Don’t Let “Someday” Become Your Biggest Regret

There’s a scene in the movie Up that says something beautiful about getting older.

Carl opens the adventure book that belonged to his late wife, Ellie. For so long, he has focused on the trip they never took—the dream they kept putting off until life got in the way. But when he turns the pages, he discovers photographs of their everyday life together. The ordinary moments. The life they actually shared.

To Ellie, those moments belonged in the adventure book, too. And she leaves him a message encouraging him to have another adventure. That scene makes me think about how we look back on our lives. We remember the opportunities we missed and the choices we wish we could change. But do we also remember to count the good? Can we appreciate the life we’ve lived while making different choices about what comes next?

At 62, I’m interested in both.

What Regret Can Teach Us

In her conversation with Daniel Pink, Mel Robbins explored a question that matters at every age: What makes a good life?

Pink’s book, The Power of Regret: How Looking Backward Moves Us Forward, challenges the idea that we should strive to have “no regrets.” His research identifies four broad categories: foundation, boldness, moral, and connection regrets.

The invitation is to examine what we wish had been different, understand what that reveals about our values, and use that understanding to guide our next choices.

That feels especially relevant as we grow older.

We have more history to reflect on. We’ve made choices, experienced things we never chose, and watched plans work out or fall apart. We also have decisions ahead of us that deserve our attention.

We cannot guarantee a future without regret. But we can notice where postponement, fear, or avoidance might be making decisions for us.

Foundation Regrets: “I Wish I Had Prepared”

Pink’s foundation category concerns the groundwork we wish we had laid earlier. When I apply that idea to aging, I think about the things we postpone because they don’t feel urgent yet. We assume our home will always work for us. We avoid discussing care preferences. We put off organizing important documents or understanding what support might cost. We expect someone will help, without asking whether they can. Then something changes, and decisions have to happen quickly.

In my work, I see families trying to figure out what their relative wants while navigating an already stressful situation. Planning cannot prevent every crisis, but it can give everyone a better starting point.

Imagine looking back and thinking:

• I wish I had considered a different home while I had more time and choices.
• I wish I had told my family what mattered to me.
• I wish I had built a support network instead of assuming my children would handle everything.
• I wish I had paid more attention to my strength and mobility before everyday activities became difficult.

These are examples of how foundation regrets might show up in our aging journey, rather than a list from Pink’s research.

For me, preparing means asking: What does the life I want require—and what can I put in place today?

I want to keep going places with Pablo, enjoying live music, and participating in life. That’s part of why I exercise. My arthritic feet may ache, but I want to support my ability to do the things I love.

It also means thinking honestly about our home, our future needs, and the conversations we should have now.

Preparing for aging is an act of care for our future selves—and for the people who may someday support us.

Boldness Regrets: “I Wish I Had Given Myself a Chance”

Boldness regrets involve opportunities we passed up because we hesitated to take a chance.

This one feels personal.

After ten years of being divorced, I met Pablo when I was 52. We met on Match, and our first date was at Union Terminal in Cincinnati. I gave myself the opportunity to find love. I didn’t sit around waiting for it to fall into my lap.

I couldn’t know where it would lead. I could have decided that chapter was closed or allowed previous disappointments to determine what I was willing to try. Instead, I gave it a chance. That decision brought so much love into my life.

Then, at 58, I lost my corporate job. I thought it would be the career I retired from, but it wasn’t.

My husband was retiring the same week I was laid off. He was thrilled about retirement. I wasn’t ready.

I had spent more than 35 years in aging services. I still had ideas, energy, and a passion for helping people age well. My gut told me this was an opportunity to build something of my own. So I went out on my own. Four years later, I don’t regret that decision. I’m more inspired than ever to help people live better, love better, and age better.

As we grow older, boldness regrets might sound like:

I wish I had taken that class. I wish I had explored a different kind of work. I wish I had volunteered, shared my knowledge, or tried the creative project I kept thinking about. Sometimes what we’re postponing could give us a new sense of purpose.

A class might introduce us to people who become friends. Volunteering might give our week direction. Mentoring might help us recognize how much we have to offer. We won’t know until we give something a chance.

What interests you enough to explore—even if you don’t know whether you’ll be good at it?

You don’t need a complete plan. You need a first step.

Connection Regrets: “I Wish I Had Reached Out”

Connection regrets involve relationships we wish we had nurtured.

It’s easy to understand how this happens. We mean to call. We keep saying we should get together. We assume there will be another opportunity. Then years pass.

As we grow older, relationships need deliberate attention. Retirement, moves, caregiving, illness, and loss can change how often we see people. Connections that once happened naturally may now require effort.

Sometimes that effort means reaching out to a friend we miss. Sometimes it means addressing a disagreement we’ve avoided or admitting that a relationship matters more than being right. But relationships are complicated, and I want to make room for that.

My relationship with my mother included love, pain, and dysfunction. That experience shaped how I think about family, responsibility, and boundaries. Mending a relationship can be meaningful when there is safety and a willingness to repair it. Setting a boundary can also protect something important.

We may regret losing touch with someone we love. We may also regret spending years accepting behavior that hurt us or giving so much that we had nothing left for ourselves.

Boundaries are my own addition to this discussion of relationships; they aren’t a separate category in Pink’s model.

The question is: Which relationships need more of my attention—and which need clearer limits?

That might lead to a phone call, an apology, an honest conversation, or a decision about what help we can realistically offer.

We cannot control another person’s response. We can be thoughtful about our own choices.

Moral Regrets: “I Wish I Had Handled That Differently”

Moral regrets concern moments when our actions conflicted with our values.

Perhaps we were unkind. We weren’t honest. We failed to speak up or treated someone in a way we would never want to be treated. Looking back can be uncomfortable. But there is value in being able to say, “I would handle that differently today.”

Sometimes we owe an apology. Sometimes we need to change a pattern or take responsibility without making excuses.

Getting older gives us more experience to draw from. It also gives us an opportunity to decide how we want to show up now.

Is there something I need to acknowledge, repair, or stop repeating?

We can take responsibility without turning every mistake into a judgment about our entire life.

Learning Without Punishing Ourselves

There’s a difference between reflection and endlessly putting yourself on trial.

Your younger self didn’t know everything you know today. You may have been afraid, exhausted, short on resources, or navigating circumstances that limited your options. Some decisions were yours. Some experiences were beyond your control. Both deserve an honest accounting.

We also need to remember Ellie’s adventure book. An unfulfilled dream does not erase the value of the life we lived. We can acknowledge disappointment while recognizing the love, contribution, joy, and ordinary moments that mattered.

The question becomes: What can I learn—and what can I still influence?

Give “Someday” a Date

In my Bold, Not Old™ framework, we move through reflection, intention, action, and accountability.

Try applying those steps to one potential regret:

• Reflection: If I keep postponing this, what might I wish I had done differently?
• Intention: What matters to me here—independence, connection, purpose, honesty, or something else?
• Action: What is one manageable step I can take?
• Accountability: When will I take it, and what will help me follow through?
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If you’ve avoided planning, begin one conversation about your future needs.

If you miss a friend, invite them to lunch.

If a relationship needs a boundary, decide what you can offer and what you need to communicate.

If you’re looking for purpose, explore one opportunity to learn, contribute, or create.

Give the next step a place on your calendar.

At 62, I want to appreciate what has brought me here, learn from the choices I would make differently, and enjoy the ordinary moments with Pablo. I also want to stay open to what I haven’t experienced yet.

What have you been leaving to “someday”—and what could you do about it today?

Aging is inevitable. How we age is influenced by the choices we make every day.

I’m still writing my story. I hope you’ll keep writing yours.

Inspired by Disney and Pixar’s Up (2009), Daniel Pink’s book The Power of Regret: How Looking Backward Moves Us Forward, and his conversation on The Mel Robbins Podcast.

🎧 Mel Robbins’s conversation with Daniel Pink:
https://www.melrobbins.com/episode/episode-398/