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.