Relationship with Money

A blog that knows “enough” isn’t a number

37 | The "Single Jump" Myth

In a conversation with a friend, my wife came up with a fantastic metaphor for pursuing career change.

The metaphor can be extended to anything where there is a vision that is grander than the current reality - assembling a group of people, starting a business, or even running a household.

Pursuing any change is a lot like trying to get from one side of a river to the other.

Our modern-day habits of small talk and social media have led us to believe that some people can make it across the river in a single jump.

No one can cross a river in a single jump...I promise.

There are two troubles with the "single jump" myth.

The first is that it makes change seem easier than it is, which is pretty discouraging when your first jump ends with a splash.

The second is that it makes it seem like there is more to be found on the far bank than there is in the river.

In reality, change is more like gradually jumping to different rocks to get closer to the far bank.

Some rocks are huge, easy to spot, and bone dry.

Some rocks are bunched closely together, and some rocks are far apart.

Some rocks are tiny and hard to spot initially but are the only way to keep making progress.

Some rocks are wobbly or slippery (or both!) and require extra care landing on them, standing on them, and leaping off them.

Sometimes your shoe, maybe even your sock, gets wet.

Sometimes you hit a dead end and must retrace a couple of steps.

Sometimes you might have to avoid the rock with the snake on it.

As I have pursued career changes, the process has made me more confident that you can't make it across the river in a single jump - all you can do is find the next rock.

The process has also made me wonder if the far bank is what we're pursuing or if the pursuit is actually the rock jumping itself.

Additional Reading

What’s the next smallest step? by Carl Richards
Reminder that scary things are less scary when you make them smaller.

You Accomplished Something Great. So Now What? by A.C. Shilton
Easy to read introduction to the "arrival fallacy".

118: Start Small by Emily P. Freeman
"Small things don’t always turn into big things, but big things always start out small."

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36 | Investments are a Distraction

Wait a second…what?!?

We just did a deep dive on how to invest and now it's a "distraction"...are you kidding me?

Nope.

Once we've cared for the basics and are prepared to behave, there isn't much else we can do when it comes to investing.

Whether it's the fact that there are infinite investment options that all converge into a similar outcome over long periods of time or...

The fact that our lived experience with money has so much more to do with how we generate income, how we spend it, and how we set it aside, or...

The fact that most details of investing are like your doctor reading you the footnotes of the research papers that led them to arrive at their proposed treatment plan.

Investments are an enormous distraction.

They are a distraction behind-the-scenes if we waste time with their administration.

They are a distraction in conversation the moment they have gone over the head of the least knowledgeable (or interested!) person in the room.

They are a distraction when we pretend that any tactical tweak is going to change our relationship with money.

The reality is that the numbers side of financial well being is mostly covered by three core themes...

At all times, do/will I have sufficient cash (blue) on hand?

On average, does/will my income (purple) exceed my spending (red)?

Over time, am I aware of how my spending (red) expectations compare to what I am setting aside (blue/gray/yellow)?

Beyond these basics, investments (and any other tactical details for that matter!) run the risk of completely distracting us from the story that we're writing with our use of money.

Additional Reading

Retirement Success Financial Independence: A Surprising Look into the Factors that Drive Positive Outcomes from the ASPPA Journal
Yes, I crossed out "Retirement Success" - the principle is the same regardless of the goal - see the first paragraph of Page 5 and the related visual

Market High Soup For The Soul by Jared Korver

Your Complete Financial Life by Carl Richards
Not a solicitation - just a powerful visual

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35 | Patient Investing, Part 7 of 7: The Secret Ingredient

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.

Forecasts rarely match reality.

Outcomes do not always align with effort.

The story in our head doesn't always align with the story that unfolds.

Patience is the only way that I know to bridge these gaps.

Patience is to successful investing what the heart is to the human body.

When you see something that challenges the fundamentals of your own way of thinking - patience to lean in, listen to the facts, discuss them with a friend or colleague, and evaluate whether your beliefs still hold true.

When you see someone else experience investment performance that appears to outpace what you are experiencing - patience to acknowledge the discomfort it may cause without abandoning your own plan.

When the world seems to be falling apart at the seams and the value of your investments seems to be free-falling - patience to make an adjustment to the things you can control without getting overwhelmed by the things you can't control.

When a new idea is promoted as the "next big thing", but in reality it doesn't seem to create real value that will ever enhance our collective life experience - patience to wait for its day of reckoning to arrive without getting caught up in the hullabaloo.

When a part of your portfolio feels like dead-weight that needs to be pruned because of recent under-performance - patience to know that each investment will have its ups and its downs, and that recent disappointment does not necessarily call for permanent abandonment.

When a decision feels so urgent and important that you are becoming paralyzed by the moment and the stakes - patience to know that buying a little more time will likely bring more clarity, more information, and more ability to make a sound decision.

Patience isn't a cute virtue.

Patience isn't convenient to have in case of emergency.

Patience is the backbone of success.

Patience is a superpower.

Additional Reading

How long is forever? by Seth Godin

Stop worrying about investments, become a better investor by Carl Richards

Staying Put by Morgan Housel

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34 | Patient Investing, Part 6 of 7: How Long is "Long"?

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.

What do you think the market is going to do this year?

What a question...

It's hard for folks not to ask and it's impossible to answer.

I literally have no idea what the market is going to do this year.

The same will be true if I'm asked again next year, or in 5 years, or in 10 years, or in 20 years.

I'll go as far as to say that someone constructing an answer to the question, "What do you think the market is going to do this year?" is taking the easy way out and only further ingraining our unhealthy desire to grasp for certainty.

If I'm forced to give an answer, I'd probably point to the left hand side of the JP Morgan chart below and say if we're 100% invested in stocks then I'd bet this year will be somewhere between -39% and +47%.

Obviously, that's not super helpful.

I think we're asking the wrong question though.

The question should never be, "What do we think the market is going to do this year?"

The question should be, "Why do we have dollars invested if we think we'll need them next year?"

Investing is not a slot machine, but the shorter the horizon, the more it's going to feel like a slot machine.

Ask me how I think the market (i.e. the collection of companies that make up the market) are going to perform over the next 10 or 20 years and now we're talking about something worthwhile.

If our outlook for investing is a single year, at some point there are going to be some pretty disappointing results - hopefully (cross your fingers!) those results don’t correspond with a significant life event.

If our outlook for investing is a couple of decades, I don't think we'll ever be disappointed by the results regardless of whether they are the historical best or historical worst for a 20 year period.

The tricky part is that for more than a couple of decades, we've been building habits of daily life and engaging with technology in ways that have made the next moment seem like the only moment that matters...

Additional Reading

Keep It Going by Morgan Housel

The delay by Seth Godin

Days or decades: What’s it going to be? by Carl Richards

Stocks For the Long Run by Ben Carlson

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33 | Patient Investing, Part 5 of 7: Be Careful What You Ask For

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.

A friend of a friend rode the GameStop wave from the bottom to the top and back to the bottom in January and February of 2021.

An initial investment of something close to $10,000 grew to something close to $1,000,000 within a few days with the biggest moves happening within hours and even minutes.

What a psychological Petri dish.

So much personal financial wealth tied up in a single stock, that for a couple of days a financial future was reduced to a slot machine with pay outs surging and plummeting by life-changing amounts every few minutes.

I think it's easy to say, "How did you not sell it when it was $1,000,000?!?", but the problem is it's impossible to put ourselves in the vacuum.

If you've made $1,000,000 in the last 10 minutes from holding something, what do you think you're going to do for the next 10 minutes?

Please don't pretend that you have so much control over your rational brain to cash out your winnings.

If you cash out and it continues to surge, you're kicking yourself for a pretty long time.

If you don't cash out and it plummets, you're kicking yourself for a pretty long time.

If you happen to cash out and it plummets, odds are pretty good that you'll have an imaginary friend named "Overconfidence" live the rest of your investing life with you helping you hunt for the next big opportunity.


The Gamestop saga certainly compressed the time and increased the dollar amount, but it's a textbook example of what's happening when we concentrate our financial net worth into a single company or investment.

If you Google "diversification", you'll get some analysis about holding 25 or 30 individual stocks.

It's not actually about the numbers though.

Diversification is about matching up your expected investment gains and losses with what your stomach can handle, knowing that we are not trying to keep from vomiting, but we're actually trying avoid chronic mild nausea.

Diversification is about knowing that in theory the upside is wonderful, but in reality the downside is completely unacceptable.

Diversification is about trusting that scar tissue is a real thing instead of believing it's something that won't impact you.

Diversification is about putting your eggs in different baskets, so that when one basket breaks, gets stolen, or spoils, you have others that allow you to keep playing the game for as long as possible...

Additional Reading

Portfolio thinking by Seth Godin

Easy Money is Money Easily Lost by Ben Carlson

Diversification Means Always Having To Say You're Sorry by Brian Portnoy

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32 | Patient Investing, Part 4 of 7: The Ceiling is the Roof

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.

The "Aura" of the Owner

Maybe there aren't that many dots to connect here. I think we all inherently know that owning something carries a different aura.

When someone says, "I work for this company", it's only so interesting and inspiring. Even someone in a key role will eventually be limited in the impact they can have and the reward they can reap.

When someone says, "I own this company", we're immediately taken to a different level. You feel it in your gut. An owner gets a different level of respect and share of the pie because they take on a different level of accountability and responsibility.

The Rewards of Ownership

When you own a business (as the sole owner or as one of many shareholders!), you get at least two things - income generated by the business and participation in the growth of the business itself.

When it comes to traditional investing, I think technology has abstracted each of these realities in distinct, unhelpful ways.

The income generated from a business used to arrive as a paper check that made it easy to see, feel, and appreciate. Now income gets commingled in an account and likely automatically reinvested making the income side of the equation feel a bit more mystical than it actually is.

The growth portion has turned into a convoluted, real-time metric that is updated every second on your smart phone, CNBC, or your Robinhood app. Instead of trusting that creation of value eventually leads to capturing of value, we've trained ourselves to believe that daily and even hourly moves of investments matter.

Even with these abstractions, the nature and rewards of owning a business have not changed one iota since the first business was incorporated - the income and growth potential that comes with ownership builds financial wealth in a way that is unmatched by being a lender or even speculating on the value of a scarce item.

As MJ would say, "The ceiling is the roof!" when it comes to the upside of owning a business.

The way that "owning-the-business-upside" plays out over time doesn't require an advanced degree to understand. In Morningstar's visual below, two lines are not like the others. That's the "different aura" showing up in the numbers.

The Hidden Side of Ownership

The sexy part of ownership is easy to sense and see.

The hard parts of ownership aren't quite as obvious.

Businesses get paid for fixing things that are broken or improving something that is sub-optimal.

This means that when a lot of things are broken or sub-optimal there is the greatest opportunity for growth.

The only way to participate in that growth is to be an owner before, during, and after the "fixing" or "optimizing" has happened.

The top lines above look great on paper, particularly relative to the lines beneath them, but the chart ignores the uncertainty and discomfort faced every step of the way.

Every bit of growth happens before, during, and after wildly unsettling things are happening all over the world.

Morgan Housel illustrates it well in this chart below. This is the "different aura" showing up in the lived experience.

A key word in all of this is "owning businesses tends to increase potential returns". Because it's not a guarantee, that's all the more reason we own a bundle of companies instead of just one...

Additional Reading

Asset allocation: Key to your investment climate by Vanguard

Stock, Bond & Cash Returns Over the Past 95 Years by Ben Carlson

Keep in Mind, Stocks Rose 1,100-fold During This Period by Morgan Housel

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31 | Patient Investing, Part 3 of 7: The Pilot Has Turned On The "Fasten Seatbelt" Sign

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.

No matter your level of belief, depth of understanding, or specific strategy, the unsettling times are guaranteed to happen.

Nobody, literally not a single person, experiences investment growth, or any kind of growth, without taking some steps backwards along the way.

Your ability to stay the course and remain invested during the periods where you are below your most recent personal high-water mark are the second most important skill you'll have to hone to be a successful investor.

One part is numbers - the best days actually come in the worst times. The depths of the Great Depression, Black Monday, the Financial Crisis, and the COVID-19 Pandemic are where the best days are found. See here.

If you miss out on those days, the implications are brutal. See for yourself...

No change in strategy or hack is making up for that gap. That is only one 20-year period, but all the other 20-year periods look the same. It doesn't matter what you did in practice, what type of equipment you're using, or what tricks your coach told you, if you can't stay in the game when it is the hardest to play, you will lose.

The numbers are easy to see. The trickier part is the psychological side - trusting simplicity instead of increasing complexity.

Doing nothing or "gritting it out", seems too easy to be right. I think this confuses "simple" and "easy".

You know what's easy...

"I think I'll wait until everything seems like it's under control and then I'll invest."

"I think I'll invest in CDs or I-Bonds to get a guaranteed interest rate."

"I think I'll switch my investments to something else because that will make me feel like I've done something productive amidst the chaos."

You know what's simple, but hard to actually do...

Have the discipline to keep enough cash in the bank to provide some cushion to navigate the unsettling times.

Have the wherewithal to acknowledge that the unsettling times are going to happen, but it's impossible to know exactly when they will happen.

Have the self control to not look at CNBC, social media, or your investment statement if that is what is necessary to keep you from making a reckless decision during unsettling times.

Have the courage to have a conversation with someone else before those unsettling times push you to the brink.

As I often like to say, if it seems hard to do, then that's probably a sign that it's the secret to success.

Additional Reading

Fees vs. Fines by Morgan Housel

Is market timing worth it during periods of intense volatility? by Jack Manley

Time the Market Game by Personal Finance Club (don't fall for Jeremy's context-less bio)

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30 | Patient Investing, Part 2 of 7: The "Other People"

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.

Whether it's a day, a year, a decade, or a lifetime - someone, somewhere will always beat your investment returns.

If we can't establish this as gospel, then we'll be second-guessing ourselves to the grave.

Some people will actually outperform, while others will only claim it.

But it's a guarantee that you’ll never know who’s for real and who’s faking it.

Either way, your ability to ignore both groups is how you'll become a good investor yourself.

Once you're cared for some basics, intentional ignorance leads to extraordinary returns.

Whether we're talking about one day, one year, one decade or one lifetime - someone, somewhere will always have an investment strategy that performs better than yours.

As Elon would say and do, "let that sink in!"

If we can't establish this as an investing gospel, then it's going to be a long lifetime of second-guessing, social comparison, and useless woulda-shoulda-couldas.

Some people will legitimately outperform and others will claim to have outperformed when they actually haven't. It's close to a guarantee that you'll never know who's for real and who's faking it.

Either way, your ability to ignore and completely block out the "other people", especially when they have allegedly outperformed you, is likely the most important skill you'll have to hone to be a successful investor.

We used to live in a world where access to information and knowledge was limited, so it made sense to go searching for better options. Some people legitimately had access to things that others didn't, so the hunt might have made sense.

The world has changed and you have access to all the information and knowledge that you could possibly need. The problem now is that it's impossible to know which information and knowledge is actually useful. Speculating about the "success" that others are experiencing is only gas on the information-overload fire.

The hunt was worthwhile when scarcity of information was the issue. The hunt is pointless, even destructive, now that abundance of information is the issue.

In a world of abundance, the competitive advantage is some combination of a mental filter that can keep the useless information from ever hitting the radar and the ability to throw on blinders so you don't get spooked when something inevitably makes it through.

Additional Reading

Hope is not an investment strategy by Carl Richards

FOMO: The Worst Financial Trait by Morgan Housel

“The market has spoken” by Seth Godin

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29 | Patient Investing, Part 1 of 7: Believe

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.

There is no "right" way to invest.

If you don't believe me, go read this book, or at least it's summary, and then come back.

There are infinite options and choices when it comes to investing and not a single one of them will work for the long haul without some level of personal conviction and belief.

There is a spectrum of belief - some people will personally know the ins and outs of their beliefs and may even have experienced something tangible that led them to believe. Others will have heard testimonies from trusted family, friends, or colleagues that have led them to believe.

In The Psychology of Money, Morgan Housel says, "Manage your money in a way that helps you sleep at night. Some people won't sleep well unless they're earning the highest returns; others will only get a good rest if they're conservatively invested."

I'd add that some people will sleep better owning index funds, some will sleep better owning actively-managed funds, some will sleep better owning individual stocks, some will sleep better owning real estate, some people will sleep better owning their own business, and some will sleep better in a mixture of many things.

Regardless of what you believe, I think the deepest form of belief is being agnostic to benchmarks and "other people" - 100% belief that the way you are invested will allow you to live the life you most desire to lead.

This doesn't happen overnight, but it can happen over time and it is worth pursuing over time because the freedom that comes from the next dollar of financial wealth pales in comparison to the freedom that comes from the ability to say "no" to the next shiny investment or to ignore what all the "other people" are doing.

The "baseline understanding" is a touch trickier because there is a risk of getting buried in the weeds.

With that said, part of belief is a high level understanding of what you are trying to believe in - even if it is only the broad strokes.

The knowledge that investment returns are only possible if you are willing to stomach investment losses is part of understanding.

The ability to acknowledge when a specific type of investment or strategy is too complex for you to trust is part of understanding.

The ability to see investing as being an owner and participating in the progress of humanity instead of viewing it as a slot machine that randomly creates winners and losers is critical to understanding.

Belief and baseline understanding ensure that we are prepared for the two guarantees of investing...

Additional Reading

Forget beating some index, instead focus on your financial goals by Carl Richards

Internal vs. External Benchmarks by Morgan Housel

My 'Too Hard' Pile Is Pretty Big by Christine Benz

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28 | I Have a Dream

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

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

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

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

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

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

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

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

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

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

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

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

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27 | Homebuying Series: The Features Always Sound Good

The features always sound good - a two-car garage, ample storage space, beautiful landscaping, extra bedrooms, etc. will sound convenient and comfortable to many people.

Zillow is going to highlight each of these wonderful features too.

In a sneaky way, this begs us to use the "features" to establish our preferences instead of establishing our preferences to evaluate the "features".

"This house has a beautiful front porch that might increase the chance we meet some neighbors" is wildly different from "We desire to rub shoulders with our neighbors on a daily basis, so we will look for a house that has a front porch”.

“This house has a large yard that will give our kids a chance to play outside" is wildly different from "We want our children to learn to play and enjoy outdoor spaces, so we will look for houses with large yards”.

"This house has tons of storage space that will be great to have in case we need it" is wildly different from "We need extra space to store things that are critical to our current and future well-being, so we will look for a house that has plenty of storage space”.

This might seem like splitting hairs, but when the house in reality is inevitably different from what it was in theory, the difference in intention dramatically impacts the odds of experiencing lasting contentment or lingering regret.

Simon Sinek says it in relation to business, but I think it applies to the modern-day homebuying experience too...

When you have a clear sense of your "why", you tend to ignore all the distracting features. When you have a fuzzy sense of your "why", you tend to obsess over all the features.

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26 | Homebuying Series: The Discipline of Renting

I once heard someone say, "There are two forms of pain: discipline and regret. You get to pick one!"

To be clear, if we're searching for a home to purchase, "privilege" is a more accurate descriptor than "pain". With that said, I think the discipline/regret concept still applies to renting before buying in a new city.

Both times we have moved, we've rented for 9 to 12 months before landing in our first home in a "new" city. Ironically, my wife and I actually grew up in the two cities where we have moved!

I've heard other friends take a similar approach and say things like...

"I never knew that neighborhood existed and I grew up in this city."

"We've been able to see where our closest community actually lives and decide to find a home closer to them."

"We realized that there are a few wonderful neighborhoods that put a lot less strain on our finances than where we were initially looking."


As painful as it is to delay feeling settled in a home, this "pain" pales in comparison to settling in the wrong home.

As painful as it is to "move twice", this "pain" pales in comparison to moving once and second-guessing your decision until you move again.

As painful as it is to live in a "less-than-ideal neighborhood" for a year or two, this "pain" pales in comparison to locking in a mortgage in the wrong neighborhood.

As painful as it is to meet people while living in a temporary location, this "pain" pales in comparison to having your home limit who you will meet.

As painful as it is to "throw money down the drain" with a rent payment, this "pain" pales in comparison to building equity in a home that doesn't match the life you want to lead.

Because of the taboo nature of money and our feelings towards money, I suspect there are plenty of people who feel the regret side of all of these examples, but struggle to name it and certainly struggle to share it.

Renting doesn’t mean you can’t afford a home and I don't think it means your unsettled either.

In a sneaky way, renting buys time, options, and flexibility that ensure we're making decisions about our money instead of money (and our home purchase!) making our decisions for us.

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25 | Homebuying Series: Wealth Is What You Don’t See

An excerpt from The Psychology of Money by Morgan Housel...

We should be careful to define the difference between wealthy and rich. It is more than semantics. Not knowing the difference is a source of countless poor money decisions.

Rich is a current income. Someone driving a $100,000 car is almost certainly rich, because even if they purchased the car with debt you need a certain level of income to afford the monthly payment. Same with those who live in big homes. It’s not hard to spot rich people. They often go out of their way to make themselves known.

But wealth is hidden. It’s income not spent. Wealth is an option not yet taken to buy something later. Its value lies in offering you options, flexibility, and growth to one day purchase more stuff than you could right now.

Diet and exercise offer a useful analogy. Losing weight is notoriously hard, even among those putting in the work of vigorous exercise. In his book The Body, Bill Bryson explains why:

"One study in America found that people overestimate the number of calories they burned in a workout by a factor of four. They also then consumed, on average, about twice as many calories as they had just burned off … the fact is, you can quickly undo a lot of exercise by eating a lot of food, and most of us do."

Exercise is like being rich. You think, “I did the work and I now deserve to treat myself to a big meal.” Wealth is turning down that treat meal and actually burning net calories. It’s hard, and requires self-control. But it creates a gap between what you could do and what you choose to do that accrues to you over time.

The problem for many of us is that it is easy to find rich role models. It’s harder to find wealthy ones because by definition their success is more hidden.

There are, of course, wealthy people who also spend a lot of money on stuff. But even in those cases what we see is their richness, not their wealth. We see the cars they chose to buy and perhaps the school they choose to send their kids to. We don’t see the savings, retirement accounts, or investment portfolios. We see the homes they bought, not the homes they could have bought had they stretched themselves thin.

The danger here is that I think most people, deep down, want to be wealthy. They want freedom and flexibility, which is what financial assets not yet spent can give you. But it is so ingrained in us that to have money is to spend money that we don’t get to see the restraint it takes to actually be wealthy. And since we can’t see it, it’s hard to learn about it.

People are good at learning by imitation. But the hidden nature of wealth makes it hard to imitate others and learn from their ways.

The world is filled with people who look modest but are actually wealthy and people who look rich who live at the razor’s edge of insolvency. Keep this in mind when quickly judging others’ success and setting your own goals.

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24 | Homebuying Series: Zillow is Not Your Friend

Comedy is both useful and funny because it says things that can be incredibly challenging to say without humor.

Thanks to Saturday Night Live, the following video probably communicates enough on its own. Please note this video could be offensive to some people and perceived as NSFW.

Browsing Zillow, particularly if you’re not actually on a house hunt or haven’t defined what you’re looking for, is a slippery slope when it comes to our collective relationships with money and contentment.

Browser beware!

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22 | Homebuying Series: Trading Floor Space for Friendship

“If you have a crisis in your life, you'll notice something. It won't be your Twitter followers who come to sit with you. It won't be your Facebook friends who help you turn it round. It'll be your flesh and blood friends who you have deep and nuanced and textured, face-to-face relationships with, and there's a study I learned about from Bill McKibben, the environmental writer, that I think tells us a lot about this. It looked at the number of close friends the average American believes they can call on in a crisis.That number has been declining steadily since the 1950s. The amount of floor space an individual has in their home has been steadily increasing, and I think that's like a metaphor for the choice we've made as a culture. We've traded floorspace for friends, we've traded stuff for connections, and the result is we are one of the loneliest societies there has ever been.” -Excerpt from this Ted Talk by Johann Hari

This felt heavy the first time I heard it, but if you look around, I think you might notice it too.

There are a bunch of big homes and there are a bunch of lonely people.

I don't believe this is a condemnation of big homes and I don't believe home size explains loneliness.

I do think it is a call to acknowledge that floor space does not correlate with quantity or depth of relationships and that the allure of a bigger home isn't always what it's cracked up to be.

A pastor friend of mine has observed a similar patter in countless families "searching for more space". Moves away from a specific neighborhood or community in search of square footage that have led to some mixture of increased loneliness, anxiety, and regret.

Because I want to be clear, I'll say it again - I don't believe this means big homes are bad and small homes are good, but double or triple checking our priorities with a home decision feels uber-critical.

If floor space is the primary driver behind a home decision, it might be a red flag worth noticing.

Instead of laboring over the ideal amount of floor space and how you'll use it, maybe time is better spent evaluating whether your home is an avenue for friendship or a barrier to friendship.

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21 | Homebuying Series: 1 decision that makes 1,000 decisions

I first came across the concept of "1 decision that makes 1,000 decisions" reading the book Essentialism: The Disciplined Pursuit of Less by Greg McKeown.

I think there are at least two sides to this concept when it comes to buying a home.

The first side is related to relationships.

The proximity and convenience of interacting with neighbors is hard to beat and hard to avoid.

Whether you’re leaving in the morning, coming home in the evening, going for a walk, playing at the local park, or sitting on your porch, you’re going to see one another living ordinary, daily life.

Your neighbors will rub off on you in more ways than you can imagine – how they interact with you and others, how they spend money, where they go to school, and on and on.

Locking in one decision on a home is like locking in 1,000 decisions on who will influence your ordinary, daily life.

The second side is related to financial freedom and flexibility.

A house is one of a few big-ticket spending items that actually moves the needle on household cash flow.

For every $50,000 spent on a home, there are 10,000 lattes or 500 date nights or 100 UNC-Duke games or 50 weekend getaways or 5 trips of a lifetime that could be pursued instead.

I realize I am not accounting for financing a house over 30 years or the interest paid or the tax deduction. Please forgive me.

I don’t think that changes the point – one $50,000 decision on a home can be responsible for an abundance or scarcity mindset on 1,000 other decisions that add the color to life.

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20 | Homebuying Series: The Myth of the “Perfect” Home

I don’t think it is possible to find a perfect home. I think homes begin to feel special, unique, and have hints of “perfection” after you have lived in them for many years and decades.

The attributes of a “perfect” home are not the features of the structure – the Instagram-able kitchen or master bath or the landscaped yard.

Beyond a relatively basic level of size and comfort, the attributes of a “perfect” home are only the memories that are created and the relationships that are nurtured within the home.

Social media, magazines, and people around us lead us to believe that the features enhance or accentuate memories and relationships, but I just don’t think that’s true.

If it were true, the people with the nicest homes would have the best memories, the healthiest relationships, and the most contentment. I don’t think it takes long to notice that this isn’t the case.

Think about it for yourself - are your fondest life memories and most formative experiences a result of the luxuriousness of the physical location where they happened?

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19 | Are You Saying It's Going to Keep Growing?

In a past conversation, I was helping someone get their feet back under them after a significant life crisis.

We spent a few months building a relationship and slowly organizing all the pieces of their personal financial situation.

Eventually, we got to the point that we needed to talk about investments.

Sadly, our team's canned investment conversation had a lot of financial jargon - equity allocation, cost basis, unrealized gains and losses, emerging market exposure, credit risk, fund manager, etc.

Even more sadly, the conversation included a PDF document that had more numbers than you would hope to see in a lifetime much less in a single hour.

After chatting through the detailed investment plan, we opened it up to questions to be sure we were all on the same page.

Question #1...

"I don't want to ask a stupid question, but are you saying it [the investment account] is going to keep growing?"

Not a joke - that really was the first question.

Chuckle all you want, but I have found there are no stupid questions when it comes to money.

Everyone, I mean EVERYONE, has the same questions whether they are willing to ask them or not and those questions are almost always of the "what-does-this-mean-for-my-life" variety and not the "can-you-clarify-what-you-mean-by-downside-capture" variety.

Shame on me for being part of a presentation that was so complex that someone had to clarify whether we hoped the investments would continue to grow!

Frankly, I think this specific conversation was just one exceptionally good example of what happens a million times a month in a typical annual investment review.

I think some people feel obligated to nod along and "track with the conversation" because it's their responsibility to "keep up with the finances" and make their family's biggest financial decisions. The nitty-gritty investment details must be part of this job description...right?!?

I think others are checked out within a couple of minutes or before the conversation even starts because it doesn't make any sense and certainly has nothing to do with their day-to-day experience with money. The nitty-gritty investment details are way too complex...I guess we'll never be "good with money"?!?

Either way, I don't think the investment review does much to address the uneasy and overwhelmed feeling that comes when most people think about money - that feeling might even be more acute than it was before the meeting started.

For too long, investments have served as a gatekeeper to real financial advice. Investments are important, but they are a fraction of our relationship with money.

When it comes to investments, I think it's OK if all you really want to know is that we're hoping they'll continue to grow.

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18 | Barometer on Burnout Risk

Burnout is dangerous.

Some of the consequences are obvious and easy to measure - the potential loss of an income stream, the stress caused by an infinite email stream, or the persistent feeling of overwhelm as you start another day.

Some of the consequences are deceptive and maybe impossible to measure - the impact of bitterness towards your colleagues, apathy towards your work, or future options slowly falling off the table.

Acknowledging it's dangerous is a start. Keeping tabs on it seems like an integral skill.

It's hard to measure, because it's the kind of line you can't see until you've crossed it.

Counting down to the weekend every Monday morning feels like burn-out risk is trending higher.

Pleasure reading about "work" topics during free time feels like burn-out risk is trending lower.

When you find yourself saying "I deserve this" as you sign off and head on vacation it might be trending higher.

These aren't the kinds of things that get fixed overnight, but they can change over years.

It's easy to think a 10% raise is the highest impact thing you can do for your finances.

It's easy to measure. It's easy to see when it hits the bank account. It might be in your control. Like ibuprofen, it relieves pain...temporarily.

A 10% reduction in burnout risk is a whole different category.

You might feel it immediately or maybe you won't.

It's certainly not hitting a traditional bank account.

But...it might help you discover something that you hope you get to do forever or breathe life into a stale routine or provide the opportunity to connect with family and friends that hasn't existed before.

You’ll never be able to measure any of these things, but maybe that’s a sign that they’re worth it.

Additional Reading:

"You Better Love This" by Morgan Housel

"Mexican Fisherman and the Investment Banker" by Unknown Author

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