When to quit that day job?

I’m on my second time of starting a full time business. The harsh reality is that it is probably a better financial decision to stay at your day job, so you need to be sure you have strong enough personal reasons to quit your day job.

For a lot of people, the regret of never giving it a go could be enough. As someone smarter than me put it “at the end of the day people regret the things the DIDN’T try.”

Make sure if you leave your day job, do it gracefully. After my first business didn’t work out, I was able to go back to my previous employer and it actually helped turn my career in a direction that I loved even more than running my own business.

Tough question, only you know the true answer for you. For me, I cut my retreat bridge before I started my business - that way I had to fully commit in mind and spirit, and I've never regretted the decision 🙂

This really comes down to a personal decision. The general wisdom is if you want to give something the best shot of success, you need to be fully committed to it.

Saying that you need to look at your personal runway - how long can your savings go. From my experience, you would want at least a full year of savings lined up, alternatively some sort of side hustle to bring in the dough if times get tough.

Seed funding can be quite challenging and can mean already having a product-market fit, you may be better off finding angel investors who can provide you with pre-seed funding early on. Keep in mind that pre-seed and seed funding from most investors would come with the assumption that the founders are not getting paid, or are getting a min-wage at most

I plan on going full-time in November with 6 months of savings and a 'make it work' attitude

Uclusion also started while we still had corporate jobs and we also came to the conclusion we had to quit those in order to make progress.

Unfortunately the only way to swing bootstrapping is to have enough earnings saved up to be able to take the risk.

However if you are already have a couple hundred users you might be able to get investors to reduce the risk without having to bootstrap long - I don't know your product well enough to say if this is an option.

Also since we are bootstrapping I hope you understand that I have no choice but to plug our product and ask to talk to you about introducing it at your startup or your day job (you are engineering managers and so definitely have the power to introduce Uclusion to your team). Note that if you are uncomfortable with this level of shameless plugging then you are definitely not ready to quit your jobs :-).