When Rob Ott and I were in college, we had to sign into the computer lab just to set up an email address. No cell phones. No inbox in your pocket. And everyone told us there wouldn’t be any jobs when we graduated.

Thirty years later we’re still friends. Our kids are hearing the same warning.

Rob is an executive coach now. Before that he built a career in cancer research and ran business operations in the corporate world. He left that role and went looking for what came next right as ChatGPT hit its inflection point in 2022. He saw it early. The technology would move as fast as it moves. The people would be slower.

That’s the heart of his new book, The Relevance Advantage. It starts with a fear social scientists now have a name for. FOBO. The fear of becoming obsolete.

You know the feeling. You built a career. You put years into a set of skills. Now a machine does some of it faster, better and cheaper.

Rob doesn’t argue with that, and I love that he doesn’t. Most AI books sell you the tool or sell you the panic. Rob concedes the speed, then points to what the machine can’t touch. If you’re mid- or late-career, you’re sitting on the answer. Judgment. Experience. Wisdom.

That’s why I reached out to him. I run my business with Claude as a systems operator. It keeps my invoices moving and my CRM current. Nobody hires me for that. They hire me for 30 years of judgment. Rob calls it a moat. What’s inside is yours. Everything outside is fair game for the tools.

His framework, TRUST, is built for the people who freeze. Target where you’re going. Recognize what’s resisting you. Undertake small experiments instead of jumping in at step 17. Steady yourself through the messy middle. Transform.

The part that stays with me is the one he’s still working out. Kids coming out of college were told the tools were cheating. Now they’re walking into offices where nobody knows how to teach them. How do you build judgment when the reps that used to build it are gone?

He doesn’t have that answer yet. He’s writing toward it.

In the meantime, he’s coaching an 80-year-old solar engineer on AI. The man is flying.

The Relevance Advantage is in presale right now. Rob is my friend, and this is the book I wish every one of my clients had on their desk. Support it here: books.manuscripts.com/product/the-relevance-advantage

Key Quotes

“It feels like this machine can do what I do faster, better, cheaper. And I think that that’s true, and I’m not going to refute that.” — Rob Ott

“A lot of people with AI will jump in at step 17 and say, oh my God, what is this? And they’ll get freaked out and close the computer and walk away.” — Rob Ott

“When you commoditize intelligence, it changes the way you’re going to build that judgment.” — Rob Ott

Takeaway

Speed was never what they hired you for. Judgment was.

Behind Darren Samuelsohn on our call sat a plastic tub. Then another one. Inside are about 200 journals, decades of a reporter writing to himself, and he’s working his way through every one of them.

Darren and I go back years. Energy, then politics. He was the reporter and I was the flack, and we’ve both changed our shade a few times since.

In late 2022, one of those journal entries saved him. His team at Insider had just won an SPJ award for Conflicted Congress, its investigation into members trading stocks. Washington is still arguing about that story. Then he was fired. He told me it sucked. He also told me it was the most he’d ever talked about it.

So he wrote. An essay called “Why I Love Journalism,” trying to talk himself into staying in the business. Somewhere along the way it flipped into a letter from journalism back to him.

Love, Journalism. Comma in the middle.

That’s his Substack now. He didn’t leave the newsroom right away. He went back in twice, to The Messenger and then USA Today, where he led White House, Congress and campaign coverage through the stretch all of us lived through. Earlier this year he walked out. His tank was empty, and had been for a lot longer than he let himself admit.

He’s clear-eyed about the business he came back to. The outlets that are thriving, from a one-man courts beat on Substack to the Times and the Post, know exactly who they’re talking to. He worries about where that leads, with everyone gravitating to their own churches. He also sees a living in it for journalists willing to experiment and fail. He’s failed before. He learned from every one.

What struck me is how much fun he’s having. A weekly podcast. Photographs of power lines out his car window. Poetry. A Bigfoot story he swears is coming. At 12, Darren wanted to be Dave Barry. Now he has the column, and Dave Barry is on Substack too.

I asked how he knows when it’s time to go. His grandfather admired people who talked about ideas, he said. So Darren checks whether he’s still learning something about himself, the world or the business he loves. At Insider and again at USA Today, the answer stopped being yes.

He says a lot of what he writes now is for the reporters he used to edit. A little inspiration. A nudge along the way.

Consider this one passed along.

Notable Quotes

“And then I got fired. And man, I’ll just say it. It sucked.” — Darren Samuelsohn

“I think the tank was empty two or three years before it was empty.” — Darren Samuelsohn

“Everyone’s kind of gravitating to their own churches, and that’s dangerous as well as a bounty and an opportunity for journalists who want to write.” — Darren Samuelsohn

Takeaway

Sometimes the love letter to the work only gets written after the work lets you go.

In 2004, Jon Seaton went door to door for Bush-Cheney with a clipboard. Can the president count on your support? Great. I can get you a yard sign. There were never enough yard signs. Somewhere in Arlington there are probably still boxes of those sheets, every answer written in pen.

Jon and I came up together in Bush world — him in the field, me on the communications side. He went on to run John McCain’s national field program, advise Lindsey Graham and launch Echo Canyon Consulting, named Best New Firm at this year’s Reed Awards. This week he came on The Friday Reporter to compare notes, four weeks out from the midterms.

The clipboard is gone. It all happens on a phone now, and a campaign knows more about a voter before the knock than we used to learn after it. Jon gives Karl Rove the credit. Rove decided grassroots could be measured like money raised or quotes in the paper: doors knocked, voters reached, events attended, every single day. That idea built the modern campaign. It also built every corporate and issue campaign in Washington that actually works.

So you’d expect a guy who sells canvassing data to swear by the numbers.

He doesn’t, entirely. Jon isn’t anti-analytics, but politics is a people business, and no forecaster can stand in 50 congressional districts at once. He reads Google Trends. He watches the national environment. Then he gets out to Phoenix or Texas, sits down at a restaurant and talks to whoever is next to him. Everybody jokes about the vibes, he told me. The vibes can tell you a lot.

What he hears out there isn’t what Washington is chasing. Not one person in Phoenix has brought up the White House ballroom with him. They want to afford groceries and gas. The campaigns that miss it are the ones that are entirely too online, chasing the outrage of the day because it feels like catnip. His fix is almost too simple. Take Twitter off your phone and listen.

I’ve worked the last four weeks of a race the same way for years. I don’t listen to Washington. I call my friends outside the Beltway.

On Election Day, Jon sends one tweet: What are you hearing? Then he waits like the rest of us, with the whole thing finally in the voters’ hands.

Notable Quotes

“They joke about the vibes, but the vibes can tell you a lot.” — Jon Seaton

“I don’t know one person in Phoenix, Arizona that cares about what the Kennedy Center is called.” — Jon Seaton

“You can question their judgment. You shouldn’t question their motives.” — Jon Seaton, on what he learned from John McCain

Takeaway

The data tells a campaign which door to knock on. The person who answers tells it what’s actually going on. Four weeks out, Jon Seaton is still listening for both.