The Big Decisions Still Need the Same Basic Question
What Is Your Money Actually For Series
We often advise that a single question belongs at the center of most financial decisions: what is your money actually for, and who is it serving? In other articles, we’ve applied that to everyday spending, to subscriptions, to family celebrations and more, as well as how the answer shifts depending on where someone is in life.
Interestingly, the same question applies to the big decisions. The ones that feel heavier because the numbers are larger and the consequences last longer. Education. Retirement timing. Major financial trade-offs that shape a family’s trajectory for years.
These decisions deserve more than a spreadsheet. They deserve honesty about what you’re really optimizing for. Let’s look at a couple of them as illustrations and then the lessons that we can take from them.
The Education Question
Few decisions carry more emotional weight for families than education. The school a child attends, and what a family is willing to invest to make it possible, touches on identity, values, sacrifice, and aspiration all at once.
We work with a number of families for whom a parochial school education has been a genuine priority, something worth real financial sacrifice because of what it represents and what it provides. We’ve also sat with families who have stretched to afford a prestigious college or university because they believed, sincerely, it was the right choice for their child.
In both cases, the numbers matter. But the honest conversation goes a level deeper. It’s worth asking: is this decision primarily about what’s best for the child, or is part of the motivation about how it looks to others? That’s not a judgment. It’s a useful question, because when people are honest with themselves about the answer, they tend to make decisions they feel better about afterward.
When a family can’t fully afford a particular school, we work through the real options together. What would a state school cost? What would the gap look like in loans, and who carries them? We’ve seen something meaningful that happen when a student has some skin in the game financially. It tends to focus attention and increase commitment in ways that a fully funded education sometimes doesn’t. That’s not an absolute rule but it is an observation worth having on the table.
Retirement Timing: What Are You Actually Choosing Between?Preview Website
Retirement timing is where this framework does some of its most important work. The question of when to retire sounds like a financial calculation, and it certainly is one. But underneath the math is a values question that most people haven’t necessarily thought through explicitly.
Retiring earlier usually means accepting less, whether in monthly income, in accumulated assets, or in both. Working longer usually means more, but it also means trading years of time and energy. Neither choice is automatically right. What matters is whether the person making the choice has actually called out and considered what they’re trading and why.
We’ve seen clients pursue early retirement as a genuine expression of what they want from this stage of life, with a clear sense of what they’ll do with the time and why it matters to them. That’s a well-made decision, even if the numbers are tighter.
We’ve also seen some clients who push toward early retirement in ways that don’t account for a spouse’s situation, or that prioritize a personal finish line over what the family as a whole actually needs. That’s a harder conversation to have, but it’s also an important one. What is an earlier retirement actually for, and is it serving everyone it affects?
Of course, there are a number of other significant decisions clients will face, from healthcare, to where they will live, to supporting family members in need, or their philanthropy. All of these and more deserve the same thoughtful and honest discussion as you move through life.
The Role of Ratios Over Rules
No matter where someone is in their financial journey, one thing we understand is that people often want a formula. A number. A percentage. “Tell me the rule and I’ll follow it.” We understand the appeal, and we do use benchmarks: distribution rates, cash flow projections, savings ratios. These are useful anchors, but life doesn’t run on monthly averages.
Expenses cluster. Unexpected things happen, though when you zoom out far enough, they’re not really unexpected at all. When you do look at the numbers, what we’ve found useful is to view your spending in averages over 24 to 36 months rather than precise monthly targets. That reframe alone tends to reduce the anxiety that comes from any single month that doesn’t look the way it was supposed to.
The big decisions, like the small ones, ultimately come back to judgment rather than a formula. What are you actually trying to accomplish? Who does this decision serve? What are you willing to trade, and what aren’t you? Those questions don’t have a universal answer. But they have your answer, and finding it is what good financial planning is actually for.
A Different Kind of Conversation
Most financial advice treats these decisions as math problems with a correct solution. Run the numbers, identify the optimal choice, execute the plan. We’ve found that approach works well for some things and falls short for others.
The decisions that define a financial life are rarely purely mathematical. They’re about what you value, what you’re willing to sacrifice, and what kind of life you’re trying to build for yourself and the people around you. The numbers inform that. They don’t answer it.
Rawe Financial is a family-owned financial advisory practice in Northern Kentucky, helping individuals and families navigate retirement. If you’re facing a big decision and would like to think it through with someone who is going to ask the harder questions, not just the financial ones, we’d welcome that conversation.