How I Learned to Finally Put Money in Its Place

Money sucks. It’s all I think about whenever I feel like I don’t have enough of it. And during the times I’m not thinking about it, I’m usually languishing, present but immobile…unhappy.

On and on the cycle goes: striving, avoiding, striving again, and avoiding once more.

This is what ambitious people do when they’re afraid.

But fear isn’t the half of it.

Money is complicated, and holds power on the psyche. Ruminating on money problems makes it impossible to attain, yet thinking about money can drive us.

Money is also one of the primary reasons why suggesting a character flaw (such as a lack of motivation or focus) is to blame for inaction is lazy and incomplete.

It was only very recently — I’m 35 now — that I realized how, when money drives my choices, success never seems to follow.

And I know this.

In fact, some of the work I’m most proud of doing was done for free or for an amount of money that is frankly well below what my professional hourly rate is at this point.

And yet, whenever I start a new project, I still can’t help but think about money. About how this idea I have could be the thing that finally breaks through, the one I finally focus on and develop pride for and pull off to the extent that I never have to work again in my life.

But of course, all of the time spent thinking about the payoff isn’t simply time spent unwisely, time during which I could be developing or selling my product or service. It’s more actively destructive than that: drooling over future riches erodes the sense of purpose required to put in the work necessary — day in and day out — to even give me a chance of living the dream.

So what’s going on? I want to be rich like everyone else, but I’m not destitute. But do I have enough of it already? Why is it so hard to accept where I am and pursue projects that simply suit my soul?

Is money the root of all evil, or am I giving it too much credit?

In this issue of the newsletter, I’m going to answer these questions. For myself, but also for everyone reading this.

Because if you don’t understand how the prospect or promise (or simply the hope) of money affects your decisions, you’ll hardly have a chance to drop your yearnings as pretext for the incessant pivots and justifications for minimally executed failures.

Stories abound about the desperate creative, stricken with poverty, who pulled themselves up by their bootstraps and “made it.”

99 times out of 100 though, money and the stress caused by its absence is one of the most limiting factors in terms of creativity and achievement.

Just look at the data. Middle-class parents raise middle-class kids. The poor stay poor, and the rich at best maintain their wealth.

This persistent mediocrity is due in large part to societal and cultural “money messages,” or narratives that persist in culture about money and its moral values, according to Loaded author Sarah Newcomb.

Each of us, Newcomb argues, was handed down loaded imagery about the essence and uses of money, and these messages pervade culture, regardless of which cultures you’re part of.

The way we talk about something is the way we think about that something. And the way we talk about money is as inflammatory (“Money is the root of all evil”) as it is noble (“Money make the world go ‘round“) as it is pragmatic (“A penny saved is a penny earned“) as it is scarce (“Money doesn’t grow on trees”).

Money has an inherent moral value to everyone.

These values, when left unchecked (as is the case for most narratives that make up our core identity) shape our worldview in ways we never think to imagine.

We see money in everything. It informs how we go about the world; how we view life and our lot, how we think about achievement, how we talk about our own sense of deserving, how we think about our parents, how we decide who is good and who is bad. It causes heartache, halts individual progress, motivates us, and everything in between.

One fact about money, however, is consistent across generations and cultures: money is more emotional than practical.

That’s because money represents our deepest needs and desires. It is our safety and security. It is also our relative inadequacy. It is how we choose a life partner. And also how we often lose that partner.

When we earn it, some might feel like there’s no more important signal of their success, while others might believe themselves frauds, or worse, evil.

I don’t mean to sound hyperbolic, but it’s true.

We love our rags to riches stories, but only if the money comes to someone we deem deserving of it. And, generally speaking, the most popular tales about a worthy character coming into money had them merely stumble on it, or rewarded it for their good deeds. For almost everyone else, the overtones of sin and losing their moral compass for the sake and drive of financial gain is clear. And these are almost always the villains…

Ebenezer Scrooge. Mr. Burns. Tywin Lannister. Even Smaug the Dragon, killing recklessly to hoard near-infinite wealth.

And there’s good reason for this dynamic. In the western world, at least, we’ve been indoctrinated in the merits of self-reliance a la Ralph Waldo Emerson. We live in a land of opportunity, of independence, where any individual can accomplish anything.

But as Newcomb says in Loaded, self-reliance is a value only available to those who have the wealth to actually be self-reliant. Which means, of course, that most of us don’t.

So naturally, most of us simply don’t value self-reliance, despite living in a society that upholds this ideal above almost all others.

As defined by Emerson, self-reliance is effectively not bowing down to groupthink. To be who you are wholly and undoubtedly, he says, is the greatest “right” a person can express. He includes in his famous 1841 essay the following exchange to show just how strongly he holds this view personally…

What have I to do with traditions, if I live wholly from within?

[To which his friend replies…]

‘But these impulses may be from below, not from above.’

[And Emerson responds…]

They do not seem to me to be such; but if I am the Devil’s child, I will live then from the Devil.

Yeah. How’s that for a deeply held conviction?

Whether or not you agree with Emerson is besides the point. There is certainly utility in the belief system that has since reigned supreme in our society. I don’t merely echo doctrine, and I shy away from dogmas whenever I realize I’m too deeply enmeshed in one.

But I do that because I can.

How Money Narratives Play Out

I grew up with a view of money that was two-faced. My parents wanted to be rich of course, but they also held a secret distrust of any public figure who had wealth, especially if they deemed that person to have come across the money unaccording to our values.

True wealth, generational wealth, was a foreign concept to us. At once a dream and a sin, I was taught views about money that left a lasting impact on me.

From Loaded…

If you believe as a child that it is hard to make money, how will you approach work? Will you feel sure of your ability to support yourself? Will you see money as something you can have personally, or will you view it as something you will struggle to obtain?

Yes. I learned early on to want wealth, but I also learned that to get it is hard. Impossible, even…again, especially if acquired in the “right” ways.

And of course this comes from excessive wealth being elusive to my parents. It wasn’t easy for them, so it must not be easy, period.

That message was branded on my core, and has stuck with me.

But I’ve held onto the dream. The dream of full-time flaneurship. The dream of living free of any financial worry.

The dream I was handed down.

Alongside the money message I was handed down.

And herein lies the conflict. To want something I feel is too hard to obtain…what wins out? Eternal despair, or shaking loose the entrepreneurial cobwebs from our family tree?

Strenuous attempt after strenuous attempt to outearn my past self, to turn the page for my financial future from one of employee to one of self-directed entrepreneur, have failed. In fact, they’ve barely ever gotten started.

Despite all the knowledge I have.

It is incredibly difficult to erase or transform our core beliefs. Especially ones that became part of us too early to question.

So Sarah Newcomb says you shouldn’t even try.

Can We Think Ourselves Rich?

As provocative a topic as money can be, when we attempt to teach others about money, we suddenly become actuarial, ceding all emotions to the practical uses and implications of it.

Financial literacy, it’s true, is at a dismal level for the average person.

But why then do we have such strong feelings about what money means?

I think it’s the same as any other psycholgical blind spot. Our core beliefs are too firmly rooted, and questioning them not only takes significant and consistent effort, but too many of us can’t even draw a straight line from our psychology to our poor money habits and unhealthy stories about it.

It’s somewhat reasonable to believe that money corrupts, to even believe that gaining significant wealth is hard…too hard.

Thinking about what it would be like to have more money, to never have to worry about it again, is also a reasonable desire. Some people, we love to believe, are living this dream of ours.

But the longer we hold onto conflicting stories about earning unlimited riches, the more we’ll find “evidence” of the narratives we were brought up to hold.

And the truth is that effectively none of us will luck our way into wealth like the stories. We won’t be rewarded with money for being a Good Samaritan, either.

So yes, we have to work for it.

But this doesn’t have to be a bad thing.

Emerson, who so effectively helped to forge the ideals of self-reliance, naturally also believes that finding prosperity without “paying for it” is not as admirable as these same stories would have us think.

From his (also 1841) essay “Compensation”…

Has a man gained anything who has received a hundred favors and rendered none?

…The highest price he can pay for a thing is to ask for it.

He saw no positive aspect in seeking something unearned, going on to say, “If you are wise you will dread a prosperity which only loads you with more.”

Although Emerson was quite the provocateur in his time, these ideas are supported by the latest science. It’s well documented that to earn something feels better than to be given that same something. It’s human nature.

So when we want the result without the work required to get it, we are setting ourselves up for emotional unfulfillment. Even living out our success story

Self-reliance is not just an optional virtue, then. It’s a prerequisite for acquiring the wealthy life we all dream of.

But if most of us are limited to communities where interdependence is valued above independence, how do we come to value self-reliance? Why is it just so hard to get this to stick?

The answer, at least for me, isn’t what you would think. I’ve spent too much time trying to “hack” my psychology with silver bullets. Only to continually berate myself for having failed (or never getting started).

I can’t, as it turns out, think my way past my core beliefs. But there’s a reason for this, and it’s what Newcomb describes simply as “culture shock.”

To Be or Not to Have: That Is Our Question

In a book called Strangers in Paradise, wealth psychologist (yes, that’s a thing) James Grubman Ph.D. explains why traversing generationally and culturally established wealth classes is so challenging.

Making money isn’t as easy as putting my pants on in the morning, but earning it — despite the stories we’ve clung to — is much, much easier than keeping the money I already have.

And this is true for most people, regardless of where in the world you live and how healthy the economy in any given moment.

But let’s leave aside all of the practical factors that an economist might blame for why most of us live “paycheck to paycheck.” We can undoubtedly tie some of our recurring issues to poor financial literacy and the rising costs (and associated debts) of higher education, among many other factors.

But these things can’t account for the perpetual cycles of gaining, and subsequent squandering, of wealth the world over.

In financial circles, it’s called the "curse of the third generation," which entails one generation earning wealth, the next maintaining it, and the third, having never witnessed the work that went into initially acquiring the wealth, losing it all.

This is not American. It’s not based on geography, or government, or culture, or even social class.

This is effectively a rule; it should be called the “law of the third generation.” Because it suggests something much deeper about work and wealth.

Grubman defines this phenomenon as the routine result of “culture shock.” It’s the same as attending a new school, or traveling to a country that speaks a different language.

Culture represents who belongs, and who doesn’t. And until we know if we do (or don’t) based on where we are, there’s no hope for elevating any other aspects of our lives.

There is no deeper human need than the one for connection. So our central nervous systems evaluate things like changing culturally biased narratives as risks for alienation.

And so many of us willingly do this. We grew up with values we are striving to undo. We have to directly challenge those that keep us safe, that make us feel part of the community we grew up in, the one we can lean on in our toughest moments.

And that…risking our own safety and security…is a scary prospect for anyone.

. . .

For many years I had been trying to tie together a view of my own seeming ineptitude. I’ve been at times too harsh on myself, and at times too forgiving. But I always knew that something deeper was going on. I wasn’t scared because I was a scared person. I wasn’t too dumb or otherwise cognitively unfit to meet my own definitions for success.

But within this theory I’ve found my answer.

I now recognize that what’d been holding me back more than anything else was a simplistic view of my own needs.

We don’t all need the same thing. But we all are given value systems before we have a chance to challenge them. And when we do, to assume that changing them is as simple as reinputting new numbers on a spreadsheet…well, this can lead to decades of anguish.

My friends aren’t people who view the attainment of wealth as a positive thing (even if they have it). Nor do my parents or really anyone else in my family.

I also have deep-seated needs for emotional shelter, “thanks” in large part to strained key relationships and losing my dad early.

This is the winning (or really losing) combination. My tribe’s conflicting values and my desperate need to not lose their support.

So for every dollar I earned, I spent it, keeping me firmly engaged with my roots. And for every opportunity I’ve been given, I’ve taken only a “reasonable” advantage of, without stepping over any firm ethical lines that I’ve been too afraid to even question.

For years I thought my path out lay in educating myself about money. But as Newcomb says about her own story (a story that, I might add, that resembles mine very closely, and which led to her publishing her book):

Learning about numbers didn’t solve my financial problems. Learning about myself did that.

The answer is not knowledge.

The answer is not even behavior.

The answer is identity. We must believe that we are secure in the identity we wish to become…for us to have a chance at becoming.

Befriending Wealth

So now, “how?” How do we change our story? How do we ultimately satisfy our biological requirements while actively striving towards something different (and in our view, better)?

Most importantly, how do we do this without* *corrupting our core beliefs, or becoming the crude image we have of the greedy villain?

Newcomb’s take is the psychologist’s take, which is to first “take stock.” Take stock in where you are right now, recognize the factors limiting your growth towards your desired ends.

And then?

Well, here’s how I’m approaching it…(and I do believe this advice will help anyone who’s striving to move up the socioeconomic ladder…)

Befriend the wealthy, stay connected to the less fortunate. There is no better way to work through deeply held personal views than by acquainting yourself with unique experiences. If you believe wealth corrupts, you must acquaint yourself with counterfactuals, in this case examples of people who were able to avoid corruption amidst accruing their own financial wealth.

I also believe (and Newcomb recommends this in her book, too) that it’s essential to stay connected to people who have less than you. This can start as simply giving, but I find it more helpful to find ways to incorporate giving as part of your taking.

Emerson’s view of wealth-building was that there is no taking without eventually giving something; the soul won’t allow it. So instead of letting fears and insecurities grip you, do something for your good in the same action as you’re giving to someone who needs it.

Establish your own family. It’s hard to become an outcast in a family whose values you’ve (at least in part) created. Whatever you’re imagining, if you aren’t yet a parent or don’t plan to be one, it’s wrong. The benefits of being a parent snuck up on me, and have — it’s not hyperbolic to say — consumed me. What I used to care about a lot now matters even more, and what I used to care about a little is now utterly meaningless.

It’s worth saying that this isn’t a value judgment on “traditional” family life; I’ll never fault anyone who deems parenthood not worth it.

But I do now understand that there are aspects of life that are too easy for overthinkers to hide from or overcomplicate, and these aspects often lead to a narrower life, one filled with less…less chance for deep satisfaction, and less chance for total devastation.

This is, however, what life is. The good, the bad, and the ugly. We can’t, as Emerson suggests, take the sweet without the bitter. And parenthood is nothing if not both, in equal parts, every second of every day.

Learn financial rules of thumb. Financial literacy at some point is required to attain, maintain, and grow wealth. I’m not a financial advisor (nor should I be), but after having spoken with a financial planner recently, it’s clear that my self-education in this area has paid off. Knowing more isn’t always better, but in most cases — including this one — knowing enough is essential to success. And rules of thumb are the things that stick. If the best gym to go to is the one closest to your home, the best advice is the advice it’s too hard to forget.

Control your spending. It is absolutely vital to not have a habit of overspending in your personal life if you expect to act the same way in your business. “There are two kinds of entrepreneurs,” someone famous who I just made up said, “those who don’t make it, and those who spend frugally.” While this quote and the person who said it are completely imaginary, the point being made is true: it’s essential to not simply understand how money works, but to know your own habits and triggers for why you spend.

One of the best ways I learned to do this is to do a “needs assessment” (thanks again to one Sarah Newcomb). Essentially, every item you have on your budget should be seen as meeting a need...even if you are an extravagant spender. Why? Because as we’ve already learned, money, including how we manage and deploy it, is more emotional than rational.

The trick is to figure out then what needs each item on your budget is meeting. And then, assuming you want to improve upon your spending, find “tactics” that enable you to meet those same needs more efficiently (read: cheaply). Do not remove an item from your budget without knowing what personal needs it’s meeting for you.

If you are too hasty in this decision, at best you’ve momentarily become optimistic about the numbers, but eventually you’ll realize that your expectations were too high, that you’re not adhering to the new budget you set, and you’ll feel even worse than when you started.

Don’t despair! This is normal. Just remember that your underlying needs can’t be clicked away. There is, however, a good chance that you will be able to meet these needs in different (cheaper) ways.

. . .

I have many more rules about money now than I used to. But more importantly, I live my life differently; I accept who I am and the values I hold deeply. I’ve worked hard to challenge them, but I’ve also left them intact.

I don’t blame anyone who wants to grab wealth when they have the chance. And spoiler: this is the best time in history to try. But before you do, remember, if you let money drive your decisions, make sure you know first who is being driven.