Reflections on 20 Years of Entrepreneurship in a Time of Crisis

I remember thinking, how hard can it be? 20 years later, the answer is really friggin' hard.

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Photo by Lauren Kress
Photo by Lauren Kress

20 years since I quit my job and walked away from a career I loved. But I didn’t love it as much as I loved the challenge to create something new, build a business, become an entrepreneur. Reflecting, I laugh at my naivety, as I started on this journey thinking “how hard can it be?”

20 years later and the answer is really, really hard.

I’ve worked harder than I ever imagined I could or would want to. I’ve thought and planned and written and talked and met and strategized and created and led for two decades. I’ve grown in ways I never imagined I would have to. I’ve worried, lost patience and spent long, sleepless nights afraid for myself, my family and the people who have come to rely on the businesses I’ve built. I’ve worried, I’ve learned, and I’ve sacrificed. A lot.

And I’ve had moments of exhilaration watching something grow from an idea to a reality. I’ve been astonished by the commitment, talent, and generosity of the communities I’ve created. I’ve taken deep satisfaction knowing that I lit the spark that started the business that created the community that has impacted so many in so many ways.

As I stare down this crisis and once again endure restless nights and a mental parade of “what ifs,” I can’t help but wonder what the next 20 years will bring and whether or not I’m strong enough, smart enough and hard-working enough to see it through.

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