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

March 30, 2018 What I Wish I'd Known Before 1 Comment

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.

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Currently there is "1 comment" on this Article:

  1. I took the Cerner buy out in 2017. Yeah your identity is tied up in your work, but fortunately I have other identities. Doing a lot of volunteer work, hanging out at the gym.
    Deleted my LinkedIn account so head hunters would not bother me. My wife and I are able to live modestly but comfortably, take a trip or two, as long as there are no debilitating illnesses, life is good. I am finally working my way through that stack of books. Two stacks, actually, the important ones I “should” read and the spy novels and murder mysteries I actually read.

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