My wonderful husband!
How to Vacation Without Falling into the Guilt Trap
By Chere B. Estrin
It was that time again: vacation time. God, what a drag. It meant I had to leave work and go have fun. I don’t have time to have fun. Who scheduled this?
Still, my wonderful husband had been dealing with some health issues lately, and stress was clinging to us like a client who found your cell number. So in a rare moment of compassion, I suggested we take a short trip to Hawaii. I knew I’d be squeezing it in between clients, candidates, webinars, writing deadlines, marketing campaigns, and possibly solving world peace but the image of lounging by the pool with a trashy magazine while a shirtless beach boy misted me with mineral water? That seemed… almost worth it.
“I was thinking Hawaii,” I said casually.
“Hawaii?” he said. “I’m on it.”
And that, friends, was the launch of The Great Client Evasion of 2025.Cue the hours of travel-site trolling. Hotel? Check. Flights? Check. Excursions, rental car vs. Uber, sunset cruise or catamaran, museum or luau, hiking or collapsing poolside? All decided. All booked. All emailed to me in a 17-page itinerary with pictures of me smiling on beaches I hadn’t visited yet.
Fast forward a few weeks, and my dear husband had meticulously arranged everything. “Are you up for Germaine’s Luau? Bishop Museum? Diamond Head? Turtles? Fish? More fish? Sunset cruise? Culture center? Hiking? Pineapple farm? Outlet mall?” (Apparently, no Hawaiian vacation is complete without discount muumuus.) “And kayaking!”
Kayaking? I can barely squat to plug in my printer. You want me to wedge myself into a plastic capsule and pretend I’m not going to flip over like a manatee in distress?
That’s when it hit me. Vacation guilt.
You know the kind. Your team’s not on vacation. Your clients certainly didn’t approve this. What if the phones ring and no one answers? What if that new client finally responds while I’m staring down a roasted pig at a luau? What if the business collapses in my absence, I’m three thousand miles and three hours behind. This was madness.
But off we go to Waikiki. Cheaper than the outer islands, more nightlife, more hustle, more… well, more honking. Traffic in Waikiki is just like New York, only with leis, more flip-flops and the smell of coconut butter. Gone were the dreamy trade winds lulling me into a soft nap. The only wind I felt was from a city bus nearly sideswiping our Uber.
The hotel? A boutique gem. Translation: the rooms were adorable in the same way a shoebox is “cozy.” No desk. No table. Nowhere to set up my laptop. “Did you bring a computer?” you ask. That’s like asking if I brought underwear. Of course I brought my computer. I’m not an animal.
We hauled in the tiny patio table, propped it by the bed, and set up my makeshift workstation. There was one usable chair in the room, so we took turns like it was a team-building exercise. First thing I did? Checked email. I hadn’t logged on in eight hours, which is basically years in recruiter time. If I hadn’t passed out on the flight, I would’ve been answering messages in Row 22B.
My wonderful husband, ever the Activities Director, pulled out his color-coded folder. First activity: hop-on-hop-off trolley. A 2.5-hour ride around the island with the option to jump off and explore every tourist trap imaginable and then jump back on. We didn’t hop off once. I checked email the entire time on the trolley. I took one photo. It’s blurry. It might be a lamppost.
Back at the hotel, we admired our “ocean view”, a generous term for the sliver of Pacific peeking through two monstrous buildings. “Look,” I confessed, “with this schedule, I have no time to work.” I pictured myself at that luau, panic-texting under the table while fire dancers flung torches overhead.
My husband, SPF 60 slathered and ready to slither poolside, was surprisingly chill. So we called it. We slashed Diamond Head, killed the luau, ditched the pineapple farm (they’re spiky, I get it), skipped the outlet (I’ve seen discount handbags before), and buried the kayaking idea six feet under.
To meet him halfway, I promised to lock my phone in the safe and turn off the ringer. I lasted eight minutes before I wanted to open the safe and check on it. You know, just to make sure it was comfortable.
“Vacations are for mental health,” he reminded me gently.
I nodded, understanding nothing. My mental health is my phone.
But slowly, grudgingly, the minutes stretched. An hour without checking. Then two. Then three. And eventually… the guilt started to fade. I remembered how to read a book for no reason. I started counting clouds instead of emails. I laughed. I wore a floppy hat. I even floated in the pool without my phone clutched in a Ziploc bag.
How to Vacation Without Falling into the Guilt Trap
Here are my expert-level, trial-by-fire tips for taking time off without melting down:
- Pre-vacation auto-responder magic: Write one that says, “I’m out of the office and fully trust my team.” Whether you trust them or not is irrelevant. They’ll step up just to prove you wrong.
- Delegate something. Anything. Just pick a task and let it go. Yes, it will be done differently. No, the world will not end.
- Make a deal with yourself. Set a work window. 7:00–8:00 a.m.? Answer emails. After that, the laptop goes back in the bag. Or the safe. Or the minibar.
- Don’t book every minute. If your itinerary looks like a hostage schedule, you’re doing it wrong. Leave room for spontaneity. Or naps. Or staring at waves until your brain finally shuts up.
- Remind yourself why you’re going. If “mental reset” sounds too fluffy, call it “executive restoration time.” Suddenly, it’s strategic.
And finally, leave the guilt in the TSA line. It’s not coming to Hawaii. You are. Preferably in a sundress, with a blue drink that has an umbrella in it, and zero tabs open on your browser.
Because guess what? The only real emergency on vacation should be deciding between mango or passionfruit shave ice.
Aloha, my fellow guilt-ridden professionals. Next time, pack lighter, and that includes your conscience.
Chere Estrin is the CEO of Estrin Legal Staffing, Editor-in-Chief of The Estrin Report, and an expert in legal career strategy. She is known for saying what most recruiters won’t. She has a new book, Power Plays for Legal Professionals: Strategies to Move Your Career Forward coming out Fall 2025. Reach her at: Chere@EstrinLegalStaffing.com.