I’ve been self-employed for over eight years. For those who’ve never tried, it’s way harder than you think. But it’s worth it.

10am Lunch

I can work anywhere. A month in Hawaii? Aloha. Six weeks exploring Greece? Pass the souvlaki. Six months in the UK? So long as there’s Wifi, cue the dancing beefeaters.

I can work anytime. If I crack all eight knuckles at four in the morning or drag in my sagging glutes at eleven, nobody cares. If I feel like a bowl of ice cream at 10am and choose to call it lunch, it need only muster the strength to walk to the fridge. If I’m feeling burned out on a Wednesday morning, I don’t even have to call in sick.

I don’t do meetings (bloody things). The inefficiency of boring, irrelevant, circular team meetings always annoyed me at corporate jobs. As an independent, I’m able to conduct small, fast, focused meetings on my own terms. Fewer gray hairs, fewer clawed-out-eyeballs, more real productivity.

I have no commute. In place of the typical 50+ minutes of vapid talk radio in traffic each day, I have the joy of walking my daughter to and from school. What would you do with an extra hour every working day of your life?

I’m there for my kids. At the risk of veering into teary-eyed sentimentalism, as a father of two young kids, working from home has given me the most precious gift of my life: time with my babies. I’ve been here for the kids at every stage, and that’s something no one can ever take away from me. I will go to my grave lingering on these priceless memories.

I make a good living. The most surprising piece of all is that I make more money self-employed than I would as an employee of most corporations. Each year I’ve earned more than I did the year before with more feasts and fewer famines, and all with a level of autonomy that I would never have dreamed.


If it were that simple, everyone would be self-employed. The life I lead is anything but easy.

The ability to work from anywhere is a problem as much as a luxury. It means that I’m never really “off,” since work follows me everywhere I go. Most “vacations” mean “Daddy’s working remotely.” Most people assume that the challenge of self-supervision would be mustering the will to keep working. For me, it takes much more discipline to stop working.

And planning vacations is difficult. If a big job comes along just as I’m heading out the door for a week off with my family, there are times when I am forced to take it. I have lots of time off, but I don’t always have control over when that time is available.

Even if I am disciplined with my schedule, self-employed means I work more, not less. It’s true that nobody can tell me when or how to work, but my need to pay the mortgage demands that I make the most of every minute of working time. Every giphy search and YouTube video costs me dearly: if I’m not working, I’m not earning.

My wife and I can’t do monthly budgeting the way other families can, because our income fluctuates week to week, month to month, and year to year. Having ample savings can be a huge help in buffering the swings, but when you go three or four months without a paycheck–as has happened to us more than once–it’s definitely nerve-racking.

It’s true that I don’t waste time in useless meetings, but the broader truth is that I hardly interact with another human on any given day. The solitude alone would have most people chewing leather scraps and talking to the walls. No watercooler conversations. Lonely coffee brakes. No bawdy jokes or inappropriate salutes, no mean post-it notes left on my monitor (unless I leave them myself), no small talk, no big talk, no trash talk. Just me.

And while it’s true that I make more money than I might as an employee, I work much harder for each and every dollar. No one arranges my health insurance, tax withholding, or retirement savings for me. I have no entitlements, no pension, no 401k matching, and private health insurance costs nearly as much as the average American house payment. Everything is more complicated when you’re self-employed. Everything is more expensive.

Pros v Cons

On balance, I love being self-employed.

I work hard and take pride in what I’m able to accomplish, and while no one is ever truly independent, I have much greater freedom and autonomy than I did when I worked corporate jobs. I spend more time with family, less time in silly meetings, and it’s hard to imagine going back to spending eight hours a day in a cell cubicle.

There may come a day when I go back to a traditional job, and I can imagine many circumstances in which that would be a deeply gratifying development. But even if I go back to conventional employment, my perspective is forever changed. I no longer think of “a job” as a necessity for a happy, productive, gratifying life, and that is incredibly liberating.

Self-employment can take many forms: freelancing, consulting, contracting, selling a product, running an online business, investing, or, best of all, a little bit of each. I’ll talk about approaches to self-employment in another article.

Self-employment isn’t for everybody. But if you’re the kind of person who can make it work, chances are you’re also the kind of person who will be very glad that you did.


Adam O'Hern is an industrial designer, designing products ranging from laptops to power tools, classroom toys to bathroom fixtures, and pro audio gear to guitar tuners. In 2008 he founded cadjunkie.com, and in 2010 co-founded EvD Media with Josh Mings of SolidSmack.com, and the two collaborate on the EngineerVsDesigner.com podcast.