I recently attended a 3-day intensive program designed to shift people’s attitudes toward money, hosted by executive coach and teacher Joe Hudson and his team.
I didn’t really know what I was in for. I went mostly to accompany my wife Lauren, who said she needed a new perspective on money and thought I might get something out of it too.
What I got was so much more profound and multi-faceted than I ever could have imagined: a deep understanding of where my mindset toward money came from, how it has shaped my life and my decisions, and how to change it to serve me better.
The origins of my story about money
Like everything in life, my stories about money began when I was a child. As the program unfolded and we spent hours examining our most deep-seated memories and beliefs toward the subject, I slowly began to uncover three core pillars of my financial mindset.
Core pillar #1: We have enough money, but I don’t deserve it
In my earliest years, I received two conflicting messages about money: the first, that we had enough of it and therefore didn’t need to worry about it.
I knew my grandfather had been a successful entrepreneur and left us with a comfortable inheritance. In my family, we always talked openly about his legacy, how much he left to us, and how we planned to manage and invest it.
The second story was that we needed to be frugal. My father was a professional artist, supporting a family of four kids in Orange County (he always reminded us), and his spending decisions reflected his constant concern for keeping us financially stable.
I reconciled these two seemingly incompatible messages by believing, “We have plenty of money, but I don’t deserve it.” In other words, I made it about me and my worth. Money became synonymous with a feeling of deservedness, approval, and love, which means I interpreted my father’s tight fist as him withholding his love from me.
As I grew up into adulthood, this subconscious story manifested itself in profligate, even wasteful, spending. I found that I could spend money on myself and instantly receive that feeling of deservedness and recognition I craved. And I didn’t have to worry about the long-term consequences, because I knew someday that sizable inheritance from my family would arrive to rescue me.
This attitude followed me throughout my 20s, and I was always on the edge of financial solvency as a result. My spending criterion was simple: if I had the money, I spent it. It almost didn’t matter what it got spent on – I wasn’t into luxury or status goods thankfully, but for travel, tech, eating out, and books and courses, I spared no expense.
But something changed in 2020 at the start of the COVID pandemic: I began making a lot of money for the first time in my life. The worldwide lockdowns created immense demand for the kind of course I’d been teaching for several years at that point, and I was perfectly positioned to reap ten-fold growth in the business.
This may seem like a fairytale ending, the perfect resolution for my chronic overspending. In reality, it exaggerated my existing habits and made my finances even worse.
The rapidly growing balance of my bank account only meant I had even more to spend, and spend I did, on everything from hiring employees and contractors to expensive video production gear to buying cryptocurrency. It was all so easy to justify in the name of “investing in future growth” and preparing for a glorious future in which our revenue would continue to grow at the same rate for years to come.
Well, it didn’t. And starting in mid-2022 our sales began a free fall. The online course market was rapidly evolving as many other live, cohort-based courses flooded the market. The end of the pandemic meant people wanted to socialize and get out of the house, not sit at their computers on Zoom. We cannibalized our own sales by publishing our previously exclusive content in multiple forms for cheap or free. I had over-hired and over-invested, and suddenly there was no underlying business to justify it all.
Looking back with a couple of years of hindsight, there was a specific moment when my stance toward money caught up to me. It was the moment I had to lay off half the team at short notice. People I cared about suddenly lost jobs they loved, lost their health insurance, and had to scramble to support their families. This was the moment that I realized my attitude toward money wasn’t just affecting me; it was hurting many others.
The cycle of shame was complete: in trying to spend money to feel worthy and deserving, I’d wasted it, leading to a self-fulfilling future in which I felt like a failure who was even less worthy or deserving.
Core pillar #2: It’s shameful to care too much about money
There was another memory that vividly came to mind as we began the weekend: I was about 10 years old, standing by our backdoor in my parent’s house, next to my father, and I told him offhand that I didn’t want to worry about money – I just wanted to earn “enough to pay the bills” and spend my time doing work I cared about.
I know this was a core memory because I can remember feeling shocked by the strength of my father’s response: he replied sharply that it was irresponsible and dangerous to not care about money. In that moment, I realized that I had believed up until that point that my father didn’t care about money, and that was why he conserved it so much. I had expected a nod of approval when I said I also didn’t care about it. His sharp response made me see that it was in fact the opposite: he cared about it quite a bit because its presence or absence determined whether he was allowed to pursue his art full time, or would be forced to make money in other ways.
In retrospect, my takeaway from that conversation was that my father cared too much about money, and therefore I wasn’t going to care about it at all. The belief I internalized was: “It’s shameful to think about, worry about, or grub after money.”
Frugality took on a negative connotation in my mind, associated with such words as “small-minded,” “fearful,” and “selfish.” It felt to me like retreating from life, like missing out on life’s pleasures. As a result I developed a judgment toward anyone who was too frugal: careful investors who analyzed every investment option, budgeters who meticulously tracked their expenses, and penny-pinchers who spent time clipping coupons or going to garage sales.
Looking back, I can see that overspending was my subconscious way of trying to escape the scarcity and fear I so strongly associated with saving money. The entire world of finances felt constrictive and limiting to me, and therefore I did everything in my power to avoid it. That included refusing to make or follow a budget, save or invest for the future, or create a financial plan.
In other words, I formed a domination relationship with money: either I dominate it or it dominates me. The main way I tried to dominate it was by refusing to give it attention, or time, and starving it of oxygen. Once in a while, when it ran out and became an emergency, I was forced to give it my attention, but only begrudgingly.
Core pillar #3: Money is easy to make
The previous two beliefs – that spending money was a way to feel loved and that it was wrong to conserve it or give it too much attention – might have led me to financial ruin, except for the third pillar of my relationship with money: that it was easy to make.
I found early on that I had a gift for entrepreneurship, probably inherited from my grandfather and great-great grandfather.
In a weird way, this third pillar both justified and amplified the previous two. I could afford to keep spending like crazy because I knew there was always more where that came from. And I could afford not to manage and cultivate my money too carefully because again, I had a way to replenish my reserves despite all the gaping leaks.
However, as long as I kept spending my money as fast as I made it, I was stuck in place. I couldn’t grow my business significantly, or outsource or delegate key functions, or invest in automation or scale. At various points in my entrepreneurial journey, I’ve had to face the fact that I am a highly-paid employee of my own company, not the owner of a true business that I can step away from.
The bottleneck on my entrepreneurial growth has never been my ability to generate revenue – it has always been my ability to generate a profit, and a crucial component of that is ensuring our expenses remain in check.
Owning my projections onto money
One of the main frameworks we used during the weekend was to treat money as if we had a real relationship with it, almost like a person. That included all the aspects of any complex, long-term relationship: past hurts and resentments, pent up rage or disappointment, recurring unhealthy patterns, as well as unexpressed love and gratitude.
This also meant that we had projections toward money, and the single most powerful exercise for me involved owning those projections.
A projection can be understood as a defense mechanism in which someone unconsciously attributes their own unacceptable thoughts, feelings, or traits to another person. It’s a ubiquitous feature of human psychology, a tool we use to avoid acknowledging undesirable aspects of ourselves (and thus avoid feeling the associated emotions) by perceiving them in others instead. It’s like judging a painting for its flaws without realizing it is in fact a mirror.
We went around the circle apologizing to money for the qualities we had projected onto it, and embracing those same qualities in ourselves instead. After a few fairly tame ones, and as my next turn approached, I began to feel an intense wrenching feeling in my gut. Tears began to pour freely from my eyes before it was even clear what I was going to say. As my turn began, I found myself saying to the others around the circle, as if with a voice that wasn’t mine, “This is the hard one guys. I’m going to need your help…”
What followed was one of the most intense and unexpected physical reactions I’ve ever had in such a setting. My whole body began shuddering, my feet stomping on the floor as I hopped up and down in my chair. Suddenly I began breathing rapidly, with sharp in and out breaths like I was running up a hill. I felt unable to speak at first, and instead made a series of animal-like growling, whimpering, and shouting noises. At one point I burst into hysterical high-pitched crying that lasted only a few seconds before abruptly stopping. I kept trying to meet the eyes of the others around the circle, but each time I encountered their gaze, my body would react again.
I remember watching all of this unfold like a spectator, my internal witness in awe of my body’s capacity to integrate a new perspective at the somatic level. I believe that’s what was happening: my body was wrestling and writhing with an idea the way a boa constrictor might wrestle with prey, or the way a woman might give birth. I knew that my ability to allow all this to happen, to let my body do what it needed to do without (too much) fear or self-judgment, was the culmination of years of work on my part. What I mostly felt was pride.
Eventually, once my body had completed its process, I was able to complete the sentence: that I had projected onto money that only it had the capacity to make change in the world, when in fact, that was just a way of avoiding facing the reality that it was me who had that capacity.
I couldn’t quite believe that this was the sentence that most triggered and confronted me. It felt almost cliche, like a motivational slogan. But in saying it again and again, each time a little more integrated and heartfelt, it dawned on me that I had never fully accepted this possibility.
I’d spent much of the last decade trying as hard as I could to make a positive impact, from teaching English in South America to working in microfinance in Colombia to volunteering in the Peace Corps in Ukraine to starting an education business on the Internet. This endless striving came from an insatiable need to make a difference, to feel like my life mattered.
I’d spent years proclaiming from the rooftops, via various globe-spanning online platforms, that I was making a difference. I’d documented and displayed the evidence proving to everyone I was making a difference, had harangued my team that we needed to make more of a difference, and plotted ever more grandiose plans to make an even bigger difference in the future.
And yet, as I was smashing down the gas pedal on “making a difference,” I was simultaneously smashing the brake with the other foot, refusing to truly let in the evidence and the feeling that I was already doing so. The feeling that my mere existence, my life, made a difference, and that I didn’t need to justify it to anyone.
This was the feeling that I had to use every bodily movement to let in: that the central driving purpose of my life had been fulfilled, and in fact was always already fulfilled. I had created the story that “I wasn’t worthy” in order to make sense of the world as a child, but since that gaping hole inside of me was created by me, it was only me who could fill it, not any external form of achievement or recognition.
Inheriting my family’s attitude toward money
Another major theme for me during the program was coming to terms with the ways my family’s attitude toward money over the generations had been passed down to me.
First, and most immediately apparent, was a deep feeling that I didn’t deserve to be the recipient of all the sacrifices they’d made. Perhaps this was the true source of my sense of undeservedness, which I had interpreted as coming from my father.
I know a lot about all four strands of our family line because my mom is an avid genealogical researcher.
We know about the 17th-century religious wars our ancestors got caught up in as French Protestants, the persecution and discrimination they fled by escaping to the Netherlands and then the UK, the difficulty of traveling across the Atlantic to Canada only to face more discrimination, the harsh years they survived as immigrants in upstate New York, and the many tragedies and hardships they endured from car accidents to fatal illnesses to broken marriages.
I know all the vivid details of how they struggled to make ends meet, and what they had to give up to provide for their families. All that information has often felt like a gigantic burden on my shoulders: Who am I to be the beneficiary of so much pain and sacrifice?
Paradoxically, having “enough” money has sometimes felt like it creates a sense of intense urgency, because I have no excuse to not realize my dreams and goals.
I realized I’d adopted a strange mindset as a result: that if I worked hard my entire life, maybe, just maybe at the end of it, I would deserve the money I’d received at the beginning. It was as if I placed the feeling of deservedness and worthiness at the end of a long road, and told myself I had no choice but to walk it. In other words, I would have to work just as hard to “deserve” the wealth I already had as if I never had it in the first place! This is what’s known as a “double bind” – a pair of contradictory beliefs held in place to ensure you can never win.
My family’s financial prosperity has made my pursuit of meaning feel harder. It has never felt like enough for me to survive, or merely prosper. The privilege of starting life’s race at the halfway mark has led me to feel like I can’t ever complain, can’t have problems, can’t relax. I’m afraid that my efforts and sacrifices won’t mean anything. I’m afraid the (even more) money we’ll leave to our kids will make their lives feel meaningless.
Considering all this in the weeks following the program, I realized that my family never left behind the scarcity mindset toward money they had adopted through the ordeals of immigration, the Great Depression, and the World Wars. My grandfather had grown up with a conservative, working-class mindset toward money, and never truly gave it up or learned to enjoy it even as he grew a successful business. He passed his money on to my father, who also refused to spend it, and is now passing it on to me with the same mindset intact.
I don’t know what exactly will change for me as a result of this weekend program, but I do already see my place in this legacy very differently: not to continue amassing wealth with no end in sight, nor to spend it thoughtlessly like it doesn’t matter. I’m starting to perceive a middle path between those two extremes: I can use the financial capacity that’s been passed down to me to heal the pain that gave rise to it in the first place. The privilege I embrace is the privilege of healing my family’s relationship to money, and moving us out of the realm of scarcity and fear for generations to come.
I can summarize my family’s attitude toward money as “Money is fine as long as we have enough of it.” I can see and appreciate how important that simple heuristic has been to help us survive through the centuries and across continents. I can also see that at some point, that becomes a limiting belief, because there is more to money than merely having enough. There are deeper and more subtle questions that I now have the freedom to explore, such as how I can invest that money and honor my ancestors’ sacrifice while still honoring my own life.
If you’d like to explore this kind of personal development work for yourself, check out the various courses and workshops offered by Joe Hudson’s company The Art of Accomplishment. You can also join their newsletter to hear about the programs they offer year-round, including one-time retreats like the one I attended, which are only open to course graduates.
To give you a taste of what it’s like to work with Joe, he has shared excerpts from his coaching sessions related to money, including how to make money doing what you love and how to feel financially safe. I can also recommend the following episodes of the Art of Accomplishment podcast:
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The post Rewriting My Financial Story: How I Healed My Relationship with Money appeared first on Forte Labs.