The Simple 10-Year Test That Prevents Expensive Regrets
How to Make Big Money Decisions You'll Be Happy With in 10 Years
In 10 years, will you regret spending $40,000 on this, or regret NOT spending it?
That’s the question that cuts through 90% of financial decision paralysis.
Most people agonize over big money choices - the house upgrade, the career change, the business idea, the family trip - because they’re using the wrong framework to evaluate them.
They obsess over spreadsheets, calculate ROI, stress about opportunity cost, and ask everyone for opinions.
And they still can’t decide.
Here’s why: they’re optimizing for the wrong variable. They’re trying to make the “smartest” financial choice when they should be asking a much simpler question.
Will I remember or care about this decision in 10 years?
That one question eliminates most of the noise and forces you to evaluate what actually matters.
Let’s dig in ↓
Why Most Financial Decision-Making Fails
Here’s the problem: people reduce everything to pure math. “Which choice maximizes my net worth in 30 years?”
That sounds rational. But it ignores a fundamental truth: you’re not optimizing for maximum net worth. You’re optimizing for a life you actually want to live.
The person who retires with $5 million but missed their kids’ childhood didn’t “win.” The person who delayed every meaningful experience until retirement and died at 63 didn’t make the “smart” choice.
Pure financial optimization without considering life satisfaction is a game you can win mathematically while losing practically.
The 10-year test forces you to consider both financial AND experiential returns.
The 10-Year Test: How It Actually Works
Before any major financial decision, ask: “In 10 years, will I remember this? Will I care about it? Will it have mattered?”
This reveals whether you’re creating lasting value or just making a decision that sounds good today.
The $8,000 Vacation
Pure math: $8,000 invested at 7% for 10 years becomes $15,740. You’re “losing” $7,740 in future wealth.
The 10-year test: Will you remember this trip? Will your kids? Will it create stories retold for decades?
If yes - the trip to Europe with aging parents, the adventure with teenagers before they’re gone - the $7,740 portfolio “loss” is irrelevant.
If no - just another forgettable beach resort - maybe the math matters more.
The test isn’t about right or wrong. It’s about conscious choice.
The $50,000 Car vs. $30,000 Car
Pure math: The $20,000 difference becomes $39,000 in 10 years, plus higher ongoing costs.
The 10-year test: Will you remember or care that you drove the nicer car? Will it have enhanced your life meaningfully?
For most people? No. Both cars get you to work. In 10 years, you won’t remember which one you drove.
But maybe you’re a genuine car enthusiast. Maybe the reliability difference reduces real stress. Maybe the safety features matter for a young family.
The test separates genuine value from status signaling.
The $400K House vs. $600K House
Pure math: The $200,000 difference invested becomes approximately $393,000 in 10 years.
The 10-year test: Will the bigger house improve your daily life? Will you use the extra space? Does it enable something meaningful - better schools, eliminated commute, home office that enables career growth?
If it’s just “nicer” without functional improvement, the test suggests the smaller house.
If it fundamentally changes how you live, work, or raise your kids - it’s worth the premium.
The Opportunity Cost That Actually Matters
Traditional opportunity cost: “If I spend $X, I lose $X compounded at Y% for Z years.”
That’s mathematically accurate but practically incomplete.
Better framework: “If I spend $X on this, what am I giving up? And will I regret that trade-off in 10 years?”
Example: $40,000 Career Break
Traditional thinking: $40,000 compounded at 7% for 20 years = $154,920. That’s what this break “costs.”
Better thinking: What happens if you DON’T take the break?
Maybe you burn out completely and leave your $200,000/year career for a $120,000 job. Over 20 years, that’s $1.6 million in lost income - far more than the break costs.
Maybe the break leads to career clarity that increases lifetime earnings by $500,000+.
Maybe you just need the break and 10 years from now you’ll be glad you took it.
The real opportunity cost isn’t just “money not invested.” It’s “what does this enable or prevent in my life?”
The Regret Minimization Framework
Jeff Bezos uses this for major decisions: project yourself to age 80 and ask which choice you’ll regret NOT making.
The Business You Didn’t Start
You’re 35 with a stable $150,000 job and $200,000 saved. You have a business idea requiring you to quit and invest $50,000.
The risk: If it fails, you’ve lost income and savings.
The regret question: At 80, will you regret NOT trying? Or will you regret the financial setback?
For most people, the regret of not trying far outweighs the regret of a failed attempt. You can recover financially from a $50,000 loss. You can’t recover the opportunity to pursue something meaningful when you had the energy and runway.
The framework doesn’t say “always take the risk.” It says “take the risks you’ll regret not taking.”
When to Optimize for Today vs. Tomorrow
Optimize for today when:
The experience is time-sensitive (aging parents, young kids, physical capability)
You’re financially on track and this doesn’t derail long-term goals
The opportunity won’t exist in 10 years
You’ll remember it in a decade
Optimize for tomorrow when:
You’re not financially stable yet (no emergency fund, high debt, minimal savings)
The purchase won’t be memorable in 10 years
Better opportunities will exist later with more resources
You’re buying primarily for status or validation
Key insight: You don’t choose one strategy forever. Optimize for tomorrow while building your foundation, then shift toward today once you’re stable.
The Real Decision Framework
Here’s how to use this for your next big financial decision:
Step 1: Name the decision and dollar amount.
Step 2: Project 10 years forward. Will you remember/care?
Step 3: Calculate the real opportunity cost. What’s the alternative? What does THAT cost?
Step 4: Ask the regret question. At 80, which choice will you regret?
Step 5: Consider your current position. Can you absorb this cost given your financial situation?
Step 6: Make the call based on YOUR values and what YOU will care about in 10 years.
Bottom Line: Money Is a Tool, Not the Goal
The 10-year test works because it forces you to remember what money is actually for.
Money isn’t the goal. It’s the tool that enables the life you want to live.
Sometimes that means spending it on experiences you’ll remember forever, even if the spreadsheet says invest it. Sometimes that means investing aggressively now for freedom later, even if it means saying no today.
The “right” answer isn’t universal. It’s personal.
But the wrong answer IS universal: making financial decisions purely on math while ignoring whether you’ll actually care about the outcome in a decade.
Before your next major financial decision, ask yourself: “In 10 years, will I regret this choice? Or will I regret NOT making it?”
That question cuts through the noise and helps you make decisions you’ll be happy with a decade from now.
Because the goal isn’t to die with the most money. It’s to live a life you’ll remember.
See you next week.
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