Founders who’ve been at it for 10+ years — do you ever wonder if you chose the harder life?
I’ve been running my business for around 10 years. We’ve been profitable almost every year, and at one point we were doing around $3M in revenue. Over the last two years, though, we’ve lost roughly two-thirds of that revenue and have had to significantly resize the business.
I’m still grateful for the journey. I’ve learned more than I ever would have in a job, grown tremendously as a person, and I genuinely value the freedom of building something of my own.
But sometimes I look at friends who stayed in corporate jobs and wonder what life would have looked like if I had taken that path.
Some of them now earn very well, have predictable careers, proper weekends, holidays where they can actually switch off, and generally seem to carry less uncertainty. Meanwhile, as a founder, even when things are going well, part of your brain is always thinking about the business.
I know I’m also seeing only one side. Jobs come with bosses, politics, layoffs, limited control and their own frustrations. And after 10 years of running my own company, I honestly don’t even know if I could report to someone anymore.
Still, every once in a while there’s this thought: was all the sacrifice worth it? Not because I hate the journey — I’ve actually loved most of it — but because financially and lifestyle-wise, entrepreneurship hasn’t automatically put me ahead.
I’m curious if other long-term founders go through this too.Do you ever compare your life with friends who chose safer careers and wonder “what if”? Is it regret, founder fatigue, FOMO, or just a normal part of the journey?
And how do you make peace with the path you chose?