What to Expect Past 60

Thanks to AI The Boomers Are Taking a Victory Lap

Boomers.

That’s everyone alive between 60 and 78.

How come I’m seeing so many articles this month about people going past 60? Is it me, or is it the algorithm? Is it the last of the boomers, bringing up the rear to cross the line over 60 and writing a lot of stories and books about it?

Once the boomer invasion starts, you can’t ignore it. Nobody was ready for the boomers. Not our schools, colleges, employment areas, airports, highways, housing, shopping malls, nor the Social Security system—all of these major institutions acted surprised when boomers showed up, and massive expansion projects followed.

It’s no surprise, then, that Substack publications are exploding with boomers who have plenty to say about their lived experiences and information that you’ll never find on the internet. It’s still in their heads, and they are writing like crazy to tell stories and give everyone a look at what you might find when you pass 60.

After all, who doesn’t want a crystal ball to tell them what to expect?We are in the middle of troubling times, and the boomers seem to be soldiering on.

They are still living large and writing about it. They still have most of the wealth in the US, for now. The wealth transfer to Gen X and Millennials has only started, so there’s plenty of time left, the boomers say, to pull out all the stops and do something big that makes a difference or leaves a legacy. If today’s politicians mess with the Social Security system, which has worked without missing a payment for 90 years, the next generation might kiss that expected inheritance goodbye because your elders need all of their money to last longer.

What Will You Find In the Over 60 Stories?

Who are these boomers, these writers, these masters of the storytelling craft?

We’ve always been an overwhelming bunch of resilient leaders who just assumed the world was ours because we had everyone outnumbered. Say what you will about boomers, here’s where we hold a commanding position at the top of the hill:

• Our work ethic and career focus is stronger than any past or future generations. Duty, achievement, and the value of our work became our prosperity drivers. And work tools? We created most of them.
• Family structures and community values are stronger than any generation since us. It shows in how we raised children, participated in local events and national associations, and took care of aging parents. We are the original community builders.
• We arrived before television and graduated from college before the internet. Our boldness made us pioneers in technology, and at the same time we can be the most resistant to technological change. It’s not that we don’t understand AI; we believe that books, nature, critical thinking, and in-person conversations over coffee are more important.

Credit Deleece Cook on Unsplash

Who Is Writing Stories That Speak to Our Curiosity about 60?

Robert Reich former U.S. Secretary of Labor, author of numerous books, and creator of Robert Reich Substack, wrote this month:

Four years ago today, I began this daily (sometimes more than once a day) letter to you.

Before I began, I told some friends I was planning to write every day. They thought I was nuts.

“How are you going to find the time?” they asked.

I’ve discovered it’s easy to find the time for something I believe is worthwhile.

“How are you going to find the energy?” they asked. “You’re in your mid-70s.”

I’m now pushing eighty, and have more energy for this than I did at the start.

Today isn’t the fourth birthday of this letter. It’s the fourth birthday of our relationship, for which I’m eternally grateful.

Mariah Faith Continelli, creator of The New Unhinged Substack, writes that she is not here to influence, here to interrupt. In her article this month, Uber ‘Til the Hip Gives Out she tells the story about the first wave of gig workers, freelancers, and side-hustlers who are about to retire.

Retire from what, exactly? There are millions of people hitting 60 with no pensions, no savings, no healthcare, and the government’s advice is to try dying quietly.

Nearly half of Americans over 55 have no retirement savings. Just arthritis. Your Social Security check covers exactly two things: a tank of gas or half your blood pressure meds. Pick one. Elders are choosing between Wi-Fi or medication, because without Wi-Fi they can’t even refill the damn medication.

She asks, Why does Congress raise the retirement age instead of asking why people are already working themselves to death?

Ron van Helvoirt created Callosom-Bridging Minds Substack and writes this month about Not of This World. It’s about turning 61, letting go, and finding what remains

Approaching 61, I find myself facing a question that cuts deeper than finances or career: Is it too late? What began as a personal doubt has opened into a broader reflection on where we stand as a society.

The past few days have been among the hardest I can recall. I’ve lived through earlier periods without work or financial stability, but this moment feels different. It isn’t just the absence of income or projects; it is the weight of age, the sense of time pressing in, and the question of whether meaning still has room to grow.

This loss of capacity explains much of what we see today: institutions locked in paralysis, public debate stripped of nuance, communities unable to respond even to urgent crises. The individual struggle — to remain relevant, to feel that one still matters — reflects a collective struggle as well. It is not only a personal crisis of meaning; it is the symptom of a civilizational drift.

And at the center of it, a single truth: being myself.

Bill McKibben, a former staff writer for the New Yorker, author of 35 books, and creator of The Crucial Years Substack, is the founder of The Third Act, which organizes people over the age of 60 to work on climate, democracy, and racial justice. In 2014, Bill McKibben was awarded the Right Livelihood Prize, sometimes called the ‘alternative Nobel,’ in the Swedish Parliament.

How many organizations have 60 or older as a requirement to get in and change the world? What do you think you can learn from becoming a valued member of The Third Act? You can look at the website but you have to blow out 60 candles to put yourself in the middle of world-changing action and conversations you’ll never have with an AI robot.

Amy Cuevas Schroeder, not a boomer, created The Midst Substack for messy middle-of-life pivots, career and relationship upgrades, perimenopause, and more.

Her article this month, MIT says this is the best age to start a business cites research by MIT and Northwestern that shows successful entrepreneurs are typically middle-aged, with the average founder of a high-growth startup being 45 years old. And, people over 55 are more likely to launch high-growth startups.

She covers the base for the 60-year-old crowd, as well.

A 60-year-old startup founder is 3 times as likely to found a successful startup as a 30-year-old startup founder — and is 1.7 times as likely to found a startup that winds up in the top 1% of all companies.

Because most of the members in our GPC community are at least 45 or dancing around that number, the data for the ramp-up to 60 is encouraging

Amy writes, A 50-year-old startup founder is 2.8 times more likely to found a successful startup as a 25-year-old founder. If you’re in your 40s or 50s and want to start a business, you’re not behind schedule. In fact, you’re more likely to succeed.

Credit shraga kopstein on Unsplash

Joe Hudson, executive coach and creator of the Art of Accomplishment Podcast, writes about the Age of Wisdom Work.

What is the greatest asset of the boomers? All of that money? Close but no cigar! It’s wisdom. It’s their ultimate ace in the hole when you toss AI into the mix.

Hudson writes, AI devours information-based roles. When knowledge is no longer scarce, what remains valuable? Wisdom. You can get answers from AI, but how you use those answers takes wisdom.

Wisdom is how to live. It is the residue of mistakes, metabolized by time and reflection. It can’t be rushed, and it can’t be copied and pasted. It is an embodied—as in felt in the body—experience, guidance from the inside.

No matter how intelligent AI becomes, it can’t live your life for you. It can’t feel your body’s signal in a high-stakes negotiation, sense the hidden fear in a boardroom, or hear the unspoken “no” behind a client’s polite words.

That’s why tomorrow’s economy will prize wisdom workers.

The three core skills of these wisdom workers are emotional clarity, discernment, and connection.

Credit chris robert on Unsplash

Still Here. Leaders of The Pack

No wonder the boomers are booming again. It’s almost like they planned it and put AI in place just in time for their greatest and final victory lap around the track of an awesome life.