Reinvention at 40 vs 82: What We Learned From Each Other
Blue and I compared notes on fear, timing, and what nobody tells you about change
I’ve been writing about reinvention for a while now.
Mostly from my perspective: mid-40s, multiple career shifts, patterns I've learned to recognize.
Then I met Blue—82, seven major reinventions, who launched her Substack a year ago: Reinvent Yourself
We realized something: our philosophies overlapped more than our ages suggested.
The questions we were asking? Nearly identical.
The answers? Sometimes the same, sometimes beautifully different.
So we decided to compare notes across four decades.
Six questions. Two perspectives.
What changes between 40 and 82?
What stays true?
Here’s what we found.
1) How do you distinguish between fear that protects you and fear that limits you?
Blue:
For centuries, fear has been associated with the fight-or-flight response, which was important for survival back then. But the fears that limit us today are different.
They’re about the unknown. Change. Possible failure. Studies show that 90% of what we worry about never happens. When I’m taking a risk, I ask myself two questions: What’s the worst that can happen? What’s the best? Then I weigh both honestly.
That’s what I did when I agreed to spend four months in Europe with a man I barely knew in a 21-foot RV. The worst was discomfort and embarrassment. The best was a larger life than the one I’d so carefully arranged. I chose the positive. I usually do.
Stephen:
I love Blue’s question: what’s the worst that can happen? I add: what’s the cost of not trying? The difference between protective and limiting fear is concrete vs abstract.
If the worst case is embarrassment or discomfort—that’s limiting fear. If it’s actual harm—that’s protective. My test: can I recover from the worst outcome in a year?
Blue took the RV trip. The worst was discomfort. The best was a larger life. Most of what stops us isn’t danger. It’s discomfort disguised as danger.
2) What would you tell someone who’s been “almost ready” for two years?
Stephen:
I thought for years I wanted to write books. I had everything I needed. I was waiting for the right moment. The right idea. Then I realized: I was rehearsing reasons not to start.
One day, I just started. I wrote. I published. Now I have two books out and a newsletter. Not because I felt ready. Because I moved. I didn’t know how much I loved it until I was doing it. The clarity came after.
If you’ve been “almost ready” for two years, stop asking “Am I ready?”. Ask “Does this matter?”. If it does, take the next step. The rest reveals itself.
Blue:
A lot of people call this procrastination. Since I am the queen of procrastination, I know better. It’s called fear. One of the ways I encourage people to take that first step is just sharing, maybe even shouting your dream out loud.
In my many changes, I’ve found that most of them wouldn’t have happened if I’d kept the dreams to myself. Becoming responsible to others who will more likely want to help you than ridicule you is a great first step. Second one? Become accountable to your own dreams. Baby steps.
3) How do you know when it’s actually time to leave, and not just a bad week?
Blue:
I have this philosophy: if something isn’t working or doesn’t feel right, I try to fix it. If, after trying three times, it’s still wrong, I move on. I learned that when I was 14 and having difficulty with my hair. After three tries, I screamed and threw my hairbrush into the bathtub. It broke. My mother was not happy.
This philosophy has served me well, both in my career and in relationships. A big part of knowing whether or not something is working is paying attention to my body. If my mind isn’t sure, my stomach or the muscles in my shoulders and neck usually provide the answer.
Stephen:
Blue’s three-try rule is smart. It separates pattern from noise. I use the Sunday test: if Sunday night dread lasts three months, it’s not a bad week. Your body knows first. For Blue, it’s shoulders. For me, it’s sleep—waking at 3 AM cycling through scenarios.
Bad weeks are acute. Wrong situations are chronic. The signal isn’t “this is hard.” It’s “this doesn’t get better even when things go well.” You know it’s time when fixing it feels like negotiating with yourself to stay.
4) What do you do when you know something has to change, but you don’t know what you want instead?
Stephen:
One summer, I was planning the usual: beach all day, parties with friends. Then I stopped. Am I really going to be happy doing the same thing again? I didn’t know what I wanted instead. I just knew that wasn’t it.
A friend called: “Want to come work at my family’s bar?” I said yes. Screwed the summer plan. Everything changed. I couldn’t have asked for better. Here’s the thing: I didn’t figure out what I wanted by thinking harder. I figured it out by saying yes to something different.
You don’t need the perfect answer. You need direction. Away from what’s not working. Toward anything that feels less wrong. Small experiments. Different conversations. One uncomfortable yes. The path reveals itself when you move. Not before.
Blue:
Stephen’s yes is one of the most important three answers I’ve learned: “Yes.” “No.” and “I don’t know.” Another one I often use when offered an opportunity, or even a slightly different challenge, is “Why the hell not?”.
In my 82 years, I’ve learned repeatedly that what I want may not be exactly what’s best for me. So, I’ve learned to trust coincidences, synchronicities and serendipitous moments. They’re nudges, or as Einstein said, “Coincidences are God’s way of staying anonymous.”
5) How do you handle people who think you’re making a mistake, or that you’re too old/late/settled to change?
Blue:
I just let them think their thoughts, feel their worries, and move forward with my life as it unfolds. Yes, I respect their opinions and try to assure them that I’m comfortable, if not yet confident in my decision. I’ve been much more of a risk taker than the “average Joan.” I don’t expect most people to understand my choices.
When I announced my retirement to Mexico at 51, my son asked me, “What if you don’t like it?” I said, “It’s not the last decision I get to make.” I’ve learned over and over in my 82 years that I cannot change other people’s beliefs, actions, or attitudes. That’s why I resonate so much with Mel Robbins’ book, Let Them.
Stephen:
“It’s not the last decision I get to make.” Perfect. Here’s what I’d add: most people aren’t worried about you. They’re worried about what your choice says about theirs. When you reinvent, you ask: what if I don’t have to stay here? That makes people uncomfortable.
Listen for the difference: “Are you sure?” is concern. “You’re making a mistake” is projection. The people who care will disagree and still support you. Blue’s right: you can’t change their beliefs. Only stay honest with yourself.
6) What’s one truth about reinvention that nobody tells you until you’ve been through it?
Stephen:
It doesn’t end. You think: I’ll reinvent myself, and then I’ll arrive. The new version. The final form. But reinvention isn’t a destination. It’s a loop. I’ve reinvented myself multiple times. Each time, I thought: this is it. This is who I really am. And each time, a few years later, something shifts again.
Here’s the truth: you don’t reinvent once and stay there. You reinvent, stabilize, then life asks you to do it again. The discomfort doesn’t go away. You just get better at recognizing it as a signal, not a problem.
The people who handle reinvention well aren’t the ones who do it perfectly once. They’re the ones who learn to do it repeatedly without losing themselves. Reinvention isn’t about becoming someone new. It’s about staying honest with who you’re becoming.
Blue:
I totally agree with Stephen. How boring life would be to me if hadn’t reinvented myself many times. I call it becoming. None of us are the same as we were a decade ago. And possibly even a year ago. We change, people in our lives change. The only two inevitable things in life are not death and taxes. They are death and change.
We may as well get used to it and learn, like I have, that anticipating change with a combination of fear and excitement makes life ever so much more interesting. Someone once accused me of being a change agent. She meant that as a rebuke. I wear it as a badge. At least as it pertains to my life. We can’t change anybody else.
Between 40 and 80
Reinvention doesn’t get easier with age. But your relationship with it does.
You stop expecting it to be clean. You stop waiting for permission. You stop needing everyone to understand.
At 40, you’re learning the rules. At 82, you’re making them up as you go along.
Change requires wanting something else more or less than what you have. Then add a bit of bravery, willingness to take that first step, and you can look back and understand what courage was.
If you’re navigating your own reinvention, at any age, I hope something here resonated.
Thank you to Blue for this conversation!
And if you want more of her wisdom, check out Reinvent Yourself
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