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From Amish Farm to Entrepreneur...

(First appeared in WRAL TechWire.)

I’m taking a hard left this week to address something that I get asked about regularly.

Many of you know that during the pandemic I left a role I really enjoyed to start my own company. And now, when I’m out and about, I’m often asked: “Girl, how did you do it?”

Sounds straightforward enough. But this isn’t really what folks want to know. The question behind the question is, “Weren’t you scared?” or “How did you know you could make it work?”

So this week I thought we might rewind and level set. Last Thursday, I invited you to think about the power of reinvention. I used the analogy of surfers getting up on their board and asked you to notice the waves of opportunity in your own life.

As a reminder, reinvention is the action or process by which something is changed so much that it appears entirely new. So, if that’s the measure, I’m an expert in reinvention. I’ve paddled out into the sea more times than I can count. Sometimes I stood up on my board, and sometimes I let the wave pass me by. And, yes, I’ve absolutely been scared.

But let’s be clear, when you do get up on that board… there’s a rush of endorphins that comes from riding the wave. The thrill of the adventure, the challenge of staying up, the excitement of the view from atop your longboard… all of this sparks something important inside.

It’s that exhilaration and the unexpected rest of letting the wave carry you that fuels your mind and body. It’s what makes it possible to not only keep going but access new ideas and dreams.

And this is why I’m passionate about reinvention. My own experience has convinced me that catching those waves leads to a more rich and fulfilling life.


I’ve reinvented myself multiple times. I’ve worked as a financial analyst at General Electric and on an Amish farm building furniture. I’ve produced events in partnership with the NFL and the NBA, wrote a book on dating and co-founded a nonprofit. All this while navigating through life’s transitions. I’ve dealt with loss and fought personal and professional stereotypes like the rest of us. But I didn’t count myself out! In fact it’s during these ‘crucible’ moments that I get more comfortable with who I am and who I wanted to become.

With that in mind, here’s how I face the fear of standing on my board.  I ask myself:

  1. What’s the end game, Jes? Where are you headed?
  2. Do the possibilities of ‘what’s next’ outweigh the safety of where I’m currently standing?
  3. How do I bring it all into focus?  In this step, I simply break down my end game into small, doable pieces – almost always in the form of 90-day sprints.  And finally…
  4. What will keep me balanced and on this darn board? At this point, I just focus on the next right step.

Now, back to the question I didn’t answer at the top, “How did you know you could make it work?” Friends, we all know there are no guarantees in life. But if I’m going to place my chips on the table, I’m going all in and I will always bet on myself. And so should you… that’s as close to a guarantee as any of us need.



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