Money Monday Blog

"We don’t stop playing because we grow old; we grow old because we stop playing." — Tag (2018)

There’s a reason this quote resonates so deeply. It’s not just a catchy line from a comedy; it speaks to something fundamental about life. My son and I watched the movie Tag the other night, the movie is based on the real-life story of ten childhood friends who, refusing to let distance, careers, or adulthood get in the way, have been playing the same game of tag for over 30 years. Every May, no matter where they are physically or where they are in life, they find a way to tag (or dodge) one another, keeping the spirit of their childhood alive.

It’s a reminder of something many of us have forgotten, how to play.

At some point, between career aspirations, back-to-back meetings, endless emails, and the all-consuming responsibilities of adulthood, we stop playing. We trade playgrounds for boardrooms, bike rides for carpools, and laughter for logistical planning. Life starts to feel more like a to-do list than an adventure.

But what if we built play back into our lives? Not just as something we do on vacation, but as a daily rhythm. What if we prioritized fun and connection with the same urgency that we prioritize deadlines? What if we allowed ourselves to be a little more spontaneous, a little less rigid, and a lot more present?

The men in Tag could have easily let their game die out, just as most childhood traditions do. But they made a conscious decision to keep it alive. And in doing so, they not only strengthened their friendships but also refused to let life become just a series of obligations.

Maybe we don’t need to start an elaborate game of tag (although, why not?). But it could simply be about adding some more fun to each day or week, something simple like…

• Make time for fun traditions with friends

• Play that silly game with our kids

• Family dance parties

• Laugh more, even when times are tough

• Games with your work team

• Pursue hobbies simply for fun

Because play isn’t just for kids, it’s for anyone who wants to feel alive. And if we’re lucky, we’ll realize that growing older doesn’t mean we have to grow old.

Tag—you’re it.

It’s funny how one sentence, just a few words, can make you rethink whole areas of your life. That’s the power of a great quote. A well-placed phrase has a way of cutting through the noise, simplifying complex ideas, and leaving a lasting impact. Here are ten quotes that have been on my mind recently, each carrying a nugget of wisdom worth reflecting on.

My Current Favorite Quotes

1. “We suffer more in our imagination than in reality.” – Seneca

2. “If you are the smartest person in the room, then you’re in the wrong room.” – Confucius

3. “The rate of return on money never saved is always zero.” – Unknown

4. “It’s never too late to be what you might have been.” – George Eliot

5. “Never put a comma where God put a period, and never put a period where God put a comma.” – Mark Batterson

6. “Care what other people think, and you will always be their prisoner.” – Lao Tzu

7. “Our life is what our thoughts make it.” – Marcus Aurelius

8. “Nothing will cost you more in life than a predetermined belief that things aren’t going to work out.” – Donald Miller

9. “Spending money to show people how much money you have is the quickest way to have less money.” – Morgan Housel

10. “Without vision, the people perish.” – Proverbs 29:18

The best quotes have a way of sticking with us, reshaping the way we think, and reminding us of what really matters. Maybe one of these struck a chord with you today. If so, let it sink in, sometimes a few words are all it takes to change everything.

I turned 47 this year. My kids turned 11 and 15. Which means, almost daily, I find myself standing in two different worlds - the one I grew up in and the one they’re growing up in.

When I was their age, it was the late ’80s and early ’90s. I remember riding my bike around the neighborhood until there was nobody left playing basketball or soccer. I knew roughly when I needed to be home for dinner. I remember there were a couple of days a year where the arrival of my report card determined whether the evening was going to be a celebration or a quiet one. My parents encouraged me to study - my mom, who had a PhD in English, gave me extra help in writing (sometimes more than a little 😀) - but beyond that, they didn’t know what I got on every quiz or whether I turned in every worksheet. If a teacher had something to say, they said it during a conference or a casual run-in. There was a kind of distance between school and home, and I think that distance gave me some space to grow.

Today? It’s different. Through platforms like Canvas, we can see our kids’ grades in real time. We can know when something hasn’t been turned in, often before they do. My wife and I know when a test was taken and how they did on it - sometimes before they’ve even processed it themselves. That space I had growing up, it’s mostly gone for them.

And the choices today are endless. Kids don’t just pick classes, they curate schedules. There are online forums, spreadsheets, and peer-reviewed methodologies for how hard or easy to make your high school experience (our son enters high school in the fall). Tutors exist for individual subjects. Strength and conditioning coaches exist for youth sports. Club teams now run year-round, and not just for the elite. Even in college, apps like Life360 can tell you whether your kid made it to class—or whether they were out too late, or spent the night somewhere you weren’t expecting.

The access is constant. And if we’re honest, so is the temptation.

We want our kids to be independent, resilient, motivated. We say we want them to create their own fun, to fail and get back up, to figure things out. But technology keeps whispering: you could intervene. You could check that assignment. You could remind them about that quiz. You could email that coach. You could fix it.

I don’t know what my parents would have done if they’d had this kind of access. Maybe they would’ve shown more restraint. Maybe not. But I do know it’s easier than ever for us to get involved - and harder than ever for our kids to get any real space.

And here’s the twist: we spend a lot of time talking about how technology is affecting our kids. But maybe it’s affecting us just as much. Maybe the constant connection isn’t just fueling their anxiety, maybe it’s fueling ours. Maybe the same tools that were built to help us guide and support them are actually amplifying our own fears and creating pressure we pass down without even realizing it.

I’ve started to wonder maybe the issue isn’t how much screen time they have—but how much we have. Maybe their games, their shows, their online worlds are a kind of escape from our constant supervision. Maybe they need a break not from tech, but from our interaction with it. From us seeing everything, knowing everything, weighing in on everything.

I don’t have the answers. I’m not sure if the answer is to delete Canvas or just check it less. I don’t know whether we’re supposed to step back entirely or just become more aware of when and why we step in. But I do know this: we can’t expect our kids to become self-reliant, self-motivated, and joyful, if every part of their lives is curated, measured, optimized, and supervised.

Sometimes, I think the best thing we can do as parents is to step back - not out of disinterest, but out of love. Not to abandon, but to allow. To give our kids the same gift we had, even if we didn’t realize it at the time: the gift of space.

And maybe, in giving them that, we give ourselves a little freedom too.

"Nothing will cost you more in life than a predetermined belief that things aren't going to work out" - Donald Miller

I’ve reflected on this quote a lot lately (I love Donald Miller), and the more I think about it, the more I realize just how true it is. It’s ironic, really—because if you’re an optimist, this message resonates instantly. But if you’re a pessimist, you might dismiss it as just another feel-good platitude. And that’s the tricky part: I’m not even sure optimism can be taught. It seems like people are either wired to see the possibilities or the pitfalls. (Side note: That sounds like a close-minded thought in a blog about optimism, but most of my experience in trying to convert pessimists to optimists have failed… converting mindsets for people hellbent on seeing the negative in life might be the only thing I’m pessimistic about).

Here’s the thing: optimists have a huge advantage in life. They see doors where others see walls. They find opportunities in setbacks, learn from failure, and believe that tomorrow can be better than today. This mindset doesn’t just change outcomes; it changes the way life is lived. There’s a self-fulfilling prophecy to it: if you believe things will work out, you’re more likely to keep trying, adapt, and find solutions.

On the other hand, pessimism can be a heavy burden. A predetermined belief that things won’t work out often becomes a self-fulfilling prophecy too. When you expect failure, you stop trying—or worse, you don’t even start. Life becomes smaller, possibilities more limited, and dreams fainter.

So, is writing about this a waste of time? Maybe. If you’re wired for pessimism, I can’t promise that a few paragraphs will change that. But if there’s even a small chance that someone might reconsider their outlook, that they might challenge their default assumptions, then it’s worth it.

Because the cost of a closed mind is just too high. And the reward for even a glimmer of optimism? Well, that can be life changing.

I'm doing a little writing on a Saturday night, and after a long week of market volatility and client conversations, I poured a bourbon (maybe two) and found myself reflecting on what 25 years as a financial advisor have taught me. I was licensed in 1999, just in time for a rocky market after equities had soared in the 90s. I didn’t have many accounts back then, but it was the first of many lessons. This was written in April of 2025 as markets volatility soared, but it could be written or read any time and is meant to be a timeless collection of thoughts.

Since then, I’ve seen:

• The tech crash in the early 2000s.

• The 2008 financial crisis, when I had a little more money under management and a lot more to lose.

• Market head fakes—like the late 2018 dip.

• The COVID crash and its V-shaped recovery.

• The 2022 bear market—uniquely brutal because bonds joined the freefall.

• And now, in 2025, we’re again dancing near the edge of uncertainty with a trade war.

These cycles have shaped me. Not just as a professional, but as a person who deeply cares about making sure clients are in the right portfolios for their goals.

Here are some of the biggest lessons I’ve learned along the way:

1. It’s Always the Wrong Portfolio... Until It’s Not: In bull markets, I wish clients were more aggressive. In bear markets, I wish they were more conservative. That’s the paradox. And maybe that’s the sign of a portfolio that’s actually well-balanced.

2. The Best Portfolio Isn’t Optimal...It’s Tolerable: Every client is really two people: present-you and future-you. Present-you wants comfort. Future-you needs growth. My job is to help those two versions of you get along. A portfolio that’s slightly sub-optimal for either one is often perfect for both.

3. Goal-Based Investing is our North Star: Long-term money belongs in stocks. Short-term needs belong in cash and bonds. Simple, clear, repeatable. It quiets the noise and protects against the temptation to time the market. Most of what makes headlines wouldn’t if we just stuck to this.

4. Advisors Are Human, Too: We’re supposed to be steady in storms and unemotional in euphoria. But we feel it too. We carry the weight of your worries, your fears, your hopes.

5. “This Time Is Different”… and it always is every crisis has a new flavor: Tech bubbles, pandemics, inflation spikes, trade wars. The storyline changes, but human behavior doesn’t. Markets panic and recover. Advisors sound like broken records because truth doesn’t change much.

6. What You Own Are Businesses, Not Tickers: One of the hardest things to remember is that buying a stock means buying a business. Unfortunately, businesses with ticker symbols get repriced every second. Your house doesn’t. A private business doesn’t. But somehow, we let the constant repricing of public stocks distort our view of their real value.

7. The Odds Are in Your Favor... If You Stay In: Roughly 75% of calendar years, stocks are up. I’m not into market timing. But if you have to pick a side, history favors the optimists.

8. Diversification - Because Risk is What You Didn’t See Coming: As Morgan Housel says, “Risk is what’s left when you think you’ve thought of everything.” Every downturn had surprises. That’s why diversification is more than a strategy, it’s a survival tool.

9. Indexing Works - Beautifully: Peter Mallouk once said, “Don’t try to find the needle in the haystack. Just buy the haystack.” In a cap-weighted index, the winners naturally rise to the top. Long-term returns are often driven by a small percentage of stocks. Indexing helps ensure you own them without needing a crystal ball.

10. The Media Isn’t There to Educate You: Jerry Seinfeld joked that no matter how much news there is, the newspaper is always the same number of pages. The news doesn’t reflect reality, it reflects what gets attention. And in markets, attention is often the enemy of discipline.

In Closing

The market may go up next week or down for months. I don’t know. What I do know is that stocks remain our most reliable way to outpace inflation and taxes. Bonds and cash give us stability. But behavior? That’s the wild card.

Advising is not just about spreadsheets and models. It’s about understanding people. It’s about helping you stay invested, not just in the market, but in your own plan. And it’s about having a drink every now and then, taking a breath, and remembering the reasons we made this money in the first place.

In our daily lives, we often find ourselves preoccupied with how others perceive us. This concern can be limiting, preventing us from living authentically. However, it’s liberating to realize that most people aren’t thinking about us anyway.

Psychologist Michael Gervais refers to this preoccupation as the “fear of other people’s opinions” (FOPO). He explains that FOPO is an anticipatory mechanism, where we excessively worry about what others might think of us, even before any interaction takes place. This fear can be a significant constrictor of human potential, holding us back from being honest, authentic, and bringing our best selves forward.

Understanding that others are primarily focused on their own lives can be freeing. Most of us (me included) can lose our ability to live in the present as we ponder the million things others could be doing or thinking and the cruel irony is they may be playing the same game in their own head. By releasing the undue weight we place on others’ perceptions, we can reclaim our personal power and live more authentically.

Embracing this perspective allows us to focus on what truly matters: our values, passions, and personal growth. Letting go of unnecessary worries about others’ opinions opens the door to a more fulfilling and self-directed life. As we get older and wiser, we let go of worrying about what other’s think… might as well start now 😀!

When most people think about leaving money to their children, they think about wills, trusts, estate planning, and what’s left behind when they’re gone. But what if the better question isn’t how much to leave but when?

The average age gap between parent and child in the U.S. is roughly 25–30 years. That means if you live into your 80s or 90s, your children are likely to inherit in their late 50s or early to late 60s. And while receiving a financial windfall at that age certainly isn’t unwelcome, it might not be when they need it most.

As author Bill Perkins reminds us in Die With Zero, the utility of money declines over time. Your ability to turn dollars into meaningful life experiences, memories, and joy is highest when you’re younger and more active. This applies just as much to your kids as it does to you.

Let’s consider the arc of life for a typical adult child. Their 30s and 40s are often filled with real financial strain - raising kids, affording a home, building careers, managing childcare costs, and trying to save all at the same time. These are the “pressure years”, when a well-timed financial boost could have compounding benefits for decades to come.

And yet, most wealth transfers happen after these years, when those dollars may be appreciated but not needed. When the struggle is mostly behind them and some of the opportunities to buy time, reduce stress, or build lasting memories have already passed.

So, why don’t more families gift earlier?

Because timing an inheritance is more than math. It’s about motivation, values, fear of enabling entitlement or robbing children of the satisfaction of building their own success. Many parents worry that giving too much, too soon might undercut their child’s drive. They want to help but not hurt.

On the other hand, they also know that giving too late may rob both generations of the joy that wealth can provide. Not just the dollars themselves, but the shared experiences they can create. A multigenerational trip. A down payment that enables a family to live near the grandparents. A business started together. A memory made in the here and now.

So, when is the right time?

There’s no perfect answer, but here are a few guiding questions and steps for families fortunate enough to be asking it:

1. Clarify your values before your numbers:

What kind of legacy do you want to leave? Is it about financial security, opportunity, shared experiences, or teaching responsibility? Your answer shapes the strategy.

2. Think in “buckets,” not just a lump sum:

Consider breaking inheritance into intentional stages, maybe some early-life support in their 30s or 40s, a larger gift later, and a final portion through the estate. Each bucket can serve a different purpose.

3. Match gifts to moments:

Rather than waiting for the end, give when it aligns with a life event - the birth of a child, a home purchase, paying down student debt, or starting a business. The impact will be far greater.

4. Consider “experiential giving”:

Not all inheritance has to be about money. Funding a family trip or creating a shared giving project can reinforce values and build stronger bonds, while everyone is still healthy and present.

5. Have the conversation:

Let your children in on the philosophy, not just the plan. Talk openly about why you’re doing what you’re doing, and what you hope it accomplishes for them and the family.

Ultimately, inheritance isn’t just about passing down money. It’s about passing down values, opportunity, love, and sometimes, time. And like most things in life, timing matters.

Giving earlier doesn’t mean giving everything, it just means giving with intention. A well-timed gift can change not just a financial picture but a life path.

So maybe the real question isn’t how much or even when, but why?

And once you know your why, the when becomes a little clearer.

Lately, I’ve found myself revisiting an important idea with several clients; an idea that Peter Tiboris explained beautifully on Will Richardson’s podcast:

Risk and volatility are not the same thing.

Yet too often, they get treated like they are.

When people think about investing, it’s natural to fear losing money. But there’s a critical difference between the risk of permanent loss… say, investing in a single company that goes to zero… and the temporary volatility that comes from investing in a diversified portfolio.

Risk is the chance that something you invest in becomes permanently impaired.

Volatility is the experience of prices bouncing up and down along the way.

Confusing the two can lead to real mistakes. For example, investing in a single small company that goes bankrupt is risk, you could lose everything. Investing in a globally diversified portfolio of thousands of businesses, however, isn’t about the risk of total loss, it’s about weathering volatility. It’s about having the emotional endurance to ride through storms without abandoning the journey.

The truth is, volatility only becomes risk when investors panic. Volatility alone doesn’t permanently destroy wealth, panic does.

This is why preparation matters so much. One of the best ways to survive volatility is not by avoiding it, but by building buffers around it. Cash, Cash Value, CDs, short-term bonds, and other safer assets give investors breathing room. Different advisors will debate how many years of safer assets you should have (some say five, some say ten), but the goal is always the same: Protect the money you’ll need in the near future so you never have to sell stocks at the wrong time. Because in a well-built plan, there’s almost never a reason to sell at a loss, unless emotion takes over.

Understanding the difference between volatility and risk changes the way you experience investing. It turns inevitable ups and downs from something scary into something manageable. And it reinforces what investing has always been about: having a plan, staying the course, and letting time do the heavy lifting.

In 2001, Jeff Bezos shared a piece of wisdom that’s stuck with me: “Stress comes primarily from not taking action over something you can have some control over.” At first glance, it’s easy to think that stress comes from long hours, hard work, or exhaustion. And sure, those things can be draining. But in my experience, the heaviest stress doesn’t come from being busy or tired—it comes from feeling powerless. It’s easy to become the victim in our own story.

Think about it. How often do we find ourselves lying awake at night, not because of what we did, but because of what we didn’t do? The difficult conversation we avoided. The decision we kept postponing. The problem we knew was brewing but chose to ignore. It’s the inaction that haunts us, that makes us feel trapped and overwhelmed.

When we don’t take action on the things we can influence, we surrender control. We allow circumstances to dictate our lives instead of stepping up and steering the course. And that feeling of helplessness? That’s where stress breeds. It’s the tension between knowing something needs to change and doing nothing about it.

But here’s the good news: action is the antidote. It doesn’t have to be massive, life-altering action. It’s about getting started - Sometimes it’s as simple as sending that email, making that phone call, or having that uncomfortable conversation. It’s about moving the needle, even just a little. Every step forward—no matter how small—reclaims a bit of control. And with that control comes relief.

I’ve found that most of my stress isn’t from doing too much but from avoiding the things I know need to be done. When I finally face those issues head-on, the weight lifts.

Maybe we don’t need less hard work or fewer responsibilities. Maybe we just need more courage to take action on the things we can control. Because when we do, stress loses its grip, and we gain our peace of mind.

This year marks my 25th year as a business owner. In the beginning, the motivation was simple: survival. I obsessed over how to take care of clients and, to be honest, how to avoid failure. There’s a certain urgency when failure feels like it’s lurking around every corner. It’s amazing how motivating the fear of falling short can be.

But as the years have gone by, the stakes have changed. While failure is always a possibility, the focus has shifted. The last 5 to 10 years have been less about survival and more about figuring out what a healthy level of ambition looks like. And that’s not as simple as it sounds.

The Double-Edged Sword of Ambition is a powerful force. It pushes us to dream big, to innovate, to grow. But unchecked, it can become an insatiable hunger for more—more success, more influence, more validation. When is ambition about honoring the talents and opportunities God has given us, and when is it just about chasing more for the sake of more?

I wrestle with this tension. I think many of us who’ve been fortunate enough to find success in business do. At its best, ambition is a way of stewarding the time, talent, and treasure we’ve been given. At its worst, it can consume us, making us forget why we were striving in the first place.

The pursuit of purpose, not just progress is the key in aligning ambition with purpose. If the drive to achieve is grounded in a desire to honor God, to serve others, and to make a meaningful impact, then ambition becomes a tool for good. But when it becomes about status, ego, or proving ourselves, it starts to take more than it gives.

There’s no easy answer to the question of how much ambition is healthy. It’s something we have to continually wrestle with, reflect on, and refine. But I do believe this: Ambition, like wealth, makes a wonderful servant but a terrible master.

My hope is that we strive, not out of a need to be the biggest or the best, but out of a desire to be faithful stewards of what we’ve been given. To pursue excellence without losing sight of what matters most.

That’s the kind of ambition worth having.