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When Should You Leave Your Job?

With more and more opportunities to become an entrepreneur and a low barrier to entry into online business, it can be a struggle to figure out the right time to leave your 9-5 job. In today’s episode, we chat about how you can prepare yourself, and some of the milestones to hit before handing in that resignation letter!


Key Insights

  • Understanding exactly what it will take to be safe in quitting your job
  • Create a “Runway” to understand how much time you will have to replace your income
  • Realize that it’s still OK to continue working, ,while you build your business. There is no rule to when or IF you quit your jb


  • [00:18] – Welcome
  • [03:10] – Mitigating risk
  • [06:02] – Understanding the reality
  • [08:00] – Safety
  • [10:17] – Planning your expenses
  • [11:31] – Hating your job does not necessarily mean you should open a business
  • [14:18] – Oftentimes, your job can actually give you experience and tools needed to become an entrepreneur
  • [20:49] – Creating a “Runway”
  • [26:28] – Milestones
  • [28:35] – Action Items

Resources Mentioned

Actions to Take

Tom Sylvester
  • Spend some time figuring out your Runway
Ariana Sylvester
  • Thinking of leaving your job? Share your “quit” date with us for some public accountability!

Tom's Bookshelf

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Tom Ariana Lifestyle Builders

Tom & Ariana Sylvester

Tom and Ariana have built 3 business and quit both of their jobs, all while raising 2 amazing kids.  Together they share their philosophies and guidance for entrepreneurs on their Lifestyle Builders™ podcast, their upcoming book Lifestyle Builders™: Build Your Business, Quit Your Job, & Create Your Ideal Life, as well as through their coaching and consulting programs.

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