Episode 44: When should you quit your day job?

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It’s THE question for every entrepreneur trying to turn their side business into their main livelihood – when should you quit your day job and pull the plug on a regular paycheck? The internet is full of encouragement to “take the leap,” but I don’t think that tells the whole story when it comes to such a difficult and complex decision. In today’s episode, two previous guests on the show talk about the struggles of quitting their day jobs and give some great advice for others considering it.


  • Why Alex did NOT take a big leap of faith… and what he did instead (3:30)
  • The importance of considering longevity in both business and life (5:05)
  • What to do if all your mental energy is spent on your day job (10:09)
  • How Kristi tried to quit three times before finally cutting ties – and what her first year of full self-employment was like (15:46)
  • Determining your level of risk tolerance (19:57)
  • What happens if everything goes wrong after you quit? (24:52)


  • Tyler Philbrook

    I put my notice in at work and my last day is June 28th. I’m excited and terrified at the same time. Thanks for this episode it was perfect timing for me.

    • You’re welcome… and congratulations! I hope things go really well for you ๐Ÿ™‚

      One thing I alluded to in the episode but forgot to mention specifically is to have a plan for your time. Paradoxically, sometimes having “too much” free time to work on your business can actually be counterproductive, and lead to feeling unfocused and unproductive. Without the constraints of a day job, I find that restricting my working hours to specific blocks (not leaving my whole day open) is helpful.

  • I fully agree with you and your guests. About 4 years ago I also decided to quit my job. I was developing and working on my own company for almost 2 years (mainly in evenings and on weekends) and then I decided to make step forward. It was one of the best decisions in my life ๐Ÿ™‚

    • Glad to hear it worked out well for you! Did you have any trouble adjusting to full-time self-employment initially, or were you able to hit the ground running?

      • In the last few months when I was working full-time job I had a problem to get some time for myself. In the evenings I was working for my clients and during a day for clients of the agency I worked for. After quitting a job I felt a huge relief and finally I had time only for my clients and for myslef ๐Ÿ™‚ I didn’t have any troubles with adjusting full-time self-employment. It was something natural to me, to leave old job and start my own business. Of course without building it for last 2 years and working full-time job at the same time it wouldn’t be possible. As you said in the podcast it also depends on risk tolerance. I left my old job at the time when I started to earn the same money like in full-time job. It was a secure income for me and that affected my decision about quitting my old job.

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