Hi. It’s been a minute. Or almost four weeks.
We went on a two-week vacation to Italy. And for the first time, I handed over the reins. Not to a spreadsheet (okay, partially to a spreadsheet–a woman has to track her budget)! Not to a color-coded itinerary I built at midnight after the kids were asleep. But to an actual human being. A travel agent.
SURPRISE. I gave up control and it did not break me.
Yes, I’m as shocked as you are.
Earlier this year, my husband and I decided to book a trip to Puglia for our 15th anniversary. I’d wanted this trip for years. I’ve dreamed about it. Talked about it. Researched parts of it. It was originally supposed to happen in 2025, but then we decided to bring the kids, which changed the location, the pace, the whole shape of that Italy experience. Puglia holds a lot of my family roots.
Somewhere around April, we decided to book this trip. And when we decide to book something in our house, I (me, myself) go into type-A, controlling, research-overdrive mode. I am a planner by profession. This is where I shine. I got myself as far as plane tickets and, with some help from AI, a few genuinely beautiful hotel picks across four locations. Then the schedule changed and I had to rebook everything to move the trip up by two weeks. I did that too. And then in June, I tapped out.
I looked at the approximately 398 mental tabs I had open worrying about everyone and everything plus the prospect of a trip navigating a whole new region, the car we’d planned to rent and drive ourselves, the research I knew I’d want to do to get it “right,” and I decided that being in control of this particular thing was no longer what I wanted, nor was it helpful.
And that’s when a small miracle happened. I finally handed the reins to a travel agent. I’d followed See Italy Travel for years, somehow ended up on their email list, and made the call. I told them I wanted everything done. Airport transportation, transfers, tours, experiences, all of it. They built the package. They delivered on it. What would have been a trip, planned by an exhausted version of me, became an actual vacation. And it was glorious.
We visited the church where my grandparents were married almost 80 years ago in Bari. I stood where they stood. We said our vows to each other again in that exact same spot. I ate family recipes in the place they came from. I connected with our tour guides–strong, bold, Italian women. I practiced my rusty Italian. My heart and my cup were full in a way they hadn’t been in a long time. A trip I could have poured myself into planning and shown up burnt out for, I instead let myself be taken care of. It was nice to have the space, for myself, for my marriage, to actually process everything I’d been carrying.
Why Control Doesn’t Actually Serve Us
My need to plan everything myself was never really about competence. I am quite competent. It was about control (and it usually is). If I built the itinerary, researched every hotel, mapped every transfer, then nothing could go wrong that I hadn’t already anticipated. The planning isn’t the point for me. It’s the illusion of safety underneath it that provides the comfort.
This shows up financially in almost identical form. A client who insists on managing every dollar herself, even though she resents the mental load of it. The woman who won’t make a hire for her business because “it’s faster if I just do it.” The client sitting on cash she’s too anxious to invest, not because she doesn’t understand the numbers, but because doing nothing feels like the one move she can’t get wrong.
We call this being responsible. Sometimes it is. And sometimes it’s a nervous system convinced that if you let go of any piece of the wheel, the whole thing goes off the road.
Buying Yourself Out of the Mental Load
Harvard Business School researcher Ashley Whillans, along with University of British Columbia psychologist Elizabeth Dunn, surveyed more than 6,000 adults across the U.S., Canada, Denmark, and the Netherlands and found that people who spend money to buy back their time, hiring out cleaning, delivery, the tasks they don’t want to do themselves, report meaningfully higher life satisfaction than people who don’t. And it didn’t matter whether they had a lot of money or very little. If anything, people with less money saw a bigger happiness boost from time-saving purchases than those with more. Dunn summarized it plainly: money can buy happiness, if you spend it right. The “right” way, per Whillans, is paying someone else to do the time-consuming work you don’t want to do yourself.
When we recognize that our time and our bandwidth are finite, non-renewable resources, and that spending money to protect them is not indulgent, but strategic, we open the door to happiness.
The Tradeoffs
The case for delegating is real. You have less mental load and more presence. Research backs the happiness gains. Handing something over to an expert usually means it gets done better than a rushed, resentful version of you would have managed. That’s just true.
But there’s a cost on the other side too. Letting go of control means letting go of the illusion that you’re the only one who can do it right. For those of us who’ve built our identities, our careers, our sense of usefulness around being the one who handles it, that surrender doesn’t feel neutral. It can feel like losing a piece of yourself, even a piece you didn’t particularly like carrying.
There’s also the actual dollar cost. Not every family has the room to hire the travel agent, the housekeeper, the bookkeeper. Part of my job is helping women figure out where that room exists in their own financial picture, because it’s usually there in some form, even if it’s smaller than they think or shaped differently than they expected.
And there’s the discomfort of a plan not being executed exactly the way you would have executed it. That’s real too. Handing over the reins means someone else’s judgment enters the picture. Sometimes their judgment is better than yours would have been under pressure. It usually is. But it’s still not yours.
Where Can You Start?
You don’t need to hand over your whole life to a travel agent, or a financial advisor, or anyone else, to test this out. Start smaller.
Notice where you’re white-knuckling something out of habit, not necessity. Is this task actually yours, or is it just familiar?
Ask what it’s costing you to hold it yourself. Not just time. Sleep. Patience. Presence.
Price the alternative honestly. What would it actually cost to hire this out, and what would it be worth to get the hours, or the headspace, back?
Let one thing go before you’re desperate enough to be forced into it. Don’t wait until you’re about to melt into a puddle. Being proactive is okay and encouraged.
The world did not implode when I handed over the reins. My marriage got a vacation instead of a trip. My kids got a mom who wasn’t buried in a spreadsheet every evening. And I got to be present for a year that has asked a tremendous amount of me in every other direction.
It’s okay to hand over the reins once in a while. It’s okay to pay for the peace of mind. The world will not implode. I promise you, mine didn’t.
Related: Your Estate Plan Isn’t Just About Your Money. It’s About What You’re Asking Your Family to Carry
