Do you live to work, or work to live?
I’ve always been a freelancer—not because I had to (i.e. I couldn’t find a “real job”), but because I wanted to. Every year I’d get job offers to work at a larger company or an agency. A few clients even prodded every now and again to see what it’d take to get me to work for them full-time (my answer was always to laugh and say $1m/year… which results in zero follow ups from them).
I resisted working for someone else because I enjoyed being unemployable. I acted with great purpose and intention to be my own boss. I didn’t want to freelance only until I was “successful” enough to start a big agency of my own, or build what I had into something larger. My end goal was always to just keep doing better and better as a freelancer. My company, of just me (and a few other freelancers to help), was the perfect size.
A few times over the years I had offers to work for someone else that were tempting. One time, many years ago, an agency that I admired reached out to see what it would take for me to join their ranks. They were pretty good at saying the right things too. Although I’d have to relocate to their head office, I could work from home some days, unless there were meetings. I’d assume a high-up position where I’d be surrounded by smart, skilled and autonomous coworkers. They’d pay me more than I was making, and give me benefits.
It was super tempting and I seriously considered it, more than most offers that came my way. But the more I continued to talk to them, to the founder, to their HR team, to other folks who worked there, I realized that there was this nagging voice inside me, telling me that while I thought all the advantages of working for them were important, there were more important things, to me specifically.
The final piece that led me to unequivocally say that I wasn’t interested was a conversation with one of their HR staffers, who went on and on about getting 3 weeks off a year to start (instead of the usual 2 most other companies offered). She was honestly and genuinely pleased with the extra paid week offered, I could hear it in her voice. The problem for me was, at the time, I was taking 2-3 months (not weeks) off work per year. Sure, it wasn’t paid time off (as a freelancer, you only make money when you’re working), but it was still time away from work and clients.
I finally realized that no amount of money could replace the enjoyment I experienced from my freedom to choose to work or not. I enjoy that I can control the freedom of my day, my work, and my life more than I could if I worked for someone else. And while it’s not complete freedom—nothing offers this except being independently wealthy (one might suppose)—working for yourself has a lot more freedom than most corporate jobs. Yes, it took a while to get to that place with my freelancing, through a lot of trial and error (mostly error), but once I was able to support my family by working for myself, that freedom became the most important thing to me.
Even though I’m no longer a freelancer (I don’t have clients or offer services), I still approach my work the exact same way. With every opportunity or choice that comes my along, I think about the trade-offs. If I proceed, will my day be filled with tasks I dislike? Will the choice lead to less freedom and control over my work? Will it impact what I value as important?
All of this, of course, comes from a slightly entitled place. The choices that are available to me are there because I’ve done well enough with work and saved enough money. I’m also a white guy in a first world country, who came from a middle-class family—and as my buddy Brendan Hufford says, I get to play life on “Easy Mode”.
The ability to make decent money working for ourselves, from home is still a fairly recent phenomena. A confluence of technology, social acceptance that working for yourself is no longer frowned upon (trust me, it was not too long ago), and the increasing number of cheap tools that help us reach more people (social media and mailing lists, for example), set up shop (legal and business services cost far less than they used to), and super cheap and easy ways to collect money online (previously you needed a merchant account which required months of hoop jumping)—all make it possible to do what we do for a living.
Really, this whole “working for yourself” as a freelancer or a company of one or whatever you want to call it, is so incredibly new, there are countless unknowns. Even for myself, 20 years in, I don’t know what things will be like for myself or anyone else working for themselves in another 20 years.
Many of us have the opportunity to choose how we want to work. Which is great, and wasn’t a real option even one generation ago. We have the luxury of thinking about how we want our work to affect both our lives and the lives of others. Do we want to work towards having more time with our family? Towards making more money? Towards fostering a creative outlet? Towards finding a way of working where a disability or health issue is no longer an obstacle? We can. Instead of living to work, we can work so that we can live. And while not everyone has to work for themselves (it’s cool if you don’t want to), many of us consider our options and decide to give it a go.
And while there are a lot of unknowns, long and short term, and while it also requires more work most of the time (because you’ve got do the work and run the business), it’s still completely worth it for some. Personally, I can’t see my life working any other way.