This told essay is based on a conversation with Outset founder Aaron Cannon, a 37-year-old who lives in San Francisco with his wife and 3-year-old son. Edited for length and clarity.
I decided to start a company while on maternity leave.
It's very intertwined. Starting a family and starting a startup happened along a similar timeline. I'm sure there are many people who think that's a bit unreasonable. that's right. There are wistful moments when you think, “What if I could have done all these things when I was 25 and single?”
And then I immediately remember how stupid I was when I was 25.
Maybe I had too much time to think about it during childcare leave. Having a baby requires all your physical effort, but it doesn't provide much intellectual stimulation. I was daydreaming about what I wanted to do with my career.
It's a very rich balance. The term “work-life balance” has a certain coldness to it. I don't have that. Every moment of the day matters. Everything other than family and work becomes a lower priority. That's painful. That's really ruthless prioritization.
It's very psychologically weird. In a normal job, you might have really busy days and then come home and say to your family, “I need to take a break.'' The problem is that my current job is busy every day. Our startup is in a crazy growth phase where everything is growing and collapsing at the same time.
I can't be present as a father if I go home and say, “Hmm, this is so intense.” I don't have that option.
Yesterday, on my way home after work, I received an intense phone call. I'm negotiating this contract. Then I pick up my kids and spend the next 20 minutes explaining the seasons to them. It started with “Do you understand what a year is?” No, where do you start? It's a crazy mental shift.
I pick him up every day so boundaries are enforced. Thankfully, my co-founder and I lead different lives. He will stay later, but I will come first. As long as we both show up the way the founders need us to, that's great.
But I'm leaving. I pick up my child from kindergarten every day. I'll take him home. I'll have dinner. I put him to bed. Then it's back to work. It's a precious few hours.
Even if I'm physically present, it's very difficult to shut it down after the busiest day of work. Even if you set boundaries in the physical world, you can still be there mentally or not be there. I want to be as deeply involved as possible.
We went through Y Combinator in 2023, and I was definitely on the old side. There were speakers and programs on Wednesday nights, but it wasn't easy for me.
Being a father gives you perspective. As a founder, it's easy to take the big and small things that are happening at face value and get attached to them. You are the company and the company is you. When I get home and have to explain the seasons, I'm reminded, “Why do we do this?” It will be zoomed out.
It also helps strengthen my motivation. I want my kids to grow up watching their dad make big career changes and try something crazy. That's the lesson and example I want to set him. You can also go make something yourself.
It's a chapter of my life, but it's not my whole life. It's intense. We should expect that to happen.
The most important thing is that I am present as a father. I haven't been back in years. He is only 3 years old and one year old.
