97 | Communicate, Communicate, Communicate!

Everyone loves to give the advice that you just have to communicate better. “Communicate, communicate, communicate!”

At times, I have found the advice to be somewhat abstract and hard to conceptualize in a practical way.

At the core, I think the advice is trying to acknowledge the gap the often grows between our whats and hows and our whys.

For some reason, it becomes more awkward to share our whys over time. Kids don’t seem to have a problem doing it, but it doesn’t feel like it’s the same for adults.

Once we stop talking about our whys, then we’re stuck trying to connect the dots between the whats and hows that we observe.

Look no further than personal finance, to find an arena that begs us to focus on the whats and hows without regard for the whys time and time again.

Recently, I was chatting with a friend who desires to care for his mom as she moves into the next phase of life.

He has a sibling who deeply cares for his mom's well being too.

In this particular case, the friend was primarily considering whether or not it made sense to buy a house for his mom to rent from him to solve her transition need.

The sibling of the friend quickly wondered why his brother even needed to be involved at all - the mom had the resources to buy anything she could need.

To add an easy layer of possible misunderstanding, there was a significant difference in financial savviness of each sibling - one was starting with the only way he could think of that might work and one knew all the ways it could work.

Not to overstate it, but it was easy to see how a single what and how was quickly taking the stage ahead of the original why and running the risk of leading to misunderstanding, unnecessary tension, and in a worst case scenario diluted levels of trust.

Refreshing each sibling’s perspective on what they were trying to accomplish was 10x (maybe infinitely!) more productive than discussing the ideal property, the impact of interest rates, the best structure of a lease, or the down payment required.

I think the abstract advice of “communicate, communicate, communicate” is really getting at tell your why and tell it with clarity, authenticity, and truth - even when it is hard or a little awkward to do.

96 | The Cost of Doing Life

The idea of 3% waste came from a friend who read it in a tweet. I’ve searched to try to give credit, but alas, I have not found the original thinker. I imagine and hope he or she would appreciate this elaboration on the idea if they were to come across it.

The general gist is that there is a baseline level of waste in everyone’s experience with money and…

That is OK.

If you’re wasting more than 3%, you’re probably being a little aloof.

If you’re wasting less than 3%, you’re probably trying to control more than can be controlled.

But for every $100,000 in income a year, we’re talking about $3,000 that will be regretted, second-guessed, forgotten, or just have less impact than originally hoped for or expected.

The 3% figure passes my sniff test, but I’d probably call it the inevitable “cost of doing life” instead of “waste”.

We’re talking about…

The convenience meal that totally disappoints.

The monthly subscription that continues many months past the last use.

The cost of groceries at a tourist destination.

The exercise equipment optimistically purchased only to collect dust in the corner.

The price increase because you waited a few more weeks to buy something that was cheaper when you first started looking.

The hidden fee that presents itself at the 11th hour of a decision.

The list is endless, but the feelings of frustration or disappointment are often eerily similar.

I think the rule of thumb is less a hall pass to freely waste, and more of a clipper for financial hangnails that have the ability to drive us crazy and even hurt if we don’t deal with them and move on.

These things don’t have to go on a permanent ledger to remind us of our mistakes.

They are better used as a mental note that might better inform the next time, and a gentle reminder that perfection is often the enemy of very good.

95 | A Gray Skill

Generating surplus and using surplus are two totally different skill sets.

In the simplest terms, generating surplus is ensuring that your income exceeds your spending over time.

It's a black-and-white skill - it’s relatively easy to measure, the objective is clear, and the feedback is direct - you either do it or you don’t.

For some people, high levels of income serve as the cornerstone for generating a surplus. For others, high levels of intentionality in spending serve as the cornerstone for generating a surplus.

It doesn’t matter which approach you take, but at some point, you have to learn how to generate a surplus.

Once you’ve mastered generating a surplus, the process of actually using the surplus is an entirely different puzzle - a gray skill.

It’s hard to know what things or experiences are worthy of surplus funds.

It’s not always clear what will be accomplished by using the funds.

Because the objective isn’t defined for us, there is a decent chance we will lose track of it.

And whether we like it or not, using surplus is an indirect way of beginning to define “enough”.

If you can’t hone the skill of generating a surplus, it’s going to be an anxious lifetime of overdrafts, counting down to paychecks, and shuffling around debt.

If you can’t hone the skill of using a surplus, it’s going to be an anxious lifetime of always-changing goal posts, second guessing, and wondering how much will ever be enough.

Where generating a surplus seems to provide a baseline level of security, peace of mind, and margin for error to accommodate the inevitable uncertainty of the future.

Using a surplus seems to help sow the seeds of purpose, contentment, and satisfaction that we all so deeply long to experience.

Two different skill sets that get at very different things - both worth refining over time.

94 | The Story is All That Matters

It’s hard to keep track of the story.

Early in life, one dollar comes in and one dollar goes out and it’s easy to say, “This dollar paid for that thing.”

It doesn’t stay this easy forever though.

The number of transactions explodes, the perspectives change, the preferences proliferate, the people multiply, and frankly, there just isn’t enough time to do this kind of accounting.

Slowly, and then quickly, the story in our head begins to diverge from the story on paper.

“Our spending is out of control” is the story in our head when the story on paper is that it’s really only a lot of $5 dollar coffees or we don’t see eye to eye on every single spending decision or we’ve had a flurry of necessary, but large purchases recently.

“We are bad investors” is the story in our head when the story on paper is that we got a little unlucky with the precise timing of investing that $10,000 or we struggle to keep track of all our accounts or we forgot about the 7 years of gains that preceded the most recent dip.

“If only we had more income” is the story in our head when the story on paper is that if we saved a little bit more or spent a little bit more intentionally or paid off that debt or boosted our cash on hand then we could feel the peace of mind or relief that we desperately desire.

More than any innocent naïveté or technical oversight, I think most financial stress or frustration can be chalked up to the story in our head diverging from the story on paper.

The good news is that just because we can’t say “this dollar paid for that thing” doesn’t mean that we can’t bring the stories back together.

93 | See Then Spend

Two of our three children have allowance jars. They get $1 per week that is disconnected from any chore or activity within the household.

My wife noticed that the jars tend to accumulate dollars when the kids are not thinking about them, but if the jars are top of mind, then there is always something to buy.

If they see, then they spend.

This feels eerily similar to how many of us still operate our financial household in adulthood.

We look at our account balances and then decide to spend dollars if there are enough there.

Or we look at our account balances and then decide not to spend dollars because there isn’t enough there.

Both modes of operating are just like a kid with an allowance jar - see then spend.

The challenge is that in either case, the money is at risk of driving the decision more than the values.

If there is more, then spend. If there is less, then don’t spend.

I think we all want the freedom to be able to spend or not spend without having to look every single time - decisions that aren’t determined by the dollars.

Of course, I’m not granting permission to spend without ever looking - that inevitably leads to a nagging shortfall of contentment or a perpetual uneasiness about viability.

I’m more describing a special freedom that accompanies a consistent routine of reflecting on spending and saving - without judgment, shame, or blame - that begins to allow values to drive decisions instead of account balances.

We can spend, then we can see.

This freedom isn’t tied to dollars in the jar, but a willingness to exchange 1,000 account balance refreshes or 100 “missed budgets” with 1 honest reflection.

Additional Reading

The freedom loop by Seth Godin

92 | Debt as a Family Member

I once had a teacher who said that any customer who makes up 25% of your revenue is a member of your management team and a customer who makes up 50% of revenue is on your board of directors.

This concept captured the hidden costs that often accompany something that seems so good on the surface.

The big contract is awesome in all the ways that you can measure, but it’s often less awesome in the things that are hard to measure.

It seems like debt can play a similar role in our own finances.

The larger it grows the more pull it has on our decisions and the more it begins to resemble an unwelcome advisor or a demanding family member.

Debt can seem so innocent and convenient until you realize that you’re the only person that can make it go away.

Debt has a way of calcifying a certain level of income as the only one that can work for a household.

Debt loves to see the future self footing the bill for the past self.

Debt has a way of delaying plans or completely eliminating the opportunity to pursue something unique, new, or different.

Debt has a way of making peace, contentment, security, and flexibility seem always out of reach.

Debt has a way of snuffing out dreams before they’ve even crossed your mind.

Debt has a way of looking your good idea right in the eye and saying “Nice try, but I don’t think so.”

Debt is tricky because it’s a useful tool all the way up to the point that it grabs the pen and starts writing a different story than the one we would write for ourselves.

91 | Good At The Things You Can’t Measure

It's easy to think that if you can measure something, then it matters.

Money is especially adept at being this kind of false proxy.

But some things, many of the most important things, will always be impossible to measure.

Your rate of accumulation is easy to measure, but knowing how and when to use what you have accumulated for more than security and peace of mind has no metric.

Checking things off a to-do list versus balancing what technically needs to be done with the mental, emotional, and relational constraints in the moment.

Knowing how much debt you've been approved for versus sensing the level where debt becomes the CFO of your household.

Knowing how to say something is a Google Search or a conversation with a close friend away, but knowing when to say (or not say!) something isn't in any manual.

Finding the cheapest option versus finding the best-fit option.

Responding as quickly as possible versus trusting that quality, consistency, and thoughtfulness might build more rapport.

Hitting the next target for a bonus versus building a business and career that is designed for the future regardless of the incentive package.

Choosing where the conversation will go versus being nimble enough to engage in the conversation wherever it goes.

Knowing the rules versus knowing when the rules may not apply or when it's more appropriate to extend forgiveness.

Putting things on the board during a brainstorming session versus creating an environment where everyone feels secure enough to get things out of their head and onto the board.

It's hard to know what success looks like for the things you can't measure, but I think it's worth discovering over time.

90 | We Are Probably NOT a Good Fit if You…

The most important thing we can do is ensure that we will work well with one another.

If we're not a good fit, we will both eventually regret it.

This business is different from any other financial planning business you have ever encountered.

It is intentionally designed to achieve different outcomes, but it is not for everyone.

We have found that there are certain desires, characteristics, and feelings that many of our clients have that make them a good fit.

We have also found that there are certain desires, characteristics, and feelings that serve as red flags for starting a relationship.

We are probably NOT a good fit if you:

Desire…

• Stock tips and speculative shop talk or someone you can call your "investment guy"
• Detailed calculations predicting the future or a promise that you'll be able to retire in a certain month in 22 years
• Complex solutions and products that you don't understand
• Control more than curiosity
• To see invested dollars only go up in value without any seasons of down along the way
• To continue paying fees to your advisor out of your account because even if they're exorbitant at least they are out of sight and out of mind

Don't know...

• How it's possible to have success with money without being in tune with where the market has been, where it is, and where it's going next year
• How you could have a real conversation about finances outside of a conference room setting
• How behavior could possibly have a greater impact on our well being than the newest tips, tricks, and tactics
• If you can trust seven colored bars to tell your financial story more completely than any other tool you've ever used

Are hesitant to...

• To block out the noise of financial social media or your most financially vocal family member or friend or CNBC
• Entertain the idea that "more" might not be the only solution
• To share all of your finances with a single person or log into an account online and share your screen in order to gather the most useful information

Feel...

• Like it's possible to game the system
• Like you should be able to figure out money on your own because, if you can't, you're not doing your job
• Like paying someone to help you make financial decisions is an expense instead of an investment
• Like a political administration is the biggest threat to your future financial well being
• Like a "one time" plan or conversation is all you need to get the ship headed in the right direction
• Like it is a waste of time to talk about the non-numbers side of your relationship with money

Appreciate...

• Getting assigned homework to do on your own instead of putting heads together to knock out tasks as a team
• Being able to talk about money once per year (or never!) in hopes that it will fix itself with time
• The personal nature of phone tag and back and forth emails over the ease of of a scheduling software that allows you to pick your best time
• Making tactical moves with your investments at the top and bottom of market cycles

89 | We Are Probably a Good Fit if You…

The most important thing we can do is ensure that we will work well with one another.

If we're not a good fit, we will both eventually regret it.

This business is different from any other financial planning business you have ever encountered.

It is intentionally designed to achieve different outcomes, but it is not for everyone.

We have found that there are certain desires, characteristics, and feelings that many of our clients have that make them a good fit.

All of them may not resonate, but if a few do then maybe it's time for us to connect.

We are probably a good fit if you:

Desire…

• To think of money as a tool to drive purpose and meaning instead of a permanently scarce resource on an imaginary scoreboard
• To pursue work that is more than a paycheck that leaves you counting down to your retirement date
• To talk about more than just investments, insurance, and/or certainty-promising retirement projections
• To buck the 9a to 5p work culture, live in a new place, switch careers, start a new business, or navigate a life transition
• To stop paying 1+% on your managed assets and still wonder what to do with the rest of your finances (even the most altruistic advisors can feel like asset gatherers!)
• To fundamentally change your relationship with money (easiest with folks in their 30s and 40s or the most nimble-minded in their 50s and 60s)

Don't know...

• The first question to ask
• Where exactly you want to go (we'll help you figure it out...over time)
• Where the goalposts are (few people do)
• How to keep the goalposts from constantly moving (you are not alone)
• Anything about investing or "the market"
• Why the dollar amount of your assets impacts how much you have to pay for advice from most other financial advisors

Are tired of...

• Trying to categorize your spending or set budgets only to be discouraged when you run out of energy to keep it up
• Feeling like the questions in your head are not appropriate to ask out loud
• Financial jargon and fearmongers
• "Comprehensive" and "holistic" planning only speaking to your investments
• Long lists of complicated recommendations that you can't get done
• DIY'ing your finances because the endless research inevitably goes in circles (and that second guessing though!)
• That feeling of leaving a meeting with an advisor and feeling like you should understand what was discussed better than you do

Feel...

• Like your income keeps growing and you keep saving, but your feelings about the future aren't changing
• Like conversations about money, particularly with people you love the most, are hard to have
• Like you’re getting a lot of conflicting advice from a lot of different parties
• Overwhelmed by the options and decisions that you have to make about money
• Inspired to change the money stories and scripts that play on repeat in your head
• Coachable and open-minded

Appreciate...

• That investments aren't the secret to financial well being
• Numbers taking a back seat to real life
• Conversations and questions more than analysis and projections
• Rolling up sleeves instead of shooting the breeze
• That simple things can still be hard to do
• That neither you or I can predict the future
• That you'll have to want it for yourself more than I want it for you (keep reading the blog if you need to appreciate how much I want it for you!)

88 | The One Pager: Why and How?

Traditional financial planning uses incomplete information to try and predict an uncertain future.

That's a bad combination.

The one pager uses complete information to prepare for an uncertain future.

The initial build of the one pager will feel like a deeper dive into your finances than you have ever done.

The information is specific, precise, and intentionally selected to tell your "numbers story" in the most concise manner possible.

Many people find that the process of building is more helpful than any other work they have ever done around their finances.

Once the one pager is built, you will have a tool to inform every single financial conversation and decision going forward.

The subsequent refreshers of the one pager will feel easy, effortless, and simple.

But there's an important distinction - it won't feel simple because it is simplistic.

Simplistic is not helpful - it is often incomplete, ignores nuance, and lacks depth.

Complex isn't helpful either - it overwhelms, distracts, and disorients. Complex is the primary residence of most financial service providers.

What you will experience is what Carl Richards would call elegant simplicity.

Elegant simplicity sits on the far side of complexity, but it is not easily attained.

Elegant simplicity is complete, appreciates nuance, and drives depth. It calms, clarifies, and orients.

The one pager was designed to cut through the complexity, embrace elegant simplicity, and change the way you think about money forever.

Here is what we will need...

Things that are easiest to gather online by logging in together…

• Balances from the start and end of the most recent year for all of your bank accounts
• Balances from the start and end of the most recent year for all of your investments accounts
• Balances from the start and end of the most recent year for all of your debt (i.e. mortgage, car loans, students loans, etc.)

Things that you may have to gather before we look at them together...

• Paystub or summary of income for the entirety of the most recent year
• Tax return for the most recent year filed

Things that we will be able to discuss...

• Summary of any real estate that you own
• Summary of any businesses that you own
• Summary of any life insurance policies that you own

87 | The RwM Checklist

This checklist is designed to help us keep tabs on our relationship with money.

It is a useful tool to create a baseline understanding of our relationship with money and to refresh every few years to keep tabs on inevitable changes that will happen over our lifetime.

Relationship with Money

• I am able to filter out the noise and identify the most important decision or next step as it relates to my finances.
• I find it easy to trust the simplest explanation or strategy for getting something done.
• I am able to tell the story or describe the "whys" behind my financial decisions beyond the objective dollar amount spent or received.
• I am able to orient within a financial conversation or decision that has many variables and emotions.
• I am able to minimize second-guessing or regretting many of the financial decisions that I make.
• It feels natural to have conversations with other people about money.
• I am able to identify the financial goalposts that I am aiming for.
• I am able to see alternatives beyond "more" - more income, more spending, more saving, or more investment return - as ways to experience financial well being.

Sustainable Income

• My income is generated by leveraging my most natural gifts and skill sets.
• My income streams have a long or indefinite horizon.
• I am able to manage the risk of burnout that accompanies my means of generating income.
• I am able to spend time doing things that matter to me.
• I am able to spend time with people that matter to me.
• I find significant pleasure in the ways I generate income.

Content Spending

• I spend money on the people, experiences, and things that are most important to me.
• I spend money on the people, experiences, and things that bring lasting contentment.
• I am aware of how my spending has changed over the past few years.
• I am comfortable with how my own level of spending compares to my perception of the level of spending of family, friends, neighbors and colleagues.
• I am confident that I could adjust my spending in the face of uncertainty without undermining the things that matter most to me.
• I am able to be generous to the magnitude that I have always hoped or envisioned.
• I experience freedom and fulfillment as a result of my generosity.
• I am comfortable with the role that debt plays in my relationship with money.
• I do not feel like debt gets a “seat at the table” when I am making financial decisions.
• I can see how dollars I spend directly enhance the relationships of people that mean the most to me.

Accessible Saving

• When my income increases, it is easy for me to increase my rate of savings to match the increase in income.
• I am comfortable with how I decide to set aside dollars into short term and longer term buckets.
• My level of cash on hand feels like it allows me to manage the stress and increase the flexibility I feel in the month to month.
• My level of cash feels like it allows my other assets to remain untouched except for the times I intentionally access them.
• I see saving as a way to manage lifestyle creep and keep my expectations in check.
• I feel like I have a good grasp on how much financial wealth is enough for the life I desire to live.

Patient Investing

• I have a high level understanding of how my dollars are invested.
• I have a high level of conviction in the philosophy that I use to invest dollars.
• In the face of uncertainty or new information, I do not question the investment philosophy that I am using.
• I am comfortable knowing that in a world of 7 billion people, many people will experience better investment returns than I do.
• I am aware of the fact that my ability to remain invested during the most unsettling times is more important and more attainable than any technical investment tactic.
• I appreciate the fact that "owners" of businesses bear more risk, but can also reap more reward than non-owners or lenders to businesses.
• I appreciate the fact that "spreading your eggs across many baskets" might limit cumulative return potential, but also limits cumulative loss potential.
• I am comfortable with the reality that my investments might not ever experience positive returns, but often do in periods that exceed 5 or 10 years.
• Many people who know me well would call me a patient person.

86 | "Houston, We Have a Problem"

We keep pretending like the same old tricks are going to start giving us a different outcome.

We're in 2023 with more insight, more wealth, more perceived freedom and flexibility than ever before and our relationships with money don't really reflect it.

Finances continue to be the number-one cause of stress for 73% of Americans outpacing other popular stressors of politics, work, and family. Gen Z'ers and Millennials take the cake with more than 80% being stressed about money. Even if we wanted to ignore it, we can’t because the ripple effect that stress around money has on everything else is always palpable.

We're as discouraged with how we generate income as we've ever been with only 32% of the workforce considering themselves actively engaged in their organization. This leaves 68% of us going through the motions or actively fighting against the system for the majority of our waking hours. It's hard to find purpose, fulfillment, and financial well being when we're barely tolerating our primary sources of income.

Collectively, we're as unaware as ever with how much money is going out the door with 65% of Americans claiming they don't know how much they spent in the last month. It wouldn't be that big a deal except for the fact that knowing how much you spend is the only way you can determine how much is enough. We tend to get stuck categorizing, budgeting, and debating the good and bad spending when adding up the total would be sufficient for most people to start changing habits.

We're as hesitant and unable to save as ever with 57% of Americans uncomfortable with their level of cash in the bank and 36% with credit card debt that exceeds that level of cash in the bank. We continue to set money aside like it's a mandatory chore instead of a stepping stone to freedom and flexibility. We're all to blame for this one, because we called our cash in the bank an emergency fund from Day #1 setting the course for decades of playing to "not lose" instead of playing to win. If only we had given it a more hopeful name like an opportunity fund instead!?!

Our investment returns are as predictable and underwhelming as ever with the average investor returning 3.6% to barely beat out inflation and cash over the 20 years ending in 2021. This one is hard to believe but it's the case every year when the statistics are refreshed. We're plagued by overconfidence, overwhelm, overreactions, over-tinkering, and overthinking in ways that are crushing our ability to generate average investment returns.

Ignoring our money hasn't moved the needle.

Annual cost of living increases or bonuses haven’t changed our level of engagement or satisfaction.

Budgeting apps haven’t changed our contentment.

Extra accounts and retirement projections haven’t made it easier to save.

Endless investment products haven’t improved our investment experience.

The same old tricks are giving us the same old outcomes.

Houston, we need to change our approach or we’re going to explode!

85 | The RwM Manifesto

When it comes to finances, regardless of level of financial wealth, almost everyone and everything has told us that "more" is the only option.

"More" will lead to abundance, security, energy, leisure, fulfillment, peace of mind, and freedom.

This is not true.

In fact, it couldn't be further from the truth.

We've been trained to...

Fixate on details instead of zooming out to see the story being written.

Increase complexity instead of trusting simplicity.

Search for tactics instead of clarifying our "why".

Seek perfection instead of embracing trade offs.

Perpetuate the taboo nature of money instead of promoting transparency.

Grasp for certainty instead of building resilience.

In a sneaky way, these default attitudes and behaviors have further solidified the idea that "more" is the only option and have ironically distracted us from the things that are most important to us.

In the process, we've replaced abundance with scarcity, security with anxiety, energy with exhaustion, leisure with busy, fulfillment with disappointment, peace of mind with restlessness, and freedom with fear.

We are here to break down this unacceptable status quo and improve our collective relationships with money so that we can move towards actually experiencing abundance, security, energy, leisure, fulfillment, peace of mind, and freedom.

84 | The Refinement of Trade Offs

This post is Part 3 of 3 of the "Embracing Trade Offs Instead of Seeking Perfection" series.

Because we've been led to believe that "more" is the only option, the idea of a trade off is perceived as a terrifying exercise in acknowledging failure.

If we can't do anything and everything then it feels like we've sold ourselves short.

We want perfection, not trade offs.

But attempting to eliminate trade offs is an endless exercise in futility and frustration - perpetual discontentment - because trade offs are a feature of life, not a flaw.

Trade offs allow us to bust the myth of perfection.

Trade offs allow black and white to become gray.

Trade offs give shape and substance amidst the ambiguity.

Trade offs force us to assign value to something and acknowledge less value for something else.

Borrowing from Godin, trade offs allow us to put ourselves on the hook.

Trade offs allow us to abandon the status quo when it is no longer the best option.

Trade offs allow us to discover things that matter more to us than we could have ever discovered without making the trade off.

Trade offs push us forward more than they hold us back.

Trade offs allow us to begin defining "contentment".

Trade offs allow us to begin clarifying "enough".

Trade offs refine us in a way that provides a peace of mind and freedom that no amount of resources can ever replicate.

83 | The Ambiguity of Money

This post is Part 2 of 3 of the "Embracing Trade Offs Instead of Seeking Perfection" series.

The line that gets us from individual decisions to eventual outcomes is twisty and usually pretty faint if it even exists at all.

It's difficult to attribute outcomes to specific factors because there are a lot of factors and because the factors are always shifting.

The shifting starts with constantly changing facts and circumstances which are further complicated by our emotions and relationships.

Once you layer on our incomplete memory of the facts and circumstances and our single-minded perception of the emotions and relationships, you can begin to imagine the challenge of re-telling the story.

Of course, we want to believe that our relationship with money is cause and effect in nature, but we're kidding ourselves when we're tricked into thinking it's that black and white.

Life experience alone sets the scene for a complex narrative and then...

Good decisions result in bad outcomes.

Bad decisions result in good outcomes.

Some decisions result in what appears to be no outcome.

Some outcomes trick us into believing that we made a perfect decision.

And we haven't even addressed luck and risk.

As Morgan Housel says, "Luck and risk are both the reality that every outcome in life is guided by forces other than individual effort. They are so similar that you can’t believe in one without equally respecting the other. They both happen because the world is too complex to allow 100% of your actions to dictate 100% of your outcomes. They are driven by the same thing: You are one person in a game with seven billion other people and infinite moving parts. The accidental impact of actions outside of your control can be more consequential than the ones you consciously take. But both are so hard to measure, and hard to accept, that they too often go overlooked."

This kind of ambiguity makes it easy for "more" to become the hammer and all our feelings about money to become the nails that need to be pounded.

But most ambiguously, ironically, and persistently of all, once we've reached a basic level of financial wealth and income, incremental additional dollars don't change our relationship with money or our feelings about the uncertain future.

"More" doesn't change our ability to manage burn out risk or make it more likely that we might find ourselves actually finding joy in the way we generate income.

"More" doesn't address the emptiness that accompanies spending once it fails to bring lasting contentment or begins to feel like dollars running through a turnstile.

"More" doesn't decrease our feelings of overwhelm or stress if we're confused about where surplus dollars need to go or wondering why extra dollars aren't changing the uneasy feeling in our gut.

"More" doesn't help our investing behavior, because "more" means that the inevitable dips in the future will feel bigger than they do today even when our wealth is substantially greater.

"More" doesn't change our relationship with money if we're not ensuring that the numbers and the story we tell ourselves about those numbers are becoming more aligned over time.

"More" is a sneaky way to avoid trade offs, but trade offs are less scary and more life giving than they seem...

82 | The Comfort of Black and White

This post is Part 1 of 3 of the "Embracing Trade Offs Instead of Seeking Perfection" series.

When things are black or white it's so comfortable - you can rest your mind, you can disregard nuance, and you can allow the absolutes to govern everything.

The decision will be right or wrong.

The options available are scary or safe.

The person is either rich or poor.

Debt is either good or bad.

The budget was met or missed.

Save this much and there's a 99.999% chance you do this thing at this precise moment in time.

In theory, absolutes feel so comfortable, nice, and tidy. Even predictable. They allow life and all its feelings and emotions to fit in a box.

The sneaky challenge with black and white is the implied assumption that there is a right answer. An ideal destination. Complete perfection without trade-offs - once we find the black or the white, whichever one we're looking for, then we'll be set.

The not so sneaky challenge with black and white is that it's not real life. It's not how the world works - there are no perfect decisions or outcomes.

You're going to buy something that goes on sale a week later.

You're going to finally pull the trigger on investing dollars only to see them decrease in value immediately after you get started.

You're going to purchase a home after properly inspecting it only to discover it has more problems than you ever imagined.

You're going to make a decision that feels exactly right and then all the facts and circumstances will change and you'll be tempted to believe you made the wrong decision.

You're going to hear a rule of thumb that feels like it should apply to you, but doesn't, and then feel uncertain about everything else.

Once the allure of black and white or the pursuit of perfect infiltrates our relationship with money, we're on a hamster wheel to nowhere with "more" money quickly becoming the only solution.

As we go about seeking perfection, the ambiguity of money only adds to the chaos...

81 | One of My Biggest Fears

"I miss when I thought chasing dreams was
Holy magic behind curtains in a sacred place
Before it was managers and lawyers
Who colored up and cashed them out
For vacation homes in coastal states"

From Heroes by Ben Rector

Yes, I had to look up the definition of "colored up" - in a game of poker exchanging many low-value chips (of one color) for fewer higher value chips (of a different color) while keeping the same overall value - but as soon as I did I had goosebumps.

I've never had the words, but this is the essence of an "anti-goal" that I have used throughout my entire career.

I've been afraid of managing and coloring up and cashing out - it's as if the very concept has been the opposite end of an invisible magnet repelling me away from some career paths and final destinations and pushing me in the general direction of others.

I've been scared of the way coloring up and cashing out would place the outcome ahead of the purpose.

I've been scared of the way it would slowly and quietly suck the life out of how I spend my days.

I've been scared of the way it would distance me from family, friends, and strangers alike.

I'm scared of the way it would sneakily place money and what it can buy above most things that are a lot harder to measure.

I'm scared of the way it would snuff out the flickering light of some of my most closely held dreams and wildest ideas.

It's not a condemnation of a manager or lawyer or any other role.

It's not even a condemnation of building financial wealth or second homes.

Borrowing from Richards, I see it as slowly allowing the game or institution or status quo to distract you from who you were created to be.

Borrowing from Buechner, I see it as slowly allowing your greatest joy to become untethered from the world's greatest need.

I've always thought that chasing dreams truly was "holy magic behind curtains in a sacred place". Something that was more magic than baby steps and reserved for the select few that knew the secret password to get behind the curtain.

As I've grown up, it seems that chasing dreams or becoming more like who we were created to be is more baby steps than magic and there's no curtain - the hardest part is not giving into the constant call to color up and cash out.

The thing is that coloring up doesn't change the value, only the appearance - maybe it isn't what it's cracked up to be after all.

80 | The Story and the Numbers

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

If certainty is impossible to deliver, then why does the financial services industry continue trying to deliver it?

Certainty (or probability of success!) will increase if…

You can make a certain level of income for the next 30 years.

You spend a fixed amount inflated by 3% for the next 30 years.

You max out your 401k and/or Roth IRA every year for the next 30 years.

You achieve investment returns of 7.5% for the next 30 years.

In theory, this work of projecting and mapping out the future is supposed to help you do “financial planning” and oftentimes this process is called a “financial plan”.

In reality, this process encourages grasping for certainty, focuses on things that are out of your control, and transforms a "financial plan" into the next item on the long list of financial services "products" that perpetuate society’s tendency to over-spend (i.e. consume) or over-save (i.e. hoard).

This process or "product", like all those before it, pushes us further away from how we were designed to interact with our money.

Real financial planning is knowing that we can only build resilience to navigate through an uncertain future adjusting course when new information is learned and improving our relationship with money each step of the way.

Resilience looks like…

Generating income from something that leverages your natural gifts and skill sets, allows you to manage risk of burnout, has a long (or indefinite!) time horizon, and allows you to spend time doing things with the people that matter to you. Income that is a pleasure to generate is ineffable.

Spending in a manner that brings lasting contentment with an awareness that every dollar spent creates some degree of expectation for the future. The ability to adjust spending in the face of uncertainty and acknowledge the sneakiness of envy are the only cheat codes for contentment. Generosity often increases contentment, debt often decreases contentment, and spending that enhances relationships with others is an investment, not an expense.

Saving, on average, in proportion to your level of income and into buckets that will be accessible in the near and distant future when you need the dollars the most. Cash on hand provides flexibility in the short run and endurance for the long run. Saving is the tool that allows expectations to remain in check and facilitates the continual pursuit of "enough".

Investing in a manner that you believe in and in which you have a baseline understanding knowing that, regardless of strategy or plan, the only guarantees are that someone will always outperform you and that how you behave during the inevitable unsettling times will be the biggest determining factor in your lifetime returns. Owning businesses tends to increase potential returns, diversification tends to make the ride smoother, long horizons tend to increase the probability of positive returns, and above-average patience is a superpower.

Grasping for certainty is inflexible, rigid, exact, unrealistic, disappointed by course correction, fragile, and ironically abstract because it tells a story with numbers that does not match up with the lived experience.

Building resilience is flexible, fluid, imprecise, realistic, expects course correction, pliable, and ironically concrete because it tells a story with numbers that matches the lived experience.

Additional Reading
The Magic Certainty Button by Carl Richards
Endless Uncertainty by Morgan Housel
God at Work in an Uncertain World by Rev. Daniel Mason

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…