Every day, we make hundreds of small choices—what to eat for breakfast, which route to take on a walk, whether to call an old friend. But some decisions in retirement feel heavier. Should you downsize your home? Is it the right time to dip into your savings for a dream vacation? What’s the best way to maintain your health and independence?
It’s easy to get stuck in indecision, especially when the stakes are high. The good news? Decision-making is a skill you can strengthen, just like a muscle. And today, we’re going to build on what we’ve already discussed by adding a powerful tool: The “Regret Test.”
The Regret Test: A Simple Way to Clarify Your Choices
One of the biggest obstacles to good decision-making is fear—fear of making the wrong choice, fear of missing out, fear of regret. But instead of letting that fear paralyze you, we can use it as a guide.
The next time you’re facing a tough decision, ask yourself:
If I fast-forward five years, which choice would I regret more—doing this or not doing this?
This question forces you to think beyond the immediate emotions and consider the long-term impact. Often, we avoid decisions because of short-term discomfort, but our future selves might wish we had taken action.
A Real-World Example: Travel Now or Later?
Let’s say you’re debating whether to take that bucket-list trip you’ve always dreamed about. The practical side of you is worried about spending the money. What if you need it later? But on the other hand, you’re healthy now, and the opportunity is in front of you.
Applying the Regret Test: Imagine yourself five years from now. Would you regret having spent the money, or would you regret missing out on an experience that might not be as easy in the future?
Sometimes, the real challenge isn’t memory loss—it’s the pressure we put on ourselves to make every decision perfectly. Instead of seeing decision-making as a test of your memory or intelligence, try viewing it as a process of discovery.
A great way to do this is by changing the lens through which you view the decision. For instance:
Imagine advising a friend – If someone you care about were facing the same choice, what would you say to them? Often, we give others clearer, more compassionate advice than we give ourselves.
Ask yourself, “Will this matter a year from now?” – This simple question can help you distinguish between major, long-term decisions and smaller choices that don’t require as much energy.
Reframe uncertainty as an opportunity – Instead of feeling stuck when you don’t have all the answers, try looking at it as a chance to explore options. Decisions are rarely final—most can be adjusted over time.
For example, let’s say you’re trying to decide whether to downsize your home. Instead of feeling overwhelmed by all the variables, you might reframe it as an experiment in simpler living. You could start by renting a smaller place for a few months to see how it feels before making a final commitment.
A shift in perspective makes decision-making feel less like a high-stakes test and more like an opportunity to shape your future in a way that works for you.
4. Break down complex decisions
Big decisions can feel overwhelming, especially when they involve a lot of moving pieces—whether it’s deciding on a new place to live, choosing between different retirement plans, or figuring out how to structure your healthcare options. When faced with such decisions, try breaking them down into smaller, more manageable steps.
Instead of tackling everything at once, focus on one element at a time. For instance, when deciding on retirement housing, don’t try to consider all factors at once—start by thinking about whether you want to live independently or in a community setting. Then, narrow it down further: do you prefer a city or rural setting? Do you need specific healthcare facilities nearby?
This shift in perspective often brings surprising clarity.
Strengthening Your Confidence in Decisions
The more you practice this type of thinking, the more confident you’ll become in your choices. And if a decision still feels unclear, try these extra steps:
1. Write it Down – Putting your thoughts on paper often reveals insights you didn’t realize you had.
2. Talk it Through – A trusted friend or family member can offer a different perspective.
3. Set a Deadline – Don’t let decisions linger endlessly. Give yourself a reasonable time to decide, and then commit.
Your Challenge This Thursday
Think about a decision you’ve been putting off—big or small. Apply the Regret Test and see if it helps you move forward with more confidence.
Remember, there’s no such thing as a perfect decision, only the best decision you can make with the information you have. Trust yourself, take action, and keep strengthening that decision-making muscles