Part 3 of 3 in the “Getting Unstuck After 50” series
So far in this series, we’ve used the “What If” Method to open up new possibilities, and we’ve talked about getting the real facts before making any big financial decision.
Now comes the hardest part. Actually deciding.
Too Many Options Can Freeze You Too
Here’s something funny about decision-making. Not having enough options paralyzes you, but having too many can freeze you just as badly. If you played the “what if” game from Part 1, you might now be sitting on a long list of possibilities and have no idea which one to pick.
So let’s narrow it down.
Step 1: Sort Your List
Go through every “what if” you wrote down and:
- Cross out the ones you already know you don’t want
- Highlight the ones you feel most drawn to
- Put a question mark next to the ones you’re genuinely unsure about
Step 2: Reconnect With Your Goals
Before narrowing any further, pause and ask:
- What are my goals in life right now?
- What are my priorities? What actually matters most to me?
- Did any of my priorities shift while I was going through the “what if” exercises?
It’s easy to lose sight of what we actually want. Getting clear on that first makes narrowing down the rest of the list much easier.
Step 3: Interrogate Each Remaining Option
For each option still on your list, ask:
- Why am I still hesitating? What exactly am I uncertain about?
- What’s the real concern here?
- Do I actually have enough information, or am I guessing?
- What would happen if I picked this option? How would my life change?
- What happens if I don’t pick it? What does that version of my life look like?
- What would I need to do to make this happen?
Tools for the Harder Decisions
For anything that would meaningfully change your life like leaving a job, starting a business, retiring early, require some deeper thinking and soul searching.
It often takes a combination of:
- Research: look into every option and every pitfall on the subject
- Journaling: do a brain dump and write down all the thoughts you have swirling in your head, write down what scares you, what you’d gain, and what you could actually do about each fear
- Quiet reflection: give yourself focused, distraction-free time to think, regularly, not just once
- Outside advice: talk to a specialist, or someone who’s actually done the thing you’re considering
I do a lot of my thinking on morning walks. There’s something about moving outside before my workday that clears the mental clutter and lets me see a problem more clearly. Also sitting still in silence in the early morning, before the neighbors start making noise, breathing deeply helps me clear my mind. Find what works for you.
Is Fear the Real Problem Or Is It Something Else?
Most of the fear we feel about decisions isn’t fear of physical danger. It’s fear of the unknown, dressed up as something bigger. The more closely you look at what’s actually scaring you, the more often you’ll find it’s simply unfamiliar, not actually dangerous.
And often, it’s really just fear of making the wrong choice.
Once you have your facts (see Part 2), ask:
- What would happen if I made this choice?
- What’s the worst thing that could realistically happen?
- How could I make sure that worst-case doesn’t happen?
- Is there a different way I could approach this?
Set a Deadline—Or You'll Never Decide
It’s incredibly easy to go back and forth between options forever and never land anywhere. That’s exactly why a deadline matters.
If you decide to “take another year to think about it,” that’s not a neutral choice. It’s a full year you could have spent learning the skill, building the business, or making progress, gone instead. Time isn’t unlimited, and research consistently shows that putting a real constraint on a decision leads to better decision-making, not worse.
Ask yourself: can I make this decision in two weeks? Set the date. Put it on the calendar.
You're Allowed to Change Your Mind
If you make the decision and it turns out not to be right for you, you’re allowed to walk it back. But if you never make the decision in the first place, you’ll never actually find out if it was the right choice or not, and it will just sit in the back of your mind and fester unresolved, indefinitely.
The more you put yourself out there and actually try things, the closer you get to understanding what you genuinely like, what you don’t, and what you’re good at.
Quick Recap of the Whole Series
- Play the “what if” game to uncover options you’d otherwise never consider (Part 1)
- Expose yourself to new information — different thinking, new strategies, people who’ve done it differently (Part 2)
- Narrow your options by getting the facts and asking the right questions (this post)
- Set a deadline
- Make the decision, and start taking action right away
What decision have you been putting off the longest and why?