211 | Don't Get Distracted

Investing is a lot like running.

We run to keep our fitness up and often measure progress by tracking our time.

Some years we trim 10 or 15 seconds off our personal record and don't even notice.

Some years we roll an ankle or get too busy and some seconds are added back to our time.

Sometimes we see someone else running faster or we hear about a new technique or we hire a coach that introduces a new regimen and our times bounce up and down.

If we're not careful, the stopwatch begins to distract us from our actual fitness.

Our 6:10 mile from two months ago doesn't make today's 6:16 mile or tomorrow's 6:20 mile a signal that our fitness is spiraling.

Don't get distracted by the times. Just keep running.

210 | Cashing in on Excitement

There are only three ways to make money investing.

• Lend money to someone who pays you while they borrow* (interest)
• Own something that makes money and pays the profits to you (dividends)
• Own something while the excitement around it grows (capital gains)

The last way offers the most upside, but it's impossible to predict.

Sometimes profits trigger excitement around a company.

That excitement rewards the founders.

Sometimes excitement surges, but a company never turns a profit and excitement fades.

That excitement rewards the lucky (or the reckless!).

Sometimes a company is exciting and profitable.

That excitement rewards the patient.

The only way to cash-in on excitement is to own the company...

While the excitement builds.

If you wait for excitement to grow, you've missed out.

If you're not a founder, be careful.

*Ideally, they return whatever they borrowed at the end.

209 | Negative Numbers

A credit card balance is a checking account with a negative balance.

If you envision it any other way, you’re confused about how they work.

Harsh? Blunt? Too direct?

That's the only option when something can escalate from fun and innocent to dangerous and overwhelming so quickly.

Travel perks don’t make it positive.

Sign up bonuses don’t either.

In fact, nothing turns it positive.

You can only get it back to zero with a transfer from a positive checking account.

208 | Shocks on a Car

Cash in the bank is like shocks on a car.

If you’re feeling every single bump – or stressed about every purchase – then adding some shocks will help.

The feeling of the bumps doesn’t mean the engine is bad.

Or we’re headed the wrong direction.

Or we need a different car.

We just need some more shocks.

207 | That Person Doesn’t Exist

"If only I'd bought ________ in 20__*, then I could kickback today."

But the person that can do those two things doesn't exist.

"Buying and riding" isn't a thing like "kicking back with your feet up".

If you stay on the ride, you're dancing with ruin on the daily.

And if you get off the ride, you'll second guess all the upside you left on the table until the end of time.

Neither sounds much like "kicking back".

At some point, you have to decide if you're investing to live life or living life to invest.

*Today's mad lib would be Bitcoin in 2011, but there are as many examples in the past as there will be in the future.

206 | Counting Days

A change that helps you quit counting days is better than a raise.

Because counting the days until you can quit is the bouncer at the door turning meaning and purpose away so the need for "just a little more" can stay.

There's no question that a bonus or a raise, especially the first one, is one of the sweeter feelings in the world.

Validation. Affirmation. Freedom. Lots of feelings that add to the sweetness.

It’s so sweet, that our attention can't help but move to the next one.

One that is barely less sweet than the one before - the taste buds likely don't notice.

But over time, the sweet has a way of fading or even growing bitter...

Especially once it's nothing more than the scissors that cut another link off the retirement paper chain.

We'll never be able to measure it, but the downsides of counting days can't be offset by a raise.

205 | What Money Allowed Us to Do

Spending is tricky.

Some is fun, some is obligatory, and some makes you want to throw up.

Some we hope to repeat, and plenty we hope never happens again.

Without a teacher to grade it or a boss to give it a performance review, it’s hard to know if we’re being responsible or doing it well.

So, we judge, compare, rationalize, or grasp for arbitrary “budgets” to try and make sense of things.

And then spending becomes a number to control or regret or bemoan instead of a dynamic story about real life.

Everyone feels these feelings – including myself.

But it doesn’t have to be this way.

So, to try and move from controlling to storytelling, here are some things that our money allowed us to do in 2024…

$1,500 to seal a cut on our 3-year-old’s forehead
Expensive for a dollop of Dermabond, but less so (as Jessica continues to remind me!) when viewed as peace of mind for 6 more days at the beach and freedom from regretting a scar

$1,900 to a handful of phenomenal babysitters
We were able to go on date nights and commit to church small groups while our kids played with a role model – said that way, it sounds like an investment more than an expense

$9,200 on two LASIK surgeries
A contact-free house and the chance to make up the cost in 6 to 8 years hasn’t disappointed yet – fortunately, this is a once-in-a-lifetime expense instead of an annual one

$5,500 to remove a couple generations of squirrels and birds from our attic
A bitter financial pill to swallow, but gone are concerns of gnawed electric wires and the scratching sounds in our ceiling 30 minutes before our alarm clock

$100 for insurance on an engagement ring and a pair of earrings
The peace of mind and lack of marital tension when one went down the drain was impossible to measure (it was eventually found!)

$1,200 for two tickets to the UNC-Duke game at the Dean Dome
“Richard’s Taylor Swift Concert” that was easier to rationalize (on the front end) with the help of a $500 Christmas gift from family and (on the back end) an electric performance by the Tar Heels

$4,500 at restaurants
The biggest month was $520, and the smallest $200 – but every month afforded connection with friends, connection as a couple, connection as a family, a little convenience, and the joy of feasting on good food we didn’t have to prepare

$500 for a summer pool membership
The cost per hour was low for an activity that anchors a summer day, teaches kids to swim, and deepens relationships for the entire family

$4,300 maintaining a 2018 Sienna and a 2022 RAV4
Over $2,000 came in November to cap off the Shore family year of deferred maintenance – not fun and easy to overlook the privilege of maintaining a car to prevent a breakdown

$6,500 for a week in Ireland
Without a doubt, the most “treat yourself”-style dollars we spent in 2024 and the agenda-less, email-less, kid-less exploration of a place we had never been made me hope we can do it again

And of course…

Some was fun, some was obligatory, and some made us want to throw up.

Some we hope repeats, and some we hope never happens again.

But more than anything - just listing them out - provides more peace of mind and perspective than judging, comparing, rationalizing, or grasping for arbitrary “budgets” could ever do.

204 | Relentless Pursuit

The ultimate career skills...

• Finding work that feels like play
• Knowing how to put it down

Because too many hours of your life are spent at work, and no one wishes they worked more once they're done.

Of course, work that feels like play doesn't fall in your lap.

But slowly making it feel like leisure begins to pull us in the right direction.

Even if it takes a couple decades or (gasp!) a dip in income, it runs circles around grinding it out until you're worn to a nub or obsolete.

It's hard to comprehend the shift that occurs.

Work that doesn't feel like "work" is one thing.

But the upside of something that's fun versus something that's tedious is 🚀.

The real risk is work that feels like play might be hard to put down.

And it's easy to blame a client or a boss or an inbox for why work owns your life.

But every field has someone who is exceptional without being consumed.

That's who we want to notice - not to uncover their 10-step process, but to appreciate the courage needed to draw hard lines along the way.

What's the secret to a good career?

Relentless pursuit of work that feels like play.

And relentless pursuit of how to put it down.

203 | Frustrated Toddlers

Brace yourself…

“64% of people with a financial advisor feel unsatisfied in terms of ‘having someone to talk to about money’”.

People with a financial advisor feel unsatisfied.

I appreciate that we have a stat to back it up, but I felt it in my gut the moment I became an adult and realized money wasn't just math.

We all feel it.

Nagging questions of "how do I spend well?" or "am I being responsible?" or "how do I know if I'm on track?” that go unanswered, while we rehash the benefits of a Roth IRA or speculate on the chances of a recession in the next 12 months.

Of course, we're unsatisfied.

Like a frustrated toddler searching for the right words, but only getting another snack so the peace is kept.

What else do we need for permission to do things differently?

202 | Dirty T-Shirts

We can talk about past performance.

We can talk about future projections.

We can talk about the nitty gritty details of our investments.

But none of it will impact how our investments actually perform.

It's a little like wearing the same t-shirt for every game of your team's playoff run to help them win.

It makes us feel like we're in control, but we all know we're not...right?

We don't jump past investment talk because we're afraid or unprepared to do it.

We move past it because anything else might convince us to keep wearing that dirty t-shirt.

201 | Riding the Wave

“I'm hesitant to invest because I don't want it to go down.”

But....

“I don't want to miss out on the next wave.”

Well yeah...me neither.

But that's the water we'll be swimming in from now until the end of time.

Investments that will go down.

And waves that will keep coming.

You don't get one without the other, and nobody knows when either will happen.

That's the main reason that we're careful when we're getting started.

Because if we get spooked on our first drop, then it's going to be harder to catch the next wave.

And riding the wave is a lot more effective than swimming back to shore.

200 | Nature or Nurture?

A scarcity mindset is hard to shake, because nature and nurture allow it to be ingrained from the start or re-introduced in every season of life.

One by nature might look like...

• Never quite figuring out how to spend less than you make.
• Or using debt as a perpetual bridge to "when it will be easier to save".
• Or cycling through jobs without ever compounding your skills enough to reap real rewards.
• Or "saving money" with cheap tipping habits.
• Or stressing over hundreds of $10 purchases while ignoring a couple $1,000 decisions.

While one by nurture might look like...

• Believing taxes are the government "taking your money from you".
• Or deferring generosity "until you have enough income to give away".
• Or expanding your lifestyle with every raise.
• Or upgrading for more square feet every time you "outgrow" your home.
• Or accumulating so much that all your effort and attention transitions to paranoid preservation.

You don't win by avoiding the mindset - that's impossible because you can't change nature, and nurture is so darn persistent.

You win by recognizing it and then pushing back on it again and again and again.

Of course, that sounds a lot like refining a relationship.

199 | A Grumpy Vet and “Handouts”

The government (and paying taxes!) make for a good scapegoat when we're financially frustrated or feeling particularly Scrooge-y.

This story from a former US Senator captures an example of the frustration too well not to share...

"A veteran returning from the Korean War went to college on the GI Bill, bought his house with an FHA loan, saw his kids born in a VA Hospital, started a business with an SBA loan, got electricity from the TVA and water from a project funded by the EPA, his children participated in the school lunch program and made it through college courtesy of government-guaranteed student loans, his parents retired to a farm on their Social Security getting electricity from the REA and the soil tested by the USDA. When the father became ill, his life was saved by a drug developed by the NIH. The family was saved from financial ruin by Medicare, and then one day, this veteran wrote his congressman an angry letter complaining about paying taxes for all those welfare programs created for ungrateful people."

Don't be that guy.

The modern-day version would be happily receiving stimulus checks and PPP Loans, enjoying FDIC insurance on your bank accounts, being amazed by a National Park, travelling on an interstate, and plenty of other things.

And then bemoaning the fact that you must pay taxes or that someone you don't know receives some benefit that you don't.

Writing out a list of all the ways that the government (and paying taxes!) - literally - changes your life, might remind us that there's a good chance the benefits outweigh the cost.

198 | How to Master Money

By acknowledging that our interaction with money, no matter the level of financial wealth or season of life, is a relationship to be refined. Not a game to win, a puzzle to solve, or a journey to complete.

Zooming out tells a story that details obscure.

Simplicity clarifies in a way that complexity disregards.

Reflecting on "why" establishes purpose that tactics overlook.

Trade-offs encourage action that perfection tends to paralyze.

Transparency disarms the fear of taboo.

And financial resilience allows us to face the inevitable uncertainty of tomorrow.

Resilience looks like…

Generating income using our natural gifts and skills sets for a long time (maybe even forever!). All while managing burnout and spending time doing things with the people that matter to us. Income that is a pleasure to generate is even better than it sounds.

Spending in a way that brings lasting contentment. All while knowing that every dollar spent builds an expectation of the future. The ability to adjust when there is uncertainty and a respect for the sneakiness of envy are the only shortcuts to contentment. Ironically, generosity often increases contentment, while debt often decreases it. And spending on relationships with others is an investment, not an expense.

Saving, or - on average - spending less than you make, is the most powerful financial skill. Because it governs expectations and jump starts the pursuit of "enough". Filling the right buckets so they are accessible when you need them is more art than science. And cash on hand provides flexibility for today and endurance for tomorrow.

Investing with some clue about what you’re doing and a genuine belief that it will work. Knowing there are only two guarantees - 1. someone will always have better returns than you, and 2. the way you behave, especially when it’s uncomfortable, will determine your lifetime returns. Being an owner offers the most potential reward. Spreading your eggs across many baskets makes the uncomfortable times less painful. The longer you’re invested, the better chance that it works as expected. And a little more patience than the next person is the only shortcut. And investments will almost always be a distraction in your relationship with money.

Predictably, as our relationship improves, it becomes clearer that "more" does not magically lead to "better".

197 | No Antidotes

There are no trade secrets.

Or silver bullets.

Or wizards behind the curtain.

The trouble is that we keep hoping a special investment or slick tool or fancy calculation will set us free.

But these things aren’t the antidote for all our uneasy feelings about money.

They're just saturating the market and our minds and leaving us without a clue of how to apply them to our lives.

It's not the best product, tool, or calculation, that we need.

We need help putting a stake in the ground, taking a couple steps, reflecting on what happened, and then repeating that cycle...

Forever.

196 | Would You Manage Investments?

I don't manage investments.

Of course, I give advice on investments - advice that rivals (and beats!) folks that manage investments.

But I don't manage investments.

If I manage investments, the investment strategy becomes a golden calf.

If I manage investments, the cost of advice skyrockets as you save.

If I manage investments, you pay way more or way less than your neighbor will pay.

If I manage investments, we're going to spend a lot of time doing things that can be done for us for free.

If I manage investments, inevitably I'll only help the wealthiest get wealthier.

If I manage investments, I limit who I can help before they've even raised their hand.

If I manage investments, I ignore what actually changes people's relationship with money.

Now that I’ve laid it all out, would you manage investments?

195 | Financially Savvy

Some people think it’s making a lot of money.

Some would say it's being frugal.

Others would consider someone who gave an in-depth market update or saved you taxes savvy.

I’m convinced that financial savvy is nothing more than knowing how to spend less than you make through various seasons of life and circumstances...

And then being able to tell the story of why you spent more than you made in the seasons that it inevitably happens.

The first part, "spending less than you make", is proof to ourselves that we know how to live within our means.

The second part, "being able to tell the story", is proof to ourselves that we're tuned into why money is going out the door and where it's going.

Once you've figured out the first part, you've mastered the technical side of finance.

But mastering the second part, is where we begin to refine the relationship that we have with money.

Once you can do both, you're savvy.

194 | Flipping the Script

Details obscure.

Complexity confuses.

Tactics tempt.

Perfection paralyzes.

Taboo intimidates.

Certainty eludes.

And "more" often misses the mark.

While…

Zooming out brings clarity.

Simplicity fosters understanding.

Clarifying "why" establishes purpose.

Tradeoffs trigger action.

Transparency combats fear.

Resilience is often in reach.

And "better" tends to deliver.

193 | The Spending Tracking Spectrum: Final Reminders

If a level isn't serving you, then move back to a previous level.

Move between levels as seasons of life change.

Or stay at one level forever.

Do what feels good to you as long as you're moving up the hierarchy of insight.

From data, "here is the list of things we paid for".

To information, "here are some themes of our spending".

To knowledge, "this spending moves the needle the most, so it should get the most attention".

To understanding, "this is why we spent the way we did and we would or wouldn't do it again."

To wisdom, "our spending reflects who we want to be, or it doesn't, so we will change it."

Because if we aren't spending well, what's the point of making and saving money in the first place?

192 | The Spending Tracking Spectrum: Level 5

We'll call this the "Buffet Level" because you can get whatever you want and your plate can be unique to you.

Within the categories of Level 4, you can make all the subcategories your heart (or stomach!) desires.

But we have to be careful - most "budgeting" efforts come to die at Level 5 because we treat it like Level 1.

“We need to budget better.”

“If we just had a budget, then I’d know what I could spend, and I’d do it.”

“How does our spending compare to other people?”

So we find ourselves diving in at Level 5 before we've perfected the other four.

And then we get discouraged because we "fail" or we accumulate a ton of data that never turns into wisdom.

Which leads to hopelessness and finger-pointing and a host of other things.

Which leaves us with a trunk full of emotionally-charged spending baggage...forever.

But if we proceed with care, after perfecting the other four levels, then the freedom of Level 5 can be real.

A freedom that makes it easy to pivot because you're grounded in reality.

A sneakier freedom from choosing to spend less in one area, so you don't have to spend less in every area.

And sometimes even a freedom that comes from seeing that you're spending as well as you can in a particular season.

Of course, Level 5 is not the holy grail of tracking spending, but only one point on a spectrum of spending well.