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I started an old-school blog. It's called Field Notes: short, rough notes on what I'm learning as a father, husband, coach, and human in this season.
I'm not posting much on social these days, so the best way to follow along is email, RSS, or directly on the site.
Link below.
How much of the appreciation you receive do you actually let in before downplaying it, questioning whether they mean it, or shifting to the next topic?
Being accepted and met exactly as we are is a deeply nourishing experience.
When we struggle to meet someone else as they are, there’s often something for us to learn about ourselves.
An edge in my coaching practice right now is knowing when to challenge and when to give space, when to stay with reflection and when to invite action.
Each can be helpful, but I’m learning to notice when it stops serving the client. Presence can become passivity. Challenge can become rescuing. Insight and action can both become ways of avoiding something.
The most skillful practitioners can sense these differences and adjust to the client, their situation, and what’s happening in the relationship. Eight years in, I’m still learning how much discernment and care that takes.
In conversations with some technical founders and leaders in transition, I’m noticing existential angst around AI.
For many builders, AI is intoxicating and empowering. They can build things they only dreamed of.
But for some of the people I’m talking with, that excitement is overshadowed by a deep sense of loss. So much of what they’ve loved about working in technology has been the process of tinkering and learning as they build. For some, shipping was secondary. The satisfaction came from working through complexity, figuring things out, and getting better along the way.
They don’t feel the same sense of exploration through prompting and waiting for the black box to spit out an answer, lines of code, or even an app. It’s like having an employee do the part they loved while they wait for the results. Yes, they can build faster, but they feel removed from the work itself. That’s left them befuddled and grieving.
I suspect more workers will experience a meaning crisis as AI takes over parts of the work they loved. And they’ll need support finding their way through it.
It’s so easy and natural to fixate on what could go wrong instead of asking what can go right.
I keep this on my monitor to remind me I have a choice.
Several friends have texted me about my return to X. I’ve come back for a few reasons:
1. Working remotely has been lonely, and I’ve been longing for more community.
2. I want to reconnect with old friends and make new ones.
3. The world is at a major inflection point, and I want to stay close to the people shaping technology and culture.
4. I’ve spent the past five years learning about coaching, transitions, and human development, and I want to share more of what I’m learning.
5. I’m launching a new executive coaching firm in November and am excited to tell you about it.
I’m really glad to be back here. Please say hello.
My dad passed three years ago today. He loved Boston sports, learning, mentoring, and his kids. I get so much of who I am from him.
He would be proud of the life I’ve built.
I never understood how someone dead can still be here. But now I do. He lives in me.
Love you, Dad.
Just bought this 2027 Himekuri Calendar from @BestMadeCo. It’s gorgeous.
These are words we rarely hear from founders and leaders:
Heartbroken. Love. Passion. Soul. Grief. Regret. Decay. Eulogy. Closure. Cathartic. Grace. Humility. Thankful.
@dens is a leader we’ve followed because he’s never been afraid to show us who he is and how much he cares.
Foursquare was acquired last month. The outcome was disappointing. It's taken me a while to write this, but I think I'm finally done grieving it. Here are some thoughts on our final years, an effort to honor the team who helped build & maintain FSQ's legacy, and my attempt to finally get some closure. teendrama.substack.com/p/som…
When I left VC 7+ years ago, I unconsciously disowned an essential part of myself.
I’m starting to appreciate him again. He was more talented than I believed at the time.
I miss those years, the optimism, and that guy. I’m going to bring more of him into what I’m building now.
A walk in the woods with @DavidSpinks. Great company, deep conversation, and peak foliage 🍂
Steve Schlafman retweeted
Life is short. Skeptics are probably right more often than they are wrong, but they also don't go on epic adventures or get to work on projects that move humanity forward. Ignore the skeptics and build the future!
Talking developmental psychology, spiral dynamics, and life goals with @tracebelll. This man is wise beyond his years.
Steve Schlafman retweeted
Ben Wilson (@BenWilsonTweets) has stage 4 cancer and 4 kids under the age of 5.
I want to help him as much as possible, so I invited him on the podcast to talk about his work studying history’s greatest leaders and what it’s like getting told he’s going to die at 38.
He’s a good guy, a close friend, and one of my favorite podcasters.
His work has benefited millions of people all across the world.
Please watch this episode and see if you can help with medicine, introductions, or donations.
0:00 What Ben has learned from making How to Take Over the World and studying history’s greatest leaders.
55:51 Living like you're dying. Ben on facing cancer.















