A Heavy Anchor

A huge shout-out to the couple that granted me permission to share this story. I pray good comes from it, and that my harsh-ish words can move the needle in their marriage!

Picture this. I'm sitting face-to-face with a couple. They are stressed, frustrated, and borderline depressed. The tension in the marriage is palpable. You could cut the desperation with a knife. Finances are killing them! Specifically, a lack of income is killing them.

Oh yeah, I should probably add one more piece of information to the picture: Their monthly take-home income is $22,000. Yeah, you heard that correctly. $22,000/month......every month. And according to them, there's simply not enough money to keep the train on the tracks. Or, as they put it, "It costs a lot just to survive these days!"

At one point in the conversation, I pointed out to them that just their monthly housing cost (plus utilities) rivals what most people in their town make in a month. They looked at me like I had an alien growing out of my forehead. Again, I tried to put into perspective just how much money they make. They continued to stare at the alien apparently bursting from my face. I explained that the client I met with earlier in the day (who coincidentally lives 1/4 of a mile from them) has a total take-home income of about $7,000/month (and is thriving!). The wife looked like she was either going to have an aneurysm and/or hop over the table to stab me.

I don't know about you, but most people don't even dream about making $22,000/month take-home. In fact, most people probably wouldn't even know what to do with that type of income. Yet here I was, talking to a couple who were lamenting that $22,000 isn't enough monthly income to even survive.

I was getting nowhere. I asked them how much money they made early in their marriage; "Probably $4,000/month." Well, that's a bit different from their current situation. "But the world has changed a lot since then." Fact check: That was seven years ago.

Here's the harsh truth. Unless we're willing to live with humility and contentment, there's no amount of income that can satisfy us. The problem with more is that every time we get more, more is still more.

I offered a few suggestions for how this couple could create financial margin. In some families' situations, it can be challenging to open up much-needed margin. This family, however, has a treasure trove of options for swiftly and materially lightening the tension in their finances. Want to know where they landed? The husband is going to pick up some extra work on the side (nights and weekends) to see if they can make a few thousand more per month.

Here's my promise to them. If they stay on this course, we'll be talking a few years from now. They will be making $25,000-$30,000 per month, yet feel just as broke, stressed, and resentful as they do now......if their marriage survives.

They deserve better than this. You deserve better than this. We all deserve better than this. Don't let the curse of more pull you down.....it's one of the heaviest anchors ever created.

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Rock Bottom

There's a saying I've been using for the last decade: "Okay is the worst place to be." There's nothing worse than being okay in xyz area of life. Okay isn't good enough to thrive, but also not bad enough to change. Slotting ourselves in the okay lane is a first-class ticket to stagnation....and eventual slow-burn failure.

I see this play out over and over again with people and money. People who are doing okay are the ones who will end up in the worst places. For better or worse, rock bottom is the blessing of all blessings. Hitting rock bottom is typically the catalyst that triggers massive change. You know who doesn't hit rock bottom? People who are doing okay.

There's one particular area of Northern Vessel that we've done okay with for the past three years on the operational side. Never good, never bad. However, it's one area I've been standing on my soapbox, yelling about how we need to step up our game. Since we've been stuck in okay land, there's no chance of making meaningful change. Something awesome happened this week, though. We hit rock bottom! We finally reaped the consequences of not handling ourselves with excellence. We screwed up, and we're paying the price. Okay quickly turned to rock bottom, and guess what (!?!?), we're ready to make some meaningful changes. As always, rock bottom will allow us to transform this aspect of our business and thrive like never before.

I never root for people to fail. However, I feel terrible for all the people in my life who live in the land of okay. I want so much better for them, but okay is their worst enemy. I never celebrate people's rock bottoms, but I rejoice in the transformation that's on the table when it does come.

I don't wish for you to experience a rock bottom, but I believe you deserve far better than just okay. I don't know what area of your life I'm talking about here, but you do. You absolutely do. Don't settle for okay, and please don't wait for rock bottom to be your wake-up call. Rock bottom will certainly wake us up, but let's not require that outcome before stepping up our game.

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Never Enough Income

Do you ever think to yourself that xyz issues would be solved with more money? If only I made $1,000 more per month! If only I made $2,000 more per month! There are so many financial priorities, and it never seems like there's enough money to go around. First, yes, if our basic needs are not yet financially met, more money will absolutely help close some critical gaps. What I'm about to talk about is the scenario in which basic needs are met, but other financial desires are at play.

I recently had this conversation with a client. This couple makes more money than ever before, yet at the same time, there doesn't seem to be enough. How can that be?!?! How is it possible to make twice as much as we once did, yet still not have enough?

Here's why. There's never enough income. Our human instinct is to conceptualize how making x more dollars per month would magically fix it all. From my experience, however, that line of thinking is futile. People who make $75,000 think more is the answer. People who make $150,000 think more is the answer. People who make $300,000 think more is the answer. People who make $700,000 think more is the answer. Believe it or not, but I've worked with people who make $3M per year who think more is the answer.

There's never enough income. I know it's a depressing thought, but I have good news. While we can't fight our way to success by driving our income upwards, there is one thing we can control. I once heard it said this way: "Wealth is the difference between what we have and what we want." In other words, if our wants keep going up and up, there's never enough money to satisfy the craving for more. On the flip side, if our wants are kept in check (i.e., contentment), what we have is enough.....more than enough.

This is the very reason why families who make $60,000 can feel wealthy while families who make $400,000 can feel financially stressed. It's not about what they make; it's about what they want.

In my 20 years as an adult living in the real world, I've learned that my financial well-being is far more influenced by my contentment (or lack thereof) than by how much money I make. It’s a humbling reality!

What about you? Are there areas of your life that you could/should want less? Is your hunger for more eroding your contentment? What steps would you need to take to widen the gap between what you have and what you want? It's a worthwhile endeavor, and fortunately for all of us, one we can absolutely control.

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Grateful For That Kid

Yesterday's post highlighted the inevitable reality that someday, future us will become current us. What seems old to us today will eventually feel young. Included in my post was a cautionary tale from an old friend who is learning this harsh reality in real time. The post ended with the following: "Yes, you're younger today than you will be someday. At the same time, however, 20 years from now you'll still be younger than you will be someday. Current you is always the youngest version of you. Please help yourself help yourself. Your future self will thank you."

In a fun little twist of fate, I had a related conversation with a client just hours after yesterday's post was published. This client, mid-40s, is in the process of making a huge life transition. Culturally, it's an odd decision. However, it's one this couple has earned through two decades of discipline and wise decisions. Here's an exact quote from the husband: "I'm very thankful for 23-year-old me."

I'm sure 23-year-old him had no idea what his life would look like in his mid-40s, yet at the same time, he respected future him enough to make some powerful, delayed-gratification decisions. Now, decades later, he's about to reap what he sowed. It's such a beautiful example of this concept.

40-something-year-old him isn't as young as 23-year-old him, but 40-something him is the youngest he'll ever be. And now, also being a 40-something, I too realize that being in our 40s often feels like being in our 20s. We feel young. We feel healthy. We know who we are. We know what we value. Life can be pretty dang awesome.

Now, this couple will spend the next season of their lives creating an entirely new reality that will forever transform their family. All because that 23-year-old kid had enough awareness and respect for his future self to live with wisdom and discipline.

No, we can't go back in time and get a do-over. I don't see any DeLoreans sitting in my driveway. However, regardless of how old you are, you're the youngest you'll ever be. You still have a chance to help your future self live the life they deserve. Please don't let them down.

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Turns Out Old Isn’t Old

Let's rewind the clock 20 years. It's 2005. Times are good. The economy is booming, and we haven't yet experienced the wrath and destruction of the Great Financial Crisis. I was 24 years old, new in my young career.

One of my friends was about six years older than me.....right around 30. Over drinks, we shared a conversation that I've periodically thought about for two decades. It's a conversation that might hit close to home for you. My friend was known to be impulsive, the proverbial life of the party. During one of our conversations, the topic of money came up. While I wasn't making the wisest of financial choices back then, I did understand one important concept: Investing for the future is imperative.

My friend had a different philosophy of life. In his words, we might die tomorrow, so we might as well have as much fun as we can now. And even if we don't die tomorrow, why wait until we're 50 or 60 to have fun, since we'll be too old to enjoy ourselves by then anyway.

Nearly twenty years have passed since that conversation. Guess where my friend is today. He's 50.....and healthier than ever. In his words, he's at the peak of his life. Just one problem: His 30-year-old self took that perspective seriously and thoroughly enjoyed life, leaving nothing for "old" him. Today, he sits at 50 and has no idea what his future will hold. Life is full of doubt, uncertainty, and stress. Will he have to work involuntarily forever? How will the bills be paid? There's not enough money to save for the future and actually enjoy life today.

I feel so terrible for him and his situation. He's between a rock and a hard place, and unfortunately, there's no redo button. That's the problem of having the attitude he had when he was younger. We ALWAYS become future us. Current me will someday become future me. A time will come when I am forced to live in the reality established by younger me. On one hand, that's the scariest concept in the world. On the other hand, it's so empowering.

Every day we wake up, we have the power to help future us. Each positive step we take is a blessing for future us, while each mistake is a curse for future us.

Yes, you're younger today than you will be someday. At the same time, however, 20 years from now you'll still be younger than you will be someday. Current you is always the youngest version of you. Please help yourself help yourself. Your future self will thank you.

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Rewriting History

What movie completely changed the way that you see the world? Have you seen any movies that fundamentally changed you? For me, there's one particular movie that messed me up in so many ways. Memento. This film was released 25 years ago and now sits at the #57 slot in IMDB's top-rated movies of all time list.

I don't want to share too much about it, as I suspect far less than half of our readers have seen it. If that's you, go watch it immediately! I just checked, and you can stream it for free on Amazon Prime. The entire concept of the movie is mind-blowing in and of itself, but at its heart is a concept that has long resonated with me: Our very human ability (and inclination) to rewrite history.

I recently spent time with a couple that is struggling. They've always struggled with finances, and money-related stress seems to be playing on repeat in their marriage. Every week, every month, every year. Stuff happens, and they can't get control of it.

Something interesting happened during the conversation. When I asked them to share what sequence of events led them to where they are today, they weaved together a peculiar story. It was a gut-wrenching story of misfortunes, unfairness, and bad breaks. Here's what makes their story peculiar to me. I knew this couple for the entirety of this 10-year stretch they were speaking about, and my recollection is much, much different than the story they shared with me. In my version of the story, each season of misfortune was triggered by a tremendously poor decision on their part. Yes, the pain and suffering they experienced aligns with my recollection, but the causes of said turmoil were a completely different story.

In my opinion, this couple rewrote their history. They didn't do it to lie or manipulate. Rather, their engineered story stems from an attempt (consciously or subconsciously) to soften the feelings of regret and resentment. It sounds wild, but I think each of us has a predisposition to do the same. It doesn't necessarily make us liars, but there's a certain risk in this behavior.

If we rewrite our history to soften our own personal responsibility, it creates the potential for us to repeat our own troubling past. When we don't face reality on reality's terms, we're apt to make the same mistakes again. When we don't force ourselves to experience the consequences of our own actions, it enables us to make more harmful decisions in the future.

This couple in front of me had a choice. They could face reality on reality's terms......or believe the rewritten history. If they continue to believe their rewritten history, there's very little chance they can overcome their behavioral and financial hurdles and end up in a good place. However, if they face reality head-on and commit to doing it differently going forward, there's no limit to the amount of beauty they can experience together.

I speak this concept as if it's easy. It's not. It's simple, but far from easy. However, some of the simplest things in the world are the most powerful. This is one of them.

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Hyperbole For the Masses

Plunged. Tumbled. Sank. Crashed. Tanked. The media has had no lack of hyperbolic words to describe what happened to the stock market on Friday. People are losing their minds! If you aren't aware, the U.S. stock market fell by approximately 2.7% on Friday. Based on the dozens of texts I've received since then, many people are anxious.

"Market Falls Off a Cliff," reads one international news outlet headline. If you're casually scrolling the web, what do you do with a headline like that? I'll tell you what many people do. They start to get scared. Is it warranted? Should people be worried? Is now a great time to be fearful?

Well, it depends on what your goals are. If your goal is to never see your account balance fall below where it is today, then yes, you should be terrified. However, if your goal is to end up in a good spot years or decades from now, no, you shouldn't be worried in the least.

One of my friends specifically asked about how badly the stock market got crushed on Friday. After all, the hyperbole used to describe those events makes it sound like doomsday. Please allow me to put it into perspective. After the market fell by 2.7% on Friday, we are down to a level that had never before been achieved since the Civil War.....until 9/11/2025. That's right. The price of the stock market today is at level that was an all-time high less than a month ago. Here, maybe this chart will serve as a clear visual:

This chart illustrates what the last five years have looked like for the U.S. stock market. That tiny little blip in the upper right-hand corner of the chart is Friday's "plunge." It's about as scary as a Halloween-themed show made for toddlers.

Will the stock market experience a far more significant decline? Probably. When will it happen? No clue. None of that is important, though. What's important is that we continue to practice the "do nothing" strategy and simply live our meaningful lives. Let the market be the market because the market is always the market. P.S., that's a good thing. We have the greatest stock market that has ever existed, and 155 years of proven data to back it up. Therefore, I love letting the market be the market because the market is always the market.

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My Collections

In yesterday's post, I confessed that I don't personally collect anything. Everyone around me seems to have collections, but my life is seemingly void of collectibles. Does that make me weird? Am I missing out? I challenged our readers to share their viewpoints and perspectives on collecting. I so much appreciate your insights.

After much consideration, it dawned on me that I do, in fact, collect things. However, instead of collecting material things like I used to when I was younger, my collections look different now. I'm not sure how I missed it so badly yesterday, but it turns out I'm indeed a collector. Here's what my collections look like:

• I collect memories.

• I collect experiences.

• I collect photos and videos.

• I collect trips.

• I collect countries visited.

• I collect food eaten.

• I collect sights seen.

• I collect first-time endeavors with my kids.

• I collect impactful moments with those whom I have the honor of serving.

I totally missed the mark yesterday when I was focused too much on the physical, and not enough on the intangible.Those things I listed above? I cherish them so much, and if I'm honest, I pursue them violently.

I recently read a study about why time seems to go faster as we age. Turns out, there's a scientific answer for it. Our brains measure time in significant events: first-time experiences, landmark moments, profound experiences, etc. When we're younger, we naturally have more of these moments in our lives. The world feels new and exciting. We're more likely to be adventurous. We have a childlike wonder.

Then, as time passes, that childlike wonder begins to fade. What once felt new and exciting starts to feel bleh. When I was a kid, I remember the astonishment I felt each time my family drove into downtown Chicago. The buildings, the lights, the sounds, the people. It was all so....intense! Today, though, it's a different experience. I took my family there a few weeks ago. This time, it was just a cool city. I still love Chicago, but the wonder has somewhat faded.

This is why it's so important for me to collect memories and experiences. The more often I approach life with a childlike wonder, the more significant events get seared into my brain. How has this panned out? The 20 years from age 18 to 38 seem like a blur, gone in the snap of a finger. On the flip side, the six years from 38 to 44, intentionally approaching life with this new mindset, have felt like two decades. I've had more monumental memories and experiences in the past six years than I did in the 20 years prior to that, combined. That's very cool to think about; that's very depressing to think about. But I'm going to focus on the cool here!

Collect memories. Collect experiences. Collect impact. The act of collecting that which is intangible is a tangible effort toward a more meaningful and enduring life. I'm not even sure if that last sentence makes sense, but upon 15 reviews, I'm gonna stick with it!

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As Simple As a Name

A few years back, one of my clients had a big, big dream. It was the type of dream that practically everyone in his life (but for his wife and me) told him was "stupid." It was "reckless," "irresponsible," and "selfish." In other words, he had a pretty awesome dream!

Like many people who pursue crazy dreams, it can be tremendously scary to walk away from a decent income and start over at something much lower. In this particular family's case, they would soon experience a 70% decrease in their monthly take-home income. Therefore, we needed to make a plan!

For each of the nine months leading up to the scary transition, the couple would set aside a chunk of cash in their emergency fund. After bulking up this fund, they would then be able to take monthly draws from it, as needed, to supplement their monthly income in the early stages of their new scary life.

One problem: the mere idea of drawing down their emergency fund felt terrible. As the husband put it, "I'll feel like I'm failing.....an emergency. I don't want my life to feel like an emergency." Even though that's what the money was supposed to be used for, he couldn't emotionally or mentally get over the idea of drawing down on his bulked-up emergency fund to feed his family.

Therefore, I suggested something ridiculous. "Change the name of the account." That's why they pay me the big bucks (haha!). They thought it was a stupid idea, but the conversation continued. If they are setting money aside for this very purpose, then drawing these funds as needed is the fulfillment of the dream. It's not a failure, but rather the realization of the dream! Therefore, I suggested they change the name of that account from "Emergency Fund" to "The Dream Fund."

While ridiculous, it's exactly what they needed. It completely flipped the switch from a behavioral science perspective. Instead of viewing the depletion of that account as a loss, they experienced it as the planned execution of the greatest adventure of their lives.

Fast forward to today, and they no longer have The Dream Fund. They made it to the other side of their scary transition, and instead of having a dream fund, they are living their best dream life. It hasn't been easy, but it's been one of the most meaningful endeavors they've ever experienced.

I'm so proud of them, and I love thinking about their story. Sometimes, it's as simple as a name. We humans are weird beings. We tell ourselves stories and twist around our own thoughts. We get in our own way and sabotage our own best interests. On the flip side, if we can hack our own behavioral quirks, we can get to the other side of a truly amazing life. Yes, it's ridiculous. But also, yes, it's awesome.

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Everything and Nothing

I was casually reviewing the finances of a young couple a few weeks ago; all normal stuff. Item by item, we checked off my list. Then, we got to savings. "How much do you have in savings?"

"We have $25,000 in our savings account."

"What is that account used for?"

"It's used for everything. We just throw money in it whenever we have extra, and that savings account is used for everything."

"By everything, do you mean nothing?"

***Uncomfortable laughter arose from both spouses.***

I want to share a massive behavioral science hack when it comes to saving. If you just blindly and arbitrarily dump money into a savings account that's intended for everything, it's actually used for nothing. Why? Because when something is for everything, then every penny spent on something is another penny that can't be spent on something else. We become paralyzed; everything becomes nothing.

The natural next step is that we simply become hoarders. If our savings account is for everything, then there's no amount of money that's enough. After all, everything is a lot of money.....infinite money. Thus, we simply hoard.

Then, if we're hoarding money into an "everything" savings account, there's a series of opportunity costs:

• We don't actually save for our future needs in life.

• We feel guilty for spending money on wants.

• We don't get around to investing for our future.

• We don't even get close to opening up our generosity.

Everything stalls at the blind saving.

Here's my suggestion. Open a series of savings accounts. Name them. Give each a purpose. Needs savings. Wants savings. Then, in your monthly budget, specifically allocate money to them. Actually fund them. If you say you're going to save $500 in your Travel Fund savings account this month, move $500 into your savings account this month.

Once that happens, it's technically already been spent: travel. Therefore, there's no doubt what that money is to be used for. It's sitting in a dedicated savings account specifically for you to enjoy on a trip. No guilt. No second-guessing. No doubts. It's already been saved. Now, enjoy! The same goes for every other category. Be specific. Be intentional. Don't psych yourself out. Honor the promises you made to yourself.

This one little hack can transform our relationship with money. I encourage you to give it a shot!

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The Benefit of Hindsight

I received several angry messages from buddies regarding my recent post about why we shouldn't time the stock market. These buddies, of course, are "investing experts." They are mirror images of the man I covered in the previous post. They believe what he believes and acts as he acts. Here's what one of them said (excluding the expletives):

"You can't invest today in good faith. The &%$#@!& market is far too expensive. Every dollar you put in is begging to be lost. Stop giving your readers &@$#% advice!"

I present to you Exhibit A:

This is a graph of the U.S. stock market (S&P 500) since 1/1/2000. As 2000 unfolded (far left side of the graph), due to the tech bubble, the stock market hit unprecedented levels of "too expensive." The market was clearly overvalued, and experts warned that it was too high to justifiably invest.

Do you see where this is going? Yeah, while the market felt a bit rich in 2000, with the benefit of hindsight, it now looks cheap. In fact, today, the stock market is 4.4x higher than it was at the peak of "too expensive" in August 2000.

It's not all roses and sunshine, though. What you'll see if you look close enough at this graph are the following rough patches:

• 46% loss after all-time high in August 2000

• 54% loss after all-time high in October 2007 (second-worst crash in history)

• 32% loss after all-time high in January 2020

• 25% loss after all-time high in December 2021

• 20% loss after all-time high in January 2025

And today, after the stock market hit a new all-time high in September 2025, we're back in the same position. Will we get our butts kicked again? Absolutely! However, with the benefit of hindsight, today's all-time high will eventually look cheap.

I say it over and over again, but please don't let the naysayers (or "experts") scare you into fear-based decisions. History always has a way of taking care of itself.....eventually. The benefit of hindsight will soon prove your patience right.

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Thanks For the Pain!

Some days I have to find my writing inspiration, and some days my writing inspiration finds me. Today is an example of the latter. As I was casually scrolling my social media feeds yesterday, I stumbled upon a post by my friend Teresa. She owns a successful business and continues to grow more excellent each day. Here's an excerpt from her post:

"I'd like to once again take a second to thank my previous employer for laying me off. Every knockdown is just an opportunity to come back even stronger."

Her story is wild, and similar to many epic stories of success, it involves profound pain. It would be so easy for her to wish away all the junk that's happened to her, but at the same time, that same junk is what set the table for what has become a beautiful story.

Had she not experienced the pain, uncertainty, and stress of a layoff (with a baby at home, mind you), I'm not sure she would have developed the vision and courage to launch the business she's now blessed with. Comfort might have lulled her into complacency. "Good enough" could have been the motto of her prime years. She might have conceded that mild misery is an acceptable way to traverse this thing called life.

Instead, though, pain met her head-on! The pain knocked her down, forcing her to take a hard look in the mirror; a glimpse in the mirror she might have avoided if things were merely "good enough."

I can relate to Teresa's experience so much, and I have a feeling many of you can, too. One of the worst experiences of my life was being 3.5 years into my dream career and learning that my company was being shut down. I had also been engaged to my wife for just three days (yeah, that was fun). I had my comfortable life all planned out when I woke up that morning, but by the time I went to bed, I was hurt and scared.

Fast forward 17 years, and I can now confidently say that the most profoundly painful experience in my life was the beginning of the most beautiful journey. NONE of what I have today would be without me having gone through the pain, suffering, and uncertainties brought on by that debacle.

Thanks for the pain! Cheers, Teresa! From one hurt friend to another, I'm so glad you're a living, breathing example of what it looks like to use one's pain for good. People are watching. People are noticing. People will continue to be impacted by your example. Keep pursuing excellence!

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Someone Should Check On Him

I had a doomed conversation in early April. One of my friends, a self-described investing expert (but with a bunch of suffixes after his name to back up his mouth), made a dire proclamation to me. In his words, "the stock market meltdown has begun.....it's time to go all cash." Translation: He, in all his brilliance, was predicting an immediate, all-out stock market crash and planned to sell all his investments to avoid losing money. Further, with his masterful wisdom, he was telling everyone around him (including me) to do the same.

Here's some added context. When he shared his "expertise" with me, it was in the midst of the great tariff scare of 2025. The stock market had experienced a few bad weeks, and people were anxious. The overall stock market was down nearly 20% from the all-time high it experienced just six weeks prior. That's when he sold.

My buddy had personally lost $200,000 (around 17%) and was now sitting on about $1,000,000 of cash in his portfolio. According to him, he was going to let the market continue to crash, and he would swoop back in to "buy the dip."

Five months have passed since he made this decision. Wanna know where we stand today? The market is up approximately 40% since he sold all his investments. 40%!!! The market has hit 24 new all-time highs since his bold proclamation, including a new one yesterday afternoon.

Had he simply done what actual wise investors do (nothing!), his $1M portfolio would be up by $400,000. In his desire to be smarter than everyone else and try to play games with the market, he lost out on $400,000 (!!!!) of upside. All he had to do was nothing. Literally, nothing. When I explained to him that his strategy has a terrible historical track record, he laughed. Today, he's $400,000 poorer because of it.

Someone should check on him. Well, I actually did yesterday. Let's just say "frustrated" would be a gross understatement to describe his state of being. He was so sure he was going to outsmart the market this time. He would have bet his life savings on it. Strike that, he did bet his life savings on it.....and lost.

He's at a loss on how to move forward. Does he now wait until the market falls? Does he just lick his wounds and get the money back working for him? Both options feel like a loss to him. These are the psychological implications of trying to play these sorts of games.

Here's what I told him: "What's done is done. You can't go back and get a redo. However, you can promise yourself you'll never do this again. Call it an expensive lesson. Humble yourself. Don't try to be smarter than everyone else. Invest your money and leave it invested. The market will take care of the rest....eventually."

We'll see where he goes from here, but it's a cautionary tale for all of us. The best investors in the world are the ones who know they aren't smarter than the market. Patience beats brains every day of the week. I have 155 years of history to prove it. Today is a great day to do nothing, and tomorrow is a great day to do nothing, too.

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Where Does It Go?

Let's dabble in the theme of death again, shall we? An interesting question was recently brought up in a group conversation. "Where do you want your money to go when you die?"

Everyone around the table quickly and instinctively answered:

• "Evenly between my kids."

• "Split between my kids."

• "To my kids. Evenly, of course."

• "50% to one kid and 50% to the other."

All four people had the exact same answer, without thought or hesitation. "Why?" I asked the group.

• "Isn't that what everyone does?"

• "Because that's what I'm supposed to do, right?"

• "I never thought about that question."

• "Are there other options?"

Nobody had a good reason. By default, we instinctively believe that splitting our assets evenly between our children is the best and correct path for each of us. But why?!?!? Nobody really seems to know.

I have lots of thoughts on this topic.......which I will share in due time. Today, though, I want you to ask yourself the same two questions:

• "Where do I want my money to go when I die?"

• "Why?"

Caveats to this question:

• Unless we're a mixed family, it's almost a given that our first beneficiary is our spouse. My question applies to the next level, after your spouse. Assume you're both gone.

• Assume your children are grown. This isn't an I-die-while-my-kids-are-young type question. Kids are grown and independent adults (i.e., they no longer depend on your financial care).

• You have something to give. Don't assume you'll have nothing. Let's pretend there's something of substance left when you pass.

Please take five minutes to think about this topic today. Really think about it. Throw all preconceived notions out the window and start from scratch. You have a blank canvas and can paint any picture you want. What does it look like? Please feel free to share your answers with me…..or keep it to yourself for now. If you want to share, you can hit “reply” to this e-mail or drop a comment at the bottom of the webpage. Then, tomorrow, I'll send part two your way (including my own perspective).

Have an amazing day, full of meaning and impact! Also, don't die. Not yet. There's still so much good work to be done.

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Deeper Than We Think

I received a bevy of criticism after yesterday's post. To summarize, I shared the story of a friend who is continually scared to spend money on wants because, all his life, he has been told that spending on things we don't need (especially expensive things) is "irresponsible." I challenged him to buy a $500+ ticket to watch his favorite team play in person for the first time ever.

The criticism:

• "You're encouraging people to be irresponsible!"

• "You should be telling people to save money not waste it."

• "Good luck retiring someday."

Do you see the irony in this? I write a piece about how a grown man who has done a wonderful job with finances is terrified to spend money on anything fun because all he's been told his whole life is that spending on wants is "irresponsible," then immediately receive a string of responses telling me that he's being irresponsible (and I'm as equally irresponsible for egging him on).

This stuff runs deep, guys! In our culture, we tend to hear the stories about people who are out there recklessly spending; it's almost become a joke. They are certainly out there! Part of the reason we talk about it is that it's so public. We often see the public side of these decisions: big, shiny, new, exotic, and fancy purchases plastered all over social media.

However, those who suffer on the other side of this coin typically suffer in silence. They often feel guilty, sometimes embarrassed, about not being able to spend money on wants. Years and years of criticism are taking their toll. Those words heard when they were children and teenagers sound as loud in their heads today as they did when first spoken.

A few encouragements today:

• If this is you, you're not alone. Find a way to break through, even if just something small. A start is a start.

• If you have influence over someone, and I suspect you do, encourage them to spend some of their resources onwants. Not all.....some.

• Lean into YOUR values. Don't spend money just to spend money. Find what matters most to you, and invest those dollars there.

• Enjoy the process!

• Have an awesome day.

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Book It

I was having a coffee with a friend. Let's call him Bill. Bill is in his 40s, humble, disciplined, and by all accounts, financially successful. His family floats somewhere in the middle class. They don't lack, but at the same time, they don't live a showy life. Bill's family is what I'd refer to as a fairly normal suburban American family.

Bill is terrified to spend money on things that matter to him. If he needs it (truly needs it), it's no big deal, done. However, whenever something veers into the want camp, especially if the price tag exceeds $100, he cowers. His hesitancy isn't caused by a lack of resources or difficulty prioritizing expenditures. He and his wife have made great financial decisions and don't need to worry about drastic negative consequences.

Rather, his mental and emotional roadblock stems from childhood. For decades, he heard the same message: "Don't spend money on things you don't need." "Don't be irresponsible." Thus, Bill views spending money on wants as taboo.

Bill loves his favorite sports team. LOVES them! During my recent conversation with Bill, he confessed that he's never actually seen his team play in person. Why? It's a want....and wants are irresponsible.

"Book it!" I exclaimed. "Buy a ticket and go." Not only that, but I encouraged him to buy a high-quality ticket. The good seats! I took it one step further. He wasn't allowed to spend less than $500 on the ticket. The mere thought of this idea made him sweat. Not only was I asking him to spend money on a want, but to do it in a big way.

Bill actually followed through! He bought the ticket for his team's first game of the year. Not only that, but he bought an amazing ticket. Fast forward several weeks, and the game arrived. That was last night.

It was a night to remember for Bill. It was everything he dreamed of these last four decades, and more. What about the money? Shockingly (to him, not to me), he doesn't feel like spending that money will negatively impact him, nor does he feel "irresponsible."

I couldn't love this more. It might seem like a silly hurdle to overcome, but this is a crippling problem for millions of people. Sometimes, you just need to book it. It's important that we practice the art and science of spending money on wants. For some, it comes naturally, but for others, it's one of the biggest roadblocks of our lives. If we can learn to do this freely, but within reason, it can unlock so much meaning in our lives.

Book it. Just book it. Try me on this one.

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Give An Inch, Take a Mile

We have a podcast called Meaning Over Money. From March 2021 through March 2025 (more than four years), we published two episodes per week, every week, without fail. We didn't miss a single episode for 419 episodes. Then, something happened: We decided to take one week off. Just one week!

The problem is that every time we give an inch, they will take a mile. In this case, by "we," I mean Cole and I, and by "they," I mean Cole and I. We gave ourselves an inch, and we took a mile. Our "we'll just take off one week" quickly grew to two weeks. Then, after just one episode, we took another three weeks off. Episode. Then a few more weeks. Episode. Then another few more weeks. Episode. Then, lastly, we had a near three-month gap.

Just like that, we self-sabotaged ourselves right under our own noses. Now, it's fair to admit that both Cole and I had a LOT of life going on. Travel, parenting, work, marriage, ministry.....all the good things. However, it's amazing how we'll use even the smallest excuse to derail ourselves if we allow ourselves.

This is one of the reasons why I've published on this blog for more than 1,000 consecutive days. I know myself well enough to know that even one day off could be the gateway to a month off. Give an inch, take a mile!

Sure, it's evident that if we miss one day, we can always jump back on the horse with little harm. That's quite true. However, our human instinct will always pull us away from our endeavors when this happens. It's sad, but true.

This isn't me saying that perfection is the answer. Perfection kills more dreams than mistakes do. Instead, what I'm suggesting is that we need to be aware of how apt we are to self-sabotage our own best interests. We'll self-sabotage our dreams like it was a trip to the dentist. That's how deeply wired this concept is in our human psyche.

So, today, draw a line in the sand and don't give yourself an inch. Whatever that project or endeavor is, stay the course. Follow through because that's what you do. You're a follower-through'er. Then, tomorrow, you'll do the same. One flawed, imperfect step at a time.

If you've never listened to our podcast before, I invite you to check it out. Today’s episode is about this very topic of self-sabotage. You can find it on APPLE, SPOTIFY, or wherever you listen to podcasts.

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The Discomfort in Comfort

During the same conversation that sparked yesterday's post about the willful pursuit of discomfort, one of my friends shared something interesting. He pointed out that there's an irony in our culture's pursuit of comfort—specifically, the pursuit of material comfort (stuff and status). The more we pursue material comfort, the more uncomfortable we actually become.

Here's how this plays out. I'll pretend I just purchased an expensive car. To pull the trigger, I probably had to spend some cash on the down payment. That cash expenditure results in me having less cash in the bank, which is a form of discomfort. Second, I now have a large monthly car payment, reducing my available monthly take-home income, which is a form of discomfort. Now that I own this nicer car, I need more expensive insurance coverage. This added expenditure is a form of discomfort.

Now that I'm driving around in an expensive car, I'll probably keep my head on a swivel, ensuring nobody gets close to it. I'll park in the back of every lot, be careful where I'm going, and constantly keep my eyes out for trouble/damage. This added attention and vigilance is a form of discomfort.

Now that I spend a larger chunk of my financial resources on this car, there are other ripple effects. I'll probably need to make one (or more) of the following choices:

• I'll have less discretionary income for travel or other fun purchases (leading to immediate pleasure discomfort).

• I'll have less money to save for future needs (leading to near-term or mid-term financial discomfort).

• I'll have less money to save for retirement (leading to long-term financial and life discomfort).

• I'll have less money to give (leading to internal discomfort).

Yes, the new and fancy car is comfortable....very comfortable! However, the consequence of pursuing this new version of material comfort is several other forms of discomfort. That's ironic, and sad!

I don't usually chat with people while they're living in the honeymoon phase of their comfort-driven decisions. Rather, I typically spend time with them after they've experienced the shadowy, discomfort-laden side of these decisions. It's not always pretty on that side.

Pursuing comfort is rarely what we're actually seeking. Instead, pursue meaning. Violently pursue meaning. That will occasionally lead you to spend money on things that can make you comfortable, but more often than not, it will lead you in some surprising directions. Please don't allow your pursuit of material comfort lead you into these unintended consequences. Life is too short to deal with that!

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On Brand

On the heels of yesterday's post about bougie purchases, I ran into a friend today mere hours after he had read that post. He shared a few thoughts about the post, then asked me about a recent bougie purchase I've made. I told him that I recently purchased Twenty One Pilot concert tickets for my family right around Finn and Pax's ninth birthday; they weren't cheap!

He looked at me for a few seconds, then responded, "Seems on brand."

"On brand." He's so right. Knowing me, it didn't surprise him that I dropped a good chunk of money for Twenty One Pilot concert tickets. In his perspective, that's exactly the sort of bougie thing my family would do. In other words, our version of bougie tightly aligns with our family's values and interests.

I also heard from a handful of readers about their version of bougie, and in every single situation, it seemed "on brand." That's a great tell! When our behaviors align with our values, we can be confident that we're making decisions that add value to our lives.

Where many people go astray is when they make culture-driven decisions that don't actually align with their values. They do things because that's what other people are doing. From the cars they buy, to the clothes they wear, to the neighborhoods they live in, to the trips they take. Without even realizing it, we allow the prevailing culture to dictate how we use our precious resources.

So, when my buddy called my bougie decision "on brand," I took that as the ultimate compliment. Whatever you're up to, whatever you're spending money on, whatever you're investing time/energy into, ask yourself the question, "Is this on brand?" If the answer is "yes," do it with confidence!

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Bougie to Thee, Not to Me

One of the most interesting aspects of my coaching business is having an opportunity to see behind the curtain of hundreds of people's financial lives. What's coming in, what's going out, and how all the pieces fit together. Most intriguing, though, is getting a front-row seat to how people perceive money. With that context in mind, I have a question for you today: What is bougie?

To start, here's the formal definition of the word: "relating to or characteristic of a person who indulges in some of the luxuries and comforts of a fancy lifestyle." In other words, bougie can be used in reference to an expenditure that's a bit (or a lot!) over-the-top; something that transcends fulfilling a mere want, and into a completely different category.

Here's another fun part of my coaching. Nobody agrees on what is considered bougie, and people rarely admit that their own decisions, actions, or purchases are bougie. Translation: Bougie is something above us that other people are partaking in.

Let me share some real-life coaching examples with you, and you can decide for yourselves. Are the following expenditures bougie?

• $25,000 for a trip to Disney

• $2,500/month on groceries

• $90,000 for a family vehicle

• $1,500/month on dining out

• $2,000/month on clothing

• $1,800/month on beauty treatments/procedures

• $1,000+/month on pets

• $5,000/month on housing (in a non-high-cost-of-living city)

• $600/month on work lunches

• $2,000/kid for Christmas gifts

These are all real-life examples I've encountered just in the past 12 months. What's your gut reaction? For each of these items, my suggestion that they are a form of "bougie" was met with shock or confusion. For those who made these decisions, these were run-of-the-mill want decisions.....even borderline "needs" in their minds. What say you?

Again, this is what makes behavioral science so interesting to me. Never underestimate our ability to shape our perspective of a broad reality based on our own narrow purview (or specific desires).

I'm not necessarily criticizing people for their decisions. After all, it's their journey, and they will reap the consequences of their choices (for better or for worse). My role isn't to tell them what to do, but rather, help them understand what they are really trying to achieve, and execute it with excellence. Where my criticism lies is how we humans so often tell ourselves a story to fit our own narrative. We can take something bougie and turn it into a mere want, then take this mere want and turn it into a need. We're so good at this (me included!).

I think the most important thing we can each do is be honest with the person we see in the mirror. Name things for what they are. Recognize bougie for bougie, a want for a want, and a need for a need. Then, through that honesty, make the best decision for our journeys. When we do, we'll make crisper decisions and go all-in on things that actually add value to our lives.

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