Should I Start My Own Business? Here's a Reality Check.

creative entrepreneurship entrepreneurship shadow work Feb 15, 2023

A few days ago, I made the video above on IG that really landed with a few of you wild dreamers, so I thought I’d expand on it and share here!

The video poses the question: Do you really want to run a business, or do you have an entrepreneurship-based fantasy in which your business (or just 1 launch) sweeps in with a cash windfall and a lifestyle upgrade and solves all your problems?


Sometimes I can hear in the way people talk about the business they want to build that they may not be relating to the idea of a business from a place of reality and maturity. Rather, deep down they relate to the idea of entrepreneurship like a Disney prince that’s going to come riding up like Richard Gere in the white limo from Pretty Woman to save them from their life.


Look, I get it.


When I was a little kid I had a fantasy about “being discovered,” that came from movies and tv shows.

Like I was gonna be playing the old slightly out of tune piano alone at lunch in the school auditorium (which I did many days) and a star-maker record exec was gonna walk by and hear me.
He’d come in and say, “Kid, I’m gonna make you a star!”
He’d tell my parents I had to go with him to Hollywood.
One montage later and I’m playing stadiums and living in a penthouse in New York and being driven everywhere in limos and my hair is always flawless.


Sadly, it never happened.


Also sadly, if it had, when I got there I’d be dealing with rehearsals, managers, press tours, people telling me when to eat and sleep and what to do, bad reviews, sleeping on planes, injuries, taxes, groupies, people trying to steal from me….yanno.

It would just be my life.

With different problems & challenges than my life at home, but still, with problems & challenges, cuz life has problems & challenges.


The fantasy was that there was another life that was less like life, where I had no problems and I was rich and everything was handed to me purely based upon people “seeing my talent” and it was easy all the time.


When you think about your creative business, is it more of a starry-eyed fantasy where your whole life is “solved” and everything is easy, or is it a mature understanding that you’re building yourself a job? 
(Maybe the best job you’ve ever had, but still a job, with all that comes with that.)


I too would love it if someone would show up at my door and hand me a tax-free no-strings-attached million dollars that I could do whatever I want with. But my business isn’t Ed McMahon. It’s my job.

It’s my favorite job. Most of my work I would do for free. I love what I get to do and the people I get to work with, and the work itself most of the time. I love getting to set my own schedule and create my own rules and be creative. 

And, it’s my job, and I still have to do things like pay taxes and solve problems and fire people and show up for appointments on sunny days when I’d rather be laying on a beach somewhere tropical.

(I also agree that none of us should have to have jobs and trading hours of our life for green paper we trade for food and shelter on the only planet we can live on is dumb. But right now that’s the game we’re playing, so if I have to work anywhere it has to be at the business I built cuz I’m obstinate and unemployable.)


On the original post, some people in the comments had their own epiphanies about how they relate to their businesses (or their fantasies!) — it made them realize that they were actually projecting a savior fantasy onto their business idea, vs actually wanting to run the business they’ve been dreaming about.


So now I’m asking you:

  1. Do you really want to run a business?
  2. Do you want to do the work of running a business?
  3. When you imagine your future business, are you picturing yourself doing the work?
  4. Deep down is “have a successful business” code for a fantasy where you’re whisked away to a different life where all your problems are solved?


Get deep with the answers of these questions before you file an LLC. Your future business will thank you.




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