231 | Missing Chapters

I’m writing a book that’s been in my head for a decade, almost two.

It started as thoughts and observations that I couldn’t turn into words.

Then it was actually helping people with their finances.

Then it was helping people and getting thoughts into words.

And the combination of helping and writing is when the book started to take shape - an endless cycle of practicing what I preach and preaching what I practice.

And all of it seems to be helping people connect the dots.

But inevitably, there are a couple chapters that leave people scratching their head because the practice isn’t quite the preaching.

Because right now, in my sliver of the industry, some sections of the book can’t be published.

The missing chapters would be too hard for the current publisher to sell.

Many days those missing chapters feel like they’re a silly thing to hold so tightly.

“Just get over them, they are too petty to make a stink.”

“Someone would have already written them if they were actually that important.”

But then there are the days that I see someone longing for them or that I have to recite their placeholder chapters as if they are the real thing.

And those are the days they seem like the key that unlocks the future that I so desperately dream of building.

I want to believe, and on the best days do believe, that the missing chapters will make it a masterpiece.

230 | Give Me Snail Mail

Technology makes things faster, but not always better.

Dividend checks used to show up in the mail every month or quarter or year.

If the market was up, there was a check.

If the market was down, there was still a good chance of a check.

Real income that repeats year after year after year…even when our investments are down in value.

That sounds sort of nice, particularly in a world of people who spend income more freely than they spend their savings.

Dividends haven’t gone anywhere, but their automatic reinvestment has made it feel like they’re being returned to sender or forwarded to the wrong address.

Instead of a paper check reminding us that we own real businesses making real money, we watch account balances move in apps like modern-day Monopoly money.

And Monopoly money is hard to spend in the real world.

Sometimes a little friction enables a lot of freedom.

229 | Market Update for Patient Investors: June 30, 2025

A market update for normal people thru the first six months of 2025.

Interest paid on cash so far this year is the blue dot. Cash is never to be confused as an investment - "no risk = no return" even if you have a good interest rate.

Since 2014, the best single year for the average all-stock (relatively more risky) or all-bond (relatively less risky) portfolio is the green line. An ongoing reminder that stockholders get the biggest rewards.

Since 2014, the worst single year for the average all-stock or all-bond portfolio is the red line. Stockholders have the most heartache too.

Folks with a paycheck often aim for the wide side of the cone, those without one tend to aim for the middle.

The gray dots below are for the average all-stock or all-bond portfolio this year. So far an above average year, despite the shock of tariffs and the doom of headlines.

Since January 1, $100k invested in stocks is now ~$110k and $1m is ~$1.1m.

Here is where it's helpful to remember our investments aren’t a black box. When we invest, we own teeny slivers of real companies operating in the same uncertain world we experience each day.

The gray dots are a blend of all public companies from all over the world - the orange x's go one layer deeper to show us smaller pieces of the gray dots.

But remember whether these six months had been good or bad, it’s not about the days or months or years when we invest, it’s about the decades. And it's hard to be disappointed over a decade. The gray and orange are annualized returns for the past 10 years - a fancy way to say it’s like you got 10% every year for 10 straight years.

In the good times and bad times, patient investing knows that…

• Basic understanding enables ignorance.
• Someone will always beat you.
• Effort ≠ Results.
• Owners get the upside (and the other side too).
• Spreading your eggs reduces the pain.
• The short term can disappoint.
• Patience is the only shortcut.
• Investments are a distraction in our relationship with money.

228 | How to Buy a Car

Buying a car never starts with 0.9% APR.

If you're trying to be cost-conscious, then you only have two options...

1. Milk more out of your existing car
2. Lower your standards by make or model or year or feature

Option 1 works unless it's gone, dangerous, doesn't function, or...the squishier.."no longer drives contentment".

Option 2 is a delicate balancing act between purchase price and maintenance. New cars are expensive, old cars break down.

Of course, "financing" is absent here, because the cost doesn't change whether we pay it now or over 72 months.

Once we've vetted our options, we can only trust our judgment and jot down our "whys" to protect us from our future self that likes to forget the uncertainty of the past.

• Why this make and not others?
• Why this model and not others?
• Why new or used?
• Why this level of features and not others?
• Why electric, hybrid or neither?
• Why now?

Then…

• Why cash or finance?

If the financing question comes first, we're not being cost-conscious.

227 | Smoke Signals

Where there is smoke, there is fire.

And two smoke signals billow up at every level of financial wealth.

Cash on hand, or the Blue bar as the locals know it, is the first one.

No matter the net worth, the most content folks are those with enough cash to ignore their next paycheck and the ups and downs of their investments.

But the lower the cash goes, the hotter the embers burn.

Savings rate, or the Green bar, is the second one.

If you aren't saving,...

• You're living beyond your means,
• You're surprised by some unexpected things, or
• You're spending now to see some benefit later

It's OK to have seasons without saving, particularly if you started it with enough Blue, but if you keep poking the embers you eventually fan the flame.

If you’re getting that “things-feel-a-little-tight” vibe, look for the smoke and then work to put out the fire.

Extra Perspectives

You Aren’t Too Big To Fail (And That’s Okay) by Jared Korver

226 | Love Letters: Why NYC?

We can't know the future before it happens.

And its unfolding can lead us to second-guess what's come before.

Especially when we're spending large amounts of money.

So to care for our future self - by reminding him what the past self knew at decision time and why he did what he did - we can write a "love letter" to him.

To be a warm hug when the future disappoints.

To be a good laugh when the future surprises.

To be a slap-in-the-face when the future makes us question.

To be an encouragement when the future gives us another decision.

Here is my love letter - to future Richard - about why we have chosen to spend July 2025 living in New York City...

Why NYC?

• So that Sara Brooke, Charlie, and Caroline (and both adults too!) experience a place that will astonish them, make them uncomfortable, expose them to a world they have never seen, see their parents fail and scramble to figure things out that we don’t know how to do, and so many other things that are hard to replicate at home
• It stands alone from any other city in its ability to mesmerize all ages
• Sam lives there right now and it is one of the few chances we have to live close to him for an extended time
• To reset the grooves that have formed in our minds and bodies around abundant space and convenience and transportation
• We have been to it before and (sort of?) know what to expect
• It is accessible by car

Why a month?

• To be able to experience the city in a daily-routine-kind-of-way and not a tourist-for-a-weekend-kind-of-way
• To experience a study abroad type setting as a family
• The cost of a week in an AirBnb was between $5,000 and $6,000 whereas a month is a little over $9,000 - at many properties the cost of a week is the same as what we are paying for our month - frankly, a month sounds less overwhelming and tiring than a week!
• It allows us to experiment with remote work and working independently
• It gets us out of our daily routine at home in an even more dramatic way than a week at the beach
• It allows us to invite family to stay with us and join us in our adventure

Why now?

• Sara Brooke and Charlie seem to be an age that they will be amazed and impacted and Caroline seems like she will be able to age up even if she won't remember it in detail
• Our family life (especially our summers) have not become as busy as our peers with other extracurriculars and this seems like an experiment in charting a new path away from typical busyness
• It feels like it provides some incubator space to allow RwM to continue growing via writing, website design, preparing for advisory council conversations, etc.

Why Brooklyn?

• It has a neighborhood feel that is different from most other places in New York City (we first discovered this visiting Sam in September 2023)
• The Brooklyn Promenade and Brooklyn Bridge are two of the most magnificent locations to experience the beauty of the city on a daily basis
• It is close proximity to Sam

Why our specific AirBnB?

• Three bedrooms allow guests to stay without having to pay for their own accommodations
• It has an outdoor space on the rooftop which feels vital as a post-bedtime escape from close living quarters
• It is extremely well connected to subway lines that lead into all of Manhattan without transfers
• The hosts allowed Sam to visit in-person and even give a FaceTime tour of the property so we could be confident before paying
• The hosts are three young folks - two teachers and a photographer - renting it out while two of them get married over the summer - way better to pay them than an anonymous person or business!

225 | Compared to What?

Money is tricky because it's a game with no real rules.

No refs or game clock.

No schedule or standings.

No scoreboard or championship.

It's missing the basic guidelines that allow us to reflect, tweak, and game plan based on a shared understanding of reality.

• This is what we'll do next half since that happened in the first half.
• That strategy isn't allowed any more so we'll have to use this one.
• We only have enough time left for this approach.
• Can you imagine how good we're going to be next season?!

Usually, we don't appreciate the value of order until it's gone.

And with money it's often MIA from the start.

So tracking "progress" is haunted by the fickle question..."compared to what?".

Yesterday?

Our neighbors or siblings?

If we'd chosen the other option?

If we were on better terms with our boss or biggest client?

If we won the lottery?

Without introducing some basic guidelines, it's as if we're learning a new sport from scratch every time we think about money.

224 | Pick Your Poison

There are really only two ways to invest - hold them all or pick a few good ones.

A lot of research here shows it's pretty hard to distinguish which approach is better.

Holding them all guarantees you don't miss the best ones, but it means you'll hold the worst ones too.

This way is almost always a smoother ride.

It's also less "expensive", which is a special way to say no one's analyzing much of anything.

Picking a few good ones can be extraordinary...as long as you pick the right ones.

If the few you pick are wrong, you'll be sad. And whether you pick well or not, it will be a wild ride.

This way is more "expensive" - sometimes in dollars, always in minutes - but intellectual or moral "consideration" is valuable to many folks.

Both approaches can, and do, work. Both have seasons of disappointment too.

Instead of arguing about the approach, it's best to pick the one that resonates most and then move on.

If it seems I’ve oversimplified it, here's the fancy version...

"The data on wealth creation suggest two strategies for portfolio construction. One is to recognize that an investor can capture the skewness, or asymmetry of a distribution, in long-term total shareholder returns by holding a diversified portfolio. Index funds are an effective way to implement this approach. While an index will include stocks with poor returns, it will also have the handful of companies that generate most of the aggregate value. The other strategy is to build a relatively concentrated portfolio that seeks to include the companies that have the potential to generate high returns and avoid those that do not."

223 | All for Naught

A big decision that falls through can make it seem as if time was wasted in the discernment.

But that's far too short-sighted.

Big decisions are one of the only ways to pave new highways for money thoughts to travel through our head.

And note that entertaining decisions - not getting outcomes - is the key action.

Honest thought given to a big decision is like downward-facing dog to your calves - something that was tight and brittle becomes loose and pliable.

Priorities that are rearranged.

Time that frees up.

Assets that are less clutched.

Debt that is less suffocating.

Income that flows more freely.

Spending that is repurposed.

All from evaluating the pros and cons or briefly entertaining the outlandish.

It's never all for naught.

222 | More Thoughts on Investment Properties

Investment properties work well for four types of people.

1. Those who pay minimal (maybe $0) closing costs.
2. Those who are handy enough to fix things themselves.
3. Those who have lots of discretionary time.
4. Those who want it for non-financial reasons.

If you aren't one of those four types, it's gonna be a frustrating road.

221 | You Don't Need a Roth to Retire

This might be hard to believe (because it's where most financial advice begins and ends), but you don't need a Roth IRA to retire.

And you don't need a 401(k) either.

Just ask the wealthiest people around where most of their wealth sits - it's neither of those spots.

It's easy for the type of account to distract us from what is happening with our finances.

The income that gets saved is the gas being pumped into the car.

The account where it is saved is unleaded 87 versus unleaded 89 - a basic shuffling of costs between now and later.

An extra quarter tank of gas is how you ensure you reach the destination - not a fuel upgrade.

220 | Financial Fingerprints

Good spending is trading money for contentment.

And contentment is about as unique as a fingerprint, but more, because you can't see it.

Some of us, whether we know it or not, define it by the clock.

How many hours of contentment does a dollar generate?

Of course, there's simple math like...

A $7 beer that lasts 30 minutes is $14 per hour of contentment.

A $15 cocktail that lasts 15 minutes is $60 per hour of contentment.

A 4-hour round of golf for $80 comes in at $20 per hour, while a 20-minute paragliding adventure for $200 is $600 per hour.

A $100,000 kitchen renovation might only be $10 per hour, and a $1,000 mattress could be less than $0.10 per hour.

But then there's the calculus of it too...

"Expectation equity", or the positive feelings around the anticipation, camaraderie, and preparation for something in the future - think about the last time you made a dinner reservation or bought tickets to a sporting event.

And to borrow from Clay "memory dividends", or the lingering positive feelings associated with money well spent - think about the stories that are re-told forever or the relationships that blossom from shared experience.

Once "expectation equity" and "memory dividends" enter the equation, hours of contentment turn into days, months, and years.

And it becomes a little easier to see contentment as a financial fingerprint.

219 | Michelangelo

To those amazed by Michelangelo's completed David sculpture, he said, “I created a vision of David in my mind and simply carved away everything that was not David.”

Our relationship with money isn't that different.

There aren't that many things to know or to do well - just ask a kid as the sun sets on his lemonade stand.

But life tends to cloud that "vision in our mind" enough to keep us from "simply carving away everything that isn't".

We digest news or misunderstand how something works and the stone calcifies.

We use generic advice or prioritize the little things and gauge out a chunk.

We see snippets of someone else's sculpture and forget that their lion isn't our school bus.

It took Michelangelo about 3 years - likely working daily - to "carve away everything that wasn't David".

We aren't that committed and we can't disappear to a studio, so we chisel for a lifetime - imperfectly revealing a masterpiece...

We shirk the responsibility of our work and the arm looks funny for a time.

We save in a way that makes sense for now and reveal the shape of a torso.

We invest in a way that's not meant for us and temporarily deform the knee.

We spend a little better and uncover a nose or ear.

David is there, but we have to carve everything else away.

218 | Financial Obituaries

Your investment experience will not define your financial life.

That is, as long as you've spread your eggs across a couple baskets, aren't using short-term debt to juice your returns, and aren't buying and selling based on daily movement.

Everyone's investment experience is too similar - all rise, all fall - for it to be any other way.

And if it’s not unique to you, how could it possibly get a line in your financial life’s obituary?

Even the worst-case scenario of everything going to $0 wouldn’t be that defining because financial wealth is relative.

And everyone else would be strapped in beside you for the ride down - leaving your relative wealth secure.

Our financial obituaries might say...

• He grew to love his work and changed the lives of clients and co-workers.
• She saw the value of things, not just the price.
• He knew money spent on relationships was an investment, not an expense.
• She never tried to predict the future, but was always calm when it arrived.
• He appreciated that "enough" was a lifestyle more than a number.

But they'll never say...

• She kept cash on the sidelines and then capitalized on every recession.
• He beat the S&P 500 in eleven different years over his lifetime.
• Their life would have been better if they'd made 2% more per year.

217 | Matter-of-fact-ness

Our finances beg us to pen an epic fiction about them.

"More income is the only way forward."

"If we aren't saving, we're falling behind."

"We can't afford to be generous."

"We have to keep cutting back until there's nothing left to cut."

"Our investments might go to $0."

Inevitably, these fictions move us from matter-of-fact understandings of our money to emotionally-charged misunderstandings.

Sadly, the financial services industry tends to ghost write more fiction - projecting unknown futures or marketing silver bullets.

Or confuse us with non-fiction - jargony post-mortems on market moves or urgent updates on tax laws and account types.

One adds chapters to our fiction and the other leaves us with nothing but the fiction in our head.

Somehow we have to add a dash of matter-of-fact-ness to disarm fiction's ability to exaggerate, invent, and pretend.

Some matter-of-fact-ness looks like...

Aggregating our accounts in one place.

Identifying when income exceeds spending, and when it doesn't.

Tracking where our dollars go.

Noticing patterns over the course of a year or two.

With a little bit of fact, our negotiations change, our spending habits change, our investment decisions change, and our saving priorities change.

And the fiction captures our imagination less and less.

216 | Out on a Limb

Everything comes back to spending - we earn to spend now, we save to spend later, we invest to spend more now and later.

Spending is as central to life as breathing.

And this is what makes "getting ahead" or "staying ahead" or “catching up” so elusive.

We can't outrun the uncertainty or feelings that creep up any time money goes out the door.

When you spend, there's always a chance...

• A better alternative exists
• A cheaper alternative exists
• Someone else will buy it too
• No one else will buy it
• Someone will have something better
• Someone will have something worse
• You're tired of buying this thing
• You didn't think you'd have to buy this thing
• You've never bought this thing before
• You haven't done enough research
• You've done too much research
• You still don't know what you don't know
• You don't actually know what you want
• Your preferences change
• It goes on sale after you buy it
• It doesn't work like you hoped
• You don't get what you expect
• You don't end up needing it
• You never receive it

It doesn’t matter whether you're 10 or 33 or 54 or 82 years old...

When you spend, you're stepping out on a limb.

215 | No Action Required

It can be painful to realize we're not in control.

And our investments are particularly adept at revealing this reality.

If you haven't noticed this time, kudos to you, you won't find a more accessible or powerful investing skill than intentional (even unintentional!) ignorance.

Feel free to stop reading here and keep living life.

If you have noticed, then it's served as a helpful reminder of why we do what we do.

Sometimes it seems overkill to be so careful with cash.

Or to start the year by understanding our entire financial life with a few colors and bars.

Or to talk about all the other parts of our financial life that are more in our control and add all the color to life.

But then uncertainty begins to connect the dots for us.

We do these things, because they prepare us for the seasons where it's better to look away for a moment than to stare.

Better to be still than make a regrettable move.

Better to see it as a workout making us stronger for the next one than a hole leaking water out of our bucket.

Additional Resources

For those who like motivational speeches, read more here.

For those who like history, read more here.

For those who like numbers, read more here.

214 | "The Market" isn't Hard to Predict

"The market" is nothing more than a live streaming estimate of the financial emotions of everyone on Earth.

Me. You. Your neighbor. That stranger in traffic. That person on TV. That person who makes you cringe. That other person who cancelled your vote in the last election. And the other 4 or 5 billion adults walking the planet.

Each of us, tuned in (or not!) to the news.

Each of us, tuned in (or not!) to our emotions.

And then…

Each of us, making an investment decision (or not!) based on one or both of those things.

It’s not the news or even the emotions that move “the market”.

But the collective “buying-and-selling” decisions of everyone in the world based on their news and their emotions…and their businesses.

If those who are encouraged by the future ("buyers") outnumber those who are discouraged ("sellers") or apathetic ("holders"), “the market” goes 👆🏻.

If the folks who are discouraged by the future outnumber the encouraged or apathetic, “the market” goes 👇🏻.

"The market" isn't hard to predict - it's the people that are tricky.

213 | Do We Have to Tell?

After years of long hours and burn out, a close friend shared that their spouse was pursuing a change at work.

The change would mean fewer on-call nights, more time with family, more baseline energy, relief from a draining routine, more unity in their relationship, and, not surprisingly, a little less income.

While celebrating the promise of relief and extra capacity, the friend said, "But we don't want to tell our financial advisor because it's not in line with the plan that he laid out and we won't be able to save as much as before."

I'd like to extend the benefit of the doubt to the advisor and imagine that our friend was exaggerating, and yet, it's a stark reminder of the fundamental flaws in the financial advice industry.

Charging a fee on managed assets means that good news for one party might not be good news for the other.

And publishing financial "plans" makes some forms of good news seem more like a misstep than progress.

Keeping good news quiet is no way to refine our relationship with money.

That's why we do things a little differently here.

212 | You Don't Need a Budget

A budget is too rigid - you either pass or fail which leads to fleeting pride or enduring shame.

It's too arbitrary - cars don't breakdown and musicians don't go on tour because our budget said they should.

It's too lifeless - budgeting stats don't typically make it on headstones.

But you have to track your spending.

Because spending is too important - all the color of life flows out of how we spend.

It's too emotional - we have to validate (or challenge!) all those feelings swirling through our heads.

It's too unpredictable - some is fun, some is obligatory, and some makes us sick. Some spending repeats and some doesn't, but no matter what, it's helpful to distinguish which is which.

And once you track, you have to reflect.

"Interesting...we spent that much last year on that thing."
"I'd love to spend less on this, so we can spend more on that."
"I wonder if that's how much we'll spend this coming year too."

With each reflection, we add a deposit to the "I-feel-freedom-in-spending" bank that an "I-missed-the-budget-again" slap on the wrist can never match.

There's even a chance that once we track it, we might get a better sense of what to expect next time.

But please don't call that a "budget", because then we're right back where we started.