by Niall Doherty

This is the fourth episode of The Foundations of Entrepreneurship. The goal of the series is to learn about the fundamental building blocks of business and entrepreneurship.

Today, we’re going to take a step back into the world of regular employment, because I know a lot of people reading this are still employees and have questions about the best way of transitioning out of that to self-employment. If that describes you, you’re going to want to pay close attention to what Jen Gresham has to say in this interview. Jen has a ton of experience helping people from all walks of life successfully navigate the murky waters of career change, whether that means finding a better job, or starting their own business.

I met Jen two years ago when I was passing through London. I had been reading her blog, really admired what she was doing and invited her out for tea. We’ve kept in regular contact ever since and even worked together for a significant stretch last year.

One of the big questions I ask Jen in this interview, which I suspect many of you would like to have an answer to, is how do you know whether to quit your job and plow full-steam ahead into running your own business, as opposed to starting up something on the side and seeing how that goes before taking the leap? Jen has really good advice on that and great answers to lots of other questions relating to career change.

Uncut interview (62m)

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3 Key Takeaways

My three key takeaways from this interview, with a focus on action. (Remember: doers get rewarded.)

  1. Define what success means to you. This is also known as figuring out your why. What are you really aiming for? Why are you doing all this? Jen mentioned that the most important thing for her is being able to spend quality time with her daughter, and so her business should enable her to do that. That’s the primary goal, ahead of making X amount of dollars per month. So take some time to think about and write down your own definition of success.
  2. Experiment with a low-risk side business before taking the leap. This is the best approach for most people, rather than quitting your job and only then trying to start a successful business from scratch. Don’t worry about finding something you’re passionate about. You want a throwaway business that will help you develop entrepreneurial skills and figure out your natural strengths. So think about what kind of business you can start today. What would be the first step you could take to try it out? Go do that.
  3. Connect with people who are out there doing what you want to do. Jen talked about how she’s a rogue in the military scientist circles. But when she goes to a meeting of non-comformists in Norway, she feels very conservative. Shaking up your environment like that is a really good thing to do, for two reasons. One, you no longer feel like a weirdo, which you’re likely to do if you surround yourself mostly with 9-to-5 types. And two, you expand your mind and open yourself up to opportunities you wouldn’t otherwise be aware of. Find at least one person who is out there living an alternative lifestyle that you’d like to emulate, and connect with them however you can.

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Oh, and last thing: Thanks a mil to my buddy Emmett Cooke for providing background music for the interview. Check out more of his work at


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