A family recently came to me with an situation that felt awkward on the surface but points to something much bigger. They have three adult children, ages 36, 39, and 40. Two of them fly private when the family travels together. The third prefers to fly commercial and has asked his parents to redirect whatever they would have spent on his private travel toward charitable giving instead.
On the face of it, that sounds reasonable. But it opens up a question worth examining carefully: when a child opts out of a gift or an experience you’ve offered, does that create a bucket of money they now get to direct?
My answer is no, and here’s why.
The Reallocation Trap
This is what I call the reallocation trap. It happens when a child feels, whether consciously or not, that declining a benefit still entitles them to something. The logic goes: “You were going to spend that on me anyway. I just don’t want it in that form. So I should get a say in how it’s used instead.”
But that’s not how gifting works, at least not in a healthy framework.
When you offer your children the experience of flying private together, you’re gifting the experience, not handing each child a pile of cash that just so happens to be spent on travel. If one child declines, that doesn’t create a redirectable asset. The gift simply goes unclaimed.
Fair, in the context of family gifting, does not mean identical outcomes. It means equal opportunity. You offered everyone the same experience. What each person does with that offer is up to them.
Two Ways to Handle the Travel Situation
There are really two reasonable approaches here, and both are legitimate depending on what you value most about these family trips.
The first is to treat the travel itself as a family-together experience, not just logistics. If that’s the case, then flying private is how your family travels as a unit, and your children are welcome to participate. On their own time, they can fly however they like. But for this trip, the expectation is that everyone travels together.
The second approach is more flexible: everyone gets where they’re going however they choose, and you’ll cover the cost of commercial travel for the child who prefers it. That’s a generous and reasonable accommodation. What it does not include, however, is any claim on the difference between what you would have spent on private and what you actually spent on commercial.
Either way, the key is that you are making the decision, not ceding it.
Why This Matters Beyond Travel
Travel is actually a relatively low-stakes place to work through this, which is what makes this situation a good opportunity. The same dynamic shows up in much more complicated forms when families start thinking about education funding, grandchildren, and larger financial gifts.
Imagine you want to pay for all your grandchildren to attend college. What happens if one of your children doesn’t have kids, or has children who won’t go to college? Does that child get a cash equivalent? What if one grandchild goes to private school and another to public school?
These scenarios follow the same pattern. Someone feels that because the gift isn’t being used in the way originally intended, there should be a reallocation. And without a clear framework in place, that assumption can quietly take root and cause real conflict.
Setting a Precedent Now
The most valuable thing you can do with a situation like this is use it to get clear about your own philosophy and communicate it. Not in a heavy-handed way, but openly. What is the purpose of the gift? What does equal treatment mean to you? What happens when someone opts out?
If you can answer those questions now, in the context of a family trip, you’ll be much better positioned when the stakes are higher. The goal is not to create a rigid rulebook, but to establish a shared understanding of how you think about generosity and what your intentions are.
That clarity protects your family from the resentment and confusion that tend to build when gifting expectations go unstated.
This post is adapted from a recent episode of the Scholar Wealth Podcast. For more perspective on family gifting dynamics and financial planning, listen to the full podcast episode here.