I have a confession to make.
My wife Bonnie and I are addicts. Not the kind that requires an intervention, exactly, but close. We are addicted to home improvement. We are always planning the next upgrade, the next project, the next thing to tear apart and make better. It gives us genuine pleasure and a profound sense of accomplishment. Bonnie leads most of these endeavours. She is remarkably capable with power tools and can pull off a tool belt like she is strutting down a Home Depot runway (aisle). Our shared obsession has even spawned a series of Facebook posts called the 2 Capable Women, where we document everything from felling trees to the deeply humbling art of Ikea assembly.
So there we were, driving in traffic, and Bonnie was telling me about her next project: removing the circa-1960 wood panelling and replacing it with modern shiplap. Mid-conversation, she went quiet for a moment and said, almost to herself, “I guess I need to allow myself the grace to fail.”
I nearly drove off the road.
You must understand something about Bonnie. She is a self-declared perfectionist. Not casually. She is committed to being a perfectionist at being a perfectionist. So, hearing those words come out of her mouth, unprompted, while discussing a renovation project, was like hearing your accountant quote Oprah. It stopped me completely.
The truth has a certain ring to it. I heard that bell loud and clear.
Because sometimes wisdom does not arrive in a lecture hall or a leadership book or a TED talk. Sometimes it arrives in a car, in traffic, from the person sitting next to you holding a coffee and thinking about shiplap.
That phrase has not left me since.
Many of us do this. We replay mistakes endlessly, convinced that self-criticism is somehow productive. We lie awake revisiting conversations and missteps, assuming that if we beat ourselves up long enough, we will emerge wiser. All we accomplish is a thorough self-beating followed by self-flagellation. Lots of noise. Zero progress. Zero calories burned.
This is not just a problem for people climbing mountains or starting businesses. It plays out in
perfectly ordinary moments. You send an email and immediately wish you had worded it differently. You make a comment at dinner that lands wrong and spend three days replaying it. You make a small error at work and carry it around like luggage for a week. The inner courtroom convenes regardless. Most of us are not failing spectacularly. We are just living, occasionally getting things slightly wrong, and treating that as evidence of something deeply and permanently wrong with us.
It is not. It is just Tuesday.
I have been thinking about this a lot lately because I am in the middle of my MBA at the Sprott School of Business. I wrote about My MBA at age 69 in Part I and Part II. Back in graduate school after four decades in the workforce, opportunities to feel uncomfortable, uncertain, and occasionally like you have wandered into the wrong building are plentiful.
A recent assignment on crafting Team Charters and enhancing my leadership skills inspired me to write a personal manifesto for my graduate studies and to take a closer look at myself. You can read mine here. While working through it, I made a surprising discovery. Most of the commitments I was making to myself had nothing to do with school. They were about life.
Read the instructions carefully. Ask for help sooner. Pay attention to what your emotions are trying to tell you. Trust your experience. Hold yourself to your own standards. And this one, which stopped me cold, and sounded very familiar: Allow yourself the grace to fail.
There was that bell again.
Those six words turned out to be the most important thing I wrote. Not because failure is something to celebrate, but because the willingness to risk it is the price of admission for virtually everything worth doing.
Failure is not a topic most of us rush toward. It is about as pleasant as stubbing your toe in the dark. Yet every meaningful thing I have ever done required me to risk it. Starting a new career. Leading a sales team. Launching a business. Climbing a mountain. Writing a book. Going back to school at 69. None of it came with guarantees. All of it came with uncertainty, mistakes, and moments where I genuinely wondered whether I had lost my mind. The jury is still out on some of those.
The irony is that failure and growth are inseparable. Dweck (2006) found that people who view setbacks as learning opportunities rather than evidence of inadequacy are more likely to persevere and ultimately succeed. Duckworth (2016) agreed, and in Grit, one of my favourite books, long-term success depends less on talent and more on the willingness to keep going after things fall apart. Neff (2023) added that people who respond to failure with self-compassion rather than harsh self-judgment show greater improvement and are more likely to try again. The friction produced by failure is often exactly what generates learning, but only if we give ourselves enough grace to stay in the game.
I see this everywhere. Professionals are staying in jobs they no longer enjoy because starting over feels too risky. Retirees hesitate to try something new because they might not be good at it right away. Students who will not ask a question because they do not want to appear uninformed. And if I am being honest, I see it in myself. Every time I hesitate to contribute to class because everyone else seems younger and sharper. Every time I catch myself wondering whether I belong in the room.
One exercise has helped me enormously. When I catch myself spiralling into negative self-talk, I imagine my five-year-old self standing beside me, listening. Would that little girl feel encouraged? Not a chance. So why do we think inner dialogue helps us?
A recent example: I made a point in a meeting that got a polite nod and complete silence. You know the silence. The one that could mean anything from “interesting” to “what on earth did she just say?” I replayed that moment for two days. Eventually, I asked a colleague how the meeting had gone, and she said she barely remembered it. The forensic investigation was conducted entirely in my own head.
I am not suggesting we lower our standards. We should hold ourselves accountable, learn from our mistakes, and strive to do better. But there is a meaningful difference between accountability and cruelty. Between reflection and rumination. Between learning from a mistake, and building a summer cottage on top of it, and checking in every long weekend.
I worry about what this means for the generation behind us.
Research by Professor Gabriel Rubin at Montclair State University found that despite living in one of the safest periods in history, Gen Z perceives risk virtually everywhere (Rubin, 2023). They have grown up knowing that at any moment, someone has a phone. One stumble, one terrible dance move, and the clip is posted before you catch your breath. Permanent, searchable, shareable public failure is something entirely new, and the consequences are showing up in surprising places.
Monocle magazine noted young people standing completely still on nightclub dance floors, phones in hand, unable to lose themselves to the music. The club has become a stage, and the crowd has become the content. Instead of dancing, people film. Instead of connection, there is performance.
This is not a small thing. Dancing is how humans have always signalled availability, built trust, and found each other. It requires a willingness to look slightly absurd. If we have raised a generation so terrified of being captured mid-stumble that they will not move to the music, we have handed surveillance culture a victory it does not deserve. Calculated risks lead to new opportunities, foster innovation, and teach lessons that comfort never could (Rubin, 2023). Risk aversion makes short-term sense. As a way of life, it quietly closes doors that were never meant to stay shut.
Give yourself and the young people around you, explicit permission to be unpolished in public. To dance badly. To say the wrong thing and survive it. The phone will always be there. So, fortunately, will the music.
Here is what I keep learning inside this MBA: wisdom arrives disguised as failure. The assignments that challenge me teach me more than the ones that come easily. The questions I most resist asking are usually the most important. I did not expect graduate school to teach me this. Then again, I did not expect to be here at seventy.
I no longer think in terms of Wins and Losses. Those categories are too simple. I think in terms of Wisdom and Learning. Success builds confidence. Setbacks build insight. Both move us forward.
Read that again.
So the next time you find yourself at two in the morning replaying something you said three days ago, ask whether your five-year-old self would find your internal monologue useful. If the answer is no, offer yourself a little grace.
Which brings me back to Bonnie.
Last weekend, she pulled off that 1960s panelling. Every last piece. It was messy and uncertain, and at several points she was unsure what she would find underneath. There were surprises. There were moments of doubt. She kept going anyway. By the end of the weekend, the shiplap was going up, clean and bright and exactly right.
She did not do it perfectly. She did it anyway. And it is beautiful.
That is the whole lesson, right there, delivered by a woman with a pry bar and a tool belt, on a weekend in June.
Failure is not the enemy. Most of the time it is just fear wearing a funny hat. And if you are lucky, it will teach you something genuinely worth knowing. Sometimes it comes from a research paper. Sometimes it comes from your wife, in a car thinking out loud about shiplap.
Either way, listen for the bell.
Writing my manifesto was one of the most clarifying things I did this year. Not because it solved anything, but because it forced me to decide, on paper, who I was going to be when things got hard. I want that for you, too.
So I created the ReWirement Manifesto: a simple template for anyone navigating a new chapter, a big transition, or simply a Tuesday that did not go as planned. It is not a bucket list. It is not a vision board. It is a set of honest commitments you make to yourself, in your own words, that you can return to when your inner courtroom calls you to order.
Download your free ReWirement Manifesto template here.
Fill it in. Keep it somewhere you can find it. And the next time you are staring at a wall of 1960s panelling, wondering if you are in over your head, remember: the grace to fail is not a consolation prize. It is the whole point.
Don’t Retire…Re-Wire!
Sue
My Book is Now Available for Pre-Order
I hope you will consider pre-ordering a copy of Your Retirement Reset for you, a friend or loved one. It's available September 8, 2026 published by ECW Press - You can now order at Indigo or Amazon. And if you love supporting Canadian booksellers, please also check with your local independent bookstore. Most can easily order it for you.
