79 | The Remembering Self

This post is Part 2 of 3 of the "Building Resilience Instead of Grasping for Certainty" series.

We're all scared of change and uncertainty, but their respective barks are many magnitudes bigger than their bites.

Complete certainty seems to be something worth longing or grasping for, but it's because we've been misled - ever increasing certainty imperceptibly transforms into boredom, loneliness, and lifelessness over time.

Uncertainty is unnerving, but it is where our most profound life moments and stories are shaped and formed.

We go to movies, concerts, and sporting events because we're uncertain of the outcome.

We go on vacations because we've never seen a place before and want to discover it.

We get coffee or lunch with people we've never met because we are curious to find out who they are.

Our greatest life experiences are often a result of living through the most uncertain of circumstances.

The uncertainty creates the tension required for the magic to happen.

The irony is that in areas of life that we could make certain, we actively seek out uncertainty and in our money life where uncertainty is the only option we desperately seek a certainty that can't exist.

With our money, we've created a system, language, philosophy, and frame of mind that has allowed the fear of change and uncertainty to control us unlike it does in any other aspect of our life.

Part of this compounding is because we've replaced a clear big picture with infinite, disorienting details.

Part is because we've replaced elegant simplicity with unnecessary, ever-increasing complexity.

Part is because we've replaced clarifying our purpose with the empty search for tactics and hacks.

Part is because we've replaced trade offs that refine us with the endless pursuit of perfection.

Part is because we've made what was always intended to be transparent completely taboo.

Part is that we've forgotten that our "remembering self" cleans up the story that our "experiencing self" so deeply fears.

As Brian Portnoy says, “The fact is that the good ol' days were rarely all that good. Even so, the stories we build in retrospect are usually very clean, with well-specified events (start and end dates), connected through a clear causal chain (this led to that) and an overall ‘this narrative makes sense’ vibe. Welcome to what leading behavioral economist [and Nobel Prize winner] Daniel Kahneman calls your ‘remembering self.’”

Change and uncertainty are more inevitable than we care to believe, but fortunately our "remembering self" knows and accommodates these realities in a way that serves as the final green light to slowly stop grasping for certainty and begin building resilience...

78 | We’re Going to Change and It's Hard to Know How

This post is Part 1 of 3 of the "Building Resilience Instead of Grasping for Certainty" series.

You take a break from work, which provides enough time to reflect on where you're headed, and the seeds of a career change are planted.

You have a child and how you allocate your time is refined in way that it has never been before.

You have a health scare and everything that seemed to matter a month-prior pales in comparison to what matters now for your well being and your outlook on life.

Your company gets acquired and the monthly expectations, income levels, and career trajectories of the former company are quickly at risk of becoming the “good old days”.

You meet a friend who leads a life that is very different from yours, but very much like one you desire to lead, and your curiosity is piqued in a way that spurs previously unimaginable action.

Some change is sudden, and some happens more organically over time.

Things that were once irrelevant become mission-critical, and things that were once mission-critical are now irrelevant.

But there is always change and it's always difficult to predict it when, where, and how it will happen.

Not only is it hard to predict, but it's hard to even acknowledge.

In describing the End-of-History illusion, Harvard psychologist Daniel Gilbert says, "All of us are walking around with an illusion - an illusion that history, our personal history, has just come to an end, that we have just recently become the people that we were always meant to be and will be for the rest of our lives."

Implied in the illusion is that our preferences will remain the same indefinitely, which begins to make "more" an enticing way to solve for things.

“If my preferences are going to remain the same, then I need to have enough to support all of them forever and maybe some extra cushion to accommodate a couple of extra preferences - just in case.”

Then the case for ever-increasing income and assets is calcified.

But what if it could be different?

What if instead of being imprisoned to a past self and his or her flawed projection of the future we accepted that change was a feature of the experience?

What if we trusted that our spending ebbs and flows - both up and down - with each season of life and that we don’t need to accommodate every past and current self's preferences and versions of the future?

What if we trusted the fact that our level of income often naturally governs our level of spending and instead of fearing a reduction in income allowed it to lead us into the inevitable change?

It doesn't have to be a never-ending battle to acquire more and we don't need a money tree to experience the good life.

For as hard as it is to get a good grasp on our future self, our "remembering self" throws us a bone that makes the prospect of change a little less scary than it may seem…

76 | She Said, He Said

In a conversation with a couple, I started with a simple question to kick things off, "What's your favorite way to spend money?"

The wife shared that going on a date or out to dinner with friends was her favorite way to spend money. The experience of getting ready, anticipating the evening, and connecting with people was second to none in this season of life.

The husband shared that he had grown accustomed to saving extra by eating on the cheap with friends in a way that had led to endless stories and deep relationships with minimal financial investment required. He acknowledged that excess spending to acquire the "experience" even seemed a bit irresponsible.

One totally legitimate perspective that will likely find saving and investing to be empty, meaningless, and detached without some spending on Priority #1.

Another totally legitimate perspective that will likely feel like they are wasting dollars and maybe even "falling behind when saving for the future" if they splurge on date nights.

I couldn't have cut to the heart of our relationship with money better had I written the script.

I think it's easy to think this question should take a backseat to more "sophisticated" topics like investments, odds of retiring on time, or the best credit card rewards.

This is a mistake.

No hack, planning tactic, or investment idea can compensate for these differences in perspective.

It's too easy to think more money is the solution, but more money doesn't change either of these perspectives - at best it allows them to be brushed under the rug still co-existing in an awkward, unspoken kind of way.

More times than not, it's not the amount of money that matters, but our relationship to it.

75 | A Deadly Combination

A common experience with our money is that our cash on hand (blue), real estate (yellow), and investments (gray) at some point can get to a level that feels like "a lot".

Of course, "a lot" is about as subjective as anything can be in finances.

Compared to $200, some people feel like $2,000 counts as "a lot". For others, $20,000 feels like "a lot" and for others it might take $200,000 or $2,000,000 to hit "a lot".

Your bank account grows to a size that surpasses the largest expense you've ever had and it feels like "a lot".

A home appreciates over a decade or two and it feels like "a lot".

Investment return in a single year is comparable to a few months worth of paychecks and it feels like "a lot".

No matter your definition, it's easy for "a lot" to feel like a good finish line and an opportunity to treat yourself, but this is where it starts to get tricky.

Without the context of our expectations, "a lot" isn’t always what it seems, and modest growth can disguise and even fuel unsustainable expectations.

Our expectations are no better represented than by our spending (red) and they have a way of growing without us even realizing it.

There is always something else that we could get or do.

Once we have something, it's never quite as satisfying as we expected it to be.

Things tend to get more expensive over time.

And the reality is that expectation’s natural state of being tends to be one of growth rather than decay.

The challenge here is that our expectations continue to grow, while our ability to support those growing expectations levels out at "a lot" - a deadly combination.

Truth be told, “a lot” is only a feeling unless it’s tethered to expectations.

63 | Less is More

This post is Part 3 of 3 of the "Trusting Simplicity Instead of Increasing Complexity" series.

You already know everything that you need to know to achieve financial well being - the hard part isn't the knowing, but the ignoring and the doing.

The list of things that are out of our control serve as great places to hide and excuse ourselves from real progress - interest rates, the debt ceiling, politics, taxes, market commentaries, daily return figures, and credit card rewards to name a few.

These things like to paralyze us. They like to consume all of our time. They like to invite second-guessing. They like to create confusion. They like to spread fear and FOMO.

Every single one of those things is responsible for increasing complexity and none of them actually matter when it comes to making real progress.

Yes, I realize that other advisors and news executives are scoffing right now, but from a numbers perspective, all financial well being (or stress!) rolls up to three simple concepts.

Ensuring you always have enough cash in the bank to live your life. Stress management.

Spending less than you make on average for your lifetime. Flexibility management.

Keeping tabs on the relationship between what you have and what you need. Expectations management.

Like it or not, if you can address these three things, there is nothing else to accommodate from a numbers perspective.

If we buy the complexity that we’re peddled on a weekly basis, then the numbers never mean anything and we struggle to reach a place of real financial well being.

If we trust simplicity, then we can focus on a couple of numbers, ignore the circus, and continually move closer to a place of real financial well being.

Trusting simplicity allows us to quiet the noise of the world and rest our minds.

Trusting simplicity allows us to see and tell our story more clearly.

Trusting simplicity allows us to move from fearing the future to constructing it.

Trusting simplicity allows us to find contentment in a world of discontentment.

Trusting simplicity allows us to move through the chaos of complexity without falling prey to its false hope.

62 | Simple is Hard

This post is Part 2 of 3 of the "Trusting Simplicity Instead of Increasing Complexity" series.

Simple is hard because deep down we want to believe it's more complicated than it is - there is too much at risk psychologically.

When we struggle on something that we perceive as simple or easy, it's demoralizing and we get stuck in cycles of shame that get us further away from where we want to go.

The mistake is thinking that simple and easy are describing the same thing.

In basketball, if you score more points than the other team then you win - pretty simple. But to call basketball an easy game would be quite an oversight.

With that said, the feedback loop in basketball is quick enough that you have an opportunity to learn the game as you go by making adjustments after a timeout, a quarter, or between games.

The scoreboard makes it easy to keep track of the objective and the natural cadence of the game allows you to make adjustments and close feedback loops.

With money, the objective is simpler than it seems, but the execution is anything but easy.

We're bombarded by alternatives, opinions, suggestions, circumstances, trade-offs, and misunderstandings that are constantly challenging our definition and perception of "enough", so the objective fades into the background or disappears completely.

And as Michael Lewis says in the Big Short, "The problem with money [is that] what people [do] with it [has] consequences, but [they are] so remote from the original action that the mind never [connects] the one with the other", so the feedback loop - for positive and negative outcomes - is nearly impossible to recognize.

It's important that we don't get confused about what we're calling simple.

The objective of the game - to have "enough" - is simple, but because of the constant noise and the missing feedback loops, the actual execution is hard.

Simple is hard because of the things that keep us from getting to it, but once we’ve experienced it and started to trust it, we come to realize that it’s priceless…

61 | Complexity is Sexy

This post is Part 1 of 3 of the "Trusting Simplicity Instead of Increasing Complexity" series.

Complexity is sexy for the person seeking it because it appears to cover over all the potential faults.

Complexity is sexy for the person offering it because it sells itself.

Complexity has been an unfortunate hallmark of the financial services industry since its earliest days.

From investments to projections of the future to insurance products, on the surface they seem different, but the underlying theme remains the same - more complexity is the only answer to a complex world and our complex feelings.

The reality is that complexity isn’t a solution, but more a symptom that we've abandoned the simple concepts that drive 95+% of the outcome.

It's a little bit like reading the textbook in school and understanding the governing principles of a topic. Once you have a baseline understanding of them, they seem relatively simple, even a little like common sense.

Then as a rookie you move into some role that is governed by those concepts, but you're too far down the org chart to see them in action and everything feels more complex than you ever imagined.

If you can't ever orient and move past the complexity of the rookie tactics and responsibilities, then you never see the "other side" where the simple concepts truly do govern everything.

Complexity is a cheap substitute for real financial well being and it torpedoes our relationship with money for at least a couple of reasons...

It's easy to assume that if you can't understand something then the person promoting it must be smarter than you are and therefore "right".

At best, this undermines your confidence and at its worst it allows many an "advisor" to continue profiting off of innocent naivete without actually improving well being.

It's also easy to think that if it's complex, then it must lead to "more".

This one is a double whammy because complexity might not (usually doesn't!) lead to "more", and even if it did, "more" isn’t always what it's cracked up to be.

Complexity is the easy way out and we all know that the easy way doesn't work in the long run.

Simple is what works, but simple is harder than it seems…

58 | The Wizard Behind the Curtain

In a conversation with a close friend, we arrived at a crossroads.

He asked/said, "The way I understand our investments is that we send money 'behind the curtain to the Wizard of Oz' and he messes with it trying to grow it to be as large as possible so we can retire, pass some along to our kids, and maybe help pay for college. Isn't this all that is happening?"

My only response was, "No, that is not right."

I wasn't abrupt because he made a mistake or because I was frustrated.

I was abrupt because he articulated a modern-day perspective towards investing so clearly and I had to be sure we didn't get further into the spin cycle that flashy marketing and a deluge of information have created.

The "grow as large as possible" and "isn't this all that is happening?" are topics for another day.

The concept of the curtain and the Wizard of Oz is what I want to lean into here.

A couple of decades ago, there was a curtain and there were keepers of secrets that could provide access or information that was important.

In what has been a positive trend for a couple of decades, the "curtain" has been removed and we have shifted into a world where everyone has access to all the information (and investments!) they could ever need.

At times, I think this trend is hard to recognize because the industry that is dedicated to improving "financial well-being" is not organized in a manner that can embrace this new reality.

The industry continues to cling to managing investments when they aren't what matters most, presenting information as if it's a secret, and promising certainty that doesn't exist.

This failure to re-organize has created one set of problems, but the attempts at "financial advice post-curtain" have only compounded the issue.

As the curtain has fallen, the industry's response has been a deluge of information in the form of tips, tactics, and products that are more redundant and inapplicable than ever before.

We've traded the curtain for confusion.

For as much confusion and anxiety as the curtain caused, I think the deluge of information post-curtain has had the same effect - maybe more.

If we're picking tools to navigate the post-curtain world, a leaf blower that can push away the cheap info is much more useful than the pre-curtain vacuum that could suck up every particle of available info.

You have all the access you need, there is no Wizard of Oz behind the curtain, and a leaf blower is more useful than a vacuum.

If we can acknowledge these realities then we can get onto the things that actually allow us to take the reins on our relationship with money. Sustainable income. Content spending. Accessible savings. Patient investing.

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...

---

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...

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.

28 | I Have a Dream

I have a dream that our collective relationships with money will radically transform as a result of having transparent conversations about our finances.

It won't start on the upper end of the wealth spectrum. The stakes will feel too high for it to start there.

It will begin somewhere down the wealth spectrum as people realize that the tips, tricks, and investment products don't actually move the needle like they have been led to believe.

One person will share their finances with another person and realize that their shoulders sit a little lower, their mind races a little slower, and their anxiety about the future dissipates ever so slightly.

Some things will feel vulnerable to share and it will be best to acknowledge that reality before they are shared.

Some things will be backed by deep conviction and appropriate pride and it will be a good thing to acknowledge this before they are shared too.

Everyone has a belief about money that could use some tweaking and a belief about money that could inspire others.

It will feel a lot like playing a card game and getting to see the hand of the player sitting beside you - much easier to play the game, appreciate different strategies, take on the right amount of risk, and have a better understanding of what needs to happen to succeed.

Financial services commercials promising peace of mind, security, and contentment will feel a bit emptier than before because it will be obvious that the promises on the TV pale in comparison to what has been experienced firsthand.

These conversations will inevitably provide gentle accountability for the most financially wealthy to keep from hoarding and inspiration for the less wealthy to slowly build to a sustainable level of financial wealth - both sides actively creeping closer to a clearer understanding of "enough".

Slowly it will creep up the wealth spectrum because the life-changing impact will be palpable and everyone will begin to realize that the same emotions and mental gymnastics happen regardless of a person's actual level of financial wealth.

Collectively, we'll begin to realize that it was never about the actual numbers, but only our underlying relationships with money.

16 | The Clear "Why"

This post is Part 3 of 3 of the “Clarifying Our 'Why' Instead of Searching for Tactics” series.

It might seem like I’m suggesting being reckless and oblivious to tactics - that couldn’t be further from the case.

The tactics matter but only to the degree that we've decided that we're committed to what we're trying to accomplish.

The specific way you finance a home or home improvement pales in comparison to the impact of choosing a specific neighborhood, honing in on a specific price point, or tying up a lot of flexibility into a down payment or ongoing mortgage payment.

The specific accounts you use to save will have minimal to no impact unless you're simultaneously saving enough to keep your lifestyle expectations in check.

The specific investments you use will have minimal to no impact unless you're able to stay invested when you see someone else outperform or another bubble begin to burst.

Without clear "Whys", the tactics - every single one of them - are sirens on a rocky shore tempting us to get distracted from the things that actually matter to us.

Clear "Whys" ensure that we remember why we are using money in the first place.

Clear "Whys" allow us to see something else that looks awesome on the surface and acknowledge that we don't have all the context or knowledge to realize that it's not as cool as it may seem.

Clear "Whys" allow us to step into an uncertain future knowing that some decisions may have bad outcomes, but that doesn't mean they were bad decisions.

Clear "Whys" allow us to recognize when a specific vocation or career trajectory is no longer aligned with what we desire at our core.

Clear "Whys" allow us to tweak our spending when our most deeply held desires are in jeopardy of not being accomplished.

Clear "Whys" ensure that we are making decisions about our money instead of having money (and tactics!) make our decisions for us.

15 | Thanks, But No Thanks, Maslow!

This post is Part 2 of 3 of the “Clarifying Our 'Why' Instead of Searching for Tactics” series.

You might be tempted to say, "Those are the basic tactics, there have to be more sophisticated tactics that are the real secret."

Nope.

The next set of tactics is even more discouraging because there is plenty of writing about them not being quite as impactful as they seem on the surface.

Tax-loss harvesting. Useful in some specific cases, certainly not all cases. See here. Sorry, Wealthfront.

Asset location. Theoretically useful, but a bit clunky and overrated when it comes to optics and logistics. See here. Thank you, Betterment.

Roth dollars instead of taxable dollars. Phenomenal benefit that is worth pursuing, but not a unicorn. See here.

Unique investment options. This is probably my favorite, because a link isn't even necessary. The average 401(k) offers between 8 and 12 fund options. There are around 10,000 mutual funds or exchange-traded funds (ETFs) in the United States. If the specific investment option was that important, don't you think we would have worked harder as a society to get the average person access to more than 0.001% of available funds for their largest bucket of traditional investments? The specific investment option certainly isn't the secret.

The endless search for tactics feels like it has to be a more productive use of time than trusting relatively simple rules of thumb and getting clearer on why we're building financial wealth in the first place.

I think the problem is that underneath the search for tactics is the underlying assumption that "more" is always better. "More" will fix everything, but "more" comes up empty when it is done without purpose.

Our typical use of next-level tactics is akin to leaping up Maslow's hierarchy of needs pyramid before we've addressed the basic physiological needs of food, shelter, and water.

In the case of personal finances, the base of the pyramid isn't sophisticated tactics, hacks, or tricks. I think the basic physiological needs equivalent is a clear "why".

14 | The Solution You're (Not) Missing

This post is Part 1 of 3 of the “Clarifying Our 'Why' Instead of Searching for Tactics” series.

It's easy to think that success with money is a matter of finding the right tactics.

A perfect combination of all the proper tips and tricks organized and assembled to achieve financial nirvana.

Google certainly contains sound tactical advice.

"How much cash should I have in my emergency fund?". See here.

"Which debt should I pay down first?". See here.

"How much should I be saving?". See here.

"Should I use a Traditional IRA or a Roth IRA?". See here.

"How should I invest my money?". See here.

All the answers are there. All the answers are sound (except the last one that is comically misleading!), but they don't seem to resolve that uncertain feeling in your gut when it comes to money.

Tactics certainly don't address how the way we generate income impacts the way we spend our time.

Tactics don't clarify how the way we spend constantly changes our baseline expectations and experience of life.

Tactics don't ensure that what we have set aside is accessible and wise to use the moment it's needed.

Tactics don't come anywhere close to helping us have more patience or less FOMO when we're investing.

There are plenty of other things that tactics don't do, but it's hard to remember this when tactics are constantly marketed as the solution that you're missing.