Past-Self Antagonism

Earlier this week, a friend pointed out something that’s now startlingly obvious—my writing is seething with contempt for Past Rob.

And I suspect this is not only emotionally unhealthy, but completely counterproductive for my business.

The problem stems from a few things. I used to be a true believer in the Online Marketing Industrial Complex. I championed all of the best practices that I now rail against. And I chased goals that were not my own, and ended up unfulfilled and disillusioned.

It’s been nothing short of joyful to break free from those dynamics over the last 18 months. But at the same time, it’s hard not to ridicule my past self for not wising up sooner. I feel a deep sense of regret for having wasted my 20s.

And that’s been showing up in my writing. There’s a clear subtextual thread running through my latest pieces of “I used to operate this way, and it was very dumb and ineffectual, but now I operate this way, and it’s great.”

Creating contrast like that is an important communication tool, of course. But the resentful tone I use when talking about Past Rob just doesn’t feel good, especially now that I’m more aware of this tendency.

I’m a firm believer in kindness and grace as first principles. That obviously applies to how we interact with others, but it’s just as important with how we treat ourselves.

Past Rob was doing the best he could. He had to go through those trials and tribulations so that I could be be where I am now. And for that, all I can be is grateful.

For me, framing it this way seems like an emotionally healthy turn to make. Deriding or shaming parts of myself has never worked out well. It usually makes my emotional health worse. Whereas when I accept and integrate those parts, I feel more whole, and at peace with myself. I suspect this will be equally true as I try to heal my relationship with my past self.

So from now on, I’m going to be more aware of this tone when it pops up, and use it as an opportunity to practice self-compassion. I probably won’t succeed every time, but that’s ok. Baby steps.

Why being a jerk to myself is bad for business

Beyond the emotional health thing, there’s another reason why I suspect this tendency towards self-ridicule is counterproductive—it’s likely bad for business.

For context, here’s a quick rundown on the vision of Ungated, and who it’s for.

Ungated exists to create a new philosophy of online marketing and business—one that’s rooted in friendliness, play, non-coercion, and cheerfully subverting the status quo.

But it’s more than just the philosophy. My content and membership are meant to be a bridge, giving people the tools and courage to cross over from the old way to the new way.

Lastly, I want Ungated to be an oasis. It should feel like a place of safety and nourishment amidst a barren landscape of online businesses trying to extract every last dime from your bank account. I want this to feel like one of the friendliest, most generous places on the marketing internet.

So that’s the vision.

Broadly speaking, the people I’m trying to reach are creators who are where I was a year ago. People who are living in the Online Marketing Industrial Complex, but feel deep in their heart that something isn’t right. People who yearn to do work that matters, practice marketing in a way that feels good, and carve their own path through the world.

If the tone of my writing is contemptuous towards my past self, it’s also contemptuous towards the people I’m trying to serve. This, of course, undermines ALL of the goals I just laid out.

It makes my philosophy feel less friendly than it claims to be. It alienates people who are a great fit for what I have to offer. And it makes my online world feel not like an oasis, but an accusation.

If my tone is off-putting, the people I’m meant to serve will be less likely to cross the bridge with me, and some of the deeper cultural changes I’m hoping to spark won’t take off.

So yeah, I should probably stop being a dick to my past self. It doesn’t serve me. And it doesn’t help me serve and connect with the creators I’m building Ungated for. Lesson learned.