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Entrepreneur Diary Series: Taking the leap


Entrepreneurship is something we romanticize but the reality is a lot of hard work and outcomes that are far from certain. I've had some great conversation's on my podcast with entrepreneurs and what they love (and don't love) about their work. I've been involved as an early management team member or advisor with start-ups in the technology, media and cannabis space. I loved the energy of these companies but while I was in the vehicle and along for the trip, I was always riding shot gun on someone else's journey. So, after years of helping companies in both the not for profit and for profit space set strategies and operationalize plans, I'm ready to take the leap. I also think we need more honest conversations about the realities of being an entrepreneur so I'm keeping a diary about the process - here is a my first entry.


August 31, 2020, 8:25am

Moving assertively to build things.

Monday. Two weeks since I handed in my final project for school and now it’s time to get a little more serious about my future. I’ve already committed to this idea of launching a business. In the framework of Gretchen Rubin’s, The Four Tendancies, I’m an Obliger – the kind of person who does best when they’ve made a public declaration and thus feel they would be letting others down if they didn’t follow through. I know that realistically, probably nobody really cares if I do this or not. If I decided tomorrow to take a job instead, I’m sure no one would say “hey, what about that business you were going to launch?” I’m sure I could write that off as a momentary lapse of judgement. Launch a business in a pandemic? What the hell was I thinking?


But…I’m trying to get better at not letting me down. There is never a perfect time to start a business. There are businesses that launch in boom times that go bust and businesses that launch in recessions that become iconic brands. I feel like this is my moment to at least try and if it doesn’t work out, well, then yes, there is always finding a job.


I’m spending the next few weeks trying to make this idea concrete. That means defining my values, what I’m trying to accomplish and writing the first draft of a business plan. One value that I’m holding is the idea of moving with care. It’s my push back on “move fast and break things” – the motto that sums up a culture which that has gotten technology companies into a lot of trouble. It’s a culture that other industries have tried to emulate in the name of innovation. Yet, moving fast to break things feels fundamentally broken itself and in a post-COVID world, it holds less appeal. Moving slowly…that didn’t seem quite right. For now, moving assertively to build things. I’m sure I’ll iterate on that idea as I go.


Resources

Gimlet Media's podcast Start Up (Season One is especially good) shares the story of Gimlet itself and other startup ventures in a very authentic, behind the scenes, way.


Jerry Colonna's excellent coaching podcast Reboot, recently featured an interview the David Sax, talking about the Startup Myth. David's new book is The Soul of an Entrepreneur.


Gretchen Rubin's The Happiness Project is a both a book and podcast. It has good advice on life happiness and developing good habits.

 
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