Trusting Your Choices: How to Make Confident Decisions

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

Simple Ways to Support Memory While Making Decisions

If you’ve ever walked into a room and forgotten why you went in, struggled to recall a name, or had a word right on the tip of your tongue, you’re not alone. Occasional memory lapses are a normal part of aging, and they don’t mean you’ve lost your ability to think clearly or make good decisions.

But when important choices arise—about health, finances, or even how to spend your time—it’s easy to feel unsure. What if I forget something important? What if I overlook a better option? These worries can lead to hesitation, second-guessing, or even avoiding decisions altogether.

The good news? You don’t need a perfect memory to make great choices. The key is to work with your brain rather than against it, using strategies that support recall, simplify decisions, and boost confidence.

Our brains don’t store information like a filing cabinet. Instead, they work more like a busy library, constantly organizing, retrieving, and sometimes misplacing bits of information. When we try to make a decision, we rely on different types of memory:

• Short-term memory holds details we need in the moment (like why we walked into that room).
• Long-term memory stores past experiences that shape our choices (like lessons from previous financial decisions).
• Working memory helps us juggle multiple pieces of information while deciding (like weighing pros and cons).

As we age, retrieving information can take longer, but that doesn’t mean we’re losing intelligence or decision-making ability. It just means we need to set up our thinking process in a way that makes it easier to access what we need.

Offload the mental load

You don’t have to keep everything in your head. One of the most powerful ways to support your memory during decision-making is to externalize your thoughts. Write things down, use a planner, or set reminders on your phone. The less effort you have to put into remembering every little detail, the clearer your thinking becomes.

For example, when making a decision about something as important as health care or retirement investments, it can be helpful to create a list of factors that matter to you. Writing down your priorities, along with pros and cons of different options, reduces the cognitive load on your memory and allows you to focus on making a choice rather than trying to recall all the information.

It might feel simple, but the act of jotting things down clears your mental space and gives you more freedom to think clearly and creatively.

2. Create routines and systems

Another way to make decision-making easier is to create routines. When certain tasks or decisions become part of a regular routine, your brain doesn't have to work as hard to process them. This is especially helpful when dealing with smaller, day-to-day decisions.

For example, if you have a weekly grocery shopping list or a set meal plan, that takes the burden off deciding what to eat each day. The same goes for organizing your financials: if you have a regular time to review your accounts, pay bills, or make investment decisions, the mental strain lessens over time.

Creating a system or schedule for routine decisions helps your brain conserve energy for the big choices that really require your attention and mental resources.

3. 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 allows you to focus on one decision at a time without overwhelming your memory, and it helps you keep track of key points as you go.

4. Use memory aids and triggers

Another strategy is using tools that can help trigger your memory when needed. These could be visual reminders, like sticky notes, or more advanced tools like apps that help you track important dates or to-do lists. For instance, if you’re considering making a large purchase, like a new car or home renovation, it’s helpful to write down your budget limits and review your priorities before making the decision.

Also, try keeping a memory journal. This doesn’t have to be a full diary—just a simple notebook where you jot down important thoughts, questions, or plans can help keep you organized. Looking back at these notes can jog your memory and offer fresh perspectives.

Another helpful trigger is associating certain tasks with a specific time of day. For instance, if you regularly review your finances in the morning, the very act of getting your coffee or tea might trigger you to sit down and look over your budget.

Trusting Yourself to Make Great Decisions

Supporting your memory doesn’t mean relying solely on external aids—it’s about setting yourself up for success. By breaking things down, using systems, and trusting that your brain is still capable of making good choices, you can navigate retirement with confidence.

In the next post, we’ll explore mental models that can make your decision-making even sharper, like considering the long-term impact of your choices and weighing consequences. It’s all about practicing thoughtful, deliberate decision-making so you feel empowered as you embrace this next chapter of life.

For now, remember: your memory might not always be perfect, but your ability to make good decisions is still strong. With a little support and some helpful strategies, you’ve got everything you need to move forward with confidence.

The Art of Thinking Clearly

Retirement brings freedom—the chance to set your own schedule, travel, or dive into long-awaited passions. But it also brings choices, and sometimes, those choices can feel overwhelming. Should you downsize your home? Invest in a new hobby? Plan for future healthcare needs? With so many options, decision fatigue can creep in, making it harder to think clearly.

But here’s the good news: clear thinking isn’t about having a perfect memory or making split-second choices. It’s about understanding how we think, recognizing common mental traps, and making decisions with confidence.

Why We Don’t Always Think Clearly

Have you ever made a choice, only to wonder later, What was I thinking? We all fall into thinking patterns that lead us astray. For example:

• The “gut feeling” trap – While intuition can be helpful, it’s not always the best guide, especially when making complex decisions like financial planning or healthcare choices.
• The “too much information” problem – The more options we have, the harder it is to choose. This is why simplifying decisions—focusing on what truly matters—leads to better outcomes.
• The “what if I’m wrong?” fear – Doubt can paralyze us, but in reality, very few decisions are permanent. Most choices can be adjusted over time.

How to Start Thinking More Clearly

One of the best ways to sharpen your decision-making skills is to step back and ask, What’s really important here? Instead of getting lost in details, try these simple shifts in thinking:

1. Look at the big picture – Imagine you’re advising a close friend. What would you tell them? This small mental shift helps you see things more objectively.
2. Take a break – Our brains process information even when we’re not actively thinking about it. Stepping away for a walk or a good night’s sleep can bring surprising clarity.
3. Trust your ability to decide – You’ve been making decisions all your life. Just because retirement brings new choices doesn’t mean you’ve lost the skill—it just means you’re learning to apply it in new ways.

The Power of Taking a Break

It might seem counterintuitive, but one of the best ways to make a clear-headed decision is to stop thinking about it for a while. When we take a break—whether that means stepping away from the problem for an hour, a day, or even just a few deep breaths—our brains continue working in the background.

Think about a time when you struggled to remember someone’s name. The more you forced yourself to think, the further away the answer seemed. But then, a few hours later, it popped into your head out of nowhere. That’s your brain at work, solving problems when you’re not actively focused on them.

The same process happens with decision-making. When we stop overanalyzing, we give our minds the space to connect ideas, filter out distractions, and prioritize what really matters.

A good way to use this to your advantage is to sleep on it. If a decision feels overwhelming, give yourself permission to step away. Go for a walk. Read a book. Spend time with a friend. When you return to the decision, you’ll likely find that what once seemed murky now feels much clearer.

A Simple Exercise to Try

Think of a small decision you’ve been putting off—maybe choosing a new activity, deciding whether to travel, or sorting through paperwork. Instead of overthinking, ask yourself:

• What’s the simplest way forward?

• Will this matter a year from now?

• If I make a mistake, can I adjust later?

Then, walk away from it for a bit. Do something else. When you return, notice if the decision feels easier to make.

The Next Step

In the next post, we’ll explore how memory challenges can affect decision-making—and more importantly, how to work around them. The goal isn’t to fight against how your brain works but to support it with practical strategies. Decision-making is a skill, and like any skill, it improves with practice.

Decision making for seniors

Over the past few weeks, I have had to make some interesting decisions and over time my confidence and clarity around decision-making became a bit clearer, but as I talked to other seniors I found that some of them were having problems with their own confidence and clarity around the idea that they were making the best decision for themselves. So, over the next few posts, I will explore the idea of decision-making for seniors. Below is the outline of what I will cover.

1. The Art of Thinking Clearly

2. Navigating Memory Challenges and Better Decision-Making in Retirement

3. Strengthening Your Decision-Making Skills

4. Thinking Ahead—And Then Thinking Again

5. Bringing It All Together

I hope you will enjoy the series, if so, let me know.