“What is the definitive answer to the question that people ask you most often?”
I was never certain how to answer this question. Especially when it came from my family.
All You Can Eat Buffet
Searching for happiness is a likely candidate for the most common hobby amongst Americans today. With the rise in social media comparison, constant distraction, and viable numbing agents – it’s not difficult to find yourself acknowledging your blessings, but then wondering if there’s still more to expect.
It’s declared for us in our Constitution – Life, Liberty, and the pursuit of happiness. It’s roots run deep within our cultural blood. The feeling lingers in our consciousness, as we wonder, “Am I truly happy?”
Nearly everyone I meet has some sort of opinion about it. Some say they have it; Some say they never thought it was achievable; others can’t seem to find it.
For most of my life, I was never certain what the heck I was supposed to be looking for.
I found myself jumping from one thing, to the next, and then the next. Each time hoping that the next thing I could pursue was going to be “it” on the other side.
When I was eight, I was convinced it was a new dirtbike.
At twelve, I had convinced my Dad that it was an Xbox.
At fourteen, it was definitely when I got a girlfriend.
When I was eighteen, it was when I could finally leave high school and go to college.
At college, it shifted to when I got my first ‘adult’ job.
At each stage, I was looking ahead to the next objective. I’d push, push, push myself (and undoubtedly, others as well) to achieve the “next thing.”
Upon landing that first job, my issues only compounded. I now had firepower – my very own, earned paycheck.
If I had a dollar in my pocket, it would burn a hole there if I didn’t get rid of it. Fancy sushi rolls, ordering food every two out of three meals, new mountain bikes, new cars, trips to here, tickets to that event there. Whatever I could spend my money on – I did.
Then the comparison game came in. I couldn’t keep up with the people who made more than me. They were accumulating things faster than I could!
I had consumed enough. I had made myself sick.
My First Sign
A full year into my corporate career – I was LOST. I couldn’t understand the reason for any projects that I was assigned to or that our team was working on. I was not connecting with anyone I worked with. Everyone seemed to be caught up in their own games as much as I was. I was hardly seeing my partner because of the role she played in her job. The only time we spent together was at the gym, where we further exhausted ourselves. And we had no money to show for any of it!
This game was wearing me out. I was unhappy with the life I was living and had no idea why I was where I was in life.
Luckily, I was presented with the opportunity to move to London for a new role. While living there, we traveled every chance we could get. I was having experiences that I’d never received with material purchases before. I had an intuitive feeling that I needed to make a change. It became apparent to me that I’d have to stop playing short-term games. I had to stop looking at material items to give me what I wanted. I told myself it was time to wise up.
I decided to gain some sense – financial sense.
On a frigid February Iowa morning after we returned to the U.S., I met with a financial advisor who was recruiting me to work underneath him in a sales role at a local Barnes & Noble. He explained that I’d have a successful career learning from him, given my athletic background and disciplined track record. He showed me the standard charts, walked me through the dry pamphlets, the whole nine yards of financial advising.
I left the meeting without any true answers to how I was going to get out of this feeling.
I walked from the small cafe tables we were sitting at over to the finance section of the books.
I flipped through five or six books. The same image appeared in every single one of them. A simple compound interest chart. The 8th wonder of the world, according to Albert Einstein.
The idea was shoveled into my awareness and transplanted like a Redwood seedling into the garden of my brain. It rocketed into a 200’ girthy specimen in an instant. I intuitively remembered the universal law of compounding and knew I needed to harness it.
He sold me on the dream. Put a little bit of money in now, and I can be happy in 40+ years when I have a huge sum.
That’s all I heard.
Happy life = fat retirement account.
The Pursuit
The plan was simple. Make as much money as possible. Save as much of it as possible. Have fat bank & investment accounts. Leave my job. THEN I was going to be happy.
My life quickly became consumed with exploring ways to save money, invest money, and make money. I’d spend 6 hours reading about how to do backdoor Roth conversions, then another 3 hours building spreadsheets modeling out how much money we’d have at each decade of our lives. I spent nights and weekends studying books on investing, scouring Reddit forums for advice, and listening to Youtube videos of anyone who spoke the “money language.”
Anybody that would listen to me also got an earful about what they could be doing with their money. Bless them.
The results were not coming fast enough. I decided again that it was time to stop messing around. Why wasn’t this working? Why wasn’t I happier?
Instead of wising up – I decided I needed to go all-in. I was convinced that I wasn’t trying hard enough.
I maxed out every single retirement or savings account that I could open up. I was funneling as much money into margin accounts as possible. We shifted to a one car couple, then eventually to only riding bicycles. I sold my partner on getting the tiniest apartment possible to continue saving money. We tracked everything in and everything out. I even started churning credit cards to get “free money.”
There was just one snag there. We didn’t even spend enough money to qualify for the credit card bonuses.
Using my systems understanding, I then switched my focus to the next constraint. I needed more income.
That pursuit led us across the country from Iowa to Seattle, then eventually to Northern California. Haddie would dream up a scenario. I would work the problem backward, reverse engineer the steps, and make it happen.
I was quickly able to scale my income and advance through the corporate finance ranks. With an analytical mind, I consistently play out scenarios in my head. This was doubly reinforced as I studied more complex financial projections and operational system theories for my work.
I was fervently attempting every key combination of a solution I could get my hands on to understand and make things work. I continued to attach myself to larger and larger problems, if merely only for financial gain.
This was an asymmetrical risk-reward. In the wrong direction. And I was still unhappy.
The Fall Out
I had been stripping away as much from my life as possible in pursuit of this goal. Everything was viewed through the lens of money. If it cost money today, I was giving up happiness in the future. We gave up many of our hobbies. We stopped doing things we enjoyed to funnel as much into our accounts as possible. We moved to different parts of the country with no personal connections, starting over in each new place, to further advance this pursuit.
Then March 2020. The Covid pandemic arises. The world is in a confused, finger-pointing, turmoil.
I found myself in conversations and arguments I had no reason to be in. I found myself at dinner parties with people I had nothing in common with. I found myself solving problems I had no interest in working on. I found myself in an industry that has a long history of controversy. I found that no one was truly communicating.
I had friction in multiple facets of my life. And somehow we had landed in the political hotbed state of California. I needed to change and eject myself out of my current situation NOW.
I had my awakening moment. I was served my medicine. The negativity had gotten to me.
Horse Dewormer
Why am I doing all of this again? Why am I here, right now?
We spend much of our lives running around making noise because everyone else is making noise. We do things because we believe others must know more than we do. We look to others to identify what it is that we want.
I went to college because everyone else went to college. I got a job because other people get jobs.
I got to my first job and everyone seemed to be ‘pausing’ their happiness to pour into this thing called a ‘401k’, so that someday they could have that happiness and leave their job.
I spent valuable time and energy on external problems before solving my own. I dangled the carrot out in front of myself to hit targets I didn’t even set myself, for the approval of others I didn’t need.
I never thought once to question it. Instead, I doubled down on it. If I could do something faster, then I would get there faster.
In doing so, I projected my own trauma onto situations I was in.
I found myself asking other people questions, hoping they’d have the answers. The issue is that I never bothered to ask myself first.
Where was I actually going… and why?
Author Luca Dellanna has a principle that he states: life is about resisting erosion.
In a similar way that water can erode a rock, drip by drip – our environment can erode us, experience by experience. Very few people come through the initial socialization phase of life unscathed.
For most of our lives, we are influenced by culture and marketing that targets our ‘old brain programming.’ We are led to believe that in order to feel worthy, to be content, to be happy, to be satisfied – it must be something outside of ourselves. Some sort of approval from others.
It must be something that I have to do. Something that I must obtain. Something that I can’t function without.
If I could just find the “hack” or the “secret” – I’ll be healed, happy, and living my best life.
This is an environmental and societal force that is smoothing our personality edges, removing our strengths and uniqueness.
I had to realize that I was creating problems for myself that were actually other people’s problems. I was setting goals to achieve outcomes that others had convinced were good for me. I was trading my own youthful energy for a promise that has no definite guarantee.
And I was achieving these things – but it wasn’t the outcomes that were satisfying to me. I couldn’t figure out why I was feeling this way. For obvious reasons, I couldn’t talk to anyone about it either. It felt like crying because my ice cream was cold.
Finally, I made the decision to solve my own problems for once. It’s a scary thought. Society always tells us to think of others first, don’t be selfish.
I channeled that relentless thirst for knowledge into learning more about myself. What I came away with shifted my entire perspective.
I realized that it is those who continually invest in their own development and growth who resist this erosion. They build back the parts of themselves that have been shaved away by others. They accept feedback, but know when to not compromise.
If the muscle is not growing, it’s atrophying. What is alive & kicking is fighting erosion, in some form or another. What isn’t, is dying.
Feeling alive means shaping our environment, rather than being eroded by it.
I stopped letting people tell me that my tendency to continually learn, test, and improve things was because I couldn’t be happy.
I found that it was the joy of the pursuit, the process of creating that I was after. I cared more about taking on the challenges of growth and expansion, than I did about some material outcome.
I started consulting businesses I could learn from. I put myself in situations that expanded me. I invested in seeing other people for who they were, now that I could see myself. I started viewing every scenario I found myself in as a mirror. I became inspired by people with visions. I focused on which games I wanted to play. I fell in love with playing the game.
So the answer to my most frequently asked question: Are you ever satisfied?
Before: When we hit the next goal, when we get the ‘next thing’.
Now: All the time. I’ll be even more tomorrow, and the next day, and the next.