episode 62

About Chris Wilson:

Self-described as “the hardest working quitter you’ll ever meet”, Chris dropped out of college to pursue professional cycling, worked summers at his family’s B&B on Cape Cod, earned his way into an online ad agency by impressing the CEO, moved into sales at Hubspot, then at Nanigans, and is now officially self-employed working on UnStuckable with friend and co-founder Stephen Warley. UnStuckable is the show that brings you “knowledge, habits, and skills to get unstuck in your career and in life”.

Chris moved from sales job to sales job, “killing it” each time and making multiple 6 figures.  The “Millennial mindset” kept him constantly looking ahead to the next great company, the next opportunity.  Along the way, he started the UnStuckable podcast with good friend Stephen Warley and began to discover that his values and his idea of “true wealth” weren't necessarily aligned with those of his peers.  Being the “software guy with an awesome side project” wasn't enough.  He was left wanting to give UnStuckable more of the attention he thought it deserved.

“Creating” his own “crisis”, Chris finally ended up being relieved from his full-time job after letting his management know that he wasn't intending to stay longterm.

After recovering from being let go from his job and “recalibrating”, Chris went all in with UnStuckable.  Now, with UnStuckable taking off, growing and developing, he's considering stepping back into sales, but on his terms and putting UnStuckable first this time.

And why not?  It really doesn't have to be all or nothing!


If it's important to you, you WILL find


What You Will Learn:

  • How to calculate (yes, we're doing math!) the dollar amount you'll need to put away in order to build your “runway” if you're planning to make the leap to self-employment!
  • The importance of merging your identity as an employee with your identity as an entrepreneur.  Don't “throw the baby out with the bath water!”
  • How the ups and downs, the tests and failures, of the entrepreneurial  journey are the way to building your confidence and gaining continual clarity.
  • How you can get your business started while working full-time.
  • The value of connecting with others who are doing what you want to do!

Relevant Links and Resources:

UnStuckable podcast – hosted by Chris Wilson and Stephen Warley,  UnStuckable will bring you the “knowledge, habits, and skills to get unstuck in your career and in life”

For more information on preparing financially for a career transition:

For more information on the power of building a strong network:

For more information on starting your own business:


Get in touch with Chris! 

Twitter:  @chrisleewilson


Your turn:

Are you currently considering or working towards a career transition?  What's the most difficult part about the transition for you?  Tell us in the comments below!

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