It Got Personal.
Editor’s Note: A number of folks have reached out to me asking why I haven’t written anything for the past several weeks. What a lovely comment to receive. I’m being missed. The truth is, I haven’t had anything that inspired me to write, and rather than just filling your mailbox, I thought I’d wait until I had something to say. It is a good practice for me to embrace.
I’m taking an AI course with my colleague, Lisa Larter, right now. It’s positioned as a marketing course, but it’s really about using AI beyond a search tool. We’ve covered prompts, research, roadmaps, and building GPTs, as well as image and video creation. And I’ve been testing different platforms, like they’re all competing for the same job.
Last week’s assignment was simple. Ask your favorite AI to write a lighthearted roast about you.
Not Nikki Glaser or Jeff Ross level. More Jerry Seinfeld or Nate Bargatze. Gentle, observational, a little uncomfortable.
I turned to my ChatGPT thought partner, Nellie. She didn’t miss.
On my work:
“You’re a psychologist who helps people figure out what’s next… while simultaneously running a multi-year internal seminar on your own ‘what’s next.’ At this point, your next chapter has a preface, three outlines, and a soft launch.”
And this one:
“You say you don’t want to be called a coach. Not a therapist. Not a consultant. You want a ‘strategic advisor.’ At this point, you’ve got more positioning statements than actual positions.”
She even went after my golf game:
“You’re out there grinding on your short game like you’re prepping for the Masters. Fifteen handicap, but psychologically? Single digit. Your wedge game needs work, but your relationship with your wedge? Fully explored.”
Funny, and fair.
Then she landed the part that stuck.
“You’ve built a career helping people make big decisions… and now you’re in that same spot, trying to make one that actually feels like it matters. So you keep refining, reframing, reworking… not because you don’t know what to do. Because you do—and you want to get it exactly right.”
What the roast exposed is that all the thinking hasn’t been about finding clarity.
It’s been about delaying commitment, because the uncomfortable part is this.
I already know what I want to do.
So here’s where I’m going to stop thinking about it and actually do something.
Over the next few weeks, I’m going to reach out to a small number of people I know and respect and have real conversations. Not the usual “how are things going” check-in, but something more direct.
How is what you’re doing now helping you get to what’s next?
Not the comfortable answer. What’s the decision you keep coming back to?
I’ll share where I am, too, because this isn’t one-sided. I’m in it as much as anyone.
If those conversations turn into something more, great. If they don’t, I still get to spend time with people I enjoy and respect.
That’s a pretty good outcome
I’ve realized the part of my work I value most isn’t refining language or building frameworks. It’s sitting across from someone, coffee in hand, working through something that actually matters.
That’s the fun. And, more often than not, that’s what actually matters.
