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Starting From Zero

Updated: Apr 19

January is by far my least favourite month as an entrepreneur. I’ve just come off 12 months of trying to hit numbers and run multiple organizations. Now, I’m a zero again. Zero sales. Zero profits. Zero time to appreciate any of it. 

How do I feel?

This is the time of year when I constantly question myself. Is this really what I want to be doing? It’s cold and dark in the mornings when I wake up. All of our clients are scrambling to get new content immediately. The team is a little rusty. Nothing is aligned. I have to forcibly push myself over the line each day to accomplish what’s needed. 

I start to feel paralyzed, thinking I’m all alone and I don’t know what I’m doing. If I make one mistake, the whole thing could burn.

Starting from ZERO.....

Then I start fantasizing about an escape plan. I could sell it all. Move to Mexico. Or work on my girlfriend’s ranch. I could be uncomplicated. I’d get a flip phone and only check emails once a week. This is the time when I'm starting from zero.

But my fantasy inevitably makes me feel even more trapped. I realize all the things I would have to give up - the freedom created by income, the ability to travel, tennis lessons, creating communities, and building real things out of ideas. And ultimately, I come to the same conclusion over and over again - the fear of having to work for someone else or depend on someone else is the worst scenario of all.

Freedom of My Own Business

When I focus on my fear of losing everything - when I lead my team from that place - I am tired and stressed all the time. I could never have enough inside of me to get everything done. Everything is a diminishing return. But when I remember the things I love - writing, creating comedy sketches, building wealth, learning how to do new things - the amount of energy I have to put towards those things becomes infinite and renewable. 

I don’t believe in the saying, “Do what you love, and you’ll never work a day in your life.” I think all work becomes exhausting. Everything is a job composed of logistics and resource allocation. If I am over-leveraged I will eventually crack.  

My Philosophy About My Work

I do believe that if I focus on the reasons why I do what I do, on the things I love, then my energy and focus are a lot more reliable. I don’t get distracted by insignificant details. I no longer care about what could go wrong because what I’m doing feels right. And if I can spend my first moments each day doing something that I love, like writing this article, I can insulate myself just a little bit from the crudeness and pressure of my more sobering responsibilities.


All this has to be negotiated in my mind every morning, every afternoon, and every evening. It’s the deal I’ve made with myself as someone who is half incredibly motivated and half scared and depressed. 

Gratitude keeps me going

Which brings me back around to the realization that this is the right life for me. This is the life I’ve chosen for a reason. In no other arena would I have so much agency over my well-being. And in no other circumstance would I receive such an education on who I am and what drives me. 

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