Striking Out on Your Own: 2 Years In

September 5, 2018 Jeremy S. Cook, ECD Contributor
As my own boss, when I wanted a standing desk, I simply built my own. Image Credit: Jeremy S. Cook

As outlined in this post from 2016, early that year I had quite a fairly stable engineering job at a medium-sized company to work for myself. While that post was hopefully entertaining and informative for what it was, the real question — “can I make this work?” — wouldn’t be answered for quite some time.

Actually, I suppose it’s never really answered, just as the question of “will I be fired tomorrow?” is never answered with a more traditional job. As of now, though, I’ve been able to make it work for well over two years, so I’d call that at least a small success. So, what are the big challenges if you’d like to make a go of it yourself as a Maker Pro, entrepreneur, tech journalist, or other profession? Read on to see what I’ve found so far:

Income: Good, but Inconsistent

While I won’t go into specifics, on average I’ve been able to make what I consider a reasonable living writing about technology as well as the occasional engineering/DIY project. The key here is average. Looking at my invoice spreadsheet for this year alone, what I’ve earned from month to month has varied by a factor of nearly two. This kind of inconsistency can be unnerving, but if you learn to live on the lower number, the good months can help pad your cash reserves, not make up for debt accrued in the previous period.

Exaggerating this effect is the fact that while I may have done XX dollars’ worth of work in month YY, customers tend to pay on different time schedules. You’ll of course need to keep track of what you’ve billed so that you can confirm that payment has been made. Related to this, one can’t get too excited—and spend too much money—if your income looks amazing one month. The next may be comparatively lean.

Insurance: Available

One thing that people seem to fear most about working for themselves is that they won’t be able to get insurance. Without getting into the politics of it, as an American you can pay for your own, likely subsidized, insurance via exchanges set up under the Affordable Care Act, or via insurance providers. Whether what you purchase will provide the coverage you want with reasonable deductibles and premiums is another question.

Personally, my deductible is quite high, and I established a health savings account (HSA) to help offset this cost with its tax advantages. Overall, it’s a bit of a headache trying to work out which doctor and how each service is covered, but you’ll see that to some extent under a normal employer plan. As with income, having cash on hand (HSA or otherwise) to help smooth out bumps in your entrepreneurial journey is quite helpful.

Loan Qualification

This year our family bought a house, after me being in business full time for nearly two years. With a good credit score and a healthy down payment from the sale of my previous residence, I assumed this would not be a problem. Unfortunately, I was initially told that I needed two years of tax returns to qualify for a loan using my business income.

The good news is that since I had been generating business income as a side job for several years before officially becoming incorporated, another lending agent was able to use this fact to push the approval along. In the end, we were able to buy the house we wanted, with a bit more stress than normal along the way. This would have never been an issue had I worked for an established company and is something that should be researched if buying a house is a possibility in the future. It also pays to get a second opinion, a theme that becomes common when doing something that’s less normal than being an employee of a business.

Routine: A Necessary Evil?

Caption: While most of my time is spent writing, this rocket launcher strandbeest was also a work project. Image Credit: Jeremy S. Cook

When one considers starting a company, the perception is that you can work at Starbucks, a cafe on the beach, or wherever you can find Wi-Fi. If you want to take the morning off to go for a bike ride or play golf, it’s not a problem. This is true, and I and other entrepreneurs have ultimate freedom as to how many vacation days we take, and how, when and where we work.

The problem is that if I don’t put the hours in, and do so efficiently, I don’t get paid. Working at a coffee shop is a good change of pace, and something that I do occasionally, but it’s hard to beat the efficiency I get out of a dual-screen setup at my home office. Besides physical location, for me it works to get up reasonably early in the morning, and work until around 4:30, then put in an hour or so after my kids go to bed. This keeps me putting in the needed time to keep things going, not wondering if I did actually put in enough effort between shopping, mowing the lawn, and other things that can take up non-focused blocks of time.

While work never really ends when you’re in business for yourself, you do have some control over what you work on, and I often make fun projects such as the Rocketbeest pictured above with the hope that they will pay off either as a subject for an article, or simply as advertisement for Jeremy Cook Consulting. Another neat benefit is that if you’re a really good “employee,” creating extraordinary value for your company and customers, there’s no argument over being compensated for this in raises or bonuses. You’re simply rewarded in direct proportion for the amount and type of work you do via direct payment by your customers.

While I certainly work more hours than I did when with a larger company, it’s my choice. I could go to the beach for the rest of the day after writing this, but I probably won’t since there is always more to be done. Still, it feels good to know that I can!

Jeremy S. Cook is a freelance tech journalist and engineering consultant with over 10 years of factory automation experience. An avid maker and experimenter, you can see some his electromechanical exploits on the Jeremy Cook’s Projects YouTube Channel!

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