As is common this time of year, I took some time to reflect on life and work. And a few different things reminded me of how incredibly fortunate and happy I am to be working at Basecamp.
But I bet you can guess the punchline — yeah, it wasn’t always like this. The year before I landed at Basecamp, things were pretty rough and I was miserable at work.
I know this feeling isn’t unique. In fact you might be feeling today how I did years ago — coming home from work tired, uninspired, unhappy, and even angry. It’s not a good look.
But change is within your grasp. It won’t be easy, but you can be damn sure it’ll be worth it. I speak from personal experience.
When I eventually reached my job-hate breaking point, the first order of business was to quit said job. I have to admit it was kind of exciting and liberating. But it was also intensely scary.
I was walking away from a good job working at a stable, respected company — a company where I could’ve had a prosperous (albeit miserable) career. I voluntarily went from having a very generous salary to one of literally $0.
Oh and by the way, as I took on this adventure of rebuilding my career I still had some huge responsibilities back at home: namely my twin infant sons and all the adulting required to keep them happy and healthy.
So you can imagine the unsettling feeling of self doubt I felt early on. More than once I wondered, “Did I make a huge mistake??”
But ultimately I realized what scared me the most was the long-term prospects of doing nothing — not just being unhappy for one year, but allowing that misery to fester over three, five or even ten years.
We spend an inordinate amount of our life at work — somewhere between 20–30% of our waking hours. How could I standby and let all those hours be filled with misery, only to bring that misery home with me every day to my family? No, if I was going to spend that much of my life doing something, those hours better be happy ones.
So I pushed aside that doubt, put my head down and got to work. I joined The Starter League and got my brain and attitude in the right space. I was learning tons and meeting great people. I felt professionally energized and excited for the first time in a long time.
I finished up my classes there and soon after I mustered up all my courage and took a long shot: I reached out to Jason Fried to ask if there was anything I could help with. We got to talking, and a few months later he invited me to join 37signals.
What an unbelievable turn of events. Going from the the worst job I’d ever had to working at my dream company wasn’t anything I’d ever expected. Fast forward 4+ years and I’m doing the best work of my career and I’ve never been happier at a job.
Now look, I’m not recounting this story as some kind of humble brag or to make myself look like hot shit. Anybody who knows me I am the furthest thing from hot shit. I’m ice cold shit.
I bring it up because I hope it shows the kinds of crazy, unexpected, wonderful things that can happen to anyone’s career if you take a chance.
I’m not special — all I did was acknowledge my unhappiness, embrace the uneasiness of change, and got to work. Yes, there was some luck involved, but even if I landed somewhere other than Basecamp, I still would’ve been happier and better off for having tried.
Of course it’s really important to remember that everyone’s situation is different, so don’t take my story as gospel.
I was fortunate to be in a position to take a chance like I did. I had years of work experience to help me recognize when to get out of an ugly situation. We were financially secure — it was a moderate risk, but I never put ourselves in any kind of precarious lose-it-all situation. And most importantly I had wonderful, incredibly supportive people around me — family, friends, teachers, colleagues, and so many others. I recognize not everyone gets the deck stacked in their favor like this.
It’s also worth noting that life wasn’t all roses and sunshine afterwards either. It took a long while to get everything back up to speed — to rebuild our finances, to re-establish my career direction, and even smooth out our family life and routine.
But in the end was it worth it? Absolutely, positively, hell yes.
If you hate your job, I’d really encourage you to consider taking action. But first you’ll need to evaluate your career situation, then decide what’s best for you and your family, now and in the future. It’s natural (and healthy) to feel scared, worried, and hesitant. Take your time, consider deeply, and take action when it’s right for you.
But no matter what your situation is, if you’re in a rough patch in your career I hope that my story gives you a spark of hope, something you can hang onto — the belief that better times await you when you’re ready.
There’s something great out there for you and your career. You absolutely deserve the happiness it can bring — go on and get it. 🤜🤛
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