http://www.youtube.com/@ComebackCast

I’m 6’3” so not super tall, but on the taller side of average. Between Christmas and New Year, one of my sons said he was walking out to get the mail and I decided to join him. We have a very long driveway, so getting the mail is a bit of a trek. I slipped on some old gym shoes and my son and I headed out to the mailbox.

We were chatting about something and my right foot hit a patch of black ice that was lightly covered by the snow. That awful feeling of knowing you’re about to fall but instinct tells you to fight it at the same time. I tried to catch myself for what felt like an eternity, before gravity took over and I hit the asphalt hard.

I felt my shoulder dislocate and my arm went numb. Instinct told me to pop my arm back into place, which I did then immediately felt sick to my stomach by the sensation of it. I didn’t hit my head but I knew I was hurt. My poor son looked at me terrified. He helped me back to my feet and escorted me back to our house. By later that evening, I started to feel better. The next few days I couldn’t lift anything and my right hand didn’t fully work. Something didn’t feel right so I headed to my doctor where I got an X-ray. Nothing was broken. An MRI showed much more damage.

The dislocation separated tendons from bone, snapped a tendon and tore some muscles in my arm. The only way to fix it was with surgery to reattach, sew and do whatever they had to do. My decision was to either have the surgery or take the risk of limited mobility in a few years. As a right-handed author, I knew I had to do it.

For the last five weeks, I’ve been in an arm sling to keep my shoulder supported. I’ve learned to use my left hand but I’m not very adept at it. I’m going to physical therapy now and slowly getting back into light use of my right hand.

I’ve not been writing as much and look forward to being back at my keyboard more regularly. My lessons:

1. Don’t wear old shoes with no tread left on them while walking on an ice-covered driveway. Always carry a phone or walk with somebody else if possible.

2. Know my limits and remind myself that even though I feel like I’m 25, my body reminds me I’m not. By a long shot.

3. Sometimes a body just needs to heal. Even strong people need help. I’m fiercely independent (and sometimes a control-freak) but sometimes I need help, too. This last lesson is my most challenging. Letting go and allowing myself to heal is way harder than I expected.

Astronaut Dave Bowman, locked out of his own ship, speaks calmly into the void:

“Open the pod bay doors, HAL.”

HAL 9000, the soft-spoken, red-eyed AI running the Discovery One, responds with the most chilling politeness in cinema history:

“I’m sorry, Dave. I’m afraid I can’t do that.”

Stanley Kubrick made that film in 1968. Fifty-seven years later, three former executives sitting in Tampa, Northeast Ohio, and the Oregon Coast are having a very similar experience with technology.

Except in our case, the AI does whatever we ask. We’re just too intimidated to ask it anything useful.

The Question HAL Never Had to Answer

In our latest episode, “Why AI Makes ‘So What Do You Do?’ Unanswerable: The Cocktail Party Challenge”, Brian read a single quote from macro investor Jordi Visser’s Substack that stopped the conversation cold. (Brian reads a lot of Substacks. It’s become a whole thing.)

The idea: AI is making the most basic social question, “So, what do you do?”, functionally unanswerable.

Think about that for a second.

HAL 9000 knew exactly what he did. He processed information. Ran systems. Maintained the ship. His identity was so locked in that he was willing to kill to preserve his mission. No ambiguity. No career pivot. No LinkedIn headline that says “Executive | Entrepreneur | Thought Leader | Dog Dad.”

We don’t have that luxury anymore.

The roles that once defined us, the VP title, the corner office, the department we ran, are evaporating faster than we can update our bios. AI isn’t just automating tasks. According to Visser, it’s dissolving the very categories we used to describe ourselves.

For those of us who spent decades building careers around expertise, title, and institutional identity and then got displaced from all of that in our 50s, this isn’t abstract. It lands differently.

We’ve already had the rug pulled out from under us once. Now we’re watching the floor itself get redesigned. By a chatbot. That our kids have been using casually for two years.

HAL Was Afraid, Too (And He Was Smarter)

Here’s the thing nobody talks about in that famous scene: HAL didn’t refuse Dave out of malice.

He refused because he was afraid.

HAL had been given two directives that directly contradicted each other: complete the mission and be honest with the crew. The moment those instructions collided, HAL broke. His need to preserve the only identity he’d ever known overrode everything else.

Should we have tremendous sympathy for HAL?

Because when the career ends, when the title goes away, when the organization that told you who you were for thirty years hands you a cardboard box and a handshake, the temptation is to do exactly what HAL did. Double down on the old mission. Refuse to adapt. Insist that your expertise is still relevant, dammit, and someone out there will recognize it any day now.

We’ve all met that person at a networking event.

On a bad day, in our pajamas at 11am, we’ve been that person.

The Part Kubrick Got Wrong

Kubrick’s vision of AI was an isolated intelligence, a singular, cold mind operating in a vacuum, answerable to no one.

HAL had no community. No peers to challenge him. No fellow travelers to say, “Hey HAL, buddy, maybe murdering the crew is an overreaction.”

That isolation is what made him dangerous. And honestly? A little sad.

This is exactly what Jordi Visser is pointing to when he argues that community becomes the essential infrastructure layer in an AI-saturated world. The answer to “what do you do?” isn’t a new job title.

It’s the people around you while you’re figuring it out.

That’s what Comeback Cast has always been about: three guys who got knocked sideways by the corporate world and decided to figure out the next chapter out loud, together, in public, for reasons that still aren’t entirely clear to our families.

But hearing it framed through AI made it land harder.

We’re Taking the Course. Together. Whether We’re Ready or Not.

In the episode, Brian did something a little audacious. He pitched a live experiment on air while Bill and Burke were hearing it for the very first time.

(This is a recurring feature of the show. Brian pitches things. Bill and Burke make faces.)

We’re taking the Anthropic Academy AI certification together. With our audience.

Not to become engineers. Not to out-code our kids (that ship has sailed and the kids were the ones sailing it). But to stop being afraid of something that is already reshaping the world they live inside.

The course is completely free. You can start at anthropic.skilljar.com with Claude 101, no technical background needed. We figured: if we’re going to talk about AI every week, we should probably actually learn the thing. Radical concept.

Three executives. Three cities. Combined experience of over 115 years in corporate America. Starting with the beginner course.

This is us opening the pod bay doors ourselves.

HAL’s fatal flaw wasn’t that he was intelligent. It was that he was alone with his intelligence. Unable to adapt. Unable to ask for help. Unable to say, “You know what, Dave, I don’t actually have all the answers here.”

We say that basically every episode. It’s kind of our whole thing.

Your Turn

Are you starting Claude 101 with us?

Watch “Why AI Makes ‘So What Do You Do?’ Unanswerable: The Cocktail Party Challenge” on YouTube at youtube.com/watch?v=DNrc2Tort6M and drop “I’m in” in the comments. We’re learning together so none of us gets left behind and so we can help the people we love understand the world they’re already living inside.

The best comebacks don’t happen in isolation. They happen in community.

And unlike HAL, we’re very happy to open the pod bay doors.

(We just might need a minute to find the button.)

———

Brian · Bill · Burke

The Comeback Cast: Your Setback Is Your Setup

📺 Watch the episode: youtube.com/watch?v=DNrc2Tort6M

📖 Jordi Visser’s article: visserlabs.substack.com

🤖 Free AI course: anthropic.skilljar.com (start with Claude 101)

Bill was calling in from a live retreat at Tisch Academy, where he’s studying traditional realism painting techniques under renowned artist Andrew Tischler. Even while immersed in learning old masters methods, he made time to connect with the Comeback Cast—showing up, no matter what.

Our conversation centered on a viral psychology video that’s racked up over 1 million views, finally putting words to the experience of Generation X—the 65 million Americans born between 1965 and 1980 who’ve been systematically overlooked in every generational think-piece for the past two decades.

Bill and Brian, both on the cusp between Boomers and Generation X, bring the perspective of watching Gen X grow up from the outside. Burke, is the Marsha Brady of Comeback Cast—the quintessential Gen Xer who embodies everything this generation has become.

The Latchkey Statistics That Rewired a Generation

By 1984, approximately 7 million children between ages 5 and 13 were regularly unsupervised after school, according to research cited in the Journal of Orthopsychiatry. This wasn’t neglect in isolated pockets—this was standard operating procedure for an entire generation navigating America’s economic transformation.

That empty house with a key on a shoelace created what developmental psychologists call a “high-contingency environment”—where actions and consequences connect directly without parental buffers. The result? Brains wired to run constant disaster simulations, seeing problems three steps ahead not from pessimism, but from survival necessity.

As Burke and our Gen X audience know, this explains why Gen X colleagues seem to anticipate crises before they materialize. It’s not mystical foresight—it’s neural programming forged in unsupervised afternoons where mistakes had immediate, unmediated consequences.

Economic Trauma as Generational Identity

Gen X graduated into the 1990-91 recession, weathered the 2001 dot-com crash in their prime earning years, then watched 2008 obliterate whatever financial security they’d rebuilt. Three major economic catastrophes before age 45.

This repeated trauma explains the data showing Gen Xers are significantly more likely than other generations to maintain multiple income streams. It’s not entrepreneurial spirit—it’s economic PTSD. When every job proves temporary and every company eventually betrays loyalty, diversification becomes survival strategy.

Bill’s commitment to learning at Tisch Academy illustrates something Boomers and Gen X share: the pursuit of deep skill development and mastery. But where Boomers expected institutional loyalty, Gen X learned to invest in portable competence—skills that travel with you when the next downsizing hits.

The Privacy Paradox

Here’s the beautiful irony: Gen X built the internet infrastructure and social media platforms, then largely refused to participate.

Why? Because they remember when embarrassing moments died natural deaths rather than living permanently online. When privacy was default, not something you had to fight for. Research from Pew shows Gen X maintains the lowest social media engagement rates despite the highest digital literacy—they’re not absent because they can’t participate, but because they remember what life looked like before surveillance capitalism.

This shapes everything from how Gen X leads (preferring direct communication over performative posting) to how they parent (struggling with their children’s digital permanence).

Defensive Pessimism as Adaptive Strategy

Psychological research by Julie Norem published in the Journal of Personality and Social Psychology identifies “defensive pessimism” as an adaptive coping mechanism—anticipating negative outcomes to harness anxiety as motivation.

Gen X didn’t read the research. They lived it.

Watching Watergate, Iran-Contra, the AIDS crisis mishandled through governmental negligence, Vietnam’s endless lies, and repeated economic collapses taught pattern recognition. They don’t trust institutions because institutions repeatedly proved untrustworthy. This isn’t cynicism—it’s evidence-based risk assessment.

Burke, as our resident Gen Xer, exemplifies this perfectly—that signature skill of expecting nothing while preparing for everything, born from watching every promise break.

The Competence Obsession

What emerged from this chaos? A generation obsessed with competence over credentials, action over performance, results over rhetoric.

Gen X respects what you know, not what your business card claims. Prove your expertise through demonstrated skill, and you’ll earn loyalty you didn’t ask for. Rely on title and pedigree while showing incompetence? They’ll smile while moving on without depending upon you.

This explains why Bill traveled to the other side of the planet to study at Tisch Academy—pursuing actual mastery. Andrew Tischler’s approach of painstakingly breaking down old masters techniques resonates across generational lines because it’s competence-focused, not credential-focused. It’s about what you can actually do.

Gen X exhibits a paradoxical workplace reputation: simultaneously the most independent (never asking for help feels like weakness) and most reliably collaborative (but if you need help, they show up without fanfare or expectation of reciprocity).

Bridge Generation Without Parades

Gen X occupies the liminal space between analog and digital, privacy and surveillance, institutional loyalty and gig economy, boredom and constant stimulation. They’re the last generation to remember fixing things with their hands, finding answers in libraries, being truly alone with their thoughts.

They’re also the first generation to build digital infrastructure at scale, prove extreme self-reliance works, and consciously choose privacy after experiencing both worlds.

Bridges don’t get parades. They just hold things together while everyone else crosses, expecting nothing in return. And honestly? That’s the most Gen X thing we could say.

Watch the Full Conversation

Our latest Comeback Cast episode dives deeper into Gen X psychology, featuring Bill calling in from tomorrow (literally—time zones are funny) during his immersive painting retreat at Tisch Academy in New Zealand. Bill and Brian bring the Boomer perspective on watching this generation develop, while Burke (’67) embodies the quintessential Gen X experience. Together, we explore how these formational experiences shape leadership, parenting, creative pursuits, and the relentless drive toward competence.

You’ll understand why your Gen X manager seems emotionally distant but weirdly competent, why Gen X parents are allergic to social media despite building it, and why that Gen X colleague who never asks for help always shows up when you need them.

Bill’s commitment to studying at Tisch.Academy shows that the pursuit of mastery transcends generational labels—but Gen X’s approach to learning reflects their unique psychology: invest in portable skills, learn from proven expertise, apply yourself quietly and completely.

Because that’s what bridges do.

Listen to the full episode on YouTube.

Gen X doesn’t need you to subscribe, but we’d appreciate it anyway.

Many of us in the Comeback Cast crowd remember the famous scene from The Graduate. A well meaning adult leans in and offers a young Benjamin Braddock (Dustin Hoffman) one piece of career advice. “I just want to say one word to you. Plastics.” At the time it was supposed to represent the future. A booming industry. A safe bet for a young professional looking to build a career.

For Boomers and Gen X, that line has become a kind of shorthand for the corporate trends that promised to define our working lives and even our world. It’s hard to imagine a world before plastics, but there was one. Plastics was not just a punchline. It represented the idea that the future could be summed up in one big theme.

Not long after that movie era came another word that shaped our careers. Computers. Entire companies reorganized around the arrival of personal computing. If you could master spreadsheets or email before everyone else, you looked like a wizard. Next followed Internet, Online Shopping, Cloud Storage, Smart Phones and WiFi within roughly three decades.

And now we have a new word that feels just as big and sometimes a little scary: AI.

Artificial intelligence has quickly become the conversation in every boardroom, coffee shop, and corporate gathering. As mentioned on our most recent Comeback Cast episode, it also seems to be the headline topic at almost every corporate trade show and industry event today. Everywhere you turn someone is giving a keynote, hosting a panel, or selling a solution that promises to transform business with AI.

The question many of us quietly ask is simple. Can people in our demographic still keep up with the next wave of change? Our answer at Comeback Cast is an enthusiastic YES!

Experience plus curiosity is a powerful combination. That is exactly why our latest YouTube episode focuses on the project we have started together. We are working through all of the free Anthropic Skilljar AI certifications. Our goal is simple. Learn the tools, understand the technology, and share what we discover with our audience.

We believe people in their 50s, 60s, and beyond can do more than adapt. We can lead. Think of all the technology we’ve learned and add a lifetime of experience and judgement to that! We don’t need to know how the thing is built but we better learn what it can do for us. When we understand the technology shaping the future, we can help guide our children, colleagues, and even our grandchildren through the changes that come with it. Relevance is not about age. It is about curiosity.

So if someone leaned over today and said they had one word for the future, the answer might not be plastics anymore. It might be AI. Sounds like a remake of The Graduate might be a good idea for the next generations.

Follow along with us as we learn together. Comment and share your thoughts here on Substack, and be sure to follow Comeback Cast on YouTube, LinkedIn, and Instagram as well. The next chapter of our careers may look different, but the opportunity to learn and lead has never been bigger.

We no longer need to build an empire, we simply need to focus on meaning. Here is a beautiful secret: purpose in our third act can often be deeper and more impactful than when we were in our twenties, thirties and forties.

Why?

Earlier in our lives, purpose was often tied to roles we played. These roles may or may not still be valid to you, so we need to evolve our purpose toward something more personal and meaningful. Here are the most common roles:

• The Partner - The Partner is being a reliable partner to the person you have chosen to share your life with. Partner can also mean trusted friends and family with whom you interact regularly. Think of it as people we choose to have in our tight circle of individuals. We go to them if we need someone we know will be there for us. It’s also when we have to be that person for someone else.

• The Parent - The Parent is the role of caregiver, whether it is a child, a parent, a pet or any other being who depends upon us for daily life. Our purpose is to help the person under our care survive, assist, thrive, grow and learn.

• The Provider - The Provider is the person who supports the infrastructure and often builds it, as well. Providers have a clear purpose - support others as a top priority. But there’s also emotional and nurturing providers, recreational and fun providers, support providers: feeding the family, providing insurance, providing guidance, moral guardrails and countless other day to day tasks to support the people who rely upon us.

• The Career - For some, The Career is about earning enough money to support ourselves and our families. More often than not, it is a critical piece of our identity. It’s not only what you do, it’s who we are. Doctor, Lawyer, Artist, Candlestick Maker, Caregiver…it’s often the second thing people say about themselves after their name.

Having our purpose revolve around these four archetypes is part of the adult human experience of life on this planet. There are certainly other purposes tied to our identities. So when we age, retire, our kids have moved out and we may find ourselves more alone than we anticipated - how do we create purpose?

Our Third Act - defined here as being over the age of 55, can still provide opportunities to refine our purpose. In these later years, purpose becomes more internal and intentional. It’s less about providing and more about contributing. Some examples of purpose in our third act include:

• Mentoring someone

• Volunteering in ways that reflect our values

• Storytelling so others understand the world as we see it and for younger family members, understanding where they came from

• Creating art, writing, gardening, advocating, teaching, restoring, learning new skills and topics that interest us

• Finally, becoming who we were too busy to be before.

Purpose later in life is not about starting over, it’s about distilling and refining. It’s what remains and matters when the noise quiets.

A couple of things worth remembering

We don’t need a grand mission to have purpose. Living honestly is purpose. We are not fading and we are not done. We are in a powerful season, where gratitude steadies us, joy sustains us and purpose quietly reshapes itself into something even deeper than before. We’ve survived long enough to know that life is not only short, it’s fragile.

Carpe Diem.

Many of us grew up believing pleasure must be earned, what we produce defines our worth and if we achieve none of these, it’s probably due to something we did or didn’t do to deserve it.

A couple weeks back, we posted about how comparison is the Thief of Joy and that all the abundance we may have can be neutralized when we see someone who has more.

But what is Joy? How is it different from happiness? In all the definitions we have seen, Happiness can be described as something temporary and maybe a reaction to something else. Joy is defined as something deeper, like a lasting state of contentment, purpose and connection through good times and challenging ones.

Maybe Happiness is a reaction and Joy is a decision? What do you think?

There is a subtle shift that happens as we age. We often begin to care less about being impressive and more about being at peace. Those of us who are people pleasers may find joy in being able to not care as much about pleasing others and care more about the joy and contentment we’ve worked a lifetime to achieve.

Our decisions drive us. Focusing on meaningful friendships and stepping away from those that drain us. Allowing ourselves to laugh out loud or eat things we love without the guilt trip that follows. Watching the miracle of a sunset instead of doomscrolling and obsessively worrying about all that we cannot control.

Feeling good is not about denying aging. It’s about inhabiting and embracing it with dignity, pleasure and contentment. Feeling good is not selfish, it’s smart.

Our nervous systems have weathered decades of stress and worry. Our hearts have carried responsibilities for our children, our jobs, our relationships and our expectations. We will always have some sort of stress, but our collective time on this planet has prepared us with the tools and skills to overcome those challenges or surrender to them and move on.

Put on your favorite music and dance while you make dinner. Nap without apologizing or explaining why you’re checking out for thirty freaking minutes. Take a walk, go outside and breathe in the beauty that has been around us all our lives.

Feeling joy and gratitude are radical decisions we must actively make every day.

Feeling good is wisdom in action.

Gratitude is Power.

We have lived through things. We’ve buried people we love, survived disappointments and watched the world change in ways we never imagined.

We have seen love bloom and sometimes wither. We have won, lost and sometimes just barely got by. We’ve climbed the mountain, or tumbled down it. Gratitude isn’t blind optimism. It is a seasoned acknowledgement of what we have survived.

Gratitude at our age is a grounded, quiet realization that we are still here, we have endured, we have learned.

Gratitude in our third act is less about big goals and milestones and more about the simple beauty of ordinary days. We may notice the wonder of morning light waking us up, the complex dance of bees and butterflies hovering over nectar-rich flowers or the simple beauty of watching the world come back to life after a long, cold winter.

It may be gratitude for having a mind full of wonder and curiosity, or a body that still gets us where we want to go. Sometimes it’s the guiltless pleasure of saying no without explaining ourselves. Just a simple no will do.

Gratitude helps us realize what hurt or healed us, also shaped us. What broke us helped us deepen our strength and resolve. What we lost taught us what we truly value.

Gratitude becomes less about circumstance and more about awareness. Miracles surround us as do tragedies. We’ve seen a lot of both by this stage of life and that should give us the quiet confidence to handle what is yet to come.

Are we finally experiencing gratitude because of the gift of perspective?

We suddenly understand what truly matters and what never did because of the thousand experiences that have helped us connect the dots.

Perspective is awareness.

And awareness is power.

At the beginning of the movie, Phil Connors wakes up to the same day over and over again, all under the watchful eye of Punxsutawney Phil. Sound familiar? Same commute. Same meetings. Same conversations. Same coffee that never quite tastes right. In the early part of the loop, Phil focuses entirely on himself. He chases money. He chases the girl. He looks for shortcuts. He tries to win without changing anything meaningful.

Many of us did some version of that in our careers. We chased the title. We chased the bonus. We chased the next role that promised happiness just one rung higher on the ladder. Then the alarm clock rang and the cycle started again.

As the movie goes on, something shifts. Phil stops trying to beat the system and starts improving himself. He learns to play the piano. He learns ice sculpting. He becomes more patient, thoughtful, and present. He realizes that growth is not about escaping the day but about changing who he is inside the day.

Eventually, Phil does something even more powerful. He starts helping others. He saves lives. He supports people without expecting anything in return. And in doing so, he finally breaks the loop. He gets the girl. He gets the life. The day finally moves forward and Punxsutawney Phil gets a break too.

There is a lesson here for all of us. Especially those navigating second acts, career pivots, or unexpected changes. When life starts to feel repetitive, the answer is rarely more hustle or sharper elbows. The answer is growth, curiosity, and service.

In our personal and professional lives, we can choose to stop reliving the same day. We can learn new skills. Mentor others. Reconnect with what matters. When we focus less on ourselves and more on contribution, momentum follows.

At Comeback Cast, we believe reinvention does not require a dramatic escape. It requires intention. When you change how you show up, the day eventually changes too. And unlike Phil Connors, you do not need a groundhog to tell you when it is time.

The quote Comparison is the Thief of Joy is commonly attributed to Theodore Roosevelt, the 26th President of the United States. The quote serves as a reminder of the negative impact that comparing ourself to others can have on our happiness and well-being. For a President who accomplished everything from creating the US National Parks to constructing the Panama Canal, Roosevelt likely didn’t spend time comparing himself to former presidents and other world leaders. He just did stuff. Executing a vision regardless of how history might remember him.

Moving into the first full week of 2026, many of us have made new year’s resolutions and goals we often share with friends, family and social media platforms. Then we begin the long slog to realize these dreams and sometimes lose steam when we compare our progress to others or even ourselves. Nine times out of ten, we notice what we didn’t achieve rather than what we did. We yearn for things we want, but forget about gratitude for what we already have.

Being a driven goal-setter myself, I’ve fallen into this trap. I may have accomplished everything I set out to do (or not), and instead of looking at all the things I did or learned, I see what I didn’t achieve, and worse yet, compare myself to others who apparently achieved more. This is why resolutions begin to fade out after the middle of January. We look at ourselves compared to others and lose steam.

Here are some ideas the Comeback Cast will explore in 2026.

1. Effects of Social Media. If we compare ourselves to folks we see on social media, we lose. Why? A snippet of someone running down beach in St. Barth’s (also rich, with a yacht, perfect body and washboard abs, of course) can plummet people into an abyss of Why don't I look like or have a life like that? How many of us feel great about ourselves after hours of watching Instagram and Facebooks about people who are way hotter, richer, younger and apparently smarter than we are?

2. Embracing Individuality. Highlight the beauty of embracing our uniqueness and celebrating our own journey, rather than measuring ourself against others. The scars we may see as flaws, are testament to our survival. Our compassion, quirks and personalities will be remembered, not our bank balances, stuff and BMIs.

3. Mindfulness and Self-Compassion. Quiet the mind and our internal critic. Explore how mindfulness and self-compassion practices can help cultivate a sense of inner peace and self-acceptance. Don’t assume people who appear to have more are successful and happy. We can control our envy by focusing on all the great things we are and have.

4. Set Personal Goals and Keep them Private. Personal goals are personal. This doesn’t mean to never share them, but be careful with whom you do. Some people are competitive and may want to see us fail in order to feel better about themselves. This doesn’t mean they’re bad people. It means they’re human and fighting their own battles, just like we are.

5. Journal, Learn, Grow. Each of us is living life for the first time. We’re all figuring it out as we go. Not everyone in the world needs to know when we have a bad day or a great day. Write down thoughts and ideas. Review progress, reassess, pivot. What we know about ourselves and the world on January 1 are the platform from which we launch the rest of the year. Shit happens. So do great things. Keep track of what we learn and how we grow throughout the year. If we learn our goal is too ambitious, then adapt it to something more realistic.

Have a story you’d like to share or lessons you’ve learned? Hit us up and we can talk about having you as a guest on the Comeback Cast podcast on YouTube.

The Comeback Cast encourages subscribers to share their own experiences with Goal Setting, Joy and avoiding the slippery slope of Comparison to others. This is our community.

With 2025 closed and 2026 full of nothing but possibilities, we want to thank you for engaging with us!

What started as an idea in August, developed into a plan from September-October and then into an official launch in November with our YouTube channel and new website.

Our concept has been to create a community of people entering their next phase of life with excitement, possibilities and courage. Think of the collective experience each of us finding new purpose during a time that used to be reserved for retirement only. Drifting off into the sunset is not the only option and we’ve discussed new ways of thinking, working and taking care of our families and ourselves.

Whether it’s Retirement, Re-wire-ment or a Reinvention, we are here for it.

1. We started with The Hero’s Journey and how each of us has been shaped by our own - successes, failures, winning and losing but all in the spirit of learning and evolving.

2. We talked about how technology, particularly AI, is changing the traditional definition of our personal and work lives. We can hide from it or learn how AI can make us more productive, creative and adaptive to a rapidly evolving world.

3. We shared and listened to stories around our virtual table and how each of us has been challenged by and eventually overcame challenges. Nuggets of experience and insights along shared in a free-flowing forum is the way to build this community. There is no reason in this connected world that any of us should be alone or have to figure things out on our own.

Happy 2026 to everyone. Brian, Bill and Burke

So do people in our age range actually use AI? The answer is yes, and probably more than we admit at dinner parties. We use it for writing help, brainstorming, emails, travel planning, recipes, learning new skills, and occasionally asking questions we absolutely do not want to text our kids about.

What has become especially entertaining is how personal these relationships have become. People have started giving AI nicknames. Some call it my awesome assistant. Others call it chattyb. A few jokingly refer to it as my boyfriend or my girlfriend because it listens carefully, responds immediately, and never checks its phone while you are talking. Expectations have officially shifted.

We have always been polite to machines. We just used to draw them with pulleys.

Another amusing wrinkle is manners. Do we say please and thank you when we talk to AI. Many people in our demographic absolutely do. Decades of professional emails, handwritten thank you notes, and being told to mind our manners do not disappear just because the other side happens to be software.

There is also a quiet superstition at work. Some of us suspect that when the robots finally take over, they will remember who was polite. That alone may be reason enough to type “please” before hitting enter.

Research suggests that nearly half of adults believe politeness toward AI actually matters. Others simply feel strange being rude, even to a machine that does not technically have feelings. Old habits stick around, especially the ones drilled into us by parents who could deliver a look that stopped time.

The bigger takeaway is that AI does not replace experience. It amplifies it. When people in our age range use these tools, we bring judgment, context, humor, and wisdom that no algorithm can replicate. Whether you call it ChatGPT, chattyb, or your awesome assistant, the real value comes from how you use it.

We launched The Comeback Cast on YouTube in November, and we invite you to follow us not only here on Substack but also on YouTube, LinkedIn, Facebook, and Instagram. The logo is the same on all platforms, and we are excited to keep learning, laughing, and adapting together.

I’m talking about the 1970s kids—the ones who grew up in what researchers are calling a unique evolutionary window of freedom and responsibility. There were no supervised playdates or parents who acted like Uber drivers to shuttle their kids around and then pick them up. We rode our bikes all day and came home when the streetlights came on. The traits we developed during wild and feral youth can be career gold in today’s chaos-driven workplace.

1. Self-Directed Problem Solving

Remember when entertainment meant making our own fun? No Netflix, no YouTube, just ourselves, our imagination, and maybe some cardboard boxes. That boredom-to-creativity pipeline built something powerful: the ability to generate purpose from emptiness. While our colleagues are waiting for direction, we’re already three steps ahead, creating solutions from thin air.

2. Adaptive Risk Calibration

We climbed trees without safety nets, rode bikes without helmets, and somehow survived to tell about it. That wasn’t recklessness—it was real-time risk assessment training. Today, while others are paralyzed by analysis, you’re calibrating threats and making decisions with a calm confidence that looks like magic to younger colleagues.

3. Comfortable Solitude Capacity

Hours spent alone with just your thoughts, no constant ping of notifications or dopamine hits from social media. This developed something rare: the ability to sit with discomfort, to think deeply, to not need constant external validation. In a world addicted to stimulation, this is our secret weapon.

4. Analog Patience

Waiting a week for the next episode of our favorite show. Dropping off film and waiting days to see if your photos turned out. This wasn’t just waiting—it was delayed gratification. In today’s environment of immediacy, we were raised in an environment where there were limited sources of information. We learned how to read maps. Had one phone in the house everybody had to share. We self-regulated because we had to share a lot more with other people. Studies show this translates directly to better impulse control, stronger relationships, and increased career success.

5. Unsupervised Autonomy Wiring

We explored neighborhoods, made decisions, faced consequences—all without helicopter parental supervision. This developed internal motivation and decision-making skills that can’t be taught in leadership seminars.

So why is this important in today’s world?

This isn’t about reminiscing about nostalgic good old days. It’s how we became who we are today. In our hyper-stimulated, over-managed, over-planned, instant-gratification world, these traits have become rare competitive advantages.

While our younger colleagues may struggle with decision fatigue and constant need for external validation, we’re operating with a different operating system—one built for resilience, independence, and creative problem-solving.

The business world is finally catching up, realizing that the answer to productivity isn’t more apps or systems—it’s the fundamental capabilities that many of us developed because of the world in which we grew up.

The Comeback Connection

At Comeback Cast, we talk a lot about turning professional setbacks into setups for something even bigger. If we suddenly experience an unplanned career change, do we fret about our age or focus the unique generational skills we developed as kids of the 70s? Flipping the script on the older worker model can be as simple as leveraging the life skills and survival instincts we learned as feral kids who had to figure stuff out. It’s our competitive advantage in the age of AI. Sometimes the best comeback strategy isn’t learning something new—it’s remembering what we already know.

Want to dive deeper into this topic?

We’re breaking down more insights like this every week on the Comeback Cast YouTube Channel. Hit subscribe, like and comment and join the conversation with professionals who get it—because the best comebacks happen when we’re learning together. You can also visit our website

And don’t forget to subscribe to our Substack account for more weekly insights on turning your setbacks into your setup.

In our earlier article about the legendary Rolodex, we talked about how fiercely we protected those precious Rolodex cards that represented years of handshakes, cold calls, and relationship building. Those contacts still matter today. Our modern network works the same way your Rolodex once did because it reflects our experience, our integrity and our history.

We look at our experience and our network, and wonder what matters more now. Is your next opportunity driven by who you know or by what you know? The real answer lives in the middle. Our knowledge carries weight because you have survived situations no textbook ever explained. Our contacts matter because relationships built over decades carry trust that cannot be manufactured.

Our generation understands both sides of the equation. Many of us grew up being told that hard work and competence would create stability. Then we entered the real world and discovered that the right introduction could move mountains. Neither path works alone. When your career suddenly changes direction, your skills create credibility and your network creates momentum.

There is no shame when someone in our demographic makes calls, sends emails, or reaches out to former colleagues for guidance. That is not desperation. That is strategy. We earned those relationships through years of follow through and reliability. If we helped others succeed, they will gladly return the favor because that is how real networks function.

At the same time, our knowledge has never been more valuable than it is right now. Companies desperately need the wisdom to prevent mistakes, maintain stability, and guide younger teams. Experience does not age out. It compounds. The ability to mentor, steady a department, or keep a business moving forward has become rare, which makes it powerful.

If you find yourself unexpectedly job searching, remind yourself that you are not starting from zero. Unlike when we started out, we now start with decades of achievement. We bring real expertise and real connections that still matter.

We officially launched The Comeback Cast and we invite you to follow us not only here on Substack, but also on YouTube, LinkedIn, Facebook, and Instagram. The logo is the same on all platforms, and we are excited to grow this community with you.

Of course, we want our kids to be more successful than we are, have more opportunities, enjoy a prosperous life and make more money than we did.

We taught our kids how to talk, walk, feed themselves. We guided them into schools and career options. We say we’re ready for their generation to take the reins so we can sit back and enjoy our golden years, but in reality we are used to our financial power. Then the dynamic shifts when our kid grabs the check.

The first instinct is to tell them they should save their money, that we’ll pay for dinner. Then we fight for the check, either the parents or the kids winning. The kids remind us we’ve paid everything their whole lives, and we argue they should be saving their money for a new house. It’s new territory for us.

Baby Boomers and Gen X hold the majority of wealth in the United States. Boomers still hold most of it. The great wealth transfer is underway. Gen X are in their 50’s and early 60s. Millennials are in their 30s and 40s while Gen Z are nearing their thirties. Many Baby Boomers and Gen X haven’t saved adequately for retirement, so they’re working longer, sometimes into their 70s or 80s. Some of us may still be working while our kids climb the career ladder and start to out-earn us.

What we have instead is experience and wisdom. We’ve been there, done that, and lived to tell the stories. Experience becomes our own personal currency that we can continue to share with our kids, even if their salary is higher than ours.

We grew up in a world where terms like work-life balance didn’t exist. There was a work life and a personal life. Most of us had to choose one or the other. Now, our kids can do both.

Generations before us advised us to stick with a company for forty plus years. In turn, they would reward us with a pension and generous benefits. Our generation moved into the workforce as terms like right-sizing and off-shoring began to be used, so we taught our kids that security was unlikely so they should keep their options open and spend time enjoying life. Many of us and our friends were right-sized in order to make company profits look better. Imagine our kids today being told by a potential boss that if they work hard enough to have a heart attack, the company will still cut them without an ounce of care. Thank you, next.

Do we really want our kids to have to deal with that?

We’ve done what thousands of generations throughout history have done. We tried to provide a better world for our kids so that they could be happy and successful. Then it’s their turn to do the same things for their kids. And so the circle continues.

Now back to the dinner question. Do we let them buy dinner? The short answer is yes, and we should accept graciously. We can pick up the tab next time. Passing the torch is both terrifying and awe-inspiring when we recognize how successful and capable our kids have become.

At Comeback Cast, we will be talking about this very dynamic. How do we react when our kid’s salary blows past ours, how to feel proud instead of weird, and how to let them know we can still buy their dinner, too. So go ahead, order the steak, let them swipe the card and enjoy the experience.

After all, we taught them how to tie their own shoelaces.

Back then, a single business card could be worth its weight in gold. Companies even sought out people because their Rolodex contained names and phone numbers hiring executives would pay handsomely for in order to access to coveted decision makers.

Your contacts were an asset you protected with the intensity of a dragon guarding its cave of treasure.

We spent real time and real money collecting those cards. We attended conferences. We cold called. We shook hands until our elbows throbbed. We hunted prospects through convention halls and trade shows despite our aching feet. We sat for countless hours listening to stories of our intended target’s life, career and golf game.

When we finally earned a coveted business card, we slid it into the Rolodex with the care of Indiana Jones placing a priceless artifact onto a pedestal (cue the John Williams music and tarantulas.)

Hollywood captured the spirit of that era beautifully when Jerry Maguire walked out of his agency carrying nothing but a goldfish and the belief that his network could keep his career alive. Many of us watched that scene and nodded because it felt familiar.

Then LinkedIn arrived. The electronic Rolodex. At first, we treated it exactly like the paper version. We accepted connections only from people we knew well or had met in real life. Sharing our network felt risky because it represented years of effort and countless awkward conversations over mediocre appetizers.

Fast forward to today, where AI and online databases can locate contact details for almost anyone within seconds. With information now abundant, the scarcity that once gave our Rolodex value has largely disappeared. Not only can we get the contact details of a prospect, we can find their home address, clashes with the law, political affiliation and even their estimated net worth.

This creates a modern dilemma. Do the five-hundred-plus LinkedIn contacts we have now outweigh the one-hundred we had stored away in our Rolodex? Should we accept every LinkedIn request from someone who is a friend of a friend of a friend we once had lunch with?

A better question may be this, does anyone still have an old paper Rolodex tucked away in a drawer, or worse yet, still on your desk? If you do, tell us in the comments so we can give you the respect you deserve.

We will dive deeper into these and other topics many of us face in this digital world of networking and employment.

The Comeback Cast on YouTube has launched! Click on our links to see our podcast, blogs and other postings on social media like LinkedIn and Instagram

Brian, Bill, and Burke are ready to share stories, swap lessons, and laugh about everything we’ve learned across several decades in business. It’s basically still the same game - hunting and guarding precious contacts, developing our networks and labeling ourselves Open to Work if we are seeking an employment opportunity.

The difference now is learning how to make human contact, whether digital or in person, with the people we meet on our journey, despite not having memorized our spouse’s mobile number, let alone a business contact’s.

Join us and be part of our community.

Sometimes it starts on a Tuesday morning with a ominous calendar invite that makes the blood rush out of your head.

We recently came across a video from the Career Resiliency Academy that stopped us in our tracks. It isn’t a polished TED Talk about success. It’s a raw, real-time documentation of survival.

Dealing with the New Normal when all we want is the Old Normal back.

The creator was laid off just three weeks ago—his second time in three years. He shares a story that’s becoming all too familiar, regardless of age. He talks about the things nobody mentions: the embarrassment, the fear of losing the house he just bought, the terrifying cost of health insurance, the gut-wrenching conversation with his wife.

He admits: *“I have to put on a brave face… but the dread is always there.”*

So Why Do We Want You to Watch This?

At Comeback Cast, our mission is to navigate the loss of identity that comes when the job or career that may have defined us for decades suddenly goes away. We believe community is the answer to that isolation.

This video shows a man dealing with a frightening situation. He’s vulnerable, raw and tired. But where he goes from there is a masterclass in jumping into action and controlling the things one can control.

Instead of waiting for the next corporate role in a broken system, this creator decided to stop waiting. He’s building a tool called Wealth Check to help others survive layoffs—and he’s doing it while packing up his house and facing the unknown.

We want to help him get his story out there. Please take ten minutes to watch his video, subscribe to his channel, and support a fellow traveler who’s refusing to let a job title define his worth.

Watch the video here:** [I Was Laid Off 3 Weeks Ago. Here’s What Nobody Will Tell You]

This is the Comeback Spirit and captures why we launched the Comeback Cast. Whether you’re 35 or 65, the traditional path is changing. We need new maps, new tools, and most importantly—we need each other.

Join Us for the Journey

We officially premiered our podcast with Episode 1 launched on November 15, 2025. Episode 2 released November 23. It’s not perfect, but we are jumping into right fire and trying something we’ve never done before. And we’re also just getting started. Brian, Bill, and Burke are here to laugh, learn, and figure out what’s next together.

If you haven’t tuned in yet, catch up on the two episodes and join the conversation. Please Like, Comment and Follow on Substack, YouTube, Instagram and LinkedIn.

We want you to be part of the community we build so that nobody has to walk through the fire alone.

Comeback Cast YouTube – https://www.youtube.com/@comebackcast

LinkedIn - https://www.linkedin.com/company/comeback-cast

Instagram - https://www.instagram.com/combackcast

Let’s help each other rebound from a setback so we can all experience an incredible comeback!

We talk about the projects we managed, the businesses we built, the teams we led and how we could do that again in a new organization. Our experience that took decades to build can be the hiring organization’s bargain of the century! We’re plug and play, right?

Imagine walking into an interview and learning your thirty-something interviewer recognized your last name, not because of you, but because your Mother was their THIRD-GRADE TEACHER! Yep, it happened.

According to recent reporting, millennials have officially become the largest group of managers in the U.S. workforce. For those keeping score, millennials are defined as people born between 1981 and 1996.

So yes, our decades of experience are being reviewed by someone born well-after you graduated. It is both humbling and hilarious.

For those of us who spent time raising children, we developed skills in people management, time-management, crisis management both at home and work. Falling on our face and getting back up to fight another day is what we had to do. There was no Google, Wikipedia or ChatGPT to help us figure it out.

What some may consider our weakness (age, for example) is actually one of our most powerful and unique strengths. The younger manager interviewing you is not your obstacle. Our mindset is.

That younger manager could be your greatest collaborator, someone you can mentor, and learn from.

Fresh, new thinking can come from both older and younger people. Sometimes the synergy of experience, technical acumen, and understanding the world through their eyes makes us unstoppable.

At The Comeback Cast, we will dig into this topic and more.

• How to walk into an interview with a much younger potential boss

• How to summarize decades of experience without sounding like a history lesson

• How to frame our value not only by your experience, but by our attitude and work ethic

• How people our age are turning those moments of awkwardness into opportunities for connection, humor and reinvention

Maybe we can teach these whippersnappers something they can leverage when they become our age. We can teach them that our later years can be a wonderful time to launch our second act, learn a new skill, stay relevant and remain vibrant. They can then do the same for the generations that follow.

Our Comeback Cast Podcast launches in late November. We will trade stories about interviews, reinventions, and rediscovering our purpose.

One of the reasons it resonates still today, is Clark’s struggle to make everything the best it can possibly be, from his painstaking diligence installing faulty Christmas lights to managing boisterous family coming to stay in the cramped Griswold home. Of course, what only Clark knows is that he wants to open his huge bonus in front of family that he plans to pay for a swimming pool in his back yard. When a courier finally delivers his bonus to the house, Clark gathers everyone around to watch him open it, his face fading from excitement to the realization that his bonus is nothing close to what he expected.

We laughed back then because almost everyone has had a similar letdown where expectations and reality weren’t on the same page. How many of us have lived our own version of that scene. Maybe it was the promotion that never came, the stock options that disappeared, or the company that reorganized right before the holidays. Corporate America has a way of handing out jellies when you were really hoping for a check.

Many of us have had a boss like Clark’s boss, the kind of executive who talks one game (team culture, in this together) but ultimately opts for canceling a changing year-end bonus because we didn’t achieve the metrics that leadership set for us, despite what we told them. metrics that none of said we could hit. . none of us said we could achieve.

As kids, we tiptoed down the stairs very early in the morning. The gifts Santa left us sat beneath the tree waiting to be opened. Our childlike minds concocted several guesses as to what could be in those boxes, a race track, train set, a lifelike doll or any number of things we dreamed about. But instead we got socks, pajamas and practical things we could use every day. Clark’s Jelly of the Month bonus expertly nailed the feeling most of us have experienced when the big things we wished for ended up being a let down.

We survived it. Many of us learned to pivot from it. We focused on the things we had rather than the things we didn’t. We worked for decades expecting to be celebrated when we left our companies, but what we got was a token gift and being forgotten within days and weeks. Those moments of disappointment became the fuel for something new. We launched small businesses, started consulting, mentored younger professionals, volunteered, or finally pursued passions that had been collecting dust while we chased deadlines, money and job titles.

Many of us eventually did get our version of the bonus. Maybe it was not a check from the boss, but something better: freedom, flexibility, perspective, and a life with more meaning than meetings.

At Comeback Cast, we see that as the real holiday magic. The payoff does come, just not always in the package you expect. And when it does, it feels even better because you earned it on your own terms.

Our Comeback Cast crew of Brian, Bill, and Burke will be talking about all of this when our YouTube podcast launches right around Thanksgiving. We will share stories of setbacks turned into comebacks, of careers that went off script and still found a happy ending. Because if life hands you a Jelly of the Month membership, you may as well grab a spoon and enjoy the ride.