compare that to my spouse who tends to get treated like just one of many in an army of workers. When you truly know your staff, you can support them every day, but then also be there when major events occur.

A teammate went out with cancer who happened to be a single mom with kids. The C-suite quietly continued to give her a paycheck for a year until she passed away. It was a huge blessing to that family, although it hurt the team tremendously because they wouldn’t let her be replaced and it was a very small team. To this day it’s still a moral dilemma I struggle with, but I’m glad they were able to support her.

Before I started in HIT, I worked at a gas station / convenience store. One of my co-workers was a single mom, barely making ends meet. One day she called the store just after leaving work to say that her car had broken down right around the corner and could she leave it in the parking lot until she found someone to look at it. My boss knew she never put more than a gallon or two in at a time so he told me to grab the store gas can and go see if the issue was that she was out of gas. Turns out that was it. We got the car back to the store and he paid for a full tank of gas for her and a bag full of groceries to boot. It was a relatively small thing, but to this day I don’t think I’ve ever seen anyone more grateful than she was at the time.

Daily encouragement and opportunities to speak up if things feel icky. Reminders of work / life balance and ensuring that, despite being a team that is all over the country / globe, we are 1 @googlecloud @GoogleGenomics

Buying an analyst a case of Diet Mountain Dew for the day of a Go-Live 😎

I gave my employee his choice of hours and location to take care of his wife with breast cancer treatment. My wife went through it, too. It consumes the individual, who really needs the support probably fears losing a high-paying IT job. I said nope, work can wait. We’ll hire some consultants for now.

I used to work down the street from a homeless shelter. Of the three brothers that owned the store, one was known for his grumpy personality. That is, until he hired a homeless woman and gave her cash to cover expenses until her first paycheck. I never let him forget that I was aware of his “soft side,” and that seeing it changed my image of him for the better.

Donating money to help a single, older employee pay for an expensive operation for a beloved pet.

When I first started out on the Rev Cycle business, the owner of the company, a small mom & pop shop at the time,  gave me a car because mine broke down. No excuses to not come to work! 🙂

When my daughter got sick, my employer allowed me to work remotely (2,500 miles away) for the past three years.

About 10 years ago, my new boss was starting our first cybersecurity department and we only had three employees. At Easter he went and bought us all very nice baskets with gourmet chocolate. Our department grew, but at least twice a year, this boss took all of us out to dinner with a guest to a local casino. After a very nice dinner, he got up and laid a $20 bill in front of each of his employees and said lets go have some fun. Just a few of the ways he supported us. Best guy I ever worked for and I try to repeat some of these items with my staff today.

My brother was killed, a victim of a robbery. Wrong place, wrong time. I was a mid-level manager in a software development organization, and had no notion that anyone would attend my brother’s funeral. I was surprised and touched that several people, including the two most senior execs and head of HR, made the 2 1/2 hour trip. My respect and appreciation for those folks rose to a new level as a result of that kindness. Thank you again Tom, Al, and Rita.

I had a project I had to complete, but the dreaded phone call from my son’s school nurse that my son had gotten sick at school. I let my manager know I’d pick up my son and finish the day from home so I could meet my project deadline. My manager assured me that my son was more important and told me to take the time I needed to finish it up. As a working parent, flexibility like this never goes unnoticed and I’m so thankful to have a manager that is so understanding and accommodating.

My last boss was a true nurturer. We had a colleague struggling with a terminal cancer. She arranged for ongoing cards to be collected, signed and sent so that there wasn’t a week that went by without kind words of support, strength, love, and family being shared. Not only was our colleague, but his entire family grateful for that support.

A boss in one division abruptly terminated my employment after many years of outstanding annual performance reviews. The only reason provided was, “I am going to take a different direction.” A dotted line boss in another division did not agree with what was taking place and brought me into his division to start a new business service line. My dotted line, now new boss, had a reputation for being very tough, having unreasonably high expectations, and impersonal. After this career changing event, I learned that you should not judge people by their outward persona. I am forever grateful for his support during an unexpected time of vulnerability and career difficulty that ultimately launched my career to the next level.

When my mother passed away several years ago, my CIO took the time to attend her calling. He had to drive for more than an hour (one way) to get to the funeral home at a time when I know he was extremely busy. He did this for just about everyone in the department who suffered the loss of a loved one.

Drove 3.5 hours one way for visitation of a co-worker’s parent. Pulled someone who had just been given bad news into their office so that person could react in private.

My boss organized my inpatient analyst team to help me move into a smaller house when I was dealing with my husband’s dementia and very poor health. I was so grateful to have the help and they really didn’t have to do that. My boss is fantastic and I am glad to be in his employ.

What I Wish I’d Known Before … Considering or Attempting Suicide or Losing a Friend, Family Member, or Co-Worker To It

I wish I would have known that I would be “judged” on my level of grief after the loss. One of my classmates in medical school committed suicide during the last half of our last year. Even though I wasn’t in his most inner circle of friends (really just his fiancée and a couple of others), we had been on many rotations together and saw each other almost every day, so I took the loss very hard. I started talking to other classmates about collecting for a memorial (our school already had a piece of art in the lobby dedicated to a previous student who also committed suicide) and was quickly approached by the dean, who told me I had overstepped my bounds and that this should be left for his friends to do.

I was shocked, and had no idea that there were different levels of grief and response which one was limited to based on one’s perceived relationship to the deceased. I certainly considered him my friend and I think that not being able to do anything “useful” in response to the loss made it worse for me. Two decades later, I still think about him – seeing him was one of the bright spots of my day, and I think about the loss for the patients who never got to experience his brand of caring and compassion. He would have been an outstanding physician.

We were brand new parents, and my husband was terribly depressed. I didn’t know it. I knew he was worried about his work situation, money, our living situation, and he didn’t like me being the primary provider. I didn’t know that as a new dad, he worried he that he’d turn out like his paranoid schizophrenic, alcohol-abusing bio-father despite the fact that he never consumed alcohol. I had no idea about the depth of his worry, struggles and depression. Certainly, no idea he was dealing with suicide-level depression – or that he’d stopped going to his crappy job during day and instead, went to his parent’s place where no one was, and that he’d pull a gun from the cabinet and contemplate killing himself. I wish I’d known what everyone wishes: That I knew. That he spoke up.

My husband didn’t end up taking his life. Two things happened that day: One, my cousin, who worked at the same place my husband had been called to see if he was feeling okay, so I knew something was up. (He hadn’t been to work in over a week.) I’m glad someone noticed he wasn’t there! Two, that day, my husband had a gun in his mouth. He heard a voice, that he was sure was God, tell him not to do it. That he was loved and needed, and that he’d be causing more pain than he’d take away. He came home, confessed/cried (without me asking where he’d been), and then we talked with family and our pastor.

That was nearly 14 years ago. He found a job he liked not long after. Our kids are 13, 10 and 1, and he’s now a stay-at-home dad for our youngest, with only gratitude for getting to stay home vs. feeling “less of a man”. It was a turning point for us in terms of depth of our relationship. We always communicate, and I don’t worry that he’d do that to me/us, and I haven’t since those early days. I wish they knew things aren’t as bad as they seem, and they can get even better.

People perceive and react differently, but these have been helpful.



I wish I’d known how incredibly cruel people can be in the wake of a suicide, as I witnessed the “friends” of a woman I know gossip about her and blame her for her husband’s suicide. It costs exactly nothing to offer condolences, mow someone’s lawn, help tidy their house and wash dishes, and keep your base thoughts to yourself. Conversely, you gain nothing by spreading malicious gossip about a family in anguish.

I don’t think it can ever be overstated – talk about it. Talk about anxiety and depression and that it can happen to anyone. It’s okay to have it, it’s okay to talk about it, it’s okay… Maybe your anxiety/depression isn’t as severe, but you should still talk about it. You’re not on an island, you’re not alone. We all have it, whether we want to admit it or not.

Two things:

The emotional bleakness that drives one to attempt suicide really will go away
When people do die by suicide their family and friends never get over it.

Over the years, I’ve lost several acquaintances to suicide and I wish they had chosen to reach out for help. Unfortunately, I’ve felt the sense of loss and tragedy when the lives of decent and talented individuals are ended prematurely. I’ve also seen the way in which it haunts their family, their close friends and any treating health care professionals. Sometimes that’s what suicidal individuals want — to make others suffer, out of anger — but plenty of others who care about the person will suffer as well. Unlike other kinds of grief where the sadness subsides and good memories predominant, with suicide one never can remember the person without those memories being tinged or overwhelmed by the way that the person chose to die.

For many years while in late adolescence and early adulthood, there was rarely a week that I didn’t consider suicide. I attempted suicide several times and was hospitalized many more. At the time, I never thought I’d live long enough to be able to legally get a drink. Finally, with the help of excellent psychiatrists who didn’t give up on me and with medications and years of weekly therapy, those thoughts went away entirely. Now I’m approaching retirement and I am genuinely happy and content. I have had a very successful career, wonderful spouse and great friends and family. And I am extremely grateful that I’ve been able to enjoy all of that.

My son committed suicide. I’m angry with him for making the last chapter of his short biography the defining event of his life, meaning that in trying to forget the painful memories of the event itself, we’ve ended up forgetting him.

I lost a cousin to suicide and a brother-in-law to suicide. My brother-in-law (JP) left two young girls in 2006. His 17-year-old daughter found him post GSW to the head. I wish I had talked to his daughters or his estranged wife to know that he was exhibiting some of the signs of suicide. He pushed his daughters away and completed the items on his bucket list in a short period of time. He was having financial difficulties and marital difficulties. He had counseled a seventeen year old against suicide in the weeks preceding his own suicide. I have witnessed the devastation this loss has put on his family and most especially his daughters. There is always the question of what if? And why?

Having been close to JP and knowing how kind, loving and dedicated he was to his family and church, it is hard to hear people speak cruelly of those that have succeeded in their attempt. I know that at the time JP died, he thought he was doing the absolute best thing for everyone and saving them the grief of dealing with his perceived mistakes. He just didn’t realize how devastating it would be for the rest of their lives. My niece still grieves deeply and asks what if and why on the anniversary of the day it happened, his birthday, Christmas, Father’s Day …

That he was suffering from something which hurt him so much that he took his own life at such a young age.

I found my girlfriend after she had taken her life in the bedroom we shared. Finding someone is a whole other subset of suicide survivorship that comes with special considerations. Talk to someone, and be self-aware and accepting that it’s okay to experience symptoms of PTSD. I let myself feel them so I can process and deconstruct them. See a professional and be honest with yourself most of all. There are many survivorship support groups to help you, take advantage of them. Take care of yourself. You become acutely aware that obligations to yourself need to sometimes take priority over others. There are a few thoughts that I’ve consciously decided to accept to help me get through it:

1) It’s not my fault
2) I’ll never know exactly why she did it, and that’s okay
3) The pain of this loss will never get smaller, will never resolve itself, will never reach some form of poetic closure. But that’s okay. Although I’ll always carry this pain, I am able to get stronger in carrying it. A mile never gets shorter, 10 lbs is always 10lbs, but as long as you practice dealing with those things in a healthy way, you will get stronger in your ability to carry on.

I try to honor her memory by being good to myself and others. I much prefer it to the alternative.

How much you blame yourself for your family members actions. You constantly question why didn’t I know, why didn’t I see, why didn’t I call them that morning, why didn’t I tell them I love them more, etc. WHY, WHY, WHY. The only thing I can do now is try to educate others to not carry the survivor guilt.

I have a perspective from both sides.

Before Considering: How much (and how many) people actually love and care about you even when you feel very very alone and unsupported. People you don’t even realize care love you. That suicide is a permanent solution to a temporary problem even when that problem doesn’t seem temporary in the slightest. That life gets better and there is in fact a light at the end of the tunnel even if you can’t see the light right now. The light may not show up immediately either but it is there and you will eventually see it.

Before Losing a Friend: How much I’d wish I would have reached out more, kept in touch better, not let life get in the way of my relationships with people and been there to support them through a hard time. Knowing how much pain someone was going through to choose suicide makes me incredibly sad. I care so incredibly much about my friends and family and really humans in general that I don’t want to see anyone hurting in that way. I am not always great at showing it but I care very much.

What I wish I’d known before before my attempt at 12: I did nothing to deserve three years of bullying and teasing. I wasn’t the “easy taaaahhhget” my mother told me I was. I wasn’t the scapegoat Teen Magazine told me I was. I wasn’t the “fat loser” my sister told me I was. I was just a shy kid who got good grades. I was actually happier than I thought I was.

What I wish I’d known before my second attempt at 15: Dear lord, not finishing my science project was not a big deal. I didn’t need to be perfect. I was actually happier than I thought I was.

What I realized while contemplating my third attempt at 38: Sure, the three years of a manipulative sister-in-law had taken its toll on my marriage and friendships, and was poised to do the same on my career once she joined my employer…but I was the only one in a position to fix myself. Considering suicide was a symptom, not an answer. People with cancer go to oncologists, and people with suicidal thoughts go to therapists. It was surprisingly that simple. I was actually UNHAPPIER than I thought I was, but years of stuffing down my emotions and trying to live up to others’ expectations had left me unable to recognize my own feelings.

I’ll say it again: considering suicide is a symptom, not an answer. It’s a flag to reach out and get help. Help is there. Keep reaching, keep trying. Suicide leaves the survivors with a hole filled with confusion, anger, loss and regret…because the person who left is more meaningful than they realize.

Logic does not work.

Taking your life ruins others people’s lives. It causes so much pain and struggle to the family/friends that you know. It’s hard to live on without that person. It’s like a massive hole in their hearts for the rest of their lives. When someone famous or someone in the limelight takes their lives the Suicide rate peaks putting suicide at the forefront of minds for folks struggling.

That a person who has many friends, and posts happy photos on FB is actually in many cases lonely and should be reached out to.

Assuming that the person did not have the courage (or could be selfish enough) to take their own life and destroy the lives of their children and family in the process.

Wish there was a way we could know that someone is so depressed they would rather not live. Good lesson of really asking someone if they are doing okay.

I lost my nephew to suicide, a veteran who suffered from PTSD and had trouble adapting. I wish I had known or understood the severity of what vets go through. I wish I would have pushed harder to have him meet with a mentor friend. I wish that our VA would listen when vets reach out for help. I don’t think them buying Cerner will help – they should be investing in more humans to serve, not more computers to record.

Suicide is not selfish. It’s a result of a sickness. Awful people said awful things about that when he died. We don’t demonize the cardiac patient for the heart attack, yet its 80 percent preventable. Depression is an illness. It made him think he was helping his family and kids by removing himself from the equation. We need more connecting and less computers and tech.

What I Wish I’d Known Before … Working in Public Relations or Marketing

Management would want entire marketing plans in 5-point type on one slide.

The number of PowerPoints you will create. My daughter thinks that is what I do for a living — make and edit decks.

That sales won’t partner with you (not everywhere, but it’s common) and you will be viewed as a source of tchotchkes and money for golf outings, or be expected to be a savior when the numbers are bad.

Trade shows are a LOT of work!

How little people *actually* read.

How little time and energy I’d have to dedicate to my personal brand while I was busy helping build someone else’s.

How the work lives in “never-done” limbo. There is always another improvement that could be made to content, always another distribution channel to explore, always another deadline looming. Silver lining: job security?

How contentious the space between sales and marketing can be and how beautiful it is when you can effectively bridge the gap between the two.

How critical having a provider that’s willing to publically vouch for a vendor company would be to gain traction with and attention from healthcare editors.

How difficult it would be juggling multiple PR and marketing initiatives on behalf of multiple accounts. I managed marketing efforts end to end for a single vendor in my past life. While my to-do list often pulled me in multiple directions on any given day, it utterly pales in comparison to how it feels to project-hop across multiple accounts with very different content needs serving distinctly different healthcare niches. The scatterbrained effects of that kind of multi-tasking can be overwhelming.

What I learned while working in technology strategic marketing and product management: “The best strategy is one that the competition can’t respond to.”

I wish I’d known how quickly relevancy dies out. Even if the content / context is good, your sales team won’t absorb it and they’ll want the next best thing you haven’t created yet.

I wish I’d known marketing would grow so expansive. The company recognizes “marketing” and thinks you can do it all.. but today, there’s all the traditional stuff, plus Content Marketing, Digital Marketing, Social Media Marketing, Influencer Marketing, Email Marketing, PPC/SEO, Video, Graphics, Website / HTML. Once person can’t do it all, and you now need both creative and technical elements in order to be successful.

Your budget will never be what you need it to be.

Everyone believes we have to do marketing and PR, but no one outside of marketing believes it can deliver measurable results.

Telepathy is at least equally important—probably more—than any other skill you bring to the table.

Everyone – I mean everyone – has an opinion. I spent hours debating the color scheme of some billboard or brochure with clinicians, even finance people. I would never tell them how to do their job, but everyone felt very comfortable telling me how to do mine.

How great of a part of any org that marketing is! As a corporate events director I am usually involved in the rally cry of the company,  so exciting and ever-changing I wouldn’t have it any other way. I am constantly educating my niece and her friends on what marketing is and the opportunities that it offers. I feel not enough of us take the time to do this.

That I would be regularly and stridently asked to make mediocre or bad products sound amazing by people with full knowledge of their mediocrity.

That I would be able to measure the impact of marketing initiatives in actual dollars. Before I had a marketing role, I looked at marketing as fluff. Once I was in a marketing role, I learned there were ways to measure the impact not only of programs, but of individual messages (split testing) in actual orders taken and dollars booked. It was a real eye-opener, and I gained more respect for the profession as a result.

People often think that since they are consumers of products and services that doing marketing is easy and that anyone and everyone is an expert. As a lifelong marketing professional, that is very irritating. Also, the field of marketing and PR is ever changing and is far more software an metrics-driven, which is good, but because of that, far too many analytical people are drawn to the field. What they lack is clear and concise writing ability and creative aptitude – which will ultimately hurt this profession.

It can be gratifying to know that you’re providing information in a useful way; information that will help people do their job better. It can be disheartening when you can’t get layperson-understandable information out of the technical and other operations teams – or when the news is bad and you have to make it sound better because otherwise senior leadership will complain.

How difficult it would be to get a happy customer to sign off on publishing a story about the successes they’ve had with your product.

How hard it is to buck the general mindset that marketing is parties and pretty designs. Great marketing is as strategic as any other business discipline and can be tied directly to business outcomes (although that takes a lot of effort). Because it does have a creative aspect to it, it often misunderstood, resulting in less respect.

I’ve worked in both. I changed careers from publishing / editorial to PR, then to health IT Marketing. I knew that it would not be glamorous, but I would learn a lot and meet great people. I didn’t know that the work would include a lot of internal paperwork, getting stalled by processes, regulations, internal tools that don’t work, and fighting internal stakeholders. The hours are long and you can lose a week at a time due to travel in the blink of an eye. Integrating IT systems with partners takes much longer than expected and the projects often don’t make it to completion. I’ve spend countless months working on integration V-teams only to have a partner or management abandon the projects with nothing to show for it. Very frustrating.

Turnover at C-level and upper management levels bog down projects, your messaging direction and priorities, partner execution, and overall direction for most projects far more than you would expect. I’ve been in health IT marketing since the mid-90s. It is never boring! I didn’t expect to meet so many customers doing great things to help patients and hospital systems. I didn’t expect to be in IT marketing for so long, or like it as much as I do. That said, I want to quit just about every month due to all of the above. The pace of change in our industry leads to burn out. But I’m not going anywhere soon!

Two things:

(1) I thought I was “settling” for marketing (long story), but I wish I had known what a rewarding but challenging career it would be. When I started, I had no idea how many different aspects of marketing there are to learn (lead gen, brand, events, PR, writing, content management, marketing technology, graphic design, web analytics, customer experience, graphics, product marketing) and how I could keep learning new things over many years. It turns out I didn’t settle after all, but have been very blessed with this career.

(2) You can be in marketing and have integrity, honesty, and compassion. In other words, it has a bad rep, but there are many of us who are working diligently to just find the right solution to our customer’s problems. Yes, really.

One thing I hadn’t expected when I first started working in marketing is the dynamics between marketing and the sales organization. In reality, there are two sets of customers: your end-user customers who purchase your company’s products or services, and your sales team. If sales isn’t on board with your offering and the support you provide them, you won’t get anywhere. Also, they are often your best eyes and ears into the marketplace. Nurture those relationships and you will be not only more successful but more happy and satisfied in your work.

You must work for a market-focused organization to have an impact. Creating shiny object messaging is not a product strategy. Working with third-party lead generation companies can be akin to used car sales”men.” Wordsmithing for the sake of a press release is like eating confetti

How uninformed, arrogant, and self-important executives are in determining the importance of company updates and events. Not everything deserves a press release, case study, or blog post. I know the content I’m putting out is chock full of buzzwords, fluff, nonsensical phrases and, more often than I’d like to admit, outright lies, but I also know my job depends on cranking out that drivel.

What I Wish I’d Known Before … Taking My First Job Managing People

The most fulfilling part of your career can be helping others advance in their careers.

I wish I would have known how good my HR department really was and how well they supported me in being a first-time manager. Every company I have worked for since then has had terrible HR resources and I’m not really sure who they were there to serve. When I had my manager hat on and needed to deal with disruptive employees, they seemed to support the employees. And when I put my employee hat on and complained about MY abusive manager, I was treated terribly. I miss that first team. They were the best.

That I’d spend 80 percent of my time and effort on 20 percent of my staff. That some people feel compelled to give details when calling out sick. That promoting someone would feel so rewarding.

I wish I’d known that managing is dealing with other people’s problems much of the time. Once I came to this realization, it became easier to plan for the kinds of things one must handle. Illness, messy personal situations, child care challenges, addictions, money trouble, and host of other things intrude on the work place and impede people who want to do a good job from being able to focus. Then there are the people who don’t really care about doing a good job. That’s another thing I had to realize. One can assume positive intent from staff, but that works a lot better after a rigorous hiring process has taken place to prevent the people who really don’t care from ever making it in the door. Another important set of lessons has to do with learning how to manage people out of the organization in a humane way. I’ve been on the receiving end enough to know that there are good ways and bad ways to manage someone who isn’t a good fit for their job. It’s still a tough thing to do but knowing how to do it right – setting fair expectations, communicating them clearly and repeatedly, and then holding the individual accountable for their performance – makes it less painful for everyone involved.

I’m in sales and love sales. I wish I had known that I like commissions more than I love managing people before I took my first management job.

That responsibility with no authority is one of the most frustrating situations to be in. If you’re responsible for getting X amount of work done, but you don’t have the people power to do it, management will say “tough cheese”. At one job, I was reduced to working nights and asking relatives to help pick up the slack from my tiny team.

Also, that a lot of people these days want so much more out of work than a paycheck. You have to be a cheerleader, counselor, drill sergeant, and about 16 other things in order to get some people to do their job.

That eventually the confluence of political correctness and regulation would make the real, personal aspect of working relationships a facade that only attempts to mimic human potential.

The skill set for managing people is very different than the skill set to do the work. You are equal parts boss, friend, mentor, confidante, etc. and there’s a fine line between the first item and the others. You will end up dealing with so many more personality and HR issues than you anticipate and you should be prepared to deal with not only workplace issues but people who can be dealing with pretty rough stuff in their personal life. I think many of us who now manage people didn’t know beforehand how much emotional intelligence you will need to be successful.

That other managers that still feel like they need to be a “boss” instead of a “leader” would feel threatened by a true leadership style of management. Although challenging at times, being a leader is highly fulfilling.

We have two ears and one mouth. Use them in proportion. Listen and engage first. Your people can provide you with all the direction you need to be successful.

That there are way more variables to consider than what you think you have learned in college and from observing others. If you don’t have a mentor, find one!

That most of the stuff (AIDS, AIDS hysteria, divorces, affairs, thefts, partner abuse, alcohol and drug addiction, mental health) were not mentioned in my MBA curriculum.

This is a tough one because there are so many things to choose from. I wish I had known that it is OK for a decision not to be universally liked. They will come around. I think also as a business owner I wish I had known how many people are poor personal money managers — save some money, people!

That “managing” people really meant being the parent to a staff of adults and my parental duties included conversations about personal hygiene, basic etiquette, and trying to instill a work ethic in them regarding the need to come to work EVERY day of the week. Also, that my “children’s” feelings would be hurt when I didn’t make it a point to tell them good morning every day. Giving up a management position to become a consultant with no employees working under me was a very good decision!

How to more effectively manage up and outside of my direct reports for an environment that would support productivity without “political” distraction.

If you are being promoted, making the transition from peer to manager is tough. I found the best approach is to be honest and humble.

You are being watched all the time. If your team sees you become anxious / freak out by bad news, they will be anxious. If you walk by someone and don’t respond when they say hi, you could ruin that person’s day. Every action is magnified, good and bad.

Being a manager doesn’t mean you have to know all the answers. You have a team of smart people that are good at their job — you should empower them.

The “my job is to make my manager look good” approach is garbage. My job as the manager is to make it easier for my team to do the job(s) they are really good at.

Managing people is more rewarding for me than being an individual contributor, but the satisfaction from watching your team grow and improve takes a long time. You sometimes have to look harder for the daily and weekly wins to keep yourself going.

Being promoted doesn’t mean you should force everyone into doing their job the way you used to do it. Set the expectations and let each person determine the approach that is best for him or her.

The huge impact that my immediate supervisor would have on my ability to carry out my responsibilities.

In my first leadership role (as a chief resident for a busy and intense residency program), I was fortunate to be supervised by people (including the departmentt chair) who were supportive yet gave me a fair amount of authority to make my own decisions (with appropriate consultation). They would back me up if the other residents tried to go higher up the hierarchy behind my back. They were also available without being intrusive and treated me respectfully like a colleague rather than dumping things on me simply because I was lower on the feeding chain. This is not to say that management was easy, but it was doable and possible to do good things (and learn to manage people) with appropriate support and guidance.

That’s in contrast to my current chair, who micromanages, second guesses, makes decisions that affect my division without telling me, frequently changes priorities and directions, and keeps everyone stressed out and on edge. The higher-level administrators see my current chair as smooth and efficient and they accept his finger-pointing and explanations of the reasons for our department’s poor performance. Though I now have 25 years of clinical and leadership experience, I am treated like a scut puppy and supposed to jump when he gives the word. I’m just grateful that this wasn’t my first experience in management or I wouldn’t have attempted it again.

How “the people” would be both the best part and the worst part of my new job.

How hard it is to get rid of poor performers.

How often managers keep poor performers around and don’t let them know they’re poor performers (either because they’re afraid of the conversation or too busy to deal with the performance issue).

How it’s harder to measure your contributions. It’s no longer about how many tickets you close or issues you resolve. It’s how you empower your team and support them and manage their work intake/output.

What I Wish I’d Known Before … Working with Doctors on Technology Projects

I wish I had known that once I crossed the line to help IT that I would be an IT person and no longer viewed as a credible physician. My former peers became dismissive of my opinions, coming up with a variety of reasons — I hadn’t been in practice as long as them, I no longer saw as many patients as them, I wasn’t in a procedural specialty, etc. Looking back on their behavior, it was bullying, plain and simple.

How often one person can derail an entire initiative regardless of the validity of the reasoning.

I wish I had known the depth of ignorance on both sides of the tech / physician engagement. Be it the languages used, the ability to decipher thoughts and requirements, the ability to say, “No, not that, but maybe this.” I wish there was more empathy on both sides of the house and more diligence in learning from each side.

From the tech side, realizing that the doc/nurse in front of you has a job to do that isn’t to interact with the computer. That our tech needs to make it easier to do that job and not harder. That clinicians have trained very hard to get where they are and that it is appropriate to ask the “why” question so you can learn from their experience — and by asking why your product will be better suited to the task and use. That when the tech side makes assumptions they need to validate those assumptions against the clinicians experience. And, that the clinical roles are not all the same — learn the workflows of the roles under development.

For the doctors, realizing that customization is expensive across the development life cycle — almost as expensive as flexibility. That there is a need to be prescriptive while still being flexible. That you should call out bad design and usability, but show them how you want to use the system. Use your active listening skills to ensure that they understand what you are conveying. Realize that we don’t hate you and aren’t trying to kill your patients or ruin your practice — even if it feels like that at times

For both, that there is a need to exchange the data, information, knowledge, and wisdom that is the potential of electronic health records. Think about how your suggestions and decisions will impact analytics, research, and semantic exchange.

Lastly, maybe walking a mile or six in the other guy’s shoes wouldn’t hurt as long as you don’t get to thinking a little experience gives you great competence (e.g. the Dunning-Kruger effect).

A savvy physician who understands IT and the challenges we face and yet holds us accountable is the most powerful and effective program sponsor I have ever had. This physician leader, who practiced emergency medicine, pushed and led our IT organization to achievements we didn’t think were possible. He provided air cover to the program with physician colleagues across the organization. He had built trust with that community over decades of steady delivery of IT-related projects that met the needs of the physician community without incorporating the latest shiny thing. His participation was invaluable. I have seen few like him, but he was worth his weight in platinum.

I wish I’d known just how many of them would tell me “I took some programming classes in college” and would then proceed to inform me how an application should be built. Cool story, doc. I took a CPR class once, so let me tell you how to treat pulmonary hypertension.

I have also worked with some great physicians who were really open to the discovery process, and in my non-scientific sampling, the ones most tolerant of unexpected or undesired behavior were primary care physicians and the least-tolerant were orthopedic specialists. I’m not sure which way causality runs, but physicians whose entire job function is the human narrative and who trade in identifying root cause from a flood of poorly-described symptoms are way more amenable to testing things out and trying them in an unfinished state than people whose entire job is fixing an already-defined problem.

The vendor is going to have its own idea of how the software implementation plan should go and this will likely include a recommendation for staff, including doctors, to watch some videos and maybe do some reading before the vendor staff show up at the office. However, the doctors will most likely NOT do this and that changes much. Never did figure out why a doc would spend many thousands of dollars on a system and not take the vendor’s suggestion. This most often leads to a planned failure or less than successful launch and more down the road issues and the aforementioned tantrums and bad-mouthing of the vendor (couldn’t be the doctor’s fault, right?)

Maybe a possible solution would be to have the doctor sign a contract outlining the vendor recommendation to study up before go-live and an agreement to pay extra for on-site staffing when things go bad if they don’t do the pre-study.

Doctors usually want to buy a system that is totally customized to their workflow and uniqueness (think lots of $$$$$) but pay for a “one size fits all” commodity software (think much less $$).

Some docs still think they can work a full day of patients and have a successful go-live.

That there are many more physicians who are helpful and positive than those that are negative and resistant. It is just that the resistant ones make a lot more noise, commotion, and are experts at getting attention. It takes strong organizational leadership and the willingness to put some teeth into the medical bylaws to hold the resistant physicians accountable for their negative actions.

Maybe to be a little more appreciative. Looking back, some of the best projects I’d worked on. A chief pathologist who never missed a project meeting, gave a personal number for emergencies, and taught us all about lab billing. Another chief pathologist who validated an ancient AP system conversion, patiently looking side by side, old and new, checking every procedure type. In the end, 25 years of data converted, no errors. An anesthesiologist who remained obstinate through an entire Lean event, pushing the team to the edge of insanity, then led the implementation and blew down barriers in the department we did not know existed. Many other great memories of physicians who were not only generous with their time but were also key contributors.

I wish that I had known that doctors are flawless beings incapable of making a mistake and that an EMR will not work and do the same task a dozen different ways every time a doctor interacts with it.

The pervasive power of delayed adolescence fused with authority, enabled by administrative leadership complicity and medical leadership effeteness.

Every doctor I’ve worked with will not admit upfront to ignorance about system capabilities or their lack of knowledge about software in general. Why would they? Start new projects with level-setting demonstrations about what your system can do (or will soon be able to do). Physicians will react to what they see presented and offer specific insights rather than speaking in generalities.

Understand your audience. Understand what the physicians and other providers want to get out of the system. Frame your language in a way that they can understand what you’re saying. I’ve seen too many people jump into wonky language when describing projects, systems, or configurations. If they don’t understand you, they will assume the worst. And then it will be much more difficult to convince them to change anything.

Practicing medicine is an art, not only a science, so there is no cookie cutter treatment for every patient and scenario. If you understand that up front, you will not be disappointed that your plans / solutions / workflows do not work with every provider or department. You need to always seek second opinion.

That all those years of babysitting and talking kids down from tantrums would come in so handy in my future.

What I Wish I’d Known Before … Firing Someone for Cause

How much stress I would feel leading up to the actual moment. I find myself spending a lot of time worrying about the impact on the person, their family, their potential future mental state, etc., particularly if I have had a good personal relationship with them and the cause is poor professional performance rather than something more obviously "fireable" like sexism, racism, theft, etc. And, in these cases, how much less stress I found myself under after making the decision, going through the documentation and attempted rehabilitation process, and then finally moving on. Having poor performers around drags down the entire team and moving them on lifts a weight from everyone else.

That I could be personally liable for the outcome if pursued legally and found in favor of the plaintiff.
That HR would not be as supportive of my needs to meet quality and project standards as in assuring they were legally protected.
Employees who should have seen it coming actually don’t, despite best efforts to prepare them.
That it is hard, even when it is fully justified
That staff who remain behind will need to be told something, or the rumor mill will take over – prepare a statement.
That staff who remain behind will glorify the employee, even if they were previously negatively impacted by the terminated employee.

I wish I had known how much the firing manager would be put "on trial" for the performance of the "firee.” Sometimes, someone is just in the wrong job, but it seems that the employee’s manager has to own all of the employee’s failings as lack of providing direction, lack of leadership, lack of mentoring, etc.

The extensive process of documenting everything to ensure there’s no lawsuit can be a pain. I’ve only had to fire one person for cause in healthcare IT and worrying about confidentiality with the reason wasn’t an issue. There was no speculation as to why “Beavis” was fired, only a general reaction of “what took so long,” even though confidentiality was maintained. I’ve worked for companies where managers would rather transfer the coworker and wash their hands of them, rather than have to go through the firing process, which really penalizes the good employees who have to work with the bad.

That you may not get to replace the employee because of attrition. The company uses empty positions for potential attrition cost savings.

Timing is never ideal when firing someone, but timing can be better than others; we terminated an employee of middle management two weeks post bringing in a consultant team. Gave the appearance that the consultant team was changing the org chart.

How hard it would be. Internally, our employees are so well protected, it’s hard to get them out based on performance – even over a lack of showing up. They are given every benefit of the doubt, and we end up down a person for months and months, yet we’re still accountable for our metrics.

Would I have done so for anybody or was this person an anomaly. Remove all personal bias and read your rationale, asking if this were X, would I do the same? If not, expect repercussions.

Regardless of the amount of documentation or agreement from those within your department, there will always be those that feel the employee was treated unfairly. You know the reasons for the firing, but that’s not something you can easily explain to others due to confidentiality issues. If you’re going to fire someone, you have to be confident in your decision and not let pushback from others impact your team’s performance.

Don’t count on your manager supporting your decision! You’re probably on your own here.

I wish I’d known how to convince my company to let me do it. They never let us fire anyone – always has to be something sneaky, like a layoff, which sometimes has collateral damage. There are bad apples out there that need to be tossed, but our HR team is dreadfully afraid of letting us do when needs to be done.

Many not-for-profits seem to treat most people with performance-based challenges as if they have guaranteed lifetime employment and it seems like everyone plays by union-like rules. That is – many write-ups. It seems like you need to have HR in the loop well in advance of the first inkling of an issue and it takes multiple performance improvement plans, sometimes with arbitration-like discussions, to move someone on.
In other cases, where the previous "model employee" is cited by someone as having caused a non-performance issue, it seems to be guilty until proven innocent. I really fear for the surfacing of potential accusations from many years back. I have yet to hear about a "statute of limitations" at my employer. These are truly crazy times.

What I Wish I’d Known Before … Creating, Defending, or Managing a Hospital IT Budget

How your organization views IS/IT should be well understood. For example, are you viewed as just a cost center or are you tied to the organization’s strategic goals? If your organization leans more to the former, focus on telling the story of cost management. For the latter, focus more on capabilities and deliverables. And find ways to build in realistic contingency. This lesson stuck from one of my college professors – "Budgets are a guess. And what do we know about guesses? They are almost always wrong!"

That doctors are not luddites but they won’t fall for the next new shiny object either.

That at any time you can and will have your budget re-allocated for the " good of the health system." Meaning, that a pet project by a key physician leader needs to get funded before they jump ship.

How much the executives were really making.

That IT is viewed as a cost center, and as such it is subject to constant downward pressure as the CEO and CFO continually chase margin. Given that IT budgets have only one real variable cost, labor, you are constantly trying to defend your staff. You have to be ruthless in squeezing your vendors – they are not your friends no matter how many dinners they buy or how much fun at HIMSS they provide. The real challenge comes after you’ve implemented your EMR and the CFO is looking for the vendor-promised 10-percent efficiency gains, never mind that you’ve implemented 6X the amount of functionality and support complexity, and BTW, those legacy systems are going to have to hang around for another six years. Best strategy I came up with was appealing to the CEO’s ego by putting him out front as a "strategy leader" in "technology driven quality healthcare," got his picture in a few trade rags with quotes, kept us safe for a couple of budget cycles.

After a go-live, be real clear with the CFO on the difference between remediation and optimization. Twenty percent on top of the original TCO for optimization in ok, but if a buzz starts that the 20 percent is just to deliver things originally promised, that’s a problem.

That a boss at a previous employer was more concerned about giving his buddy some business he would move around project priorities based on which vendors got the bid rather than actual need. Which is how we ended up buying a metric crapload of servers and networking gear but no racks or power distribution to actually install them.

That leadership would not stick to the budget and would always find a way to fund special projects without any considerations of the resource planning that had already taken place. Especially when leadership bends the budget for non-IT departments to purchase new IT-dependent products without allowing for any increase in the IT budget for implementation and support.

That finance sets the rules and will let you know when you are not following them but do not necessarily tell you what the rules are. Always add a minimum of 10 percent to your best-guess cost projection to cover the unknown.

Previous budget data, operational metrics, and how more/less efficient the proposed budget is.

What I Wish I’d Known Before … Taking College Courses While Still Working Full Time

That taking classes when you’re over 40 is pointless. Few, if any, employers believe that those over 40 have anything left to offer, regardless of one’s interest in continuing their education and staying current.

Nothing. I was glad I earned my MBA while working when I was 24-25 years old. At the time I knew it would be a short-term sacrifice for long-term gain and it was. I started the program part time in the evenings while I worked full time and concluded full time while working part time for eight months. To those of you in your mid-20s thinking about earning an advanced degree, get practical work experience for a few years first. It will make the degree more valuable as you will apply professional experience to course work and learnings from the program immediately in your work setting.

I wish I had known just how little sleep I would get! I went back to school after a divorce. I was a single parent working full time, carrying a full load of at least 12 credit hours, and it was a huge test of my stamina. However, it was the most rewarding experience. I wish there were online programs when I did it, I had to physically go to school.

I encourage all of my employees to follow their dreams and go to school as well. One finished her MBA, another just graduated with a BA, another is in school now. They all found programs that are online and that seems to be more manageable.

It’s worth doing. Time management, prioritizing and letting the unnecessary stuff go are the keys to sanity. And remember, there is a light at the end of the tunnel. Just get through one class at a time and eventually you’ll be done.

Engage with your full-time college student peers sooner — they can help you through. I worked full-time nights as a nurse, taking graduate-level business classes in the morning. I was so tired I didn’t sense how curious the ‘regular’ students were and how much they wanted to get to know me. Once I made the effort, they became a great support system.

I tried to do it 20 years ago with young kids, a more than full-time job, and travelling. Not surprisingly, I could not sustain the effort and was unprepared for the amount of non-class time I would have to commit, so that effort ended. Fast-forward to 2016, and tried again, this time with a completely online program. The coursework was still extremely challenging (more so than I remember from my brick-and-mortar experience), but the flexibility made all the difference in the world. Bottom line: be ready to commit the time and be realistic about your current life situation before jumping back in.

The course that seemed so valuable to gain new expertise ends up being little more than a high-level theoretical overview of the area. After a day of professional work with software, a computer science course seems like a step backwards, learning old techniques and theory. I find myself questioning the expertise of the professor compared to my professional colleagues. After a week of full-time work, I rarely have much energy to spend on deep learning, so I find myself doing the bare minimum to get by. I’m surprised at the low-quality work that is acceptable to get a decent grade.

I wish I’d had the foresight to schedule time for social activities when I first went back for my master’s. If I don’t look for opportunities to meet up with friends early, I either end up becoming a hermit or accepting last-minute invitations too close to class deadlines.

I wish I’d known how helpful programs like Khan Academy and even YouTube channels can be for brushing up on the basics. My advice for anyone going back for another degree after a long time out of academics would be to put pride aside and find a way to test how much you may have forgotten.

That I would immediately want to quit my job and go to school full time, forever.

It’s 100 percent worth it when you’re done. MBA.

You will be forced into TOUGH choices. After a while, it becomes hard to juggle school, work, and family. Additionally, I had travel related to school and for work. I ended up quitting work midway through the degree because my employer didn’t care about my MBA and I felt that I had reached my ceiling there. That helped me regain sanity.

I wish I’d known how much effort it would be. I knew college courses were hard, but I signed up, waxing nostalgic over going to college full time. Working then going to class after was totally different. It was basically paying a ton of money to do extra work. It feels especially hollow when you realize there are a dozen courses online where you could learn the same things for free.

That as time-consuming as it was, it wasn’t as bad as I thought it would be. I had put off getting my master’s degree for years because I thought I wouldn’t be able to handle all the extra hours. Once I got into my new routines, it was challenging but doable.

That success in school meant getting up early before work to read, staying up late to complete assignments, eating lunch at my desk at work while reading, and basically using every free moment to pull out my tablet and/or phone and chip away at assignments. Oh, and doing schoolwork on every vacation for four years, including on cruise ships.

Even though it was hard, it was worth it.

Academia is very different then real world and professors have a book perspective on leading business. Look for a school that has professors who have worked in your field and can provide real-world perspective.

There were three things I wanted to do well: work, family, and school. I found that one of these always suffered, and since family had the least-noticeable short-term consequences, that’s usually what I sacrificed. In the long term, however, the family impact was significant and I ultimately stopped taking classes. For anyone who is married or has a family, I would ask them to seriously consider whether a lack of degree is truly what is holding them back in their career. For me, it was not, and school was not worth sacrificing family time. If you’re single, go for it!

I wish I had known that my academic medical center’s (!!) implementation of software and a third-party vendor was done to suppress the usage of their highly-touted education benefits. I stopped taking classes after it became too much of an exhausting chore to utilize the “XX credits per year free!” benefit. (The “Benefits” [sic] department kept insisting I needed to pay for classes and fees that should have been covered by the education benefit.)

That it is well worth it – should have started sooner! Don’t be afraid to take more than one course at a time so you can finish your degree.

That I would be giving up my personal time completely for three years to complete my graduate degree. Online and flexible sounded wonderful when I started, but on top of a 50-hour work week, it didn’t take long for me to be on the computer every waking hour just to keep up.

The struggle was worth the effort. It took me five years to complete what would have been a full year on campus, but having that BS degree allowed me to move on. Without it, I would have not been eligible for most of the positions around the country that I have enjoyed and friends I made along the way. Now getting ready to retire from this life in HIS-land after 41 years.

That it was going to take five years for a master’s. I would still do it; it was the best thing I did for my career.

That work levels are exponential with more classes when you have a full time job. One class seems like a class load of work, two seems like four, and three seems like eight. I suspect with so much time taken up with your real job, being a full-time student makes the impact on limited free time more forcefully felt.

If there was an option to move the registration of the course to incomplete, audit, or pass/fail when work falls apart. Time allowed for completion of incomplete.

I had a very positive experience in completing a master’s degree while working full time. But it could have been a very different experience and outcome if it weren’t for the following factors:

  • The program was an asynchronous distance learning program, so I could do the work at night regardless of when I finally got home.
  • There was a lot of flexibility in the time for completion of the degree, so I could limit myself to one course at a time.
  • The faculty were excellent. I was impressed by the other students in the program. The topics, even in the required courses, were interesting, all of which kept my motivation high.
  • I had some flexibility in juggling my work responsibilities as I wasn’t doing full time patient care and my work deadlines tended to have some advance notice.
  • I had very minimal travel requirements for my job and for the degree.
  • My spouse was supportive in every possible respect

Taking two+ courses while working full time is incredibly difficult, especially if you come home from a day at work mentally exhausted. My tip: wake up early and get schoolwork done before you go to work. It’s tough, but it can be done! I would not recommend taking more than two courses at a time.

I did this in my late twenties while earning my MBA and enjoyed it thoroughly. Having context for the classwork in my daily life kept my engagement level high and helped to develop my time management skills. I would not necessarily recommend approaching undergraduate work this way, as there are important social aspects to a college education.

What I Wish I’d Known Before … Selecting a Consulting Firm for EHR Implementation or Optimization

Make sure consultants have a basic orientation to your organization, especially around acceptable use policies, communication, security.

They don’t know everything — trust, but verify.

Don’t let them burn billable hours with your vendor or other consultants without your participation or approval.

The #1 job of consultants is to create fear, uncertainty, and doubt (FUD) that you can survive without them.

Don’t be fooled by the sample resumes. In most cases, it is unlikely those will be the resources on your project. Bait and switch is common.

Don’t forget to factor in travel expenses — the more distance, the more $$$. Make sure they find your travel guidelines acceptable.

Call lots of references. Not the ones they gave you, but others on their “we’ve worked for every health system in country “ logo slide. Find out who is on their A team and get them.

Check their quoted number of employees (many firms are 70 percent temporary people). Go to LinkedIn and see how many people actually list them as an employer. Find out their turnover rate (both senior management and staff consultants) — again, LinkedIn is useful for this.

Unless they’re sharing financial and other risks with you, they’re not your “partner.” Let them do something small successfully, then sign them up for something larger. Interview their consultants and ask hard technical questions.

Always remember that they know more about you than you know about them. Consulting firms are notorious at being opaque. Beyond them really screwing something up and you spreading the word, they have very little accountability.

That they’d then try to get me fired so they could put their replacement in as interim leadership and bill for it.

How they vet their consultants.

I wish we’d had more perspective on the specific skill sets those working with us would have to ensure they fit the roles as we’d defined them.

What I Wish I’d Known Before … Serving on the Board of a Company or Non-Profit

That the Robert’s Rules of Order my Dad had occasionally instigated at the dinner table would be so yearned for when pandemonium decimated meetings run by the unaware.

How critical it is to have goals and milestones. We are over a year into a new non-profit and just now getting a board of directors in place. If I had it to do over again, I would sit down at a organizational meeting and put 4-5 big goals on a sheet of paper or electronically with a timeline.

How few of the non-profit board members read the written materials sent before the meeting.

I wish I had known more about the company’s ability to actually focus on, and be accountable to, their strategic mission. This relates to the balance of operational needs, strategic directives/promises, and monitored deliverables.

After being on the executive team of a large hospital and taking up a board spot on a non-profit, I wish I had remembered how little impact (rightfully) the board has on operations. It’s frustrating to offer suggestions and get ignored.

That I would quickly come to hate the comment “we’re all volunteers” as an excuse for why people couldn’t get things done and no one was held accountable.

How complex the interpersonal relationships can be and how much of an impact those interpersonal relationships can have of the function or dysfunction of a board.

How much I would have enjoyed it and how much I learned from a management / leadership standpoint. No kidding. Maybe it’s the non-profit organization itself or the fact that my fellow board members are easy to work with and for the most part share similar goals for the organization. I am going on 12 years serving for this organization in some capacity (eight years on the board) and I love every minute of it. One day I will have to step aside and let another person get as much out of it as I have.

I joined the board of a non-for-profit charity to give back. I didn’t realize just how much giving I’d be doing and what the annual give/get really meant.

I wish I’d known that I’d be working with some other board members who were only on the board because they were busybodies and had no intention of reading relevant documents, including legal depositions, that we needed to make decisions on and vote. Ugh. Never again!

The backstory on infrastructure acquisitions and their political import. Local politics are horrific.

What I Wish I’d Known Before … Retiring or Career Downsizing

Clearly the hit on the paycheck is the first thing that comes to mind. But honestly, when I look at ROI between continuing to work and no longer working, it makes it all worthwhile. Which is to say, the incremental difference in the paycheck to continue to work does NOT offset the pain and retiring and giving up that paycheck was the right thing to do. As much as I enjoyed my job in the latter years, it was not so much because of my managers, but because I figured out how to make it work. I’m glad to be retired honestly. And don’t even miss the paycheck!

Wish I had known devastating effect of having your life and ego wrapped so tightly around the work you’ve done or who you do it for. Working for a prestigious company gives you an identity to colleagues, friends, and family. When that goes away, part of you goes with it. You quickly realize that you no longer have a big name attached to big resources.

How much I would miss the daily interactions and problem-solving. The sense of trying to accomplish something as part of a team is difficult (impossible?) to recreate sitting at home. Also, my failure to create a meaningful alternative hobby during my (limited) spare time while working. Be sure to get an engaging interest outside of the office and family.

Perfect time to pick up a new hobby such as programming, web / app development. If you already know a computer language, learn a new one. There are some amazing new tools to play with out there: Python, SQL, Angular, MongoDB, Web2Py, etc. All free, open source. Pure fun. Expanding your mind to new levels, not to mention acquiring some needed skills as well. As the song goes:

“Go ask Alice
I think she’ll know
Remember what the dormouse said
Feed your head
Feed your head”


I went from working full-time to retirement in two days. Wish I would have / could have worked part-time for a while to ease myself into it. I also should have tried harder to find another job before I retired. Biggest reason I decided to go when I did (which was about three years before what Social Security considers full retirement age) was because of an insufferable department director and an incompetent CIO, both of whom were gone roughly a year after I retired. But it’s all good now. I love retirement.

Although the finances are OK, I think I’d like to have built up a little bit more reserve and know how busy I’d be. It has been nearly 10 years since leaving the workforce. Time is spent on things that I never even thought about doing (genealogy research is a huge time-suck), and at the same time, being more “available” for whatever short- or long-term project needs to be done among friends and family versus trying to squeeze it into weekends. Some of these (house fix-up) projects span a few weeks, others a few years. Have not been bored at all, but also have not had time to take a nap, which was a weekly thing after a 65-hour work week.

I wish I’d known how much I would enjoy downsizing my career from being a large system CIO. The quality of life improvement made me realize how much I was missing, and not having to constantly play politics was a huge relief. Having said that, I do miss a lot of the people that I worked with, truly some dedicated professionals who are really trying to make a difference in healthcare.

That once you have a “5” in front of your age, you suddenly become the least desirable applicant for any job in your profession. It seems employers think that once you hit 50, all your knowledge disappears. I would never have downsized had I known that I could never go back.

I retired “early” primarily because I was on the verge of burning out, both professionally and personally. So it’s more what I did know before retiring and that I had prepared myself for the transition. Best move I ever made. I am a recovered workaholic and quite content.

I haven’t done it yet, but an planning on getting off the corporate (software vendor) rat race as soon as my youngest graduates high school in three years. I’ve been through countless acquisitions, layoffs, VC, PE, and makeovers over my entire career. It takes its toll. Career downsizing will be a sacrifice, but selling the house, not buying a new car, and moving back to Florida and living out on the slow lane near the beach is my dream. My advice to the young up and comers: the price is not worth the prize.

I wish I had known before retiring that retirement REALLY would be one more of life’s major change experiences, similar to entering kindergarten, going away to college, beginning the first job, getting married, having a baby, getting a divorce, losing a loved one through death, etc. No matter how much I planned or expected certain events to occur, it was (and is) challenging.

Even though I had prepared myself before retiring, I was surprised at how quickly I became irrelevant.

What I Wish I’d Known Before … Being Admitted to a Hospital or Being Seen in the ED

How much my ambulance / ED / hospital bill would be for a three-day emergency admission at an academic medical center in Tokyo. Being an American, I spent much of that time stressing about how much it would cost me, assuming I’d be presented with the usual five-digits-or-worse sums we get slammed with in the US. Turns out I didn’t need to stress out so much The ambulance ride was free, courtesy of Japan’s taxpayers. The ED workup, including tons of labs and imaging orders plus the three-day stay, ended up being about $2,000. I expected at least one more digit on that number. The standard of care and facilities was actually better than what I’ve seen at most US hospitals. A good reminder of just how absurdly out of hand healthcare costs in America are by comparison. In related good news, my employer’s surprisingly generous health insurance plan reimbursed the full cost, no questions asked, probably because it was way cheaper than paying for a comparable situation here at home.

1. In the Emergency Department, even though I confirmed with the reception-triage nurse that my physician earlier had called into the ED to discuss my condition and to refer me to the ED and hospital, my medical record, under referring physician, listed SELF-REFERRED.

2. For the next 5 1/2 hours, while I was waiting for a decision to be made about my painful condition and hopeful admission to the hospital, two or three of my “neighbors” in the Emergency Department room were seen and admitted to the hospital. In addition, an Emergency Department staff nurse who complained of flu onset was immediately admitted to the hospital in an available pediatric bed.

3. After another three hours, finally a call was made to the gastroenterologist on call, a Fellow. She never came to see me. I was told by the attending Emergency Department physician 1) that GF did not think I needed to be admitted; 2) that except for requiring a blood transfusion, which would be risky, I was “healthy” and I should be discharged home.

4. Three days later (after the weekend), when I appeared for a rescheduled Clinic appointment, I was immediately admitted to the hospital with intractable diarrhea, failure to thrive, iron deficiency anemia, and a urinary tract infection. I remained in the hospital for TEN days.

5. After discharge, ONLY one day later, the home health nurse, my referring physician, and the on-call hospital physician advised me to return to the ED so I could be readmitted to the hospital.

6. This time in the ED, an NG tube was placed down my throat. From the time I received the NG tube to the time I was finally re-admitted to the hospital, eight and a half hours transpired! I was told that the reason for this intolerable delay was that the Medicine and Surgery Department physicians could not determine what was really wrong with me, and so they argued back and forth about which service should admit me!

Information about your condition and treatment will be verbally communicated to you regardless of your ability to comprehend or retain it due to pain and medication. And your care is overseen by a series of non-employee hospitalists that come and go, leaving nothing but a bill and an 800 number where you can leave a message but never hear back.

Upon discharge, you will be given a paper prescription for three days of medication and instructions to contact your PCP that wont be able to see you for a week.

Within three weeks, the bills for out-of network providers that you don’t remember seeing begin to arrive and will continue to arrive over the next year.

The only coordination of care that exists is what you personally enforce so take notes as best as you can keep copies of what little information is shared with you.

I took my wife to the ED late at night one time. After a thorough examination of her condition (ectopic pregnancy / ruptured fallopian) and in consultation with her OB practice’s on-call physician, the ER team decided to wait for my wife’s personal OB to come in for his morning rounds to see her. So they admitted her, without really consulting us and considering any alternative options, for the few hours until he came in and could get prepped for emergency surgery. She had a private room for all of about four hours, but of course that resulted in a significantly larger bill. I wish we had known more about this plan and had an opportunity to weigh in on the admission decision.

My wife was admitted following a skating fall and a early evening broken wrist. The ED did not tell us that a doctor would not be available to set the break until the morning, when we could have gone to a nearby hospital and had it done right away.

Admitted after about twelve hours in the ER bay (not too much of a complaint, they’re a busy hospital) to a room shared with a women with an altered mental state who rang the nurse call button about once every half hour.

I was brought a hospital gown and trousers, which were left folded on a chair that was past the end of my bed. I was hooked up to an IV on one side, and a heart monitor on the other, so I couldn’t even crawl to the end of my bed to try and reach for them.

The main light in the room was a bright overhead fluorescent light that spanned the width of the room, directly over the head of both patient beds, meaning that every time they checked on her in the middle of the night, they turned on a light that shone through my eyelids.

Eventually they stopped turning it off altogether, so I had to try and sleep with a pillow over my eyes, while hooked up to a drip and a heart monitor.

Similar experience with meals: I was moved to a new room that was “private” (until the next patient moved in) and when dinner came around it was a fruit cup and nothing else.

  • “That’s what you ordered.”
  • “I didn’t order anything, I just got here.”
  • “That’s what the last person in this bed ordered.”
  • “They were discharged, they aren’t here to eat their dinner. I am.”

The nurse felt really bad for me and rustled up something a little more substantial, but the total lack of coordination and apparently awareness that beds turn over was startling. I made sure to order a nice full meal before I was discharged so that whoever came after me got at least something they could eat.

Being provided instructions by the nurse on how to make my own bed with new linens. I don’t know what to make of that. On the one hand, nurses aren’t maids, so it seems weird to be churlish that the nurse wouldn’t be making a bed, but on the other hand it definitely seems weird to ask a patient (who is still hooked up to a heparin drip with a heart monitor in the gown pocket) to do it.

I wish I had known that just because nurses don’t get technology doesn’t mean they can’t give you excellent care. At the time I was doing desktop support at a hospital and went to the ED with a particularly virulent GI bug. Due to a combination of factors, they decided to admit me after six hours in the ED. I went to the floor where I felt the nurses were particularly incompetent based on the interactions I had had with them about their computers. The care I got was wonderful and I was incredibly grateful and humbled.

The difference between being admitted and being observed.

That the hospitalists may not be in my insurance plan and I don’t really get to choose the one that will see me.

That the doctor treating me while at an in-network hospital was actually out of network. Then that HDHP out-of-network charge single-handedly emptied my HSA for co-pay and co-insurance.

Even though the wait at the ED seemed shorter than at urgent care, by the time you add in waiting around for the doctor to get results and then actually share them with you, it ends up equaling out, except from a money perspective. ED is definitely more expensive.

As CIO, I was shocked at how folks taking care of me used the systems we had deployed. In discussion with them, it turned out their training was not adequate or they were told “this is how we do it.” What disappointed me most was that my staff was well aware of it and had done nothing to improve the situation, including giving management a heads up. Turning that around took a long time.

I’m probably not a very good person to answer this one, but I honestly felt very prepared for my inpatient surgery a few years ago. I owe this to a pre-op surgery instruction program I attended which was hosted at the hospital a month or so before the actual day of surgery. My doctor and his staff were also very organized and on top of their processes before the day. I had all my questions answered, fears allayed, and was pretty ready to go on D-Day. In fact, my care while at the hospital was so good, I almost didn’t want to come home. Yep, I know, this sounds like a paid advertisement. But I think it was my own initiative to educate myself and the the doctors’ / hospital’s efforts to plan how to educate patients to be ready.


What I Wish I’d Known Before … Taking my First Hospital IT Executive Job

That shifting organizational culture takes time and patience. When you actually succeed and the culture starts to change, your employees who were barriers to change will start to leave the organization.

That budgets are boring and the software in the space doesn’t help. Where’s the digital disruption in the budget planning space?

How political and backstabbing a faith-based healthcare system can be. And how adeptly a CFO can play the game.

Hospitals still may not value the role of IS leadership. Control of budgets can be limited to the point of requiring approval for PC purchases and everyone in the department is viewed as a help desk function. Strategic vision and focus on critical topics such as information security are lacking. In those cases, your role as an IS executive is to prove your department’s worth and role in the organization and drive cultural change. This effort takes many years with seemingly slow progress.

That even as a physician executive, my clinical credentials would be a point of debate among all the physicians with whom I had to interact. They challenged my authority constantly because I didn’t see as many patients as them, didn’t see as sick of patients as them, didn’t see patients in their specialty, etc. They had a host of excuses for why they shouldn’t listen to me and unfortunately our senior leadership wasn’t willing to tell them they were full of bull and needed to just get in line. I had the last laugh though when I led the (successful) initiative with the operations side of the organization to change their contracts to require compliance with EHR use and tied it to their bonuses. Surprisingly, they all got in line after seeing a drop in their bonuses once the new contract was in place.

Not much because I did a consulting project for them before they offered me the position. So I had a pretty good idea what I was up against and how long I would want to work in that type organization. I also made it clear that if they did not agree with the recommendations in my report, they shouldn’t hire me. I’d recommend that approach (if available) to others to minimize unknowns.

That the same projects I rolled out quickly and successfully (1-2 weeks) in the mid-sized physician office where I was the boss would take months to years to complete in a hospital-owned ambulatory setting. Change management is easier when everyone is on the same page, but much harder when duties are dispersed over multiple locations and individuals with varying skill levels. Partnering with a strong operations administrator with experience helps ensure success.

Healthcare IT is messy. Gaining physician cooperation in institutions where they are not employed (which is the majority) ranges from tough to nearly impossible. Healthcare economics are messy.

As a CIO, how much of my job would be pure politics, trying to placate high-production specialties practices and physicians whose productivity (and income) was negatively impacted by EMR implementations. That and the realization to whatever lip-service we received from the rest of the C-suite regarding “innovation” and “investing in technology to improve patient care,” IT was always viewed as a cost center, and when the inevitable cuts came, IT is at the front of the line. Having said all that, given all of the challenges, discovering how rewarding it could be when you accomplished despite the obstacles.

Most hospital CIOs are politicians, and as such, are reluctant to measure the value of their projects, like ROI.

Existing politics and relationships can be your death knell. When you arrive to your first C-suite job, be mindful about these two items. If you are not, it can put you in a very bad position. My advice is to use the two ears-one mouth ratio to listen and observe to figure out what is what. There are many reasons the team you just joined is there. They have most likely figured out how to keep their high-paying, high-perk jobs and they are not about to let the new person on the team mess that up.

Real power does not always lie with the obvious titles. Try to become aware of who is really running the show and who the CEO really relies on. Also, some CEOs promote politics more than perhaps they should. It then becomes high-stakes gaming where you, as the newbie, will lose if not careful. It is a harsh reality of many C suites, but it exists. I have worked in six organizations with various levels of C-suite politics. Four of them were fraught with really messed up, toxic behavior. Two were not.

Even with that said, I would not trade any of those experiences as it has helped prepare me for the job I have today. In my current role, while I have our office and company politics fairly figured out and know when to speak up and when to duck, it is a constant part of the job to help ensure I am not a casualty from an ill-timed or ill-placed remark or taking a stand when I could have just let it go. It is truly an art at this level and takes a lot of practice, observation, willingness to not die on every hill, and of course a bit of luck.

What I Wish I’d Known Before … I Quit My Job to Go to Work for Myself

How much you need to understand your strengths and weaknesses, and that just because you are great at a particular skill in your industry, it doesn’t you’ll be great a running a business in that industry.

That I would work harder and longer for myself than for any other boss or company. And that I would have more fun and freedom! Too bad healthcare insurance availability and costs for small businesses are pushing me back to working for an employer.

That I haven’t done it yet. “I don’t have an idea, what if I fail?” Fear is a shitty thing. For those who have, give those of us who haven’t hope, but don’t sugarcoat it!

I knew the cost of health insurance would be a large expense. However, I didn’t project that the cost would more than double from one year to the next.

I should have done it SOONER!

I wish someone would have hot me over the head making sure I comprehended the true cost to do business. Business registration at the state and local level, general liability insurance including automobile insurance, you’re your own technology shop, meaning you will have to buy and install all your software and hardware and configure it so it works. It is probably 25 percent more expensive than you think to start a new company.

Before I quit my job to go to work for myself, I wish I had known that 30+ years later I still would be happy having made that important decision.

That my finances were going to take a larger hit than I expected not because my business didn’t take off (always a known risk), but because it took me longer to get back into the job market than I had expected. Although I had very competitive job opportunities, my personal situation had changed while working for myself, precluding most travel or moving out of the metro area I was in.

That I had the skills, knowledge, expertise, and professional network to quit an established position and start our own firm. Wish that I’d had the confidence to do it a few years earlier.

That it doesn’t matter how successful you are right out of the gate — hire a salesperson. I didn’t because a series of old clients signed with me just after starting my new company and I became overconfident in my success. I know now that selling while you are successful sure beats trying to catch up when those early contracts start expiring. Also, as the owner, president, and chief guru, it takes a full time salesperson and you won’t have time to be that if you’re doing everything else, too.

Nothing. If I’d not been naive and ignorant, I probably wouldn’t have started the company. My ignorance allowed me to ignore the risks and take the leap.

Everything takes longer than you think. It is not easy for organizations to decide to work with small firms, even if the individuals at those firms have stellar resumes. The security blanket of a big brand name drives revenue, even if the quality of services from small firms is generally substantially better.

The sheer terror of the roller coaster ride of income and no income. It’s debilitating and drains every last ounce of downtime from what is already an oversubscribed schedule. Say goodbye to relaxing at the weekend or even on Sunday — you spend 24/7/365 working or thinking about work and where the next penny will come from. As for the clients and choices, it’s amazing how cheap companies can be when considering payment. They all seem to forget that at least 50 percent of any fees go directly to basic costs that are not covered when you are not an employee (billing rate vs. take-home rate).

Chasing after unpaid invoices is definitely one of the most unpleasant aspects of being self-employed. One positive impact I didn’t anticipate, however, is the way it makes you think about time and making every minute count, whether you’re working or not. Also, the sense of satisfaction gained from building your business and knowing you’re helping your clients is extremely gratifying.

You wind up being put in the tough position of actively having to sell your services simultaneous to having to wind down your existing assignment. That puts a strain on you, and for those of us who got into being solo to do more as opposed to sell more, it could be awkward to have to wear both those hats. It also reinforces the message that, as a solo practitioner, when you are not working, you are making zip. No PTO, nothing like that. A little extra pressure!

In a startup of one employee, I loved setting my own schedule, driving to my own goals, and working from home. But I realized I missed the interaction of other co-workers, being part of a team, and having my home be a home. If i was building a product, I would have stuck around longer to foster it, but I was doing consulting and contracting, which is hard to scale.

How much happier I’d be. I’ve observed two kinds of consultants – those doing it to stay in the flow (and make some money) while waiting for their next real job and those for whom it is their real job. No right answer, but it helps to know which you are. Today’s technology (Google Apps, Dropbox, VOIP, Upwork, and more) make it easier than ever before. A few pointers: Get a domain name – Gmail suggests you’re not committed. Consider forming an entity like an LLC or S-Corp. There are great retirement benefits available such as solo 401(k), if your revenues allow it — remember that any savings match comes from you, so need to take it seriously. If your business can support it, a virtual assistant can give you great leverage for scheduling, invoicing, and other routine tasks. Take advantage of the flexibility it provides in your life, though the flipside is you can always be on call.

The cost of being self-employed. There are direct costs, such as self-employment taxes and insurance benefits: life, health, disability, and professional liability insurance, and indirect costs, such as handling business development for the next assignment while executing the current assignment. And handling contracts is brutal. I once had a government organization ask me to sign an 80-page contract for a job that was worth a couple of thousand dollars. We eventually got it down to three pages because I refused to sign a document that would cost me more in legal advice than the job would pay for my services.

You will need an accountant. You will pay for an accountant. Even if you think you can do it yourself or fall victim to the “QuickBooks will do my taxes for me” idea, you will need an accountant.

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Reader Comments

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