When the Blues Comes Knocking

I was a migrant Southerner living away from home in Boston, leading a start-up tech firm. We had tons of press, a game-changing business model, and a few brand-name clients. We were on the verge of breaking out, but we were coasting on fumes with less than 4 weeks of cash. My family hadn’t seen me in months, I had 3 kids in college, and we were mortgaged to the hilt.  Welcome to entrepreneurship.

Growing a private business is an emotional roller coaster. Self-doubt, discouragement, and setbacks are part of the journey. There are days when getting out of bed is a challenge. I call it the “entrepreneurial blues”.

In “Entrepreneurial Leap”, Gino Wickman says “Fighting like hell for 10 years” should be expected by every entrepreneur going through the journey. In “The Dip”, Seth Godin says “The middle of anything feels like a failure”.

In my story, we were able to raise additional capital from outside investors long enough to fight another day, but there were many other close calls and sleepless nights.

Today, the entrepreneurs I work with as an EOS Implementer have massive self-confidence and energy. They’re also human beings with their own doubts and fear. They inspire me with their determination, but each of them (and their families!) suffers while building their businesses. If we could listen to their thoughts, the self-talk would sound like “I’m the boss, I’m the one who needs to radiate confidence and be ready with the answers to everything. What if I’m wrong? Do I have the right model, the right team, enough money, enough time, and enough know-how?”.

My EOS colleagues and I are dedicated to helping entrepreneurs navigate these questions with critical structure, a proven process, and a community they can lean on for support. The Entrepreneurial Operating System can provide a bulwark against self-doubt with tools and support when their motivation and energy are depleted. The EOS community can offer experienced coaches, leaders of other EOS companies, and a library of best practices to restore their confidence and level up the “entrepreneurial blues”.

Smart leaders never stop seeking mentors, connections, perspective, encouragement, and great tools. For them, EOS is more than a system. EOS is a community of people who’ve been all been through Hell and can help you get through it too. Check out www.eosworldwide.com and you’ll find people who get it, want it, and have the capacity to do it.

Get in Touch with this Implementer

EOS Worldwide

Let’s Talk!

Request a FREE 90 Minute Meeting with me and let me show you how EOS can eliminate common business frustrations, or just contact me with any questions.

"*" indicates required fields

I would like to…*
I prefer to be contacted by:*
This field is for validation purposes and should be left unchanged.


Base Camp


Client Portal



Search the EOS Worldwide Blog

Generic filters