Every few days, Parker will say something that stops me in my tracks.

I first noticed the shift a few years ago and didn’t think much of it. Kids experiment with language.

But over time, the pattern sharpened. The frequency increased. And now it’s hard to ignore.

It happened again this past weekend.

“Boys are weird.”

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It lands harder each time.

Other variations have popped up too — “crazy,” “chaotic,” even “psychopaths.”

At first, it sounds like harmless shorthand, the kind of blunt observation kids make as they try to understand the world. But repeated enough, silly sayings have a way of settling into lifelong beliefs.

That’s where my concern begins.

This isn’t about policing a phrase or overreacting to a moment but about recognizing how language, especially repeated language, quietly shapes perception.

What starts as “boys are weird” can, over time, become a default lens that filters new experiences. The brain is efficient like that. It notices what confirms the pattern and overlooks what doesn’t.

Left unchecked, that kind of thinking doesn’t just describe reality — it distorts it.

I’ve seen the progression up close. There was a time when Parker just wanted to play … with anyone. Then, somewhere around first or second grade, the separation began.

Boys over here. Girls over there.

It’s a typical transition, but it’s also when kids start sorting people into groups instead of seeing individuals. Tribes form. Lines get drawn in the sandbox.

Now, as sixth grade winds down, Parker says things like: “You guys crash out too much.”

Some boys do act in ways that are confusing, loud or immature — just as some girls do. The issue is the leap from behavior to identity. From “that was weird” to “they are weird.” A small linguistic jump with outsized consequences.

Because once identity gets attached, curiosity often disappears.

That’s the habit I want to interrupt. Not her voice, but the shortcut her thinking is starting to take. The goal isn’t to correct her into silence but to guide her toward seeing people as individuals first, patterns second.

We’re living in a time where broad generalizations between men and women are getting louder, sharper and less forgiving. In some corners, the divide is framed as inevitable, even justified.

That’s not a mindset I want Parker to inherit unexamined.

The way she learns to talk about people now will shape how she relates to them later. And reducing people to categories rarely leads anywhere constructive.

If she learns to reach for labels first, those labels will start doing more of the work than she does. If she learns to slow down and look at what actually happened, she’ll carry that habit with her into friendships, into conflict, into everything that involves another person.

That’s what this really is for me. Not correcting every phrase, but paying attention to her thinking while it’s still forming.

Because it becomes habit long before it ever looks like one.

A funny Reel made the rounds on Instagram earlier this year.

The headline alone was handmade for Money Talks: “It will cost you $15,000 a year to have a girlfriend,” it read.

In the 2 1/2-minute clip, a young man describes what he calls “the bare minimum boyfriend.” He breaks down what guys must do as a boyfriend — and how much it will cost monthly and annually.

It’s a comical rundown, only I don’t think the guy is joking.

Check it out, and judge for yourself.

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If ever there was a Money Talk that I didn’t belong at the table, this is it.

The man in the video breaks down a woman’s routine maintenance and needs like they’re monthly bills.

💸 $250 a month for hair

💸 $150 twice a month for nails (manicures and pedicures)

💸 $80 for lashes once a month

💸 $150 for dates once a week

The rundown probably sounds ridiculously inflated to most people reading this, but the Reel received 100,000 likes. The man must have struck a chord.

I had no idea and never subscribed to such behavior, which is probably why I’m single. But plenty of men do, and there’s a new sucker born every day.

More power to them.

But in what world is it a man’s job to pay for a woman’s upkeep, especially his girlfriend’s? That’s not among the things I was taught about money, and it’s not what I’m teaching Parker.

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Near the end of my last relationship, I stumbled across a phrase that said, “Men save money being single; Women save money being in relationships.”

Only then did I even give the gender roles much thought. I had grown tired of paying for dates with strangers. I never considered — or cared about — the financial undertaking when in a relationship.

Those societal norms and expectations make me think twice about jumping back into these dating streets.

There’s a real cost attached — and it’s far greater than financial.

There’s time, which is the No. 1 resource I no longer squander. Energy, both mental and emotional. Effort, which could go toward other productive things. And attention, which is always finite.

It all adds up.

There’s more.

A different Reel that I saw recently isn’t as humorous, but it hits the nail on the head. It gets to the heart of what a real relationship is all about, and you won’t hear the words “mani” or “pedi” anywhere in this 53-second clip.

In the video, a man shares that a great relationship isn’t free and will always cost you something. He started with his pride and ego, saying it only works if both are equal and on the same team.

“It cost me my arrogance and self-centeredness,” the man said. “Don’t tell me you want a passionate and connected relationship with low conflict, but you aren’t willing to pay the price for it by learning how to listen and validate each other’s pain.”

Whew.

“Don’t tell me you want intimacy inside of the bedroom,” he said, “but you aren’t willing to fill their emotional bank account outside of the bedroom.”

Bars!

This is a Money Talk that is so much bigger than money.

Always has been. Always will be.

So before you tally up what dating or a relationship is “costing” you, ask yourself what you’re actually investing — and what kind of return you’re creating.

If you’re single, maybe the question isn’t what it’s going to cost you to date, but what habits you’re bringing with you that make connection expensive in the first place.

If you’re in a relationship — happy or not — take inventory. Not of what you’re spending, but of what you’re withholding. Time. Attention. Patience. Accountability.

Because most relationships don’t fall apart over $150 dinners or $80 lashes. They fall apart over missed calls, short replies, half-listening, ego and effort that quietly fades.

And if there’s a real price to love, it’s not on your credit card statement. It shows up in the moments you don’t think to count — the text you don’t send, the apology you delay, the conversation you avoid.

That’s the bill most people keep running up.

At some point, it lands in your hands.

The question is whether you’re finally ready to pay it — or keep pretending it’s not yours.

I used to think about turning my old dating adventures into columns — but never seriously.

It always felt a little off, like I’d be turning private moments into superficial click-bait. So I left it alone, and for much of the past four years I wasn’t in that world at all.

Then I got out of a long-term relationship and found myself back in these dating streets.

Now there are things the new me can’t unsee: how quickly time gets allocated, how expectations form almost immediately, how money starts moving in ways you don’t notice until you add them up later.

Seen in that light, talking about dating openly stops feeling like sleazy storytelling and starts looking like what it’s always been: another Money Talk.

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And it’s rarely dramatic in real time.

One drink turns into another. A conversation runs longer than it needs to.

The downside is it adds up. Time, mostly. But money and energy too.

But the reality is I’ve got more of all three now than I used to. More time, more space and more resources. At some point, you’ve got to do something with it. I’ve still got to live.

So I’m back out here.

Not with any big plan or reinvention of how I do things. Just back in it, figuring it out as it goes, like most people do.

I don’t want Parker to make the same mistakes, so maybe keeping romantic lessons to myself isn’t the best idea.

Although she did fall over in her bed and play dead when I asked her thoughts about me dating again.

Still, think about how much money gets wrapped up in courtship, dating, engagements, marriages and divorces.

And how much of the fallout, emotional and financial, could be softened if people were just a little more honest early on.

I owe Parker that, in an age-appropriate way, whether she’s enthusiastic about it or not.

And I don’t mind dating. Not when it’s respectful and reciprocal. I learn people, I learn myself. I end up doing things I wouldn’t normally do, and I usually walk away with a story worth keeping, one way or another.

But dating has never been cheap, and it’s only getting more expensive.

Recent data from the BMO Real Financial Progress Index revealed that Americans spend $189 on an average date, including pre-date grooming and gas money, up 12.5% from $168 in 2025.

Forty-seven percent of singles say dating is not financially worth it.

We’ll see. This will be my first time truly dating in my 40s, so I’m interested in seeing what that looks like from here.

There’s a drawback to stepping out as this version of me, though, and it has nothing to do with my age.

It’s simply that I don’t move like most people anymore.

I’ve committed to doing things most people won’t, which naturally narrows the field. So the question becomes less about who’s out there and more about who actually fits the way I move.

That’s a much smaller number than it used to be.

And I feel it — in what it means for the wife and life I want.

But there’s only one way to find that person and build that life. So I’m back in these dating streets, embracing experiences.

Maybe I’ll write about a few of them along the way.

“If you want to make God laugh, tell Him your plans.”

Triest is gone.

She left.

And I … I …

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It already feels like a distant memory.

Between one geopolitical headline after another, it’s easy to forget how strong the market actually was to start the year. But Q1 ran hot, especially in January and February, and that forced me into a decision I don’t naturally make.

I took profits.

I trimmed my position in VTI, the Vanguard Total Stock Market Index Fund ETF.

Not a full exit. Just enough to skim some off the top while the market was sitting near all-time highs.

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That decision carried more weight than it probably should have.

Because I’ve been on the other side of it before, holding too long, watching gains disappear and wishing I had secured profits when I had the chance. So this time, I told myself I would.

And I did.

But it didn’t feel clean.

Frankly, it felt like I was trying to time the market.

What if the market kept rallying? What if I stepped out too early and had to buy back in higher? Would I even know when to get back in? And more than anything, could I trust myself not to take that money and chase something worse?

That was the tone for most of the quarter: conflicted.

Not unsure of what I should do — but uncomfortable actually doing it.

There were some clear wins mixed in there too. On Feb. 12, I deposited the final $1,635 to fully fund my Roth IRA for 2025 — the second year in a row I’ve done it. This money move now feels less like a stretch of the imagination and more like a standard. And the consistency is quietly doing its job in the background.

That part felt right.

The rest of this quarter wasn’t nearly as clean, but I was more intentional than I’ve ever been.

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I didn’t expect the best money move I made in March to show up in a small Amazon box.

But on March 25, it did.

Two days earlier, I finally bought a smartwatch, something I’d been considering for at least six years. I’d always come to the same conclusion: “nah, I’m good.”

I’d gone this long without it, so why start now?

But I was tired of carrying my phone everywhere just to track steps. Tired of guessing how well I slept. And tired of having no real system for something I keep saying matters most: my health.

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So I kept it simple. I found one on Amazon, hit “Buy now” and two days later it was on my wrist.

Setup took 10 minutes. No stress. No overthinking.

And honestly? This thing is amazing. It’s exactly what I needed.

It’s the Amazfit Bip 6 Smart Watch (14mm). It has a 14-day battery life, and at $79.99, it didn’t require much internal debate — or a payment plan.

The battery life alone feels like a win. I charge it and forget about it for days. In an age where everything can feel like a drain, that’s a small miracle.

It tracks my steps, which has turned into a quiet competition with myself. I’ve absolutely paced around the house at night just to hit my number. No shame.

It tracks workouts, too — whether I’m at the gym or convincing myself a long walk counts as cardio.

It tracks my sleep, which has been… humbling. There’s nothing like thinking you slept well and then checking your watch and seeing five measly hours. Still, it’s made me more aware, and that alone has helped.

My favorite feature? The hourly reminder to get up and move.

At first, I was offended. Now I respect it.

There’s also the alarm — a gentle vibration on my wrist instead of a loud phone. It’s a much better way to wake up.

But then there are the notifications.

Calls come through, although I haven’t quite figured out how to answer them yet. Social media alerts show up too — which was fine in small doses on my phone but a nuisance on my arm. Those, I’ll probably turn off.

There’s also a little cheat code. If you swing your arms — even sitting down — it counts as steps. I’m not saying I’ve used it… I’m just saying I know it exists.

Here’s the real point.

This wasn’t a flashy purchase. Nobody cares what watch I’m wearing.

But it’s useful. Every single day.

It reminds me to move more. It shows me how I’m actually sleeping. It keeps my health top of mind without requiring much effort.

That’s the return.

March was about learning to say yes — not recklessly, but intentionally. Out of everything I spent money on, including an uncharacteristic $1,000 month of shopping, this was the best decision I made.

It wasn’t exciting. It was quietly brilliant.

We talk a lot about spending on experiences, comfort and joy. And we should. But sometimes the smartest money move is the one that makes the small, ordinary moments of life noticeably better.

This watch does that for me.

Because wealth means nothing if you’re not healthy enough to enjoy it.

Last month, I did something that doesn’t come naturally to me.

I spent more money than I usually allow myself to — and I did it on purpose. Not because I lost control. Not because circumstances forced me.

I did it because I said I would.

Before writing about learning to spend a little, I knew there was only one way to make that message honest: I had to live it. I had to step out of the comfort zone that discipline has built for me over the years and actually practice the mindset I’ve been talking about.

So in March, I walked it like I talked it.

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Most of my purchases go on a credit card so I can rack up airline points. A few essentials — like rent, gas for my vehicle and apartment, electricity and my $10 monthly gym membership — are paid separately. Tracking expenses this way lets me monitor spending in real time, and each month I share my progress, for better or worse.

If you compare my March 2026 spending to March 2025, the difference is clear. I spent more this year. Not dramatically or irresponsibly, but enough that the old version of me would’ve paused or talked himself out of some of these decisions. This version didn’t.

Instead, I leaned into something unfamiliar: permission.

I bought new pillows — the kind you don’t think twice about until you finally upgrade and realize what you’ve been missing every single night. I replaced towels that were perfectly functional but far from enjoyable.

For years, “good enough” has been my standard. March was about raising it, even in the smallest areas of my life.

I added in things that serve no purpose other than making life feel better in the moment — scented candles, scented lotion, a new fragrance. These purchases won’t change my financial future, but they improve my daily experience.

I can’t remember the last time I spent this much in one month on shopping.

I also booked two getaways for April. Nothing over the top, nothing designed to impress anyone. Just intentional breaks from the rat race — something to anticipate, something to experience fully.

That’s what March gave me: small, tangible reminders of what the money is for in the first place.

Because I’m realizing the purchase matters less than the practice behind it.

March wasn’t about pillows or candles or even booking trips. It was about shifting a mindset that defaulted to “nah, I’m good” for most of my life.

No has served me well. It helped me build. It kept me disciplined. It protected me from many of the financial traps that catch people off guard.

But “no,” over time, can also become a limitation.

So March became an exercise in learning how to say yes — carefully and intentionally but consistently.

Yes to comfort. Yes to enjoyment. Yes to choosing what I actually want instead of settling for what simply works.

Yes to myself.

And maybe the timing of that lesson wasn’t a coincidence.

While I was loosening up in March, a financial storm was brewing in the background. By April, it arrived, but that’s for another day. What matters is that I’m prepared.

The years I’ve spent being disciplined — the long stretches of saying no — already positioned me to handle what’s on the horizon. I’m not scrambling. I’m relying on what I’ve built.

I still have the discipline. I still know how to go without. That hasn’t changed — and it’s still my greatest advantage.

But now it’s balanced by the understanding that life can’t only be about restraint. It also has to include allowance.

March didn’t change my finances in any dramatic way. It did, however, change my relationship with spending.

I didn’t go overboard. I simply gave myself permission.

After years of saving, stacking and saying no, March reminded me that the whole point of this journey is having the freedom to say yes.

I’ve learned I have an advantage when it comes to money, and it’s not what you think.

It’s not a secret strategy or some hot stock tip.

It’s simply that I can go without.

I never considered the power in carrying that mentality before I started this journey. Going without has always felt natural to me. Most things don’t tempt me long enough to become a decision. The kinds of trappings that derail other people financially rarely get a foothold with me.

That’s made a bigger difference than anything I’ve ever calculated — or any strategy ever could.

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I don’t need much. I probably want even less.

I’ve built a life on discipline. On saving. On cutting back. On being responsible.

And it’s worked.

But my advantage doesn’t end there. I’ve also lived. Really lived.

I’ve traveled the country and around the world. I spent the first half of my professional life in entertainment, a world full of energy, access and opportunity.

I’ve tasted more cuisines than I can remember, attended more concerts than my ears appreciate and rubbed elbows with people the world calls famous.

Those experiences aren’t just memories. They’re part of who I am. They remind me I’ve been there, done that.

I’ve already seen how big the world can be. Knowing that makes me unbelievably comfortable sitting my butt down and building.

Discipline laid my foundation, but the life I’ve lived gives me the calm to stay put and keep growing without fear of missing out.

Yet, part of building a good life is knowing when to spend.

Not recklessly. Not to impress anyone. But intentionally.

On experiences. On moments. On yourself.

I’m learning to treat myself in ways that feel deliberate, nourishing and completely guilt-free. Not the easiest feat for men anywhere, let’s be honest.

I’ve learned to spend without hesitation or regret on rest and relaxation. Because real rest isn’t a luxury. It’s essential maintenance for the life I’m still building. A weekend getaway, a massage or an afternoon at a spa. They recharge me in ways nothing else can.

I’ve learned to spend without hesitation or regret on majestic memories. The kinds of moments that stay long past the final bill. A few years ago, it was my first cruise. Last year, it was our first daddy-daughter trip to Disney World. Those moments are worth every cent.

I’ve learned to spend without hesitation or regret on promoting peace. Anything that consistently brings me back to myself. My $10 a month gym membership has become non-negotiable, and lately I’ve been thinking about upgrading from the bare minimum at Planet Fitness. I’m also researching wellness retreats.

Before reaching my mid-40s, I did more than I ever imagined I would.

And now? All I want is peace.

My home has become my sanctuary, and more often than not, I have to push myself to leave it.

The very habits that got me here are now threatening to hold me hostage.

But I remind myself each month: get out. Do something. Go somewhere.

Order the meal you actually want. Book the trip, even if it’s short. Maximize the moment.

Discipline is vital, but so is delight. Spending intentionally — on experiences that recharge, memories that inspire and peace that restores — isn’t indulgence. It’s part of building wealth itself.

So spend a little. Enjoy it fully. Then get back to the grind.

Because the goal was never just money.

It was always to build a life worth having.

My first target was $5,000. I pushed myself to grow nothing into something.

Then it was $20,000. Then six months of expenses. That’s the amount experts almost universally recommend for cash reserves, even while research shows that 43 percent of Americans couldn’t cover a $1,000 emergency with their savings.

I never wanted to be like most people. Less than four years ago, I was at rock bottom financially — broke, drowning in debt and directionless. My daughter, Parker, became my inspiration. Life was quickly becoming bigger than just me.

As the youngest of four boys, I was accustomed to being babied. My mother had always been my fallback plan, but relying solely on her — now 78 — was no longer sound. I needed to prepare. I needed a plan. So, I tucked away $334 each month, with one rule: the money was for emergencies only.

Then, an unexpected gift arrived. My mother returned $20,000 to me. The sum nearly doubled the amount I had originally borrowed and repaid to cover divorce debt. That gift pushed me past the $20,000 milestone in liquid cash for the first time in my life, and it almost immediately changed how I thought about money.

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I began calling the savings my freedom fund because as my balance grew, it was important to me to use the money to thrive, not just survive. A magical daddy-daughter trip, for example, will never be skipped due to the possibility of a problem arising. I’m fortunate to feel this side.

If you’re struggling to build your emergency fund, strategies that helped me (before my mother’s benevolence) included tracking spending, canceling unused subscriptions, cooking at home, scaling back on drinking and smoking and finding creative ways to increase income. These are all things I continue to do — because they absolutely work.

By the time you reach this stage — I’ve since doubled that $20,000 — you’ve built so much discipline and routine that the desire for material things fades. Spending starts to feel less like a reward and more like a chore. You begin to play a different game, with completely different rules.

The payoff? It’s transformative.

Here are five ways clearing $20,000 in your emergency fund can change your everyday financial life:

1. Covers unexpected expenses — From car repairs to medical bills, you’re prepared without going into debt.

2. Reduces financial stress — You can make decisions from a position of strength, not panic.

3. Protects your investments — There’s no need to sell stocks or retirement funds during a pinch.

4. Provides flexibility — Whether it’s a surprise expense or a market dip, you have options.

5. Offers clarity and control — You know exactly where you stand financially and can act with confidence no matter the circumstance.

But the No. 1 thing I’ve learned from building a healthy freedom fund?

It’s OK to use it.

It’s a tool, not a trophy. That’s why I grew intentional about what I call it. There are many benefits to building an emergency fund, but mine is designed to give me freedom — the freedom to act, to breathe and to face life’s surprises without fear.

Whether it’s a last-minute trip with Parker, an unexpected bill, or simply the peace of knowing that, finally, I’m prepared, my freedom fund lets me live life on my terms.

A five-figure nest egg is not easy to achieve, or else the statistics wouldn’t be as grim as they are.

First, believe you can do it. Set your goal. Start small. Stay consistent. Every dollar brings you closer to your own freedom fund. The clarity, control and confidence you gain is worth the commitment.

Once you cross the $20,000 milestone, you’ll see it as a turning point — for your money and your life.

Editor’s note: A year ago, I introduced my niece Bryana after she returned from her first trip to Africa, already dreaming about where she might go next. Today, I’m introducing her twin sister, Marilyn Mayberry. The older of the two, Marilyn — like Bryana — graduated from high school last year, and now they are taking very different paths.

Two sisters, only 10 minutes apart, raised in the same home with the same values, are carving out their own directions. Bryana chose higher education, leaving in early March to attend school in Poland, while Marilyn chose a gap year.

On their father’s birthday, Marilyn reflects on nearing the end of that year — and what it has meant to invest in herself and boldly forge her own path.

My father has asked me for as long as I can remember to write down how I saw myself in the future. At the time, I thought it was a pointless thing to do. What was the use of writing down what I wanted to do when I already knew what I wanted to be when I grew up?

But, during my senior year of high school, when it came time to actually make a decision, I realized that knowing what I wanted to be and knowing how to get there were very different things.

Everything I had thought about for my future had always just been the end goal. I knew I wanted to make art, but I had no idea how to do it sustainably. There were careers I was mildly interested in, but they were never things I was passionate about.

This began a cycle of doubt no one else in my grade seemed to be experiencing. I had goals and dreams, but I had never thought about what I’d need to do to actually reach them. It didn’t help that I was prone to procrastination or that I struggled with putting myself out there, and I didn’t know how to ask for help or explain my thought process until it was too late.

All of this, and the fact that going to college would feel like a waste of money if I didn’t know what I wanted, is what led me to waiting till the last minute to admit that I wasn’t ready for college, and eventually led to my decision to take a gap year.

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During my research on what to do during a gap year, I was stuck. Most of the articles I read and videos I watched suggested going on a trip — something I couldn’t afford, or getting a prestigious internship — which was difficult when I didn’t know what I wanted to do, and a myriad of other things I wasn’t interested in, and didn’t know how to start.

I eventually decided I would stay home and work instead of doing something extravagant, to save money and adjust to adult life, but I still wanted to do what all of these people seemed to do: they found experiences and opportunities that helped them grow as people, often in ways they wouldn’t have been able to while in school.

I spent the first few months after graduation trying to settle into a routine that wouldn’t have me sleeping in or lounging around all day. So, I finally did what my dad had suggested. I sat down and thought about what I wanted my life to look like in the future.

I knew that I wanted to focus on the things I enjoyed, but also be stable financially, which was difficult when I knew living as an artist isn’t easy. But I was determined to use this break from school to work on the life I wanted.

I’ve been working two jobs during this year — one that I started toward the end of high school, and while it didn’t pay very well, I stayed to have additional income. The other paid better and was in a field I’m interested in — early education, at a Montessori school.

Having two incomes was a good way for me to save money, and it helped that I could stay home and not pay bills right out of high school, which I’m incredibly thankful for.

I was able to save the money I made at the higher-paying job and use income from the other as spending money, while still keeping it within the financial limits I set for myself.

I learned to track my spending in an app, something I had never thought to do before, and it helped with impulse spending when I knew I would have to write down why I spent that money later on.

Working so much has been a good chance to focus on earning and saving money and learning to work in different fields, something I wouldn’t have had time for if I was in school as well.

But even while I was earning money and learning new things, the jobs were taking up my time and energy on things that weren’t my passions. And while I was OK with it at first, it took away from what I wanted from the year.

My dad gave me a good perspective on deciding what my time is worth: Would I rather get paid $8 an hour for a job that didn’t make me happy or spend that hour making something that could earn me three times that?

It gave me a good view on how to prioritize my time for what would benefit me. My schedule, and the coincidental locations of both jobs within a 10-minute walk of each other, allowed enough time that I wasn’t incredibly busy, but my days were still pretty packed.

I would typically leave to catch the bus early to work a morning shift, taking a break at lunch to go home or wait nearby, then going to the Montessori in the afternoon. I’d take a bus home and sometimes have enough time and energy to still work on personal projects.

While my schedule is definitely more than I was doing in school, something about creating my own schedule made it easier and more manageable. Having such a detailed schedule compared to school also made working on my time management an important skill to learn, and using a planner is a habit I’ve grown used to.

As I’ve started prioritizing what was important to me, I dedicated more time to growing my art business, working on a website and applying for places to sell my art. I started to take the time to schedule a day each month to go enjoy time alone at a coffee shop and plan for my month ahead, to reflect on what I had accomplished and how I had been working towards my goals.

Looking back on this year, I feel I’ve met those goals in many ways because I’ve seen growth in so many aspects of my life.

I’m more productive, and my stress levels are way down from when I was in school. I’ve improved with spending and saving money. I’ve gotten much better at overcoming fear and social anxiety, something that held me back too often, and I’ve been able to do all of it because I had time to really focus on myself, which I think is important for anyone leaving high school, gap year or not.

I took time to intentionally learn skills I know I’ll use throughout my life, from big things everyone should try to learn, like managing my time and money, to personal ones, like learning how to do my own hair. I’ve also had the chance to try things I’ve never imagined being able to do, simply because I’ve gotten more comfortable trying new things.

There is so much that has happened this past year simply because I didn’t let fear stop me from going for things I wanted like it used to.

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I messaged someone about the job at the Montessori, got it and have ended up loving it.

I applied to a big art market and got in despite my doubts about it.

I entered my art to sell in a local shop, and I got accepted for that.

I’ve worked on being OK with the possibility of rejection, something that had stopped me from trying things before, and it resulted in me getting closer to my goals simply because I put myself out there.

While I would suggest to anyone preparing for life after high school not to wait as long as I did to make a decision, I think it was ultimately the best choice for me.

I learned to balance work, to have time to work on my art, which has gotten me opportunities that I wanted to make money.

Although it’s not conventional, and maybe not for everyone, taking a break from school is a great opportunity to focus on bettering yourself and to open yourself to new opportunities that will help you for the rest of your life. It’s given me a new view of what I want in life and how to get there.

Now, as it’s nearing the time again to think about the big decisions I need to make for my future, I feel less wary. I’ve had time to explore my interests and find out what works, and it’s given me new perspectives on what I can do.

I want to keep growing with my art business — finding ways to make money from it and get better. I’m considering taking courses for Montessori schooling, a study I’ve gotten to learn more about this year.

I don’t know yet if the full college experience is for me, but this year has shown me that I don’t have to rush on trying to decide my future, and that there are more paths to take than I originally thought.

So, consider taking a few minutes, especially before reaching the last year of high school, to write down where you see yourself next year, in five years, and in 10 years, and what steps you’d need to take to get there.

It might help more than you think.

Loss hits hard, often when we least expect it, rocking our worlds in ways we never imagined.

In Episode 23 of the Money Talks podcast, Parker and I sit down to explore how losing people close to us has left a mark.

This Money Talk pulls back the curtain on the raw emotions that follow a shattered dream. We dive into memories, lessons learned and even my one big regret.

We also honor what was, while finding a way to carry on. The discussion is personal yet universally relatable, offering perspective for anyone who has faced similar experiences.

Episode 23 is an invitation to pause, reflect and consider the lessons and resilience that come from life’s more difficult moments.

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Click the play button below to listen now, or find the Money Talks podcast on Spotify. For your convenience, here is a timestamp of Episode 23:

🎙️ Episode 23 — Timestamps:

0:01: Backstage
0:49: The Money Talks jingle
2:20: Parker shares an important update
4:25: Parker has adopted a new money personality
7:18: Feels about Friday the 13th?
8:45: What y’all reading?
12:15: Dealing with pain, sorrow and grief
21:25: A heartfelt thank you to Parker from dad
22:45: Outro

Editor’s note: This is Part 4 of a four-part series, “What Money Says,” looking at how life’s events — from becoming a parent to starting over after divorce — can reshape our relationship with money. | Part 1: Becoming a parent | Part 2: Buying a home | Part 3: Changing careers

I didn’t think about money when my marriage ended.

I thought about survival. About my daughter. About how I was supposed to rebuild a life I never planned on losing.

The financial side felt distant at first. There was too much to process: court dates, piles of paperwork, conversations that went over my head, documents I didn’t fully understand and didn’t have the capacity to question. I showed up. I signed. I just wanted to move forward.

And then, slowly, reality set in. It showed up in invoices. Court orders. Withdrawals. Loans. Obligations.

And it didn’t stop coming. It still hasn’t.

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Divorce has cost me a small fortune.

Well into six figures — and counting.

Money that didn’t build anything. Didn’t grow. Didn’t return. It might as well have been launched into Lake Michigan.

It’s hard not to think about what that capital could have become now that I actually know what to do with it.

That’s when money finally started talking.

I remember standing in the courthouse during a break, listening as the attorneys went back and forth.

At some point, the conversation turned to what I could pay. My attorney pushed back. Said I didn’t have the funds.

The response came quickly.

“Well tell him to take it out of his retirement.”

I was close enough to hear it. Close enough to know it wasn’t friendly advice.

That’s when money started talking in a new language. Divorce had rewritten the question like nothing else before.

Now, it was different. Sharper. Harder. Colder.

Money started asking: Who do you trust?

It wasn’t myself anymore. Money was just how that distrust showed up in my life. For more than five years, I froze.

I avoided my accounts. Retirement funds sat untouched. Investments went unmade. Interest charges accrued.

Every dollar felt like a decision I couldn’t afford to make — not just because I didn’t know what to do, but because I didn’t trust that it would matter. That it would stick. That I could rely on anything lasting.

It wasn’t just money I avoided. It was myself. Every decision felt like a trap.

Could I even rely on my judgment? Could I make a choice that wouldn’t blow up later? I didn’t know anymore.

I stopped trusting others too. Attorneys, court staff, even the so-called experts I was paying felt like liabilities. Every interaction felt heavy, carrying stakes I couldn’t fully control.

The system was supposed to protect me, but instead, it reminded me how vulnerable I was.

Beyond that, I questioned everything else. Who was I if I wasn’t just a father providing for Parker? What was my purpose?

For years, I didn’t know. Survival mode was where I was stuck.

The mental and emotional toll naturally bled into the financial. I paused my dream career, taking a demotion and a pay cut to fight for my family.

Before long, I lost my passion for the only job I had ever known, ever wanted. Each morning on the elliptical, I watch colleagues I grew up with appear on television, in studios I once dreamed of calling home.

But the world suddenly felt bigger than my own plans, and problems I hadn’t anticipated kept surfacing.

I was suffering in silence, toiling away as both a workaholic and a functioning alcoholic.

But I’ve always been a supportive father, and that’s what kept me going.

I owed it to Parker to provide a life beyond survival. I had to start small. One article. One podcast. One book. One account. One rollover. Tiny acts reminded me I could still make wise choices, and each step chipped away at my insecurities.

Each choice taught me I could trust myself again.

That I could rely on systems if I took the time to understand them.

That money could be a tool, not a warning.

Slowly, I began to see a life beyond simply providing for Parker — a life that was mine to shape, not just survive.

Divorce didn’t just cost money; it reset everything I thought I could count on.

It took time and intention, but now I make each choice deliberately.

And I’ve learned to trust myself. Finally.

Editor’s note: This is Part 3 of a four-part series, “What Money Says,” looking at how life’s events — from becoming a parent to starting over after divorce — can reshape our relationship with money. | Part 1: Becoming a parent | Part 2: Buying a home

Two summers ago, I dropped a sentence on my supervisor that stopped him in his tracks.

“This is going to be my final season covering the Bulls.”

He blinked, trying to process it.

“Does that mean you’re leaving the company?”

I froze, unprepared for the counterpunch. The honest answer was: “I don’t know, but I had to find out.”

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All I knew was that I couldn’t do another season of more of the same.

I had built a career doing work I genuinely loved — covering basketball, telling stories, living inside the rhythm of a professional sports season.

It was my dream job. The kind of gig many people spend their careers chasing.

I lived that dream for 20 years.

But somewhere along the way, the work that once energized me began to feel heavy. I was restless, frustrated, ready for something different.

And once that feeling appears, it’s hard to ignore.

Because changing careers isn’t always about chasing the next opportunity.

Sometimes it’s about acknowledging that what you once loved no longer brings the same satisfaction.

For me, the decision wasn’t about money. It was about meaning and purpose.

Work takes up too much of our lives to ignore when that feeling changes.

Still, career changes come with financial consequences whether you worry about them or not.

Changing careers is one of the few financial decisions that forces you to confront uncertainty head-on. When you step off the path you know, the numbers stop behaving predictably.

The paycheck might change. The timeline for promotions resets. Your value has to be proven all over again.

This wasn’t my first time changing lanes professionally. I’ve shifted roles twice in my career, both times moving from writing into editing.

The first time, I took a pay cut, though a portion of it returned after subsequent promotions. This time, I was luckier — I kept my previous salary, even as I stepped into a new role and a new set of challenges.

For a while, I had no idea what would happen next. I didn’t know if I would even still have a job at the company.

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I remember sitting with that uncertainty and thinking: I could walk dogs, coach youth basketball, do anything that felt worth my time. Money barely registered. It wasn’t that I didn’t care. It just wasn’t driving me.

I was fortunate. By then, I had been investing aggressively for nearly two years and dabbling in stock options for the previous nine months.

I had watched money move faster than I ever imagined, and I carried an almost reckless confidence about my own abilities in the market.

Even with confidence in my investments, uncertainty lingered. Money was no longer just a tool or a reward. It morphed into a life-defining question:

“Are you willing to risk stability for meaning?”

Before this shift, money asked simple, comfortable questions: What do you want? What can you afford?

After this shift, it asked something harder: What matters enough to take a leap — even if the numbers aren’t guaranteed?

I had served my time. Dollars mattered less than what I wanted my life to feel like.

Before / After: Changing Careers

Before the shift:
Money asked: What do you want?

• Stability.

• Predictable paychecks.

• Progress along a familiar path.

• Comfort in routine.

After the shift:
Money asked: Are you willing to risk stability for meaning?

• Satisfaction in work that energizes you.

• Freedom to take unconventional paths.

• Tolerance for uncertainty in exchange for purpose.

• Awareness that every financial choice carries a new weight.

  ---

Of course, not everyone’s career change is as tidy as mine. Some people take leaps without a safety net. Some take pay cuts they can’t recover from. Some don’t know whether they’ll even land a role that brings the satisfaction they crave.

The pursuit of fulfillment can be as messy as the pursuit of a fortune.

But the questions we ask — and the way we answer them — shape the trajectory of both.

Before my shift, money mostly asked about comfort and predictability. After, it asked about courage, priorities and trade-offs.

It forced me to confront what I valued most, what I was willing to risk and what I refused to sacrifice for the sake of perceived stability.

Career changes aren’t just professional decisions. They are financial decisions, emotional decisions and ethical decisions all at once.

They expose assumptions we make about safety, success and happiness, and they force you to weigh them carefully. Some moves will feel reckless. Some will feel overdue. Some will feel like a miracle.

But in every case, money has a voice, reminding you that staying stuck often costs more than stepping forward.

Editor’s note: This is Part 2 of a four-part series, “What Money Says,” looking at how life’s events — from becoming a parent to starting over after divorce — can reshape our relationship with money. | Part 1: Becoming a parent

We were standing in the kitchen chatting and snacking when we heard a strange sound.

It came from the living room.

A steady tapping.

For a brief moment, we wondered if someone had gotten inside.

As we turned the corner, water dripped from the ceiling onto the couch.

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A bathtub upstairs had been left running, seeping into the structure of the house and spilling onto the first level.

By the time we shut off the water, it was too late.

In crisis mode, we rushed back downstairs, moving furniture and salvaging what we could — only to watch the ceiling collapse under the weight of the water.

When I bought my first home, I thought I understood the cost of owning it.

I understood the mortgage.

I understood the property taxes.

I understood the insurance.

What I hadn’t yet experienced were moments like this.

Buying a home felt like the milestone. Signing the papers. Getting the keys. Making it official.

Owning it was something else entirely.

The first surprise came with the bills I hadn’t accounted for: closing costs, new flooring, renovated bathrooms, furniture and decorations.

The purchase price was only the beginning.

💸 Costs beyond the purchase price

• Closing costs — Legal, title and escrow fees.

• Renovations & upgrades — Flooring, kitchens, bathrooms or cosmetic improvements.

• Furniture & décor — Outfitting your new space.

• Utilities — Electricity, water, gas and internet.

• Homeowners association fees — If your community has them.

• Insurance & property taxes — Ongoing, often rising expenses.

• Maintenance & repairs — Plumbing, HVAC, roofing and general upkeep.

• Unexpected disasters — Floods, leaks, storms or other emergencies.

  
  💡 Owning a home isn’t just about the purchase price — it’s about everything that comes after.

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Then came the lessons not on any spreadsheet: two floods, repairs and the slow wear of everyday use.

Still, owning a home meant we had a space to call our own — a place where, despite disasters, we could rebuild, repair and make it feel like ours. It offered a quiet comfort and control that, for some, can make it feel worth the effort.

Houses, however, don’t just sit there quietly. They interact with water, gravity and time — and they charge for it.

Predictable costs weren’t predictable. Utilities rose, taxes increased, insurance ticked up. The ongoing costs stacked quietly, relentlessly, until I realized the math I had done on paper barely scratched the surface.

Buying a home feels like the financial event. Owning the home is the real financial event.

Even the predictable homeowners association fee reminded me that ownership comes with obligations beyond the mortgage. The HOA was a pain for me, and it has scarred me into not wanting one again. Even after the home is paid off, that monthly fee still lingers.

Owning a home taught me something I hadn’t fully understood before: the cost of owning never ends. Repairs, maintenance, utilities, taxes, insurance, unexpected disasters—they all arrive in waves, some predictable, some not, but all real.

A house is not just a purchase. It’s a relationship with expenses that continues long after the papers are signed.

Financially, homeownership can be a terrible investment. Between mortgage interest, property taxes, insurance, maintenance, repairs and unexpected disasters, the money you pour in often outpaces the equity you gain — at least for a long time.

The excitement of owning fades quickly when you realize that each improvement, each repair, each routine bill adds up faster than the value of the home itself.

Homeownership isn’t a milestone. It’s a Money Talk that never stops.

Before owning, money said: “Tell me what you want to spend.”

After owning, it said something different: “Tell me how you plan to fix this.”

Owning taught me that the price on paper is never the full cost, and fees never stop.

Owning taught me that floods, repairs and disasters don’t wait for your schedule or budget.

Owning taught me that every choice carries consequences long after the purchase.

But above all, owning taught me this: buying a home feels like the finish line. In reality, it’s the starting point.

Editor’s note: This is Part 1 of a four-part series, “What Money Says,” looking at how life’s events — from becoming a parent to starting over after divorce — can reshape us and our relationship with money.

Thirteen years ago, I got the biggest surprise of my life.

I found out I was going to be a dad.

Parker wasn’t part of some carefully constructed life plan. There was no five-year forecast, no moment in early 2013 where I decided the timing was perfect. She was unexpected.

But from the moment I knew she was on the way, something else happened that I didn’t anticipate.

My relationship with money changed almost overnight.

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Before Parker, money was mostly about my lifestyle. It funded the things I enjoyed: electronics, video games, new gadgets, nights out, the occasional impulse purchase that made life a little more fun.

I wasn’t reckless, but I was optimizing for the present, living my best life.

If money asked me a question back then, it was usually a simple one: What do you want?

That question works fine when the consequences of your financial decisions mostly stop with you. But once Parker entered the picture, the question changed.

Suddenly money wasn’t about what I wanted anymore. It was about what she might need.

In a quiet but profound way, money stopped being about lifestyle and started being about stewardship.

Some of the changes were obvious. Guilty pleasures started to take a backseat. I still enjoyed technology and the occasional night out, but they stopped being priorities.

Expenses that once felt optional suddenly had competition from things that weren’t — healthcare, savings, childcare and a larger cushion for the unexpected.

Now, at 12, Parker’s needs guide more of my decisions than I ever imagined. The shift didn’t happen all at once. It showed up gradually, as I realized how impactful my choices today will be for her life tomorrow.

Every poor financial decision, whether big or small, wouldn’t just affect my bank account; it would be unfair to Parker. She reshaped the way I manage money, time and priorities.

Before Parker / After Parker

Before Parker:

Money asked: What do you want?
Electronics.
Video games.
New gadgets.
Nights out.

After Parker:

Money asked: What will she need?
Savings.
Investments.
Insurance.
Stability before excitement.

But the bigger shift for me wasn’t really about spending.

It was about risk.

Children don’t just change your finances. They change your tolerance for uncertainty.

Before Parker, risk mostly meant inconvenience. If I made a poor financial decision, the downside might be a tighter month or delaying a purchase. The stakes had been low. I could absorb mistakes.

After Parker, the stakes felt different.

Risk no longer affected just me.

I remember thinking more seriously about things that had once felt distant or abstract: Building a larger emergency fund. Making sure I had the right insurance. Thinking about the stability of income in a way I hadn’t before.

I hadn’t suddenly become more cautious by nature. Someone else now depended on the outcome of my decisions.

Parker made me want to do everything better and work harder for as long as necessary. I wanted to earn more, plan more carefully and give her opportunities I never had myself.

The Shift

• Lifestyle ➡ Stewardship

• Spending ➡ Planning

• Freedom ➡ Responsibility

• Optimizing today ➡ Protecting tomorrow

When you’re only responsible for yourself, financial decisions are mostly personal. When you’re responsible for a child, they become structural.

You start asking different questions. Not just about what today looks like, but about what tomorrow might require. You think more about provisions, stability, optimization and resilience.

Before kids, money tends to ask: What do you want?

After kids, it asks a different question entirely.

What will they need — today, tomorrow and long after you’re gone?

Everything I do now is measured against that question.

There’s a phase in every successful journey that doesn’t look impressive from the outside.

No big wins. No grand celebrations. No dramatic life changes.

Just consistency. That’s the stage I’m in right now.

My February spending tells the story. Compared with February 2025, I spent $809 less this year. And when I looked closer at my credit card statement, more than half of my spending went to groceries and my tithe.

Spending doesn’t get much more mundane than that.

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Right now my focus is simple: buying assets, staying disciplined and avoiding lifestyle creep. Even though my diligence has created a growing monthly surplus, I’ve resisted the urge to upgrade my lifestyle.

Living below my means remains the key to unlocking my long-term financial goals.

Spontaneity has taken a backseat to structure and routine. It hasn’t always felt comfortable. But I can already see the payoff — mentally, emotionally, physically and, of course, financially.

Still, I’m learning balance. I’m working to shake the scarcity mindset that shaped how I’ve viewed money for most of my life.

When you don’t come from money, two things can happen once you begin to acquire it: recklessness or fear.

I’ve gravitated toward fear.

Even in my 40s, I’m still learning how to properly treat myself. As the year goes on, I hope to get better at it.

But what happens when you have everything you want and no longer feel the urge to spend? What happens when living below your means transforms from a money hack into a way of life?

How do you break free from the rigidity that’s led to life-changing results?

This journey is still just getting started. And making money is only the first step. Keeping it is just as important — and I can’t keep anything if I’m careless with it.

So I’m cautious.

Maybe even a little fearful.

But it’s working.

Here are six lessons I’ve learned during this “boring” stage of building wealth.

There’s power in boring habits

I used to think financial progress required big moments. A raise. A lucky investment. Some breakthrough strategy.

Instead, it comes from repetition — tracking my spending every month, investing regularly and resisting the urge to treat every dollar like it’s a reward.

Turns out the boring habits are the ones that actually move the needle.

Buying assets changes how you see money

Once I committed to buying assets, every dollar started talking to me. It asked me a simple question: Spend me or grow me?

That mental shift has made everyday spending decisions much clearer.

Lifestyle creep is always lurking

The funny thing about generating more income is how quickly your life tries to expand around it.

Better restaurants. Nicer clothes. More subscriptions.

So far I’ve managed to keep my lifestyle mostly where it was — and that discipline is the only reason the surplus exists today.

The scarcity mindset doesn’t disappear overnight

Even when the numbers improve, the old instincts don’t vanish.

When you’ve spent most of your life worrying about money, it’s hard to suddenly relax around it. Security takes time to feel real, and I’m navigating this reality on the fly.

Living below your means can become your default

At first, living below your means feels like a financial strategy.

Eventually it just becomes how you live. That can be a slippery slope if you’re not careful. Sometimes I have to force myself to remember that the goal of investing is to improve our quality of life — and actually do it.

Discipline needs a little joy

Structure and routine have transformed my finances, but I’m learning they can also squeeze the fun out of life.

That’s why I’m making a point to build experiences into the year — small trips, dinners and as many intentional moments that break the routine as possible.

I refuse to let the boring days turn into ho-hum weeks, and monotonous months stretch into forgettable years.

Our wealth shouldn’t just grow quietly in an account.

It should show up in our lives, too.

People sometimes wonder why I became a vegetarian.

I tried being veggie in April 2025. But a week later, a friend told me that I could become a pescatarian, and I didn’t know what that was, but she told me that it’s basically where you are a vegetarian but you eat fish.

I thought that was cool, and I told my parents that day and went pescatarian. Recently, I realized that I’m good on fish, and I became a vegetarian.

Many people think it’s because I have to.

Few people think that I wanted to become a vegetarian.

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But here’s the real reason. Well, there are a few.

The main reason is the animals themselves, they are dying for our own good and pleasure. I mean, imagine you had this awesome best friend, like they knew you inside and out and you knew them inside and out. The kind where you know what each other is thinking about at 2:30 in the morning. But the next day they are missing, and they didn’t even tell you that they were leaving. You find out later that a human ate them for a sports game!

Hopefully you feel like that was unfair, because it is unfair.

Another reason is there is more in the world that tastes just like meat. Vegetarian and vegan people are not missing out on much. One of my favorite plant-based foods is Tofurkey. They have many varieties of great plant-based foods. If you know a vegetarian or a vegan person, I would encourage you to get some for them!

The last reason is discipline. I don’t usually stick to something for a long period of time. But when I started, I felt like I could not go on. But after a couple months, I started to adapt to it. And I felt better and was not craving meat that much. Like when I did the 5 a.m. club.

Now don’t get me wrong, I still remember what meat tastes like; really good, but I have to remember why I’m doing this. It takes discipline to give up things like burgers, bacon or fall-off-the-bone ribs, but I’m committed.

It’s another kind of investment because it’s pouring into myself. It’s teaching me how to be patient and helping me to be healthier.

It also saves more money because you don’t have to worry about the price of beef getting higher. Or as my dad says, “Every year, my Doritos are getting more expensive.”

Some other helpful websites and recipes are Forks Over Knives and Beyond Meat if you’re interested in becoming a vegan or vegetarian, or supporting someone you know.

It’s OK to eat meat, even though I personally prefer no one eat meat, I can only change me.

I’m going to try to stay a vegetarian for as long as I can.

I want to do it forever, but honestly, there are times when I don’t want to be a vegetarian.

My plan is to try to help the earth forever — no matter what.

In December 2022, two months into her investing journey, Parker bought her first individual stock.

It was her birthday.

She had just turned 9.

While most kids would have been focused on cake and candles, Parker was digging into charts and displaying conviction.

Her pick? Roblox.

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At the time, the stock was hovering in the mid-$20s, not far from its floor. Parker was buying what she understood.

She knew the platform. She spent hours on it. She knew other kids who did too, which only strengthened her belief in Roblox’s staying power.

So she bought one share.

It took nine months later — until September 2023 — for the stock to retrace back to her entry price. She bought a second share.

Fast forward to last July, when Roblox shares surged to an all-time high of $150 per share. On paper, Parker was sitting on a gain north of 400 percent.

Four. Hundred. Percent.

Naturally, I did what any responsible investing parent would do — I suggested she consider taking some profits.

She refused.

Not out of stubbornness. Not out of naivety. But because she had something many grown investors struggle with: a long time horizon and the discipline to match it.

Parker understood, even then, that time in the market, not timing the market, is what swings the odds dramatically in your favor.

At 9 years old, she already grasped that compounding needs patience. She was comfortable sitting back and letting her assets cook.

That moment — watching her hold steady while I nudged her to sell — said everything about how investing should work.

Today, the stock sits well below its peak, closing Wednesday at $68 — a 54 percent drawdown from its all-time high.

Parker hasn’t panicked (she’s still up 135 percent!).

She barely even peeks at her portfolio.

Another sound strategy.

In Episode 22, we unpack what Parker has learned in her first few years of investing and how she thinks about opportunity, risk and conviction. We also put her framework to the test: When should you jump at an investment? When should you slow down and ask harder questions? And how do you tell the difference between a green flag and a red one?

Click the play button below to listen now, or find the Money Talks podcast on Spotify. For your convenience, here is a timestamp of Episode 22:

🎙️ Episode 22 — Timestamps:

0:01: Backstage
1:19: The Money Talks jingle
2:15: Parker shares a few important updates
9:22: What y’all reading?
14:00: How to spot a good investment?
17:35: Parker’s 5 steps to picking a good investment
19:00: 5 important questions to ask before investing
22:35: Mini-game time!: “Green flag or red flag?”
26:00: One final thought about investing
26:25: Outro

Disclaimer: The information contained on Money Talks is not intended as, and should not be understood or construed as, financial advice. I am not an attorney, accountant or financial advisor. These are my personal experiences, and neither this website, newsletter nor podcast is a substitute for advice from a qualified professional.

Sunday night, Bitcoin broke $65,000, and I shrugged.

There wasn’t a hint of second-guessing or even the thought of panic selling.

Three weeks ago, I decided to go all in on a simple habit.

I’m buying Bitcoin every single day for the rest of 2026.

Not recklessly. Just consistently. A daily, disciplined accumulation.

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This pullback looks like the perfect time to do it. But I’m not trying to time a bottom. I’ve built a routine that removes that question entirely.

By dollar-cost averaging with automated buys, I remove the guesswork. If the price drops, I buy. If it rises, I buy.

And if Bitcoin eventually returns to its previous high around $126,000, every dollar I’m converting today will nearly double in purchasing power.

That makes daily accumulation at these levels feel obvious.

On Feb. 5, when Bitcoin broke $70,000, I committed.

My conviction isn’t only practical — it’s intellectual.

Over the past year, I’ve been studying money in ways I never have before. I recently finished “The Bitcoin Standard,” which followed “Broken Money” and “The Hidden Cost of Money.” Together, they’ve reshaped how I understand scarcity, trust and the very concept of money itself.

I’ve supplemented that with documentaries — “The Hidden Secrets of Money,” “God Bless Bitcoin” and “Money Masters.”

Each one added layers to my understanding and connected dots on how history, policy and technology collide to create — and destroy — value.

The more I learned, the clearer it became: digital money isn’t a gamble. It’s the next logical step.

That growing belief pushed me to take another step: self-custody.

On Feb. 13, I bought a cold wallet to move my Bitcoin into my own control.

For me, that was a line in the sand. A popular catchphrase in the Bitcoin community is “Not your keys, not your coins.” Holding my own keys means stepping away from intermediaries and embracing personal responsibility.

It’s not just about potential upside anymore; it’s about sovereignty. About protecting what I build. About safeguarding my wealth without relying on anyone else.

Practical changes also helped cement the daily purchase habit.

Earlier this month, Cash App rolled out updates that made buying Bitcoin cheaper and simpler: no fees on purchases of $2,000 or more, and no fees on recurring buys.

I’d been paying another platform $29.99 a month since last July just to avoid fees. That charge is set to renew on Friday, and, of course, I’m canceling beforehand.

I don’t know what will happen next.

Bitcoin could dip further. Or it could take off.

Either way, when I look back on 2026, I won’t have regrets.

All indications are that I’ll be glad I leaned in.

Disclaimer: The information contained on Money Talks is not intended as, and should not be understood or construed as, financial advice. I am not an attorney, accountant or financial advisor. These are my personal experiences, and neither this website, newsletter nor podcast is a substitute for advice from a qualified professional.

Fifteen months ago, I was calculating what 75 shares of Hims & Hers Health (HIMS) could be worth if everything went right.

Now I’m calculating how much pain I can tolerate if things keep going wrong.

I started buying around $19 in November 2024. I watched it run. I watched it hit $70. Twice I had real profits sitting there.

Twice I did nothing.

Today the stock is $15. I’m down 39%. And I’m feeling every bit of it.

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Because this hasn’t been a gentle pullback. It’s been one headline after another.

Regulators circling. Powerful enemies taking notice. A stretch where it feels like half of Washington and Big Pharma decided my stock needed to be taught a lesson.

Shares are down more than 50% in a single quarter. More than 60% in six months. Momentum didn’t just stall, it hit me like a cousin slamming down a Draw Four at a cookout.

This is the part nobody brags about.

This is the life of a long-term investor.

This is the risk that comes with picking individual stocks.

This is the peril of never taking profits when the screen is glowing green and your conviction feels bulletproof.

Hims had been riding a wave. Its recent growth leaned heavily on high‑demand treatments, including certain weight‑loss medications. Revenue and enthusiasm were climbing.

Then scrutiny hit.

First, Amazon’s online pharmacy entered the chat as a direct competitor, expanding its offerings in November 2024 that threatened to cut into Hims’ business.

That alone made many investors run. Things have only gotten worse.

Last week, Novo Nordisk filed a lawsuit against Hims, claiming its weight‑loss drug strategy infringed on its patents and harmed its business.

Then the company was referred to the U.S. Department of Justice, amid concerns that its plan to mass-market a low-cost compounded weight-loss drug might violate federal law. The DOJ could pursue civil or even criminal enforcement if violations are found.

A drawn-out court battle could cripple the company. A quick loss would be just as devastating to Hims’ profit margins.

Oh yeah, Hims founder and CEO Andrew Dudum tweeted a 👀 emoji in October, as retail investors were hyping the stock — and then sold a sizable block of shares shortly after, frustrating many holders.

I had numerous chances to exit. For now, I’m weathering the storm.

Of course, none of this should have been a surprise. These risks were always there, quietly waiting in the background. I just hadn’t felt them yet.

When you invest in a company trying to shake up an industry, the wins can be huge. The pushback can be just as intense — and when it arrives, it stings more than you can imagine.

I’ve been on a rollercoaster with this position. I started buying around $19 in November 2024. The stock shot up to about $60. I even took a screenshot to savor the unrealized gains.

By April 2025, it had pulled back to the $20 level, a 220% unrealized gain wiped out, leaving me nearly flat.

Since then, I’ve added 58 more shares. Today, that same position shows an unrealized loss of nearly $2,500.

Why didn’t I take any profits? Because I believed in the future of telehealth, and my emotions tricked me into thinking $100 per share was just around the corner. I never want to be in the stock that keeps running while I sell too early, but now I’ve also lived the pain of never selling at all.

Now all I can do is hope — against common sense, really — that Hims’ earnings report on Monday brings some clarity, maybe even a little relief.

I’ve made a few dollars over the past two weeks buying put options on Hims in anticipation of the stock continuing to fall. Nowhere near the $7,200 unrealized profit I had when Hims hit its all-time high just below $73 last February.

The lessons are brutal but clear.

Individual stocks can soar. And they can tank just as fast.

Conviction is no shield against headlines, lawsuits or regulatory fire. Never taking profits feels heroic when everything’s green, but it can leave you staring at losses you swore you’d never see.

I’ve paid tuition in real dollars and emotional wear and tear. I’ve also gained a firsthand education in market swings, risk and human behavior. Lessons no article or podcast could teach as vividly.

So yes, I’m down. Yes, it stings.

But I’m still here. Still watching. Still learning.

Because that’s what being a long-term investor really means.