A Century, the Enlightened Executive, and Invisible Immigrants

Hi Friends!

Are you new here? Good. Welcome. I love newbies, and I'm glad you're here.

I organize this newsletter into a few consistent sections: ideas I'm practicing, things I'm loving, people I want to shine a light on. If that sounds like your jam, read on. If not, you can always unsubscribe here.

August is that place where we feel the tipping point begin. Summer hangs on in many parts of the country for another month, but if you have kids, the return-to-school prep has already started. (Welcome back, badly formatted, text-heavy emails.)

I hope you're still sitting outdoors and lingering by a fire pit. I hope you're leaving early on Friday afternoons. I hope you're reading books that have nothing to do with business or money or building companies.

I'm reading one a friend gave me called Theo of Golden. I'm watching Love Story about JFK Jr. + Carolyn Bessette. And I'm drinking wine in the backyard, most nights.

Enjoy these long days of summer.

Let's jump in.

- Jess

The Century.

Fewer than 0.5% of the world's population has completed a century bike ride. Last Sunday, I did. 100 miles.

I rode with an old friend I've known since we were 13. She doesn't wear makeup, buys her kit secondhand, zero drama. The kind of cycling partner you want next to you at mile 80.

Five wooden covered bridges through the rolling hills of the southern Willamette Valley. Beautiful weather. No mechanical issues. 7.5 hours on the bike. Muscles felt great the next morning. We’re not promised tomorrow. So, I am immensely grateful my body can do this, today.

Since April, little by little, I did the hard thing. It wasn't about heroics. It was about building a system, working the system, and having good people around me.

If you believe you can, you will. It’s that simple.

LinkedIn is actually (occasionally) serving up content that's meaningful and relevant to me. Does this still happen for you? The kind of thing you learn from and want to share, unprompted. Isn't that what social media was supposed to be for in the first place? Turns out there are still glimmers of it left, even in 2026.

Props to Adam Joseph for the inspo.

Executive comms has long been thought of as getting your CEO on a stage at CES or Cannes. Social media has long been dismissed as twentysomethings making videos that entertain and little else. Podcasting? For influencers.

But the wise executives know better. Here's how you can tell:

If this is you, CONGRATULATIONS. You're ahead of 90% of leaders in America.

We should know each other.

I get up her way all the time. Clients, friends, ferries. Lots of reasons to visit Seattle. Julia rarely drives south to Oregon, so how exciting to hear she'd been accepted to speak at DisruptHR Portland. No question I'd be in the front row. 🙌🏼

Julia wisely used her Microsoft background to frame her talk: "We're Running 2026 Businesses on Windows 95 Managers." We're patching an old operating system instead of architecting a new one. She killed it. 20 slides, 5 minutes, done.

I'm not that interested in being on stage anymore, but I love being the wing woman. It's gratifying to watch a friend and former work buddy push herself to do something that takes real courage. So proud of you, Julia.

If you want Julia on a stage or in a conversation, find her here: brightworthy.com

Outliers usually come down to two things: they believe they can do something others can't, and they work relentlessly to make it true. - Malcolm Gladwell

Here’s my secret, not so secret: I have an idea for a book. The working title is The Invisible Immigrant.

The subject has little to do with my profession or the business I’m building. Rather it’s something I’ve been chewing on for most of my adult life. Books like Educated and The Glass Castle both sit on the shelves next to my desk. But those stories expose vulnerabilities and situations many of us hide. Still, they reminded me I wasn’t alone. In fact, I thought I might have something to add to the conversation.

This book won’t further Co-pilot’s prospects and may make little money, but something in me says there is work to put out.

Here's the idea.

We talk a lot about parity with regard to race, gender, ability, even age. Here's what doesn't get talked about enough: class.

Who among us isn’t familiar with the equity vs. equality discussion. Meritocracies don't really exist, so let's go fix that, the thinking goes. I'm still working through how I feel about it. Do I want equity? No question. Do I want to be offered a job because I'm a woman? Not really.

There's also a lot in the air right now about prejudice against people perceived not to be here legally, and the terrible cascading effects on legal immigrants and American-born people with brown skin. I have a number of friends who are first-generation Americans. I love learning about their food, their holidays, their families. Our lives are richer when there are differences among us.

But in all this discussion about the groups we get tagged as, we’re forgetting what it feels like to sit next someone in a conference room who grew up driving a parent’s Land Rover when you grew up standing in line for government cheese.

Scott Galloway talks about this. He was raised in a single-parent, working-class immigrant home before landing at UCLA, then Morgan Stanley, then corporate boardrooms. He says he “fooled them” into letting him in. His read on the culture shock of that jump feels very close to home.

Working-class people who land in rooms with pedigree often feel like they're missing some cultural fluency everyone else was born with. The unspoken etiquette. The shared references from schools they didn't attend. I remember one time I was at dinner with a client. He got up to use the restroom. I thought I’d refill our wine glasses. The wine was in a decanter, which I’d never poured from before. I didn’t realize how fast the wine would come out. Very different from a wine bottle. I spilled the red wine all over the linen table cloth. No way to hide that before he would return.

It’s these moments that build a quiet, persistent fear that you've fooled everyone and will eventually be found out. “Why was I so dumb to believe I belonged here?” But who is there to teach us? Our parents can’t help. Most of our childhood peers aren’t in those rooms either.

Galloway's answer: flip it. That discomfort isn't a sign you don't belong. It's a sign of ambition. “You should have a little bit of imposter syndrome,” he says, “because if you're not in rooms where you sort of don't deserve to be, you're not trying that hard.” Feeling intimidated means you pushed past your comfort zone into a room full of people who have real reasons for wanting you there.

And the leaders already sitting in those chairs didn't start with some flawless, built-in confidence either. They learned to tolerate the same self-doubt until it stopped being loud.

I call this being an invisible immigrant. I think my generation, and certainly Millennials and Gen Z, are living through the evaporation of the middle class, the skyrocketing cost of college, and the disappearance of the communities where mentors used to be found just by being around. It leaves the few who do move between classes in a lifetime feeling strangely invisible. Alone, even.

DM me your thoughts on this one. I'd genuinely love the feedback. Have you seen this in your own circles?

Somewhere that straddles UK and US culture, known for manners and kindness, paints its bike lanes red, and lakes so blue- you’d think you were in the Caribbean.

Reply and guess. I'll feature the winner next month.

Thank you for being here. See you in September. 💛

— Jess

Bet on yourself.

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