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.

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