Photo credit: Austin Neill on Unsplash

If you’d asked me twenty-six years ago where I thought I’d be today, working in my mechanic’s waiting room would not have been one of the answers.

Here I am anyway.

Turns out, flexibility of location is an enormous benefit of self-employment. You learn to work practically anywhere: in my office, a client’s office, the aforesaid mechanic’s waiting room. In libraries, airports, airplanes. In restaurants, hotel rooms, hotel lobbies, churches. On my porch, at my mother’s house, in the back of an airport limousine. Pretty much anyplace with a flat surface is a place where I can work. (I once took a stack of documents to a dance recital so I could keep reading while waiting for the curtain to rise.)

Another benefit is flexibility of schedule, but this comes with limitations. When you bill by the hour as I do, there’s no such thing as paid time off. Any hour not spent at work is an hour not spent earning a living. As a result, I rarely meet anyone for lunch; it simply takes too long. By the time I drive to where we’re meeting, we have lunch, and I drive home, usually close to two hours have elapsed. That means either I’ll be working two hours later that night or the price of that lunch now includes what I’d have earned in two hours on top of what I actually paid for the food. As a result, if I take time out of my workday for a non-work appointment (medical, vet, Mom stuff), I automatically calculate the true cost of that appointment. (It is not always easy to convince people that there is a very real cost to my out-of-office time, especially when they’re wed to the notion that “you can do [whatever needs doing], because you’re self-employed, so you can take off whenever you want.”)

As to other aspects, the cost/benefit analysis is a little harder to classify. For example, I’m solely responsible for all my equipment. I’m writing this on my 2018 Surface; God forbid this device fails, I’ll need to shell out funds for a new one, because I learned early on that a backup device is one of those things I absolutely must have, second only to a pen. When you earn your living by using a computer as I do, you cannot afford to have only one machine because when that one fails (as it inevitably will, usually on the eve of a deadline with little or no warning), you’ll be in a very difficult position. You also can’t afford to run out of toner or other printer supplies. You need a reliable smartphone so you can check email and messages from anywhere (including any of the above-referenced locations) and download documents if you need to review them before returning to the office. As for smaller expenses, I note that in the past year, I’ve replaced a desk lamp, obtained a riser for the desktop monitor, and purchased an easel to support a free whiteboard. Whatever you need to operate your business is something you need to acquire; when it fails or runs out, you must replace it. Luckily, such expenses are deductible, but as I learned early on, nothing is deductible until you’ve first paid for it.

Which brings me to professional support. The self-employed person needs a support system. Back when I was a W-2 employee, I didn’t need an accountant to handle my taxes, but now I do. I also have regular computer support available. My insurance agent handles not only my car and homeowner policies, but my malpractice insurance. I also have an adviser to guide me in managing my retirement account since one of these days, I’ll probably want to stop working. Some people can manage some or all of these things on their own, but one thing I learned early on was to identify what I know how to do and hire out the rest. Not only does it protect me against the effects of my ignorance, but it’s more cost-effective: in the hours it would take for me to produce the same tax returns and quarterly estimates my accountant does each year, I can easily earn far more than I pay her for those services.

Are there downsides to self-employment? Of course. Chief among them is uncertainty, especially financial. Some clients will pay promptly; others will take their sweet time, and some will try to avoid paying altogether. It’s been many years since I’ve needed to sue someone for payment, but I remember the stress involved—not to mention the amount of otherwise-billable time I had to invest in chasing down fees I’d already earned. Of course, even if the clients are paying appropriately, the cashflow might be slow simply because there is a lull in the work. (Summer, with its vacations and long weekends, is an especially popular time for such lulls.) Businesses fail all the time for want of customers or clients. Especially in the early days of the pandemic, my clients weren’t getting paid by their clients, and so they weren’t asking me to do work they might have to pay for out of their own pockets. Had it not been for the federal programs protecting small businesses, I could never have stayed afloat until business picked up again.

One consideration when setting up a small business is scaling. In other words, can you create something one time (such as writing a book) and then have it continue to make money for you while you’re doing something else (writing the next book)? Or are you in an non-scale business where an hour’s work produces an hour’s income so that the amount that can be earned is limited by the hours worked? My main business (legal research and writing for other lawyers) is non-scale because it’s entirely about the personal service I’m providing, but my side business (writing and publishing fiction) scales. It’s something to think about when you’re trying to decide how to structure your business.

Another consideration is expenses. Take hiring, for example. Over the years, I’ve periodically hired file clerks to tend to clerical functions like closing and storing files. I’ve also hired subcontractors to do research or analyze data when my workload exceeded the time available. I’ve never hired a permanent employee, though. For one thing, I don’t need to, and the cardinal rule of self-employment is never spend money on something you don’t need. For another thing, hiring someone doesn’t mean you never have to think about what you’ve delegated; employees or independent contractors still need direction and oversight. So there’s an expense of time and attention as well as funds, and you need to consider whether the benefits of hiring help outweigh the costs.

In the past few years, I’ve applied for several jobs. The primary purpose was to lock in some security of income as some of my clients have begun to slow down, retire, or (in one case) die. Somehow, though, none of these jobs worked out—either I didn’t get the job, or it came with unacceptable conditions.

And so here I am, twenty-six years after that Monday morning in June when I woke up and—for the first time in my adult life—I did not have to go to work in someone else’s workplace. I had one client and enough work to last me two days. On Day Three, I wrote my first (and only) marketing letter and sent it to a dozen small law firms.

I had no idea what might be on the horizon, whether my attempt at self-employment would pan out or fail. No one ever does.

So far, so good.