134 | The Next, Next One

Once I get the next $1,000 or $10,000 or $100,000 or $1,000,000…

Then I’ll do ____________.

The list of risky things that can fill that blank is endless and unique to each of us.

The problem is that once you get the next one, it’s usually going to feel better to wait for the one after that.

Of course this happens…

Because the amount of money is just a scapegoat.

Either the thing isn’t what we actually want, or no amount of money will ever be enough to start.

131 | Bigger Barns

The "how much is enough?" question has been around since the advent of money and it will remain til the end of time - it's too personal and abstract to work any other way.

One place that many people have referenced to try and construct an answer is the following passage of the Bible...

Luke 12: 13-21
Someone in the crowd said to him, “Teacher, tell my brother to divide the inheritance with me.” Jesus replied, “Man, who appointed me a judge or an arbiter between you?” Then he said to them, “Watch out! Be on your guard against all kinds of greed; life does not consist in an abundance of possessions.” And he told them this parable: “The ground of a certain rich man yielded an abundant harvest. He thought to himself, ‘What shall I do? I have no place to store my crops.’ “Then he said, ‘This is what I’ll do. I will tear down my barns and build bigger ones, and there I will store my surplus grain. And I’ll say to myself, “You have plenty of grain laid up for many years. Take life easy; eat, drink and be merry.” ’ “But God said to him, ‘You fool! This very night your life will be demanded from you. Then who will get what you have prepared for yourself?’ “This is how it will be with whoever stores up things for themselves but is not rich toward God.”

Maybe you read that passage and think it's out of date and doesn't apply to our conversations and relationships with money.

Maybe you read it and find it quite easy to see a bank account, a 401k, real estate, or an ownership stake in a business as modern-day barns that store our surplus assets.

But even if the metaphor is easy for you to see, the practical application of it is as complicated and nuanced as it gets.

Reducing the concept of "bigger barns" to an individual “heart" issue seems like a cop out - like we are letting ourselves off the hook for transparent conversation and real transformation in our relationship with money.

But attempting to quantify it with hard numbers seems like a fool’s errand that ends in arbitrary lines and harsh judgments of our own or others' relationships with money.

As I reflect on it, I don’t pretend to have any answers, but I have so many questions…

If financial wealth is what we need compared to what we have accumulated, how do our thoughts about what we need impact whether we have a second barn or not?

Can you create a second barn by needing less so that what you have accumulated stretches further?

Can you eliminate a second barn by needing more so that what you have accumulated doesn’t last as long?

Does the nature of what you have accumulated - cash, investments, real estate, or owning a business - impact whether your assets are more or less like a second barn?

Does living off only the income of the assets you have accumulated count as a second barn?

What about accumulating enough assets that you never again have to reduce your spending or or even reflect on the quality of it?

If you don’t know you have a second barn, does it count as second barn?

If one person has a second barn, and another person has an identical financial profile, then do they also have a second barn?

If someone passes away and you receive the equivalent of a second barn as a result, do you immediately have a second barn? Or can it become a second barn over time?

Can a certain level of income count as a second barn, particularly if what you need is only a tiny fraction of that level of income?

Even if you give away most of your income, is that income stream like a second barn because you experience the security and power that comes from retaining control and discretion over the resources?

If you use accumulated assets to purchase an income stream, does that make them more or less like a second barn?

If your income is more variable than someone else with the same accumulated assets, does that that make your assets feel like less of a second barn?

Still no answers - only questions that feel like they are worth discussing.

105 | The Cost of Availability

As a kid, I remember friends’ parents who were doctors and carried a pager around when they were on-call.

Maybe I’m unique, but the pager did not seem cool. Maybe it was novel, but it wasn’t cool.

Any time I saw someone interact with a pager, they were being disrupted, they were annoyed, or their stress level changed pretty quickly.

The cost of this kind of availability was extremely high - missed sporting events or recitals, baseline dread of the next notification, tension in a marriage, shuffling of schedules, disappointment, miscommunication - the list could keep going if we wanted it to.

I think most people could recognize that being available around the clock, even for a day at a time, had a high intangible cost - it was obvious to see because the person had to physically leave whatever they were doing in order to “pay the bill”.

It’s funny how in a couple of decades, we’ve transitioned to every person on the planet carrying a “pager” around.

Slowly, we’ve all opted into the novel (not cool!) doctor lifestyle without realizing that the cost of availability hasn’t changed.

We don’t have to leave the space, we don’t get an invoice, and we don’t even have to swipe or tap to pay the bill, but you better believe that the vendor is getting paid in full.

103 | Hindsight is Not 20/20

I don’t think hindsight is 20/20.

Yes, if you have a good memory, the technical facts of the story are easier to retrace once you have seen them play out.

But remembering the precise emotions, priorities, consequences, trade offs, relational dynamics, or rationale of a decision or event does not get clearer as time passes.

I think it gets infinitely fuzzier, because you can't ever fully recreate the moment right before something happened.

Whether it’s replaying the result of a game.

Or a hard conversation.

Or a job change.

Or reflecting on a big purchase.

Or reviewing past investment decisions.

Or criticizing the decisions of leaders and individuals in March 2020 or October 2008.

Considering hindsight 20/20 discredits the past self and torments the current self.

After the fact, we know what went according to plan and what created other challenges.

After the fact, we can’t recreate the moment in a way that respects the adrenaline-, emotion-, anxiety-filled decision that was made when the outcome was actually up in the air.

After the fact, we can’t objectively re-simulate the decision or event because this time we’re able to ignore the hypothetical worst-case scenarios that didn’t happen after the first take.

Hindsight makes it too easy to woulda-shoulda-coulda our way through life wondering why we, or someone else, didn’t get it more right the first time.

Once we can acknowledge that hindsight isn’t 20/20 then it becomes a little easier to extend ourselves some grace and put the what-ifs to sleep.

102 | The Cost of Convenience

Convenience used to be the cherry on top, but it’s beginning to feel more like the ice cream itself - the primary ingredient instead of a nice bonus.

I think it’s become that way because proximity and speed are easy to measure, so in a data-first world, it's only natural to calibrate the scale to measure closer and faster.

But there is a little more going on under the surface.

Every time something is more convenient than the last time, you can’t help but fall deeper into a game that can’t be won.

It can’t be won because convenience is a relative game.

Each “improvement” further closes the gap between wanting it and getting it, but it’s a gap that can’t be completely closed.

No matter how convenient life becomes (or how much our financial resources grow!), today’s desire will never be met yesterday. And this moment’s longing will never be satisfied a minute ago.

The tricky part is that there isn’t a ledger that tallies up this cost of unmet desires.

Instead, the costs reveal themselves very slowly and in ways that are hard to see.

Daily expectations that were once reasonable and dynamic are now unrealistic and unmet.

Slightly less convenient alternatives that used to be a good substitute become silly, even ridiculous, to consider.

Patience that was once a calling card is now perpetual frustration with the system.

And “throwing someone a bone” is replaced with a desire to cancel the people who can’t keep up.

Just because it’s easy to measure doesn’t mean it’s easy to optimize. And just because there isn’t a price tag doesn’t mean it’s free.

Additional Reading

The half-life of magic by Seth Godin

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.

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.

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.

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...

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…

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.