Money Monday Blog

I watched a TED Talk by Jordan Daniels the other day and it got me thinking. On the screen was a grid of dots, each dot representing the remaining months in an 18-year-old’s life if they live to 90. At first, it looked like a lot of time. But then Jordan began shading in the hours we spend sleeping, the years in school, the decades we spend working, even the time that disappears into eating, commuting, and chores. What was once a wall of possibility quickly became a sobering picture of how little free time is actually left.

One part of his talk focused on screen time. The average 18 year-year old is projected to spend 312 months, or said another way, 93% of their remaining free time on a screen. This point was meant to provide a reality check rather than guilt. It's a call to action. We don’t control how many dots we get, but we do control how to spend the ones we have left, especially the ones today.

So here’s the question worth reflecting on: Will your dots go toward time with family? Adventures you’ll tell stories about years from now? Building something that lasts? Or will they be lost in distraction, in autopilot, in “someday”?

Screen time is real, but it’s also a metaphor for distraction. When we lose sight of making each day count, we lose perspective on how precious each dot of time really is.

Every dot counts the same on the calendar, but not all of them carry the same weight in our story.

So, how will you spend the time you have left?

"The sad part about parenthood is that you’re raising the one thing you can’t live without to be able to live without you.”

I read that quote online last week and couldn't find its original author. It resonates in new ways as our kids get older (our kids are 15 and 11).

When they’re little, you’re their whole world. They need you for everything, from tying shoes to navigating nightmares. But the quiet truth is that every bedtime story, every carpool run, every life lesson is slowly preparing them to not need you anymore.

And here’s the tension: success in parenthood is measured by our own obsolescence.

When your son or daughter walks confidently into the world, whether it’s the first day of kindergarten or the moment they leave for college, that independence is evidence of a job well done. But it also leaves a hollowness in your chest. The very thing you poured yourself into for years is meant to walk away.

Bittersweet is the only word that fits, we aren’t personally there yet with our kids, but I can’t imagine it feels any other way.

This is the paradox of love: we give everything knowing we’ll eventually have to let go. And when they do leave, that ache in our hearts is matched only by the pride in seeing them stand tall.

For me, it’s a reminder that parenthood is less about holding on tightly and more about teaching how to let go gracefully. We are not just raising children, we are raising adults who can thrive without us.

It's humbling to know that in business and parenting, our ultimate legacy is our ability to prepare the next generation to do it better than we could.

We recently had our LiveWell 10x Summit with 130 people in town, it was an incredible few days. We had a variety of speakers, and one of the highlights came when Brad Weeks, LiveWell Partner & Private Wealth Advisor, presented a book review on Die With Zero. The presentation was outstanding.

Afterward, Angie (one of our teammates and one of the world’s best humans) came up to him and said something that stuck with me…

“I think the book is really about dying with zero regrets rather than zero dollars.”

That simple reframing changes the way I view the book, and it actually makes it even better.

As financial advisors, it’s easy to read Die With Zero and focus mechanically on how to spend your money down, how to time your withdrawals, how to sequence experiences, how to make sure your balance sheet matches your lifespan. That’s important. But Angie’s insight points to something even more powerful: living every day in a way that minimizes regret.

Jeff Bezos once said he built Amazon around a “regret minimization framework.” He asked himself, "When I’m 80 years old, will I regret not having tried this?" That’s the kind of question that shapes not just companies, but lives.

In his book, Bill Perkins challenges us to stop hoarding money for a future we might never fully live into. Instead, he pushes us to invest our resources, like money, time, and energy, into experiences, relationships, and impact while we’re able. But if you take Angie’s lens, the call goes deeper: don’t just allocate dollars, allocate your days. Don’t just manage wealth, manage meaning.

Here’s what that might look like in practice:

• Saying yes to a trip with your kids, even when work feels overwhelming (because it always will).

• Reconciling with someone before the silence hardens permanently.

• Choosing experiences over things.

• Building a financial plan not just for security, but for significance.

Money runs out, but so does time. And when the clock hits zero, the balance sheet won’t matter nearly as much as saying I don’t have many (or hopefully any) regrets.

Maybe that’s the ultimate financial plan, dying with zero regrets.

I’m 47, and with my parents approaching 80, age starts to feel more tangible. It’s easy to slip into thinking age defines how we act, but what if we don’t let it?

When I first heard “Don’t Let the Old Man In,” I initially liked the song before knowing the full context. Then I discovered the story behind it: Toby Keith and Clint Eastwood crossed paths at a charity golf tournament in 2018. Eastwood, then 88 years old, was filming The Mule. Toby, in his late 50s, marveled at Eastwood’s drive and energy, and asked the secret to his vitality. Eastwood’s reply was simple and profound: “I don’t let the old man in.” He went on to say that every morning an old man is knocking at the front door and he has a choice of whether to let him in or not. That thought lit Toby’s creative spark, and he wrote the song on the spot.

The song went on to be featured in The Mule, reflecting themes of aging, legacy, and purpose. It’s a ballad about resisting complacency: “Don’t let the old man in” becomes a metaphor, urging us to stay engaged, curious, and alive, even as time marches on.

That phrase, "Don’t let the old man in", isn’t just for the silver-haired. It’s a mindset, a daily choice to be energizing rather than defeated, open rather than closed.

Why this matters for us today:

• Age is just a number: We can choose how we show up, vibrant and optimistic or resigned and passive.

• Productivity isn’t age-bound: At 88, Eastwood was about to start a movie; that speaks volumes about purpose.

• The key to life is often having the wisdom to know what we let in and what we don’t: Just because the old man’s at the front door doesn’t mean we have to let him in.

Last year, Toby Keith lost his battle with cancer at 62. A reminder that everyday is a gift and everyday we have a choice on what we do with that gift.

Here’s a link to Toby Keith’s official music video:

https://www.youtube.com/watch?v=yc5AWImplfE

I heard a concept the other day from one of my coaches that stuck with me, he called it Life 3.0 (A concept he learned from Doug Fagerstrom).

Now, there’s a book out there with that title about artificial intelligence. This isn’t that. And I’ll be the first to admit, I’m not smart enough to write about AI anyway. But this idea of Life 3.0 made me stop and think.

The way he described it:

• Life 1.0 is our school years, our training years.

• Life 2.0 is our working years, careers, building families, striving, and providing.

• Life 3.0 is what we might traditionally call retirement, but I think it’s much more than that.

Life 3.0 is the season of reinvention. A time when the pressure of providing may fade, but the deeper questions come rushing in:

• What kind of relationship will you have with your spouse when you’re together more than ever before?

• How will you invest in adult children and maybe grandchildren?

• What rhythm and routine will shape your days?

• Will you nurture your health, volunteer, mentor, create, or even launch a second act?

I spend a lot of time with people in Life 3.0. And here’s what I’ve noticed: most have prepared financially, often over-prepared, but few have prepared for the life part of Life 3.0.

The transition can be bumpy. I’ve seen many men especially struggle, because their identity was tied so tightly to work. Women, in my experience, often move through it more gracefully, perhaps because their identity was never fully anchored in career alone. But when someone’s whole sense of purpose is wrapped in a job title, leaving it behind can feel like falling off a cliff.

The people who thrive in Life 3.0 almost always share something in common: they were already thriving in Life 2.0. They didn’t wait until retirement to figure out who they were or what mattered most. They invested in relationships, causes, and curiosity long before they stopped working. They retired to something, not just from something.

That’s the key. Because Life 3.0 isn’t the end of the story, it might be the richest chapter yet. Society seems to think people in their 60s, 70s, and 80s are “over the hill,” but I think that’s wrong. It’s often the season where wisdom, purpose, and perspective are at their peak. And if that energy is poured into mentoring, giving back, or building into others, then everyone wins.

So maybe the best way to prepare for Life 3.0 is to live Life 2.0 with intention. Build the life you’d want to keep living, even if the job disappears tomorrow.

Because the truth is, you don’t just stumble into meaning. You practice it.

We live in a time where our brains are trained to chase certainty, but the truth often requires us to hold two conflicting ideas at once. That’s called cognitive dissonance, and it might be one of the most important skills for thriving today.

Two writers I admire, Scott Galloway and Morgan Housel, helped me sit with this tension.

Scott Galloway: The Case for Pessimism (even though he is a pretty optimistic guy)

Scott Galloway, NYU professor, author, and entrepreneur, often reminds us that today’s young people face unprecedented headwinds. Using 1987 (the year he graduated college) as a baseline, he shows how much harder the path has become:

Avg. admission rate at top schools: 27% → 6%

College debt as % of first-year income: 31% → 53%

House price-to-income ratio: 4.4x → 8.5x

Wages haven’t kept pace with inflation (especially for low and middle income)

His point is sobering: this could be the first generation in modern U.S. history where children are not better off than their parents.

Morgan Housel: The Case for Optimism

Morgan Housel, author of The Psychology of Money, reminds us that discontent isn’t always about absolute reality, it’s about expectations.

We look back on the 1950s as a Golden Age, but the facts tell a different story: the average American home was under 1,000 square feet, air conditioning was rare, medical care was primitive by today’s standards, and most families had one car, if any.

By nearly every measure, healthcare, safety, technology, convenience, life is better today than it has ever been. Yet, as Housel puts it, “your expectations grow faster than your income.” We feel poor not by reality, but by comparison.

How Can Both Be True? That’s the paradox.

Galloway is right: Relative to their parents, today’s young adults face a steeper climb.

Housel is right: Relative to history, we’re richer than ever.

Progress has raised the floor but also lifted the ceiling out of reach. Young people aren’t starving, but they’re staring up at lifestyles that feel unattainable.

The Takeaway

We don’t have to pick a side. The healthiest posture may be to live inside the tension: to acknowledge the structural challenges while also practicing gratitude for the abundance we enjoy.

Progress and struggle coexist. Gratitude and realism are not opposites. And maybe teaching ourselves and our kids to hold both truths is the most valuable education we can offer.

Some team members believe that detailing every obstacle makes them appear smart. But to an entrepreneur, that’s usually exhausting and unproductive. They’re not begging for a list of roadblocks, they want someone who says, “I got this,” and delivers. Because there’s no proven benefit to analyzing problems beyond defining them. Action does the solving, and solutions move the needle.

Cue RSF: Relentless Solution Focus, this is my favorite mental model from Dr. Jason Selk. My favorite problems are the ones I never even knew about, because a teammate already solved them.

Introducing Dr. Jason Selk’s RSF (Relentless Solution Focus):

Jason Selk’s RSF is a simple but transformational mental framework:

1. Recognize: Catch yourself when you’re slipping into negative thinking or over-focusing on the problem.

2. Replace: In 60 seconds, shift from the problem to a solution-oriented question, “What is one thing I can do right now to make this better?” (The key is putting a 60 second limit on talking about the problem. How many meetings have we all been in where entire meetings were spent complaining about the problem with no solution in sight?).

3. Retrain: Practice this consistently. Even a few minutes per day can rewire your brain to default toward solutions (RSF tools like a Success Log take less than three minutes).

Why the 60-second window? Because staying stuck in a problem triggers cortisol, a stress hormone, which impairs creativity, confidence, and performance. Interrupting that dip with a solution-oriented thought prevents the downward spiral.

Why RSF Works for Entrepreneurs

• Empowers action. You don’t need another breakdown of obstacles, you need someone who can pivot and tackle them.

• Builds confidence. The mindset of “find a fix” reinforces ownership, trust, and results.

• Beats perfection. RSF favors incremental progress over paralysis by analysis.

• Trains resilience. With daily practice, even three minutes, you turn solution-focus into instinct.

Final Thought

There’s no evidence that endlessly talking about problems solves them. But there is evidence that with RSF, success becomes your default. In the face of uncertainty, pressure, or complexity, entrepreneurs don’t need problem experts, they need solution executors.

This past weekend, I had a once in a lifetime opportunity (thanks to one of my business partners, Toby Eng) and I went to a charity event at Michael Jordan's old house in Chicago. It was everything I thought it would be and there was a Jump Man logo in many areas of the home to remind me where I was, if I ever forgot. It was an epic night, and it got me thinking about the GOAT. It is the inspiration for today's blog.

We even have this debate in our office, and it’s almost always generational. For some, LeBron is the obvious answer. For others, there’s only one GOAT, Michael Jordan.

I was a teenager during Jordan’s prime, and I can tell you, it was fun to be a basketball fan then. The NBA wasn’t just entertaining, it was electric. There’s a stat that perfectly captures it, during the two seasons Jordan stepped away to play baseball, NBA TV ratings fell by nearly 50 percent. Not just for Bulls games, but for the entire league. That’s how much his presence elevated the sport.

Jordan played 15 seasons, made six NBA Finals, and won all six, taking home the Finals MVP trophy every single time. LeBron? He’s made it to 10 Finals and won four with three different teams. He’s the all-time scoring leader, a model of durability, and one of the most skilled, intelligent players the game has ever seen.

LeBron might be one of the nicer superstars ever, Michael could be brutal. He was relentless, demanding, and sometimes downright hard on his teammates. But he made everyone around him better. He raised the standard so high that excellence was the only acceptable option.

That was the magic of The Last Dance (released for streaming during COVID). Decades later, you could still feel it, that competitive fire, the refusal to lose, the extra gear in the biggest games. From the Flu Game in ’97 to that shot over Bryon Russell in ’98, Jordan’s defining moments weren’t just highlights, they were proof that when the stakes were highest, he was at his absolute best.

In business and in life, you want people on your team who show up for you in the big moments, who have confidence not only when things are easy but when the stakes are high, and when the pressure is on. I think that’s also what you want in a financial advisor, a steady hand when you need guidance during life’s biggest decisions. Whether it’s selling a business, navigating a career transition, or deciding how to secure your family’s future, you want someone who rises to the moment when it matters most.

LeBron is greatness personified, but, for me, the GOAT will always be the one who never blinked in the biggest moments.

“You are the average of the five people you spend the most time with.” — Jim Rohn

It’s one of those quotes that’s so simple, it’s easy to scroll past. But when I reflect on it through the lens of parenting, it takes on new meaning.

Every time we encourage our kids to join a team…

Every time we nudge them toward the kid who’s kind, focused, and curious…

Every time we gently steer them away from the chaos…

What we are really doing is helping them choose a new kind of normal. Because normal is just what you’re used to.

When your friends study hard, it feels normal to study hard. When your friends are chasing big goals, that feels normal too. But when your group shrugs off effort or mocks success, that becomes normal just as quickly.

And here’s the weird part: You’re the one who picked those friends in the first place. Which means you chose your normal.

This has been bouncing around in my head a lot lately, not just as a dad, but as a grown up.

In the last 30 years, I’ve been fortunate to have some great friendships. Not always perfect. But consistently filled with people who hold me to a higher standard. Who dream big, do hard things, love well, and challenge me to do the same. Their version of normal? It’s shaped mine.

I don’t think we talk enough about this as adults. We spend time thinking about our diet, our money, our habits, but who we spend our time with? That’s shaping all of the above.

So maybe the question to ask isn’t just “What do I want out of life?” Maybe it’s: “Who already lives that way?” And then: “How can I spend more time with them?”

Choose your people. Choose your normal. Choose your life.

One of the hardest parts of advising clients in retirement is knowing when to say “yes” and when to say “pause.”

I love seeing clients finally buy the boat they’ve always wanted, take the dream trip, remodel the kitchen they’ve been talking about for years. These moments are why they saved. They’re why we plan.

But when you’re retired, you can’t just earn more money. Every big expense pulls from the same pool of resources that has to last decades. One “just this once” is fine, but a series of them can quietly become a pattern.

Most advisors plan in straight lines (similar monthly expenses every month), but real life plays out in curves. It’s also hard to anticipate and financially model how many “just once” things may come up in a client’s lifetime.

The tension is real. Say “yes” to everything now, and we might be forced to say “no” later when it matters most. Say “no” too often, and life passes by with a pile of money and a list of missed moments.

A solid financial plan, portfolio and the right financial tools are a large part of the the solution. The harder part is the human element, knowing when the additional spending or purchase leads to more happiness and knowing when it is more for more’s sake.

That’s why this job isn’t just about math, it’s about nuance. I’m not just managing money, I’m managing possibility. And the art of advice is living in that uncomfortable middle, helping “today you” enjoy life without robbing “future you” of freedom.