How to Make Big Life Decisions in the Second Half of Life Without Losing Yourself
I don’t think I ever had the stereotypical midlife crisis. Or, at least, it was delayed. I turned 59 in May and reflecting back on the past couple years makes me realize that midlife crisis idea hit me at the end of my 50s!
The “questioning life” phase people talk about after turning 50 hit me in the past couple years instead. Life events around me reminded me how fragile life is, and that our time is limited. I started having lots of questions.
How happy am I really with my day-to-day? Does my career still excite me? When is the right time to explore branching out on my own full-time as a bridge to full-time retirement? Am I listening and acting on my core values in everything I’m doing? (These values have changed over time for me.) What’s the right next step for me?
Maybe you feel the same. The chaos of the world around you may have you more afraid than usual to take a big step and pivot to something new. What if it doesn’t work out? Can you go back? Do you know what you want to pivot to? Suddenly, staying put can feel safer than stepping forward.
I try to look at these questions as avenues to explore and answer for myself. A life pivot is inevitable no matter your age or the state of the world. Now is my chance to choose, on purpose, how to spend the years ahead. Studies say our sense of meaning peaks around 60 — I’m 59, and that both excites and unnerves me.
In this post, I’m sharing tools that have helped me and others navigate the big, messy questions of what’s next:
Using a values filter to clarify what really matters
Trying a visioning exercise to picture your ideal future
Applying the “Regret Minimization” framework to think long-term
Using mind mapping to expand your options
Using a Values Filter to Clarify What Really Matters
Clarity rarely comes from thinking harder. It comes from paying attention to what matters most now.
Our values may have shifted at this age. In fact, they probably have shifted or changed considerably since our earlier years. Maybe status has given way to peace. Maybe growth looks more like balance. That’s worth noticing.
One tool I use with clients — and myself — is a values filter. Start by naming your top five values. Then ask: Does this choice support those, or pull me further from them?
A values filter won’t hand you an answer, but it will ground your decision in what’s true for you today — not who you were ten years ago.
Visioning Your Future
Sometimes the best way to make a decision isn’t by analyzing the present, but by imagining the future.
One exercise I return to often is this: picture a day in your life five years from now. Not a highlight reel—just a regular Tuesday. Where are you waking up? What fills your calendar? How do you spend your time, and with whom? What does your day look like?
That imagined day can tell you a lot. Get specific in imagining what the day is like. What activities are you engaging in that bring you joy? How are you treating your mind, body and soul? Notice what you imagine. It may not be perfect, but it can shed light on what you want more of in your life and help shape your perspective and decision making today. Pay attention to the things you imagine or daydream about during this exercise and note what excites you.
Take a quiet moment and a willingness to be honest with yourself. I’ve found that when people start describing their future life out loud, clarity starts to rise. It can be messy, or it can flow with ease because you've been daydreaming of it for so long!
If nothing else, visioning pulls you out of the loop of “Should I stay or should I go?” and into a more expansive question: What kind of life do I want to live next?
Minimizing Regret: A Future-Focused Framework
When I’m stuck between two options, I try a simple mental exercise: I picture myself 5 years from now, looking back on this moment. Which choice would I regret not exploring? It's easy to look back from today and point out where you may regret a decision, but doing that from 5 years in the future turns things around.
It’s called the Regret Minimization Framework — and I’ve found it surprisingly clarifying. It helps me cut through fear, noise, and perfectionism by shifting the question from What if it goes wrong? to What will I wish I had done?
Sometimes we get so caught up in overthinking that we forget to ask the one question our future self might care about most: Did I try?
I encourage clients to write a short note from their future self — the one who’s already lived through the decision. What does that version of you say? Does it thank you for going for it and not waiting?
That little shift — from fear of failure to fear of regret — can change everything.
Mapping Possibilities: Getting It All Out of Your Head
Sometimes even when we know what we want to avoid, we still struggle with seeing what’s possible. That’s where a good brainstorm with a mind map can help.
When you feel stuck between a few options—or overwhelmed by too many—sometimes the best thing you can do is get it all out of your head and onto paper.
Mind mapping is one tool I come back to again and again. It’s simple, visual, and surprisingly effective. Start with a central question in the middle of a blank page: What could come next? Then branch out from there. Capture ideas related to work, creative interests, location, lifestyle, values—whatever shows up. Let it be messy. Let it surprise you.
The goal isn’t to “solve” anything yet, but to empty your head and capture the ideas. Let the exercise widen your lens and make space for ideas that might’ve been hiding beneath the surface. I've used mind maps for all sorts of things like decision making and mapping my life according to main focus areas important to me.
You don’t need the answer. You just need a starting point. A mind map helps you find it.
From Reflection to Action: Taking Small Steps Forward
All the reflection is powerful, but it's not the end goal. Insight is only the beginning. The real change comes when you do something with it.
I’ve seen this in others as much as I’ve experienced it myself — someone feels stuck for months, maybe years, turning a decision over in their mind. Then they try one small step and something shifts. There's a click that nudges them toward what’s next. The click for me was talking to a Life Coach about getting certified myself. I’d worked with coaches and self-studied for years, always thinking about getting certified myself, but never doing it until recently.
Eventually, you have to pick a moment and step into it — even if it’s imperfect.
If one of the tools in this post stirred something in you, don’t let it sit. Pick one and do something with it. Jot down your top five values. Sketch out a mind map. Write a note from your future self. Or simply set a tiny, doable goal for this week that moves you an inch closer to what you want.
Want a little help getting started? You can download my free worksheet, or reach out and let me know what step you’re taking. I’d love to hear from you.
You don’t need to know the whole plan. You just need one small move. Let that be enough for today.
