I Asked 3 Successful People How (And Where!) They Vacation

A former financier, a multi-hyphenate strategist, and a skincare founder dish their favorite vacation spots in the US and Europe.

Aug 03, 2026

Welcome to Reframed by Ashley Rudolph. One idea, every week, that changes how you see your career.

Last week, I published 10 Lessons That My 30s Taught Me. Over the years, I learned that editing myself doesn’t always pay off, that there’s a difference between passion and anxiety, and that rage quitting was rarely worth it. If you're a millennial and you’re feeling angst about your career or otherwise, I get it.

What successful people do when they’re “off the clock”

I talk about work, maybe too much.

How to get promoted.

How to get a raise.

How to network.

How to position yourselves for the opportunities that you want.

I live and breathe this stuff and I’d be lying if I didn’t say that I love it. I do.

But more recently, I’ve been feeling curious about what people are doing when they’re not “on”. That wondering led me to today’s newsletter. I sought out 3 people who’ve reached impressive levels of success in their careers and asked them 2 simple questions:

What’s your favorite vacation spot and why do you love it?
What’s one thing you actually do (or refuse to do) that helps you unplug once you’re there?

Hopefully there’s some inspiration for you as you plan your own PTO this year :)

David Roberts

David spent nearly forty years in finance, most of it in investment management, then walked away to become a writer and a grassroots philanthropist focused on fighting poverty. He writes Sparks from Culture. Some of my favorite essays of David’s explore wealth, literature, and family. I couldn’t resist asking him about where he escapes.

What’s your favorite vacation spot and why do you love it?

My favorite vacation spot currently is our place in East Hampton. The sky, the air, the light, and the greenery are beautiful. And yes, traffic getting there can be challenging, but we’re able to spend a week at a time, and door to door it compares favorably to most other destinations.
The vacation place I miss is the Four Seasons Resort on the Big Island. We used to go there for ten days or so each August as a family, when our kids were still in school. Now, arranging a trip like that is too challenging logistically; the kids are adults with families of their own. Maybe in 5 years or so, when our grandchildren are a bit older.

Anna Eleri Hart

Anna is a digital strategist, influencer marketing expert, interiors planner, and content creator. A true multi-hyphenate — Anna has spent 15+ years devising digital plans for brands big and small, and has documented it all (house restorations included) on her social platforms.

What’s your favorite vacation spot, and why do you love it?

Probably Ibiza, because it has everything you could want. Yes, there are the big nights out, but there are also the remote hills, cliffs, and the ocean. I’ve been there lots of times for many different reasons: girls’ holidays, bachelorettes, my mini-moon, boat trips, a yoga retreat, and a weekend break. I’ve had nights with 30 minutes of sleep and nights with 10 hours. It’s the perfect destination, and the locals are the nicest people in the world.

What’s one thing you actually do (or refuse to do) that helps you unplug?

My husband and I have a rule: expecting to completely switch off on day 1 isn’t realistic. We both work for ourselves, so the reality is our careers bleed into our personal time a little. We give ourselves the first day of our holiday to “tidy ourselves up,” meaning we don’t book any fixed-time activities and we each do our own thing. By the time we have dinner, we both feel able to put more intention into quality time together.
I also keep a notepad with me, because I always, without fail, come up with an idea for work when I relax. I think it’s an extension of “the best thoughts come to people in the shower.”

My best thoughts DEFINITELY come when I’m in the shower or on a walk. I love the notebook idea.

Rachel in Greece, hello isn’t this incredible?!

Rachel Liverman

Rachel is the founder and CEO of Glowbar, the fastest-growing skincare brand redefining facials: 20+ studios, two consecutive Inc. 5000 appearances, and a $10M Series A. She’s also a third-generation esthetician: her grandmother, Catherine Hinds, founded the first accredited esthetics school in the U.S. in 1979.

Confession: I am a Glowbar member. They hooked me with the concept of a quick 30 min facial every month — I love it.

What’s your favorite vacation spot, and why do you love it?

The Greek Islands. Cliché for a reason — the water, the food, the relaxed vibe of the locals and guests just makes your shoulders drop away from your ears. I also do feel like the Mediterranean water is healing!
A closer-to-home favorite: Hotel Lilien in the Catskills, hiding out for a full weekend upstate to really disconnect.

(She also offered to share a couple of vintage stores with no WiFi that “really help you disconnect.” Rachel Liverman we need the list.)

What’s one thing you actually do (or refuse to do) that helps you unplug?

I refuse to be on my phone for part of each day. I also don’t make plans. I know that sounds odd, but I live so scheduled (literally every minute of my day has a calendar item when I’m home) that when I’m away, I don’t even want to have to be at dinner at 8pm.

As for me?

Kamalame Cay in the Bahamas. If you know, you know. And they allow dogs depending on how you arrive, so that’s Ailey in our golf cart :)

Reading through these responses was a reminder for me that work will still be there. It always is. For better or for worse, that’s the most dependable thing about it lol. And because it’s always there, it’s easy to default to prioritizing it.

My advice for you this week is: book the vacation. Book the girls trip. Go somewhere solo. Take your PTO. You deserve it.

Good luck! See you next week.

Ashley

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