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Ask Dave

Time to leave the day job?

Steve has two side jobs in addition to his regular job. He asks Dave how to tell when the time is right to leave your day job, and make a go of the things you really love to do.

QUESTION: Steve makes $25,000 a year at his day job, and he has side jobs as a personal trainer and a DJ. He has paid off almost all his debts, and he asks Dave how to tell when he’s ready to leave his regular job and concentrate on the other two.

ANSWER: I always tell people to first get to a point where their side hustle is generating almost as much money as their day job. I want the boat pulled as close to the dock as you can get it, so that when you make the jump from the dock to the boat you don’t hit the water.

In your case, I would want the $10,000 you earn from personal training to look more like $20,000. When you reach that level, combined with what you’re making as a DJ, it would create a pretty safe situation for you to quit your day job.

Maybe you could cheat a little on the personal trainer money, because you’re making as much or more as a DJ as you are in your day job. Otherwise, you’re giving up $25,000 for $10,000 and only hoping the personal training gig will grow. That’s not a good idea. I’d like to see that hope proven a little bit more before you walk away from a day job.