Knowing When to Quit Your Day Job and Pursue Your Passion

CareerQ: At what point should a budding entrepreneur with a side business go “all in?”

When you become only mediocre at both jobs.
“I was in this position when I started my first business. I had a great full-time job at the age of 24, but I always wanted my own software company. I needed my full-time job to make ends meet. I kept both going for about 14 months before I was getting really burned out — and my performance suffered both at work and with my venture. It was obvious that it was time to fully dedicate my time to my business.” Tim Maliyil, AlertBoot

When it’s too risky NOT to do it. “You should go ‘all in’ when you have an opportunity for success, and it’s just too risky not to do it! Too often we assess the risk of doing something. Challenge yourself to assess the risk in not doing it. This might be before your side business is producing a living wage. Yet, if you believe in it and the chance to create and grow is in front of you, that’s when you go all in.” Andrew Thomas, SkyBell Doorbell

When everybody is ready for you to step out.
“I recently stepped away from a company I built and grew over the last decade. I had a side business speaking and coaching. I stepped away from my original business and went all in when I knew my team was ready to run without me. They now run without me and run it better without me. The correct leaders are in the right places, empowered and writing the next chapter of our company story.” Matt Shoup,

The second you find that thing you love.
“People running side businesses should immediately recognize that in order for something to truly be successful, it’s going to take 100 percent of their being. ‘All in’ should happen the moment they realize that they would rather be doing this new thing rather than the other. To me, the decision to be an entrepreneur isn’t about finances; it’s about passion/risk on a well-calculated plan.” Michael Spinosa, Unleashed Technologies

When it makes financial sense for your individual situation.
“It’s a lot easier to take the leap when you have no bills, no kids, no mortgage or any real obligations to attend to. If you have a side business that is making you enough to survive, then take the leap. If you have bills, expenses and other people that you are responsible for, then focus on sales to break even in your business to then quit. Do not quit without any income coming in!” Chris Brisson, KickaConference

When it becomes an obsession.
“At some point, if the idea is right, the entrepreneur will get to a crossroads where the venture is keeping him or her up at night and that is the only thing that they are able to think about. This is when you need to make the leap.” Reza Chowdhury, AlleyWatch

As soon as you can support yourself.
“If you can lower the cost of living to a rate where you can reasonably support yourself on your side business without having to burn through savings, then you should go all in. That might mean not going out to restaurants for a while, or eating frozen meatballs every day for lunch (what I did), but it’s necessary in order for your business to succeed.” Mattan Griffel, One Month

Right now. “If you are waiting for that right opportunity to go all in with a side business, you do not have the ideal mindset to be a successful entrepreneur. Successful entrepreneurs have incredible tolerance for social risk taking and don’t need things to be perfect to get started. The time is now if you are on the fence to jump in and make it happen. Stop thinking and go all in right now.” Kristopher Jones,

When you have triple the savings.
“If the only thing keeping you from going all in is the illusion of stability that your day job gives you, then calculate the savings you’ll need until your side business makes you enough money. Multiply that by three (because it always takes longer than you think to make a decent profit, and you want to play it safe). Then, once you’ve hit that savings goal, go for it. You’ll be ready to go all in.” Dave Nevogt,

(Source: TCA)