For years, I assumed that making good financial decisions meant avoiding unnecessary purchases and staying focused on long-term goals.
Then we bought a boat.
From a purely financial perspective, it wasn't an especially compelling investment. Boats depreciate, require maintenance, consume fuel, and create ongoing expenses. There are plenty of reasons financial planners can think of to avoid buying one.
At the time, however, our family found itself in a unique season of life. It was during COVID, our children were teenagers, and many of the activities that normally filled their schedules had disappeared. Like many families, we were spending more time at home, but not always spending that time meaningfully together.
Then, one night at dinner, one of our kids excitedly described a day he had spent on a friend's boat. Somewhere during that conversation, I casually suggested that maybe we should get one too. I meant it as an idea worth discussing someday. My husband apparently heard it as a directive. Three days later, he towed a boat into our driveway.
Before long, our weekends started to look different. Our kids spent less time on their phones and more time together. We invited friends, spent long days on the water, and created memories that became part of our family's story.
Looking back, the experience forced me to think about a question that comes up frequently in financial planning:
Once you've built financial security, what do you want your money to accomplish?
When You’ve Spent a Lifetime Being a Good Saver
One of the challenges of financial discipline is that the habits that help people build wealth don't necessarily disappear once they've accumulated enough.
People who have spent decades saving, investing, sticking to a budget, and delaying gratification often reach a point where their financial goals are on track and their retirement is well-funded. Yet spending a meaningful amount of money can still feel uncomfortable. The behaviors that contributed to their financial success remain in place long after the original goal has been achieved.
I've seen this with people who have done all the right things financially. They have sufficient assets, a solid plan, and a high degree of confidence that they will be able to meet their long-term objectives. Yet when an opportunity arises to spend money on travel, family experiences, charitable giving, or something they've wanted for years, the first instinct is often hesitation.
At that point, the question is no longer whether they are saving enough. The question becomes what they wanted all that saving to accomplish in the first place.
For some people, the answer is security. For others, it may be time with family, travel, flexibility, generosity, or the ability to help the people they care about. Most often, it's some combination of those things.
A financial plan can help determine whether a purchase is affordable. It can also help evaluate how that decision fits alongside other priorities, such as retirement, healthcare needs, long-term care considerations, charitable goals, or the legacy you hope to leave behind. Deciding whether a purchase is worthwhile is often a different question entirely, but understanding the financial tradeoffs can provide valuable context.
A Different Way to Evaluate a Purchase
The question isn’t whether every experience is worth the money. Our boat would have been a terrible decision if it meant jeopardizing retirement, carrying debt we couldn’t responsibly handle or giving up something our family valued more.
Meaningful spending still requires discernment. And once a financial plan gives you room to spend, I think there are a few questions worth asking that don’t appear on a traditional balance sheet.
1. What are we actually buying?
Years before we bought the boat, I remember telling a financial advisor that I wanted one someday when I had kids. He kept asking why, and I struggled to answer the question. At the time, it sounded like I wanted an expensive toy.
Looking back, I think I understood the outcome I wanted, even if I didn't have the language to describe it. I wasn't focused on the boat itself. I was thinking about family time, shared experiences, and creating reasons for everyone to want to spend time together.
That conversation has stuck with me because it applies to far more than boats.
When evaluating a significant purchase, it can be helpful to look beyond the item itself and consider what role it will play in your life.
For our family, the boat created opportunities to spend time together during a stage of life when that was becoming increasingly difficult. For someone else:
- A plane ticket might create an opportunity to spend time with aging parents.
- A vacation home might become a gathering place for multiple generations.
- A kitchen renovation might support the way a family hosts, entertains, and spends time together.
The purchase itself is only part of the decision. Understanding what you hope that purchase will make possible can provide a better framework for evaluating whether it aligns with your priorities and is worth the cost.
2. What does saying yes require us to say no to?
Every dollar has an opportunity cost. What are your savings and spending habits teaching you to value?
If spending the money means postponing retirement, carrying high-interest debt, or giving up another goal you value more, that matters.
Depending on your stage of life, other considerations may matter as well. How is your health? Have you planned for potential long-term care needs? Do you have sufficient liquid investable assets to support both this purchase and the goals that remain important to you? Are there charitable causes, children, or grandchildren you hope to support in the future? These aren't necessarily reasons to avoid spending, but they can provide important context when evaluating the tradeoffs.
But if the financial plan comfortably supports the expense, then the decision becomes less about whether the expense aligns with the goals and priorities that matter most to you and more about whether this particular use of money reflects what you care about.
Instead of “Can I technically afford this?” ask, “Is this one of the things I actually want my money to accomplish?”
3. Is there a window for this experience?
This one is more significant than we sometimes acknowledge, and this is the question I think we underestimated before buying the boat. Our teenagers weren’t going to be teenagers forever. There would only be so many summers when they were home, available, and willing to pile into a boat with us for the entire day.
The timing of an experience can matter as much as the experience itself.
Parents age. Kids grow up. Health changes. Careers get busier. Families spread out geographically. Grandchildren stop thinking you're the coolest person alive.
Planning for the future remains important, but some opportunities are time-sensitive. Recognizing those opportunities can be just as important as preparing for what comes next. It is a difference between being patient and assuming every opportunity available today will still be available ten years from now.
This can create an interesting planning tension. The same factors that influence long-term financial decisions, including age, health, family circumstances, and evolving priorities, may also influence how long certain opportunities remain available. Sometimes the question isn't simply whether you can afford an experience. It's whether waiting significantly changes the value of that experience to you and the people you care about.
4. If our financial plan supports it, what is keeping us from spending the money?
For lifelong savers, watching an account balance grow can feel deeply satisfying. It represents security and discipline and years of good decisions.
That feeling is real.
For many people, seeing assets accumulate reinforces a sense of security. Spending those assets can feel inconsistent with the habits that helped build them. But I also think there are moments when money has already accomplished the thing you asked it to accomplish. It created security and gave you options. There are times when money has done its job. Now one of those options is to use it.
When clients face these decisions, it can be helpful to model multiple scenarios rather than relying on instinct alone. Financial planning software can help illustrate how a significant purchase might affect future retirement spending, gifting goals, healthcare expenses, or assets ultimately left to heirs. Seeing the numbers in context often provides confidence that a meaningful purchase fits within the broader plan.
The value of some financial decisions may never appear on an account statement. Sometimes it becomes apparent years later through the experiences, relationships, and memories those decisions helped create.
What Do You Want Your Money to Become?
The answer is different for everyone. Maybe your money becomes financial independence. Maybe it becomes an education for your children or grandchildren. Maybe it becomes philanthropy, travel, time away from work, care for a parent, long-term healthcare security, or the chance to bring your entire family together once a year.
Maybe part of it becomes a boat.
The reality is that most families are balancing several priorities simultaneously. They want to enjoy life today while also preparing for future needs and considering what, if anything, they hope to leave behind.
The right answer will be different for every person and every family. There isn’t one correct way to spend wealth. The important part is making sure the way you use it reflects the life you actually want.
Sometimes that decision begins with a conversation, first with yourself about what matters most, and then with a trusted advisor about how those priorities fit within the broader financial picture.
Financial discipline creates options. Eventually, we have to decide what to do with them. The point is to make the decision consciously and intentionally.
For our family, one of those choices sits in the driveway for part of the year, costs us money every time we use it, and makes very little sense if you judge solely as an asset.
And I’d buy it again.
Because a life well-planned should leave room for both financial security and actually enjoying the life you've worked so hard to build.
