Whether it’s a month abroad, a multigenerational family trip, or finally stepping away from the business, here’s what the planning actually looks like, and what most people forget until it’s too late.
Key TakeawaysIs a big trip a money question, an emotional one, or a logistics one? Usually all three, but in our experience, money is rarely the real obstacle. Most clients who can afford the trip talk themselves out of it. Our job is often less about running the numbers and more about giving them permission to go. What do people most often forget to plan for? Taxes, healthcare coverage, mail, and life insurance timing are the ones that catch people off guard. The logistics feel obvious in hindsight, but only after they’ve been missed. How does having a financial team change what’s possible? It means the market can move, a rebalance can happen, and a decision can be made, all without interrupting your trip. For most of our clients, that peace of mind is worth more than any specific financial benefit. |
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When a client tells us they want to take real time off, a month away, the big family trip, the multigenerational adventure everyone keeps talking about, our first move isn’t to pull up a spreadsheet. It’s to ask questions.
Where do you want to go? Who’s coming? What do you think it’ll cost? How are you thinking about paying for it? Most clients already have the trip mostly worked out in their minds. Our job is to understand how they’ve thought about it, meet them where they are, and then help them see what they’ve missed, or what they don’t need to worry about as much as they think.
Sometimes that conversation is about creating a runway. Sometimes it’s about giving someone permission to spend money they’ve already earned. And sometimes it’s about saving them $5,000 in credit card interest they didn’t know they were about to pay.
It’s Rarely Just a Money Question
When clients come to us with a trip in mind, the financial piece is usually solvable. What’s harder is the emotional permission, especially for clients who have spent decades building something and feel guilty about spending down the wealth they’ve built.
We had a client in her thirties who wanted to take six months off work. She was highly paid and, financially, it was doable, but she needed to see it on paper before she could let herself believe it. We adjusted her investment plan, shifted some non-retirement savings into a more conservative allocation to preserve the cash she’d need, and showed her the full picture. Once she saw it was real, she went. The plan didn’t make the trip possible. It gave her the confidence to take it.
We see this pattern all the time: the issue isn’t the money itself, it’s feeling comfortable giving yourself permission to spend it.
When a Trip Feels Out of Reach
One of the more memorable conversations along these lines involved a couple who had dreamed for years of taking their adult children on a trip back to their country of origin. They’d immigrated as infants and had no real memories of that time, so they wanted their kids to experience it before everyone got too busy with their own lives.
The trip they envisioned cost around $50,000, and they’d never spent that much on a vacation. They were still carrying student debt from graduate school, in their 50s, while simultaneously paying tuition for kids in and out of college. On paper, it looked like the wrong time.
However, they’d just come into an unexpected windfall, and they asked: do you think we can afford to do this now?
The answer, after looking at the full picture, retirement savings, two Social Security checks, a pension, was yes. Not probably fine, but genuinely yes. They were in better shape for retirement than they realized. And the window for this trip wasn’t going to remain open forever: the kids were finally old enough to appreciate a trip like this, but not so grown that their own commitments would make it difficult.
Take the trip. That was the advice. And they did. Without that nudge, they may well not have taken the trip, and very often we see situations where our clients are better situated than they realize.
Related: Preparing Kids for Wealth: A Guide for Intentional Families
What People Often Forget
This is where the planning gets specific. Most clients think about flights and accommodations. Fewer think about everything else.
Taxes and cash flow. If you’re self-employed or have significant investment income, estimated taxes don’t pause while you’re away. Make sure quarterly payments are set up in advance, and that someone knows to flag anything time sensitive.
Healthcare coverage. If you’re taking extended time off and leaving an employer plan, you need a bridge. COBRA, a marketplace plan, or travel medical coverage, are options depending on where you’re going and how long you’ll be gone. This one surprises people every time.
Mail. It sounds small. It isn’t. We had a client who did a retirement account rollover right before a long vacation. The check arrived after she left and sat in her mailbox for a month. For a trip of more than four weeks, either hold your mail, forward it to someone you trust, or, better, time major financial transactions around your departure.
Life insurance exams. If you’re in the process of applying for life insurance, take the medical exam before you travel, not after. We had a client who came back from a two-week cruise and failed his blood work. Not because he was unhealthy, but because two weeks of vacation eating and drinking had temporarily skewed his results. He ended up with a worse underwriting outcome than he deserved. Also worth noting: if your travel plans include certain destinations, some insurers will decline coverage outright, so apply early before you’d have to disclose that you plan to travel to a country on the “do not insure” list.
Power of attorney. For extended trips or international travel, having someone authorized to act on your behalf isn’t just useful, it can be essential. A deal needing a signature, a financial decision with a deadline: these things don’t wait. Set it up before you leave.
Handling the Money Conversation
When one family member is covering the cost of a trip for a larger group, the financial dynamics can get complicated fast. The best thing you can do is have the conversation upfront, before anyone commits to booking a flight.
We’ve seen this done well: a client covering an Airbnb and groceries for an extended family stay, with a simple message to the group, here’s what we’re taking care of, here’s what’s on you. No ambiguity, no awkward moments mid-trip when someone wonders if they should offer to pay for dinner. Everyone arrives knowing the framework.
It doesn’t need to be a formal conversation. A quick text works. What matters is clarity, for the person paying, who now knows the commitment they’re making, and for everyone else, who can plan accordingly. The goal is to protect the experience, not just the budget.
And sometimes, when clients have the means but haven’t considered the idea, we introduce it. One client had been talking for years about that one trip the whole family took together. She had the assets, she had the desire, she just hadn’t given herself permission. We did. Now it’s an annual tradition.
What It Means to Have Someone Watching
One of the quieter benefits of having a financial team is what it makes possible when you’re unreachable. Markets move. Rebalancing opportunities come up. For most of our clients, we have the discretion to act without needing to interrupt a vacation for a phone call.
That matters more than people realize until they experience it. You can be out on the water, off the grid, genuinely away, and know that if something needs to happen, it will. You don’t have to be available. You don’t have to be worried. You just have to be present where you are.
Related: Our Process
For clients who keep finding reasons to delay the trip: the planning isn’t as complicated as it feels. Most of what needs to be in place can be handled in a single conversation. The harder part is deciding the trip is worth taking.
Not working with TNLPG yet? Schedule a complimentary SWOT Session to learn more about how we help turn moments of hesitation into moments of clarity.