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  • Writer's pictureTerry Dockery

The Happiest Entrepreneurs I Know

My longtime friends John and Jane Doe (no, these are not their real names) are the best and happiest entrepreneurs I know. They're retired now, but let's look at how they did it and take inspiration from their example.

From the research in Positive Psychology, they did a good job on all four of the major sources of happiness:

A caring relationship with yourself


  • Ate healthy food, exercised, and practiced meditation regularly

  • Maintained a healthy balance between their work and personal lives

Caring relationships with others


  • Met in graduate school, fell in love, and got married

  • Have three grown children who are successful and happy as well as a bevy of cute grandchildren

  • Have lots of friends (and throw great parties)

  • Were, and still are, active in their community

Work you love doing


  • Were both professional service providers who were passionate about their work

  • Are satisfied they have made a positive difference in the lives of others as their legacy

Enough money to pay your bills with some left over for fun


  • Bought a house in a rapidly gentrifying area which is now worth 4X what they paid for it

  • Worked for the same company for several years, and then launched their own company (which was a two-block walk from their home)

  • Managed their money wisely during their earning years

  • Are comfortable financially and have the time and resources to visit their children and grandchildren as well as take adventure trips

High-Performance Habits

  1. Include being happy in your definition of being a successful entrepreneur--otherwise, what’s the point?

  2. Learn how to “work smart” rather than “working hard” so you can maintain balance and enjoy your entrepreneurial journey.

  3. Don’t live your life in such a way that you wind up with a lot of regrets on your deathbed--be clear on your priorities and live them now.

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