57 | Why a "Financial Coach"?

Frankly, it's hard to know the best title for someone that helps people with their financial well-being in this day and age.

"Advisor" sounds a little stale, a little formal, and a little out of date.

It's used by too many people that might not have any impact on improving your real financial well-being and I think it implies some unique ability to control the markets that no one actually has.

"Planner" sounds a little too focused on the numbers, a little too rigid, and a little too specialized.

It's closer than "advisor", but I think it still implies some ability to predict the future by crunching the numbers a little better than the next person or doing the impossible task of drawing up a plan that eliminates uncertainty. Yes, as a CERTIFIED FINANCIAL PLANNER™, I do appreciate the irony of this perspective.

"Coach" sounds a little informal on the surface, but it is exactly how I hope to interact with every client.

With a coach, there is no doubt that he or she is 100% on your team.

A coach is an integral part of the story, but never the hero.

A coach empowers the player.

A coach helps the player see things that can't be seen when they are playing the game.

​A coach knows all the rules and strategies to use in the game even if he or she doesn’t use them all the time.

A coach knows that the gameplan has to be flexible - sometimes in the first minute, sometimes at halftime, sometimes in the final minute, but always flexible.

A coach knows that even if it's discussed or practiced, it still might not happen in the game and that's OK.

A coach directs focus to the things that matter the most.

A coach knows that you can control the process, but you can't control every outcome.

A coach's impact can be felt on a single play, but is most significant over the course of a season or an entire career.

A coach does not see you as who you are today, but who you can and will be someday.

A coach is with you in the wins and in the losses.

Over time, a good coach shares enough life experience, builds enough trust, and earns enough respect that you can't imagine playing the game without them even though you probably could.

Additional Reading

Don’t worry about playing a game better when there’s a better game to play by Paul Davies

How to deal with investing blind spots by Carl Richards

56 | Love The Game Beyond The Prize

To this day, intramural flag football remains one of my top memories of time at UNC-Chapel Hill.

I played on men's teams and co-ed teams. I played multiple seasons with my wife, my brother, and my sister on the same team. Some of our very best friends to this day played on these teams too.

I can still remember specific plays like they happened yesterday.

The Anderson to Hill hook-and-ladder to win our first men's championship. Anderson's toe-dragging interception in the endzone to seal a win in a rainy semifinal game. Rebecca's diving catch to extend a game-winning two-minute drill. Keith's punt return touchdown to clinch a semifinal win. The list goes on and on...

Many of these games established a rivalry against a team named Red Bull Carolina. We played them in the semifinals or finals nearly every season and the game always served as the de facto championship game.

During my final year at UNC, we joined up with Red Bull Carolina to play in a national tournament in New Orleans over New Year's. Some of their players and some of our players - the 2010 version of a college intramural super team.

In the weeks leading up to the tournament, we practiced by the twilight of the moon and street lights trying to mesh two teams. We got to know one another personally. We invented new plays. We told stories of previous tournaments. One story that stuck out was a prior year loss to the University of Nebraska team who went on to win the championship.

In the final days before Christmas Break, we were particularly focused on ways to beat Nebraska if we were to play them again.

All of us carpooled from North Carolina to New Orleans a few days after Christmas. We arrived and explored the city together, did final walkthroughs of plays, and were ready to roll when the tournament started.

We blew through our opponents in the first couple of games. I can't remember who the schools were as we were locked in and only concerned about getting the opportunity to play Nebraska again.

The night before the Nebraska game I can remember our whole team congregating in one hotel room to talk about the game. Clay, our team captain, told us the story of losing to Nebraska the year before. We also all shared stories of how our perceptions of one another had changed over the last few weeks as we had turned from rivals into teammates. It was a powerful team building conversation.

Weeks of technical prep, years of experience, high levels of confidence, and trust in one another - we could not have been more ready and prepared for the game.

Game day had finally arrived and we came out rolling on all cylinders. By halftime, we were up 31-9. They had no answers and we made all the plays.

We were well aware of the fact that the game wasn't over. They had extremely athletic girls who could catch every ball thrown their way. They had a guy who was 6'5", 250 pounds who could haul in a catch over our entire group of 5'10"ish, 160ish pound guys. Plus they were the defending champs.

Early in the second half, they scored a couple of times to make it a less than one possession game (touchdowns involving a girl were 9 points for anyone fact checking!).

I can still remember a play call that I made that was a deep pass to my sister. In the huddle, I drew it up specifically to be on one side of the field, and when we broke the huddle the whole team reversed the way I had it laid out in my head - poor communicator, not bad listeners.

As we lined up, I shrugged it off and proceeded anyway. I threw what I thought was a perfect ball to my sister and it was intercepted in the end zone. If I could do it again, I would call timeout and reset.

Sure enough, we held on to a 4 or 5 point lead heading into the final minute of the game. Nebraska had the ball and was driving the field with an opportunity to score to take the lead and win the game.

We forced them to a 4th down and goal from the 5-yard-line for the final play of the game. Score they win, stop we win.

There was no question what the play call would be: fade route to the corner of the endzone to Mr. 6'5", 250 lbs.

My brother, Hill, was our best athlete and the only player for us who could even try to challenge the catch.

Sure enough, the ball was snapped, the receiver came off the line headed to the corner of the end zone, the quarterback lofted it it up for a jump ball in the corner.

Hill, close by the receiver, followed for a couple of steps and then leaped up in the air timing his jump perfectly to swat the ball out of the air before the receiver could touch it.

The kind of defensive play that couldn't have been planned or executed any better except for the fact that a player, who was not part of the original play design, happened to be standing on the two-yard-line, caught the tipped ball as it fell to the ground and simultaneously stepped across the goal line to score the touchdown.

Game over.

Talent. Years of experience. Weeks of prep. Team building. Motivational pep talks. Game-planning. Seemingly perfect execution.

None of it could account for the fluke chance that there would be a girl trailing the play who could catch a perfectly defended ball for a walk-off win.

---

As Carl Richards says, "Risk is what's leftover after you've thought of everything."

All the talent, practice, game-planning, and even near-perfect execution couldn't account for every possible way we could lose.

In the same way, all the planning and forecasting of the future can't protect us from all the ways we could be surprised with our finances.

Whether it's the global things like a tech bubble, a financial crisis, a pandemic, or a wild housing market.

Or the personal things like an unexpected dip in income, the loss of a big client, a medical diagnosis, or an unforeseen expense.

Every single one is out of our control, all-but-impossible to predict, and likely to change our outlook on life in obvious and imperceptible ways.

At some point, there is a diminishing return to the game-planning, predicting, and accommodating for an unknown future because there will always be a surprise that can't be accounted for.

Instead of grasping for certainty, we can really only build resilience, refine our whys, and try to remember the advice from my grandfather a few hours after we had reported the heartbreaking outcome home...

---

55 | The Story of the Mexican Fisherman

Sometime in the last decade, I read the following story on the wall of a Jimmy Johns while waiting on my #5 Vito to come off the line. My perspectives on my career and my relationship with money have not been the same since.

---

An American investment banker was at the pier of a small coastal Mexican village when a small boat with just one fisherman docked. Inside the small boat were several large yellowfin tuna. The American complimented the Mexican on the quality of his fish and asked how long it took to catch them.

The Mexican replied, “only a little while."

The American then asked why didn’t he stay out longer and catch more fish?

The Mexican said he had enough to support his family’s immediate needs.

The American then asked, “but what do you do with the rest of your time?”

The Mexican fisherman said, “I sleep late, fish a little, play with my children, take siestas with my wife, Maria, stroll into the village each evening where I sip wine, and play guitar with my amigos. I have a full and busy life.”

The American scoffed, “I am a Harvard MBA and could help you. You should spend more time fishing and with the proceeds, buy a bigger boat. With the proceeds from the bigger boat, you could buy several boats, eventually you would have a fleet of fishing boats. Instead of selling your catch to a middleman you would sell directly to the processor, eventually opening your own cannery. You would control the product, processing, and distribution. You would need to leave this small coastal fishing village and move to Mexico City, then LA and eventually New York City, where you will run your expanding enterprise.”

The Mexican fisherman asked, “But, how long will this all take?”

To which the American replied, “15 – 20 years.”

“But what then?” asked the Mexican.

The American laughed and said, “That’s the best part. When the time is right you would announce an IPO and sell your company stock to the public and become very rich, you would make millions!”

“Millions?" asked the fisherman, "Then what?”

The American said, “Then you would retire. Move to a small coastal fishing village where you would sleep late, fish a little, play with your kids, take siestas with your wife, stroll to the village in the evenings where you could sip wine and play your guitar with your amigos.”

---

The first time I read it, and every time since then, I've gotten goosebumps. It paints a picture of the ultimate form of sustainable income - complete work-life integration.

To be clear, this is very different from work-life balance.

There is no scale measuring the amount of work or life.

There is no mental clock keeping track of time allocated to work or life.

There is no black and white distinction between what is work and what is life.

It's nowhere close to being a "workaholic" for any skeptics out there.

There is no finish line, because a finish line would be disappointing.

Work-life integration flips the retirement equation on its head and slowly quiets the longing for “more” and amplifies the call for "better".

The integration leads to generating income from something that leverages natural gifts and skillsets, allows for managing risk of burnout, has a long (or indefinite!) time horizon, and allows time to be spent doing things that matter to you.

That has always seemed more appealing to me than "grinding it out" to a finish line and then calling it quits.

54 | Seesaws and "Enough"

Our kids love a seesaw - the constant ups and downs seem like Roller Coaster 101 for those under the age of 6.

The "pivot point" in the middle of the seesaw on which the entire board rests is the fulcrum.

The closer you get to the fulcrum, the harder it is to lift the other side.

The further away from the fulcrum, the easier it is to lift the other side.

A 4-year-old way out on one end can lift someone many times his or her size if that person is close to the fulcrum.

And vice versa, no amount of force applied near the fulcrum is going to lift the 4-year-old into the air.

Of course, I see a connection to finances. How can I not?

Income that is not accompanied by an ability to spend less than 100% of it is like applying force at the fulcrum of the seesaw while "enough" is sitting way out on the end.

Even for folks, especially for folks who have the highest levels of income*, the reality holds true.

The force matters, but only if the fulcrum is in a place to leverage it.

If the fulcrum is in the wrong spot, no amount of force is bringing the other end off the ground.

It's not about applying force, or generating ever-increasing amounts of income, until you retire, burn-out, or quit. It's about slowly adjusting the position of the fulcrum to see "enough" begin to come off the ground.

Of course, no seesaw is ever perfectly still, but once we know the mechanics, it's easier to predict which way we're headed.

When it comes down to it, I think deep down everyone just wants to have "enough", but it's all too easy to forget the role of force and the role of the fulcrum.

*I caught myself typing "fortunate enough, lucky enough, talented enough to have high levels of income" and realized my own biased towards "more" being the default best case scenario.

53 | Thinking Like a 10-Year-Old

Investing seems like it should be so much easier to understand.

As a kid, I felt like I understood it pretty well.

When you have money, you can choose to buy shares of stock of a company and over time you hope that money will grow to an amount that is bigger than what it was when you started.

I can still say I think I understood it as a kid, but man, did the world try to convince me that I didn't for a bunch of years.

No single thing can be blamed, but there are a bunch of things that can shoulder some of the responsibility for abstracting my 10-year-old self's definition.

The marketing of financial services firms. The fear-mongering of the media. The endless "fine print". The by-the-minute price quotes. The infinite number of options. The complicated terminology. The tax rules. The statements. The account types. The fake investments.

Every single one of those things slowly obscured that simple, accurate definition of "investing".

The reality is that even with a good baseline understanding of what it means to invest, the circus that is modern-day "investing" is mighty adept at leaving us dazed and confused.

It leads some to think investing is...

Riding the roller coaster of a single stock.

Sitting in the safety of a money market fund.

Making money without the risk of losing any money.

Doubling or tripling your money in a couple of years.

Borrowing to invest only to see it all slowly go to zero.

Trying to time the bottoms and tops of the market cycle to "buy low and sell high".

Hunting for the next hot investment or meme stock.

Buying and holding an index fund for the rest of time.

No wonder investing seems so hard - the way each of us define it is as if we're trying to say that badminton, soccer, basketball, and swimming are more similar than they are different because they are all "sports".

If we can get back to understanding and promoting the definition of "investing" that we all had when we were 10-years-old, I think it'll make us all better investors.

52 | Toilet Paper and Gold

In March 2020, during the peak moments of uncertainty and fear surrounding the COVID-19 pandemic, there were shortages of every imaginable consumer item.

Many things impacted small groups of people, but one shortage impacted every single human on the planet.

Toilet paper.

I can recall neighbors dropping individual rolls of toilet paper on other neighbors front steps to help share the available supply.

Sadly, there were some bad apples that saw the shortage as a business opportunity. Newsweek tells the story of one of them here.

It didn't take a genius or an expert economist to realize that hoarding toilet paper during a pandemic was pretty messed up.

There are some folks that had a medical reason to get more toilet paper than the average person at the time - I am not dogging on them.

I am dogging on the few folks who were hoarding a scarce resource in anticipation of everyone else having to beg or pay them for their abundance.

When toilet paper was the resource and a pandemic was the challenge, it was easy to see the lunacy and self-centered nature of the hoarding.

In spirit, the theoretical "holy grail" moment for gold isn't any different than hoarding toilet paper in March 2020, it's just become a little more socially acceptable through the generations.

Historically, I have found the economic arguments against owning gold compelling enough to pass on it.

Gold doesn't generate income like a business does year after year after year.

Gold has no practical role in improving our daily lives as a society.

If it doesn't do either of these things, then why own it?

But the part that really moves the needle for me is the fact that its value is primarily derived by society's aggregate fear of the future.

When you buy gold, you're hoping to profit off the fact that someone else will eventually be more scared than you are - it's the ultimate opportunity to round trip the fear-greed spectrum in a single decision.

That's not exactly a characteristic of a fulfilling life in my mind, so no, I don't own or plan to own gold and I don't plan to own stacks of toilet paper during the next pandemic either.

51 | The More Things Change, The More They Stay the Same

This post is Part 3 of 3 of the “Promoting Transparency Instead of Perpetuating Taboo” series.

Progress continues to be made, options continue to proliferate, information continues to become more accessible, convenience continues to be ubiquitous, and yet we're still plagued by the same money problems.

These money problems existed 1,000 years ago and they will exist 1,000 years from now, because they are fundamental to the human condition.

Our lifetimes are marked by constant movement along a number of money spectrums - overconfidence vs. paralysis, fear vs. greed, regret vs. pride, contentment vs. longing, scarcity vs. abundance, control vs. chaos, and so many others - that can't be "figured out" or solved "once and for all" because our daily life experience is constantly changing our position on them.

Every single person is faced with the same unanswerable money questions - How much is enough? Am I ahead or behind where I am "supposed" to be? What is the "right" type or amount of spending? Why is it so much harder to spend out of my savings than out of my income?

Every single person's life experience is wildly unique to them and also only really known by them, so the layers of nuance that are then baked into our individual relationships with money are hard to comprehend and impossible to map out on a piece of paper.

And yet financial hardship, at every level of wealth, can be pointed back to three basic principles...

• Running out of cash on hand.
• Spending that exceeds income for too long.
• Expectations of the future that outpace the ability to support that future.

No matter the point in history or the amount of wealth, the same three principles explain every hardship that someone has experienced with money.

They’re not complicated principles and they don’t require much technical knowledge, but they continue to perplex human after human - not because we haven’t found the tactics, but because the tactics aren't the missing piece of the puzzle.

Every single one of us has the final puzzle piece in our possession, it’s just too scary and hard to place in its spot.

The final puzzle piece is the willingness and courage to begin slowly chipping away at money's taboo-ness so that we can actually begin changing our collective relationship with money.

Not recklessly talking about it, but discussing it with intent and legitimate desire to change our relationship with it.

Conversations that are characterized by more listening than telling. More questions than answers. More accountability than advice. More encouragement than judgment. More awareness than correctness.

Common languages for discussing it that span household, age, and dollar amount.

Common tools that stop measuring, bench-marking, or promising certainty and instead provide context, comparability, and promote resilience.

50 | More Context, Please!

This post is Part 2 of 3 of the "Promoting Transparency Instead of Perpetuating Taboo" series.

There are two primary ways we communicate about money that compound its taboo-ness.

There are the things we say that only serve as gas on the fire of things we observe...

"We can't afford" when we've actually just chosen to spend on something else.

"We really screwed up" when it wasn't actually a bad decision, but only new information that came to light and made hindsight 20/20.

"Once we 'catch up' or 'get ahead' then everything will be better" without acknowledging that "more" doesn't actually change our relationship with money.

The list of phrases is endless, but the themes are eerily similar every time - emphasis on non-critical, ambiguous details, single points in time, and things that are out of our control.

Then there are the things we don't say that leave us all filling in the blanks with an infinite list of "whats" and no accompanying "whys".

What we have experienced in the past with money - good or bad.

What we have observed family and friends do with money - good or bad.

What part of our finances feels like a function of luck - good or bad.

What part of our finances we wish was different - good or bad.

What we know about the future - good or bad.

What we don't know about the future - good or bad.

The reality is that these thoughts and feelings actually drive our decisions and feelings of well-being, but our tendency to reduce money stories to "I-see-what- they-bought,-so-I-must-know-their-story" leads us to believe that "more" spending means "more" wealth which means "more" well-being.

What we observe and discuss only perpetuates the taboo nature of money and obscures the fact that, regardless of our actual level of financial wealth, the exact same emotions and challenges impact every single one of us…

49 | The Teeny Sliver

This post is Part 1 of 3 of the "Promoting Transparency Instead of Perpetuating Taboo" series.

Morgan Housel says it so well, "People are good at learning by imitation. But the hidden nature of [financial] wealth makes it hard to imitate others and learn from their ways.”

Observe someone playing a sport. You can probably figure out how to score.

Observe someone raising a child. You can probably snag some pointers.

Observe someone doing a good deed for stranger. You can probably replicate it.

Observe someone interacting with their money. Take it with a grain of salt.

The reality is that we "see" a fraction of a fraction of how people interact with money - a teeny sliver of how they spend it.

Toss in the fact that we tend to compare other's highlight reels to our own blooper reels and that teeny sliver of spending becomes even more misleading.

Everybody has to maintain their car and pay utility bills, but the vacation or nice house or restaurant is what gets filed away in the observer's brain.

We don't see how much cash they have on hand.

We don't see how much equity they have (or don't have!) in their home.

We certainly don't see any investment balances.

We don't know their income level.

We don't know what else they spend.

We don't know their savings rate.

We don't know what their investment experience has been.

The funny thing about the teeny sliver of spending is that, if anything, it's a glimpse into what is preventing someone from building financial wealth.

Drawing conclusions about someone's financial well-being by observing their spending is like assuming someone is physically fit because you have seen them lounging on the couch or eating a piece of cake.

If incomplete, irrelevant observations are the embers on the fire, the way we talk (and don't talk!) about money only fans the flame...

48 | Pricing Land Mines

I took our two older kids to the movies for the first time. We ate more popcorn and drank more Sprite than we ever would at home. We experienced the magic of watching a movie in a theater. We took a picture beside the cut outs in the lobby. We had a shared experience that all three of us added to our memory buckets.

It doesn't really matter if the popcorn was $5 or $15 or $30 of the $45 that we spent for the experience.

The funny thing is that it's easier to say that than it can be to actually feel that way.

It's all too easy to focus on the specific price because it's easy to measure, while appreciating the general value is harder because it's impossible to measure.

Movies aren't the only place it's easy to get stuck on the price. There are little "pricing land mines" everywhere that can ruin an experience if we don't maneuver around them or disarm them ASAP.

A professional sporting event costs $20 to get in and sells a beer for $15. How different would it feel if you paid $35 at the door and received a free beer ticket?

An online retail item costs $70 and then on the next screen you realize that shipping costs another $10. How different would it feel if the list price was $80 and there was free shipping?

A hotel costs $300 for a night and then charges $30 for self-parking on-site. How different would it feel if the room cost $330 and the parking was complimentary?

It's hard to recognize when you might step on a "pricing land mine" until it has already exploded.

A few ways to navigate them are...

Observing how often you or someone you're around talks about the specific price of things - notice whether it emphasizes the price or the value received.

Zooming out and describing the experience as a whole instead of the individual components. Name the value of the things that you're getting - they're not always obvious and they are different for everyone.

Acknowledging that the "whats" are much easier to discuss than the "whys", but the "whys" are what actually drive contentment. Name the "whys" behind the decision to spend in the first place.

Remembering that someone else's price doesn't have to change your experience.

47 | Keeping Tabs on the Story

This post is Part 3 of 3 of the "Zooming Out Instead of Fixating on the Details" series.

The risk is not that we will miss an important detail with our finances.

The bigger risk is that we get lost in the details and lose track of the bigger story.

The reality is that there are only a handful of things that need to be addressed from the technical side of our finances.

Beyond those few things, the rest of our relationship with money consists of the stories that we tell ourselves to fill in the gaps and make sense of our lived experience with money.

When we get lost in the weeds, we start to lose track of the story.

When we push on a rope, we start writing a different story.

When we zoom out, we give ourselves the best chance to keep tabs on the story.

Zooming out allows us to quickly see if we're caring for the technical things.

Zooming out allows us to orient when the details try to overwhelm.

Zooming out helps us call out feelings that are not in line with reality.

Zooming out helps us to rewrite narratives that have gotten out of whack.

Zooming out ensures that we're all seeing and talking about the same things.

Zooming out allows us to recognize when we need to change course and instructs us on what we should change first.

Zooming out ensures that the story we're telling with our finances matches the story that we're trying to live out in our lives.

46 | Pushing on a Rope

This post is Part 2 of 3 of the "Zooming Out Instead of Fixating on the Details" series.

The weeds have an ability to disorient us and then lure us into focusing on things that don't actually move the needle.

We take action, but inevitably that action doesn't do anything to address the uncertain feeling in our gut around money.

At first it might, because doing something feels good.

The trouble is that that "good feeling" doesn't always imply "good progress".

Eventually, we circle back to the same old feelings of...

"We've been here before."

"Well, that didn't really change anything."

"Why does the hole still feel so deep?"

"Why does it feel like we are still 'behind'?"

If being disoriented leaves you overwhelmed and confused. Putting energy towards the wrong things leaves you tired and frustrated.

Changing companies for modest income boosts without addressing our risk of burnout or increasing the horizon on our ability to generate income. Eventually, we'll discover that we're pushing on a rope.

Trying to control spending by saying "no" to hundreds of $5 decisions instead of saying "no" to a few $500 decisions. Pushing on a rope.

Trying to save what is leftover at the end of a month or year instead of setting aside the money on the front end to "pay yourself first". Pushing on a rope.

Chasing hot investments and accidentally establishing the dreaded habit of "buying high and selling low". Pushing on a rope.

Inevitably, pushing on a rope leads to no real progress, consumes all of our energy, and leaves us exhausted and bitter.

Instead of trying to get every single little detail right and hoping it will change our relationship with money, we're better suited to zoom out and focus on the things that actually matter...

Additional Reading

Staring at decisions by Seth Godin

The perils of investing based on past performance by Carl Richards

45 | Lost in the Weeds

This post is Part 1 of 3 of the "Zooming Out Instead of Fixating on the Details" series.

One of the first challenges with money is orienting to what matters and what doesn't matter so we can experience real financial well being.

Because finances are complex and hard to talk about, it's easier than ever for conversations about money to get lost in the weeds.

Once you're lost in the weeds, it's hard to get out, it's easy to become overwhelmed and feel like you "don't have what it takes to succeed", and it can seem like the only solution is "more".

Sadly, much of the financial services industry begs us to dive further into the weeds by emphasizing and marketing undifferentiated "products" - investments, financial plans, and tactics - as the things that you're missing.

We don't need experts driving us further into the weeds, because the reality is that any conversation about finances is always at significant risk of getting lost in the weeds...

We find ourselves evaluating different banks trying to squeeze out an extra 0.20% of interest thinking it will make a difference - "more" must be better! - instead of acknowledging that the fact that we have cash set aside and available at any moment, not its rate of return, is what actually matters.

We find ourselves haggling or stressing over the last few thousand dollars in the sale or purchase of a home - how much "more" can I capture? - instead of realizing that 99% of the financial implications of the decision are already water under the bridge.

We find ourselves wondering if we, or an advisor, can find the handful of investments, of the tens of thousands that exist, that will provide the most return - "more" has to be better! - instead of acknowledging that as long as we care for a few basic things that infinite combinations of investments can be good enough.

We find ourselves wrapped around the axle on the precise level of this year's raise or bonus - "more" today must be better! - instead of assessing and reflecting on the trajectory and sustainability of income over the next couple of decades.

We find ourselves defeated and discouraged when we exceed an arbitrary monthly budget for any category of spending - if only we had "more"! - instead of intentionally observing the spending over a longer period of time and evaluating its role in driving lasting contentment.

We find ourselves perplexed and overwhelmed by the different types of accounts that we could use to save - which one will lead to "more"? - instead of knowing that the fact that we're actually saving is the ice cream sundae and the exact account to which we save is only the cherry on top.

We find ourselves ruminating and socializing on the daily, weekly, or monthly moves in the stock market - "more" must make these emotions go away? - instead of accepting that the short term moves don't mean a thing and that they will never go away.

Getting lost in the weeds in one category can hijack our relationship with money, but society makes it hard not to get lost in the weeds in every single category.

Once we're lost in the weeds, then any effort to address the feeling of disorientation, overwhelm, or discontentment is a lot like pushing on a rope...

44 | The Urge

The urge is real.

The urge is strong.

The urge is persistent.

The urge is for the "deliverable" - the tool, tactic, analysis, projection, or product - to solve everything and allow us to surpass the underlying emotions and feelings that define our relationship with money.

It's a two-way street.

The urge is the easy way out for the one providing advice or counsel.

Once we've identified or felt enough of the tension in the conversation, we can point to the "deliverable" to make the tension go away and then subconsciously cross our fingers!

The trouble is that this runs a substantial risk of missing the mark, pulling us further away from what we actually need, and discouraging us along the way.

"I am feeling significant angst trying to buy a home in the current housing market." Well, here's a summary of your investment performance over the past 12 months and a commentary on what outperformed in your portfolio.

"We feel significant tension making spending decisions and often find that we can't reconcile differences in our perspectives." Well, here's a projection of what you can spend over the next 30 years to be sure you don't run out of money.

"We want to save for college for our kids, but we're not sure if that will be in the cards for them and we're hesitant to designate so much money to this one goal." Well, here are all the tax benefits of saving into a 529 account and thoughts on why it's a good idea.

The "deliverable" is the cheap way to get out of the real conversation.

The urge is the easy way out for the one receiving advice or counsel too.

When we're feeling the typical overwhelm that so easily accompanies our experience with money, we subconsciously cross our fingers and hope that someone will point to the "deliverable" that can make the tension go away!

The trouble is that this "magic bullet" does not exist and pretending that it might only expedites our journey to a disappointing day of reckoning.

No commentary about the current job market finds you a new role.

No budgeting app assesses the level of contentment in your spending.

No future projection does the saving for you.

No investment product protects you from the uncertainty of the future.

The "deliverable" is a crutch to making real progress.

It sounds like I am suggesting that tools, tactics, analyses, projections, or products are not necessary for financial well being. This is not the case.

The reality is that fancy "deliverables" are much less necessary to financial well being than we've been led to believe and, if we're not careful, they run the risk of distracting us from our relationship with money.

43 | Why So Many Bank Accounts?

Any time I see a bunch of bank accounts within a single household...

I cringe a little bit.

Yes, I understand the mindset of segregating money for a specific goal from everything else.

I see how having separate accounts in a relationship could allow spending to happen seamlessly without a value judgment being placed on each purchase.

I also know that a business owner needs to keep the business finances separate from personal finances.

Certainly there are other advantages that I am not listing.

I can buy into each of these advantages if they are done with clear intention, but it also doesn't have to be this hard.

The number of disadvantages to allowing your list of accounts to grow without pruning seem infinite and hard to measure from a psychological perspective.

When everything comes into one place, and everything goes out of one place, it makes it a lot easier to do something that is important in finances...

Keep track of how much is coming in and how much is going out.

This sounds so simple, but it's so easy to overlook.

When funds are spread across a bunch of different accounts…

It's a lot harder to keep track of what is real income and what's a transfer between your own accounts.

It's close to impossible for the average person to keep tabs on where dollars are being spent.

It's a lot easier for things to run on autopilot for many months or years longer than they were intended to run in the first place.

It's a lot easier to panic when an account balance gets low even though your collective account balances are more than enough.

When it comes to the number of accounts, "Less is more!".

42 | Running on Empty

This past weekend, my dad and I were riding down to Pinehurst to meet up with my brother for a weekend of golf, college basketball, and quality time.

Pinehurst has been a special place to all three of us for many years - U.S Opens, golf weekends, and visits to my grandparent’s-in-law house.

Over the past 15 years, I'd bet that I have driven the route from Winston-Salem to Pinehurst somewhere between 25 and 30 times.

I know the route well - the food options, the golf courses we pass along the way, the exits with tons of options, and the exits without much of anything but an on/off ramp.

About seven miles away from the traditional turn off, we passed an exit with our last gas station option. As we drove under the overpass - the exit officially behind us - Dad said, "I think we should be able to make it to the next exit before we have to fill up."

At this point, the warning indicator read, "1 Mile to Empty".

For a few minutes we chuckled as we discussed the decision - how long has the light been on? Does the light coordinate with the mileage counter? Does "1 mile" mean 1 mile or does it mean 35 miles?

Based on prior experience, we sensed that we had some leeway, but the exact amount of leeway was unknown and the previously casual discussion quickly pivoted to how far we were from the next gas option.

After a few minutes, we began approaching the normal exit and saw big, orange barricades across the entire ramp - "EXIT CLOSED".

The innocent chuckles and "what ifs" of a few miles back pivoted further into somewhat nervous laughs and a quick glance at Google Maps to assess the reality of the situation.

At this point, we were winging it on what seemed like a gallon at the most and fumes at the worst.

The innocent decision to pass on an easy gas stop seemed like no big deal until the next option, which had been available every time before, was not available at the precise moment we needed it.

---

The reality is that cash in a savings account is a lot like gas in your car.

With a full tank of gas, you can access exponentially more destinations than you can even with a half tank. The next fill up is way down the list of things you need to be concerned about and you have the freedom to dream and adventure without being too concerned with immediate logistics.

When you're driving on fumes or even a gallon, you are constantly thinking about when, where, and maybe even if you will be able to fill up again. You're completely susceptible to any uncertainty that is thrown your way. Even routine trips begin to feel reckless because there's a chance it won't go as smoothly as it always has.

With the gas tank, it is easy to see the cause and effect. With money, that relationship is not as obvious.

Ample gas in the tank, or cash in the bank, can feel like such basic advice that it's easy to overlook under the presumption that you'll always have the ability to fill it back up.

No matter the car, if you run out of gas, you're stuck.

No matter the level of wealth, if you run out of cash, you're stuck.

---

Fortunately, the next exit was only a couple of miles down the road. It didn't have a gas station, but we were able to navigate back to the closed exit in a roundabout kind of way to fill up the tank and grab lunch.

For us, the worst outcome would have been waiting on the side of the road for AAA and possibly missing a tee time for the afternoon. A bummer, but not a life changer.

With finances, the stakes can escalate much more quickly. The AAA equivalent when you run out of cash in a savings account is carrying a balance on a credit card out of desperation, selling investments at an inopportune time, or being forced to say "no" to something that might have been an automatic "yes" with more cash on hand.

Don't run your household on fumes!

Additional Reading

How your bank balance buys happiness: The importance of "cash on hand" to life satisfaction by Peter M. Ruberton, Joe Gladstone and Sonja Lyubomirsky
"Could liquid wealth, or "cash on hand" - the balance of one's checking and savings accounts - be a better predictor of life satisfaction than income?"

How I Think About Cash by Morgan Housel
"When chaos hits, nobody has enough cash."

41 | Who’s Throwing the Peanuts?

Don't model your life after a circus animal. Performing animals do tricks because their trainers throw them peanuts or small fish for doing so. You should aspire to do better. You will be a friend, a parent, a coach, an employee -and so on. But only in your job will you be explicitly evaluated and rewarded for your performance. Don't let your life decisions be distorted by the fact that your boss is the only one tossing you peanuts. If you leave a work task undone in order to meet a friend for dinner. then you are "shirking" your work. But it's also true that if you cancel dinner to finish your work, then you are shirking your friendship. That's just not how we usually think of it.

In May 2012, I clipped this excerpt from an article in the Wall Street Journal called 10 Things Your Commencement Speaker Won't Tell You.

It stuck out to me as a 24-year-old trying to find my way in the real world and it still rings true today.

Typically, before you are responsible for supporting yourself financially, you're spoon-fed metrics that streamline measuring progress - grades on report cards, scores on exams, win/loss records in sports, diplomas and degrees, etc.

It can be pretty difficult to orient in a world that doesn't have a standard way of measuring progress - a lot of career and even financial frustration can probably be pointed back to “failure to orient”.

Because it's so hard to find metrics in the real world, it's easy for income - one of the few things that spans household, profession, industry, and age - to become a default metric of progress.

Some level of income is vital, but beyond that level, it is a pretty lousy metric that doesn't account for the things that add all the color to life, particularly the quality of our relationships.

The line that hooked me was, "But it's also true that if you cancel dinner to finish your work, then you are shirking your friendship."

The quality or strain of a relationship is pretty easy to feel, but impossible to objectively measure.

With enough shirking, I think it's possible to get "fired" from a relationship. It's just a lot harder to recognize when we're on the brink in a relationship because there aren't any peanuts being tossed.

Oftentimes, work must be prioritized - not minutes at work, but real, value-creating work.

Oftentimes, a relationship must be prioritized too.

The nuance isn't in knowing precisely when to lean into each one.

The nuance seems like knowing that the peanuts aren't the only way to measure progress and figuring out creative ways to assess progress for the things that might not have peanuts.

40 | Why Do We Save?: The Most Powerful Reason

We save to keep our expectations in check.

A dollar that is not saved is spent - creating expectations.

A dollar that is not spent is saved - creating options.

The challenge is that every dollar gets assigned to either expectations or options - you can't pick "both" and you can't pick "neither".

This fact alone makes it the most complex relationship in our personal finances and the thing that most financial well being hinges upon.

A weekly coffee, a monthly streaming subscription, an annual trip, a specific school, a specific style of decorating a home - each has a different purpose, magnitude, and frequency, but every single one creates some degree of expectation.

When expectations grow out of control, eventually there is a day of reckoning and reality forces us to push the reset button.

When options grow out of control, there are a number of downsides too, but they're a conversation for another day.

The purpose here is not to determine an objectively correct level of spending/saving or make a value judgment on different types of spending.

Both are impossible tasks.

The purpose is to acknowledge the power of saving and its role in a world where expectations are easier than ever to create and as painful to change as they have always been.

39 | Why Do We Save?: The Underrated Reason

We save in order to keep flexibility in our finances.

A habit of saving - income (purple) consistently exceeding spending (red) - is the equivalent of playing a card game with wild cards.

The flexibility and combinations that come from having wild cards in your hand completely changes every hand, every decision, and eventually the entire game.

If you have an established habit of saving then you can...

Take a pay cut to make a career change or shift to part time without changing your underlying lifestyle.

Say "yes" to a once in a lifetime opportunity without crunching the numbers or wondering if you're being reckless.

Spontaneously give money to an organization or person that means something to you because you want to or because they have a specific need.

Temporarily re-direct funds that have historically landed in a bank or investment account and for a season cover college tuition or a car purchase or a trip.

The flexibility afforded by saving can be hard to wrap your mind around, because we think of "saving", or "not spending", as constraining.

It's too easy to think that "spend whatever you want" is flexibility.

In actuality, "spend when you want" is a truer form of flexibility that comes only from a habit of saving.

Additional Reading
Overstuffed by Seth Godin

38 | Why Do We Save?: The Obvious Reason

We save to set aside money that we can spend later.

OK...?

Tell me more please...

Not saving is like...

Routinely running your gas tank to empty. You're always looking for the next gas station, you're limited in how far you can travel, and you're always susceptible to a tiny change in plans or expectations leaving you stranded on the side of the road.

Buying food for your next meal only. There's no slack in the system in case you’re unable to go to the store tomorrow, someone else decides to join you unexpectedly, or you find out the food has gone bad.

Operating with only the roll of toilet paper that is on the holder. Once you get to the second half of the roll, you're going to be pretty aggressive with conservation and pretty selective with who you'll call if you happen to run out.

We have no problem operating with a little more gas or food or toilet paper than we need for the next moment. We're also pretty adept at not hoarding any of them.

In reality, money doesn't need to be any different, but for some reason it feels much more complicated.

With money, it's easy to do the equivalent of always operating on E or towing a tank truck of gas behind you so you never run out. Finding the right middle ground is so much harder.

Inevitably, every dollar spent over a lifetime is not perfectly timed with an offsetting dollar of income. This is the essence of why we need to save something.

What's challenging is that if this is the only reason for saving, eventually we're going to get burned out, forget why we're saving, or struggle to determine how much is enough.