Going all-in

There's a never-ending debate in online startup circles about when you should quit your job to go all-in on entrepreneurship. The current consensus seems to rally around the idea that you should build a business on the side (often called a "side-hustle") while you prove that it the water is safe enough to make the dive into the deep end.

Although this is now pretty close to the consensus wisdom, it is often sold as a contrarian take or "unpopular opinion". This is likely because it goes against the prior generation's wisdom that was more rooted in dotcom era startup culture, which was basically, quit your job and go for your dreams, everything will work out fine. And of course, in many cases with early internet companies, things didn't go just fine, and lots of people got burned and I assume had to go back to some kind of day job.

My take is more contrarian if compared to the current consensus. All of my attempts at building something on the side ventured into the realm of daydreaming instead of actually building something that could generate enough revenue to make a living. Without the pressure of needing that revenue, my focus was always on endlessly tweaking my website before launching it, instead of doing things that would move the needle.

For me the right decision was to quit my job and go all-in, otherwise I would have never gotten anything off the ground. However, the difference is that I went all-in on my skills, not on an idea. I was happy to take on freelance work that combined my technical skills and prior business skills as long as it was generally related to the direction I wanted to go with my startup. Even now after 2.5 years, my actual product revenues are only about 1/3 of the total company revenues, but by using my whole set of skills I can continue to develop my startup ideas without the pressure of running out of runway.

The problem with the traditional startup advice is that it makes it seem like you should go all-in on an idea. That's probably not the way to go for most people. Build your skills on the side and then take the jump when you're ready to go all-in on your skills.