Achieve and Maintain a Work-Life Balance Entrepreneurial Lifestyle


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A great deal of the businesses we sell at Quiet Light are founded by entrepreneurs looking for the rush of finding the next thing. Sometimes they look to sell because of burnout and sometimes it’s just boredom. Today’s guest’s business is designed to help entrepreneurs really question the goal of the businesses they run.

Jason Zook earned social media fame and experienced that burnout while on his first entrepreneurial ride after walking away from his day job. For five years Jason ran IWearYourShirt, creating thousands of videos, photos, posts on social media, and had countless media outlets talking about IWYS during the early days of social media marketing. At some point, Jason realized he had almost created a self-made work prison for himself. He and his creative wife started their company to guide owners towards financial freedom and a business they actually want to work on. Jason’s focus is now on working to live rather than living to work. He strives for entrepreneurship with a healthy balance.

Episode Highlights:

  • The backstory on Jason’s current company, Wandering Aimfully.
  • Why the t-shirt business had to end.
  • The things Jason learned from that business and his subsequent years of starting and growing companies.
  • How Jason and his wife formulated the idea for the business.
  • The importance of setting a mark and working towards it.
  • What the “enough” number means to Jason and his wife.
  • How to create the balance between getting ahead and falling behind.
  • How that balance applies to the business creep that can often take over work-life balance.
  • Ways Wandering Aimfully helps people build their business impactfully based on what they need,
  • How Jason uses challenges to create habits.


Joe: Most of the businesses that we sell Mark … well maybe not most but a great deal of them are businesses where someone bootstrapped it, put all their energies into it, got it up to a certain level, and then looked around and thought “man, this is kind of work now I’m not loving this day to day anymore; I’m not happy with this challenge and I’m getting burnt out”. It happened to me. I had a cushy gig, I was working 20 hours a week, easy business, recurring revenue, and I looked around and said this isn’t fulfilling me, I’m burnt out I need to move on. A lot of buyers that are from the corporate world don’t understand that. Those people that are in the entrepreneurial world know that they need that new challenge, that exciting challenge. And as I understand it you had Jason Zook on the podcast; a husband and wife team actually and they talked about working to live not living to work and trying to overcome that burnout challenge.

Mark: Yeah, Jason got completely burnt out with one of his 1st businesses and one of his 1st businesses; really simple concept, he would wear a t- shirt that was a sponsor. It would be their company on the t-shirt and he would wear a t- shirt every single day and put up a YouTube video of that and the prices increased every single day for that sponsorship. And so as he put it he said I was doing daily videos before Casey Neistat made that cool to publish daily videos on YouTube. He said it was great initially and he was making money by just wearing t-shirts and having people follow him around with cameras. But then this organization grew and it grew more and more and his whole life every single day was being documented and he built this prison. And I think as entrepreneurs a lot of us can relate with this idea that you build prisons sometimes for yourselves with the businesses that we’ve built. And so he naturally got completely burned out on that and now his whole focus and life as entrepreneurship but wit

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