Afraid of my own ambition

If you haven’t noticed, I’ve made this next phase of my career about helping entrepreneurs plan their businesses with intention. It’s something I learned way too late in the game after shooting from the hip, which I only learned the consequences of once it was too late. 

I’m not really here to talk about plans, but instead about fear of success. See, my team and I are heading into a 3-day intensive strategy session next week to dream up visions of the future and plot out how we’ll make them a reality. To plan. 

The opportunity to make a dent in the online education space is huge, but also tricky. The current landscape consists primarily of cheesy “info marketers,” legit universities, and MasterClass. While there’s plenty to learn from each of them and their successes, we want to be none of them.  

The white space we could occupy is exciting, opaque, and big. 

Big is a word that––and I hate to admit it––after 15 years of building big things and inspiring others to do big things, scares the shit out of me.

I didn’t go to college, but I do have a Ph.D in the PTSD of entrepreneurship. I’m terrified to go big again. But I’m fucking possessed. And I’m hell-bent on, at all costs, preserving my autonomy as much as possible so I can, hopefully, for the first time in my adult life, control my time. 

I know the general thinking is that entrepreneurs work for themselves, have flexible schedules, and work their businesses around their lives. And some do. But for 99% of folks running massive enterprises, their businesses are like big babies. Oh shit, it pooped and you’re on vacation? Sorry, gotta get on the horn and clean it up. Spilled cereal? Roll up your yoga mat and deal with it. Plans with a friend? Well, it’s throwing a temper tantrum, so put down that spicy marg because if you don’t nip this in the bud, you’ll be maligned on Glassdoor. 

I want to be sure to acknowledge that it’s only with huge success that one has the privilege of encountering these issues. And ultimately I’m extremely grateful to have had them. 

But as we head into next week’s planning session, I’m clear on one thing, and one thing only: I never want them again. 

Don’t ask me how I’ll dodge my own masochistic drive to build something big and preserve my time, but I’m going to figure it out. I’ve never been one to pussyfoot and I’m not about to start, but I do want to walk before I run, maybe for the first time ever.

Wish me luck.

Wheels up,

Sophia