Not sure. Let’s find out.
That’s mostly why I’m here. You put words somewhere and see if anybody bothers to stop what they’re doing and read them.*
* Full disclosure on the timing of this: there’s an article about me in the works, and my publicist pointed out that a guy being written about ought to have somewhere to write back. (Ought is her word, not mine.) So this is me being managed. She’s right, of course; she usually is, which is worse.
So. Hello.
Once upon a time, I worked with an organization that encouraged me to start a Slack channel.
The exact instructions in a meeting about our people were “give them some perspective, I guess.” HR-ish and I/O Psych-adjacent. Something more for the younger employees on the team, but something for everyone. A place for the things that didn’t fit into town halls we didn’t have, performance reviews we didn’t do, or one-on-ones with managers who kept looking at the clock because they had a “hard stop.”
Sound familiar?
I said yes, mostly because nobody told me what it was supposed to be. And since I don’t mind ambiguity, my fingers didn’t stray far from the keyboard. On a plane to San Juan. On a train to Manhattan. In a pub in Galway. In my office. In a castle. In bed.
Or, as Dr. Seuss may have put it:
I wrote on a plane. I wrote on a train. I wrote in a pub with a Galway refrain. I wrote in a castle. I wrote in my bed. I wrote it all down because nobody said.
Either way, you get the point. I wrote.
A lot.
The eye rolls lessened after the first few posts. And eventually, it resonated, even if they didn’t want to comment publicly in the threads. The validation (not that that’s what I was looking for, or needed) came to me in DMs or on the phone, which should have told me more than it did at the time.
It found its purpose the day someone vented to me about their job. They were holding back tears. They felt stuck and unhappy. Not lazy, not checked out.
Stuck.
They couldn’t see a path forward in their role and couldn’t tell whether that was the company’s doing or their own. What was making them crazy, they said, was that the business itself was in an all-out sprint. Launches, deadlines, pivots. Everything felt frantic, yet nothing was moving.
Controlled chaos. That was their phrase. I nodded in agreement. I’ve used the term many times over my years sitting on both sides of an executive table.
Somewhere in there, I understood why the Slack channel worked, and it had nothing to do with providing answers.
In a world full of “How did we get here?” moments, it dawned on me in that conversation that I had more of something than they did.
I had... a before.
Most of the time, that’s the only thing I have that they don’t in those conversations.
Perspective.
It helped that I wasn’t their manager. No reviews, no promotions, nothing that could be used against them later. Nobody put me in charge of them, which left me free to be useful to them instead. That’s probably why they felt comfortable telling me half ot the things they did.
Perspective is a funny thing. It is not necessarily intelligence, and it is not necessarily work ethic, either. I’ve watched twenty-five-year-olds outwork me on my best day, go to the gym, and still make it to a 7:30 dinner reservation on time.
Perspective is inventory. It’s the pile of shit that already happened to you, filed in your hippocampus, available for comparison.
When you’re twenty-three, and everything and everyone is moving except you, that feels like a crisis. When you’re forty-three, and everything and everyone is moving except you, that’s the third time that’s happened to you.
The third time’s familiar. It’s the relationship you gave one more chance than it deserved. It wasn’t great; you knew how it would eventually end, but you lived to tell about it.
You know roughly how long the sucky parts suck. You know which of your feelings about it are information, and which ones are just the ten-day weather forecast, wrong half the time.
Nobody can hand that to you, not honestly anyway.
You can’t read your way to a before of your own, and you can’t fake your way there either. You put your nose down, put in the time, and struggle through what feels in the moment like death by a thousand papercuts. Or you don’t get to have it to reference later.
Gaining perspective has something in common with karma; it can be a patient bitch.
You can borrow someone else’s, though. That’s what the Slack channel turned out to be. My borrowed inventory.
My borrowed brain.
We’ve all been there before. Some of us are just further up the road and can yell back about what’s around the bend.
So you know whose road this Substack’s paved on: Over twenty years in business. Operations first, a cup of coffee in finance, then the better part of a decade-and-a-half in HR/People. An M&A play somewhere in the middle took apart a culture I had taken for granted and eventually pushed me out the door. A few successful stints in Private Equity firm exits followed.
I work on the other side of the table now, mostly with founders and family-owned businesses, startups, and PE- and VC-backed businesses, as well as small- to mid-cap businesses. PE is the wild child. I also co-founded a company built on AI, so take my opinions on that however you wish.
That’s the résumé portion. But I promise that won’t come up much.
Here you get the stuff nobody says outside a bathroom stall at work, or on an urgently scheduled field trip to Starbucks with their work bestie.
Why the reorg actually happened. What your manager is really optimizing for. How decisions get made in rooms you’re not in yet and how you eventually get into them. Careers as a long game, which moves compound, and which ones only feel productive. AI, which you’ve been told will either eliminate your job or hand you a career and is currently doing neither of those things.
Leadership, mostly from the angle of what it costs the person doing it. And postmortems on my own bad calls, where I have a deep bench. Like, Sixth Man of the Year deep.
Goodness, I’ve made some stupidly bad calls over the years.
You will not get a lecture about how much harder it was in 2006 than it is in 2026. Because it wasn’t harder.
It was just different.
If you’re early in your career, the thing I most want to convince you of is that you’re not behind. You’re just early (and maybe lied to or underprepared about how work actually works these days). And, from the inside, those things feel very much the same.
If you’re further along in your journey, spar with me. A good amount of what I think I know is probably a mix of survivorship bias and hindsight bias, and you’ll likely spot it before I do.
How often? As often as I have the time and the energy.
That’s unsatisfying, I know.
So here’s the calculus.
Someone calls me dad. Dissertation done and prepping to defend in a few months. I keep a handful of client businesses running. Sitting with professionals working through things they can’t take to anyone inside their own building. Co-founder. And there’s got to be some time for date nights, when my calendar permits and theirs cooperates.
If I promised you every other Tuesday, I’d be lying to both of us by mid-September. So, when it’s ready.
None of that is an apology. I learned early, and hard, that the workday doesn’t get to decide what else is happening in your life. Work/Life Balance was never the right term for it, and still isn’t. There are 24 hours in a day. Everything competes inside them, and the sooner you stop pretending you have two separate lives, the sooner you can be honest with people about what you actually have to give. If you’re a leader who says leave work at work and home at home, I’m happy to have a conversation with you about how you’re entitled to your opinion, but you’re probably a dinnertime conversation for all of the wrong reasons.
A founder told me recently that one of his strongest people had lost her commitment. He was wrong, and the reason he was wrong was none of his business until she decided to make it his. He got quiet when he found out. Find out what’s happening to someone before you decide what it means, and you’ll be wrong about your people a lot less often.
Years ago, my team spent a week with a small, non-technical business walking them through a change program. We left what we were sure were clear instructions. We came back the next week, and nothing had been done. Not. One. Thing.
They hadn’t understood any of it, and not a single person in that room was willing to speak up. Fear first. Embarrassment a close second.
One of the most valuable lessons I’ve ever been handed, and it wasn’t about them. What we handed them was just too complicated. We’d built a model that made perfect sense to the people who built it. If the room doesn’t follow you, that’s on you. We rebuilt it. Simpler. And it worked like a charm. I’ve been suspicious of complexity ever since. It’s usually somebody protecting their position.
But back to the question at the top.
I don’t much care whether people still read (unless you’re my son). I care whether a generation that now tries to resolve things in nine seconds with an AI prompt can be talked into something that can’t.
An argument that doesn’t make sense until the fourth paragraph. A career that takes four years to bend. A stuck problem that doesn’t announce when it’s over, and makes you sit in it looking like an idiot while you wait.
Nine seconds is about how long a prompt takes. Or to find a “coach” while doom-scrolling on social media, who hasn’t lived a day longer than the person watching them.
What do they have in common besides mostly bad advice? Neither one can hand you a before.
If you get three paragraphs in and drift off, I’m going to assume I wrote it badly.
That’s the deal I’m making with you. That’s the experiment.
You’re the control group.
Welcome to Sincerely, RB
P.S. That Sixth Man of the Year reference... I was all-in on the 2026-27 Philadelphia 76ers roster before LeBron James was, so that should tell you something about my capacity for commitment.