Financial Insecurity

5/15/24

I turned myself in today for lying on my expense reports. 131 times over 4 years totaling $13,760. I know these stats because I just went back and counted. When I started the review I expected to find ~10 times… Nope! 131 times that I embellished the truth of the situation or flat out lied in order to buy meals for myself or friends (without my friends’ knowledge).

Side note: it’s amazing how my conscious mind minimized the scale of something that it wanted so bad not to remember.

What started back in 2020 as a single time tiptoeing into the grey area, eventually became 131 times that I opted to choose greed & excess over honesty & modesty.

As I walked into the office today, I had an out-of-body experience. Despite walking into such a familiar place, this time it was different. I was different. I went straight up to our exec’s office. I didn’t want to see any of my colleagues first. I sat on the couch outside his office, anxiously awaiting this dreadful conversation. When a couple friends strolled by and struck up conversation, I’d never felt more awkward. Trying to bite my tongue for the last few moments before I spilled it all out for real. But it felt like these friends already knew. It felt like I was just waiting to be “found out,” even though I was the one turning myself in. I gave myself a guilty charge. The shame had already crept in.

I’ve gotten so used to that guilty feeling though. The undertone of it. That feeling that maybe today would be the day that I get the call from our finance team, saying, “Hey can you explain this expense?” 

However, I’d gotten so good at covering my tracks that I knew they’d probably never catch me. I always had a clear alibi. I always had a go-to reason. If I took a walk with a company in the afternoon, then that would become the subject of my “company dinner” that evening. I could name the “attendee.” I could share the work content of what we discussed. And yet the act of expensing that dinner was a lie. We didn’t eat together that night. We just walked that afternoon. The act of expensing that meal was across the line, my line. You know how I knew? Because I felt guilty as I did it. This wasn’t a crime of ignorance. It was a crime of ignore-ance. I’d ignore the guilty feeling I felt every time I crossed the line. A little pang in my side that was trying to say, “Why do this? You have enough. Why is this one meal worth your integrity?”

I learned to quickly quiet those concerns, responding, “Oh come on. You earned it. Look at all the value you’re driving for the firm. That was a great meeting. And you’re breaking even on this day anyway. You probably even made us money! You decided to go on a walk rather than have dinner with the company? That’s money that was planned to be spent at the beginning of today. So why not treat yourself to a nice dinner? What’s 100 bucks in the grand scheme of things?”

Justifications abound. Justifications could always be found. They clearly didn’t cover over my guilt though. I knew when I was crossing the line. I knew when it wasn’t right. My body would tell me. My mind just became an expert at silencing that sensation.

My body would get a bit queasy. My stomach would turn ever-so-slightly (not the ideal sensation as you’re about to indulge in a delicious dinner). But that became my reality. Expensing excess meals that I never got to fully enjoy because of the disdain I felt for myself every time the check came.

If there was a companion at this dinner, then I’d get subtly pissed off at them after I’d paid the bill. I’d never vocalize my resentment because 1) they didn’t know what was going on and 2) I wouldn’t dare disrupt the praise that came after I said, “Oh I can get it.” 

I was so addicted to being in others’ good graces that I risked my entire career that I’d worked so hard to build, in exchange for a little bit of recognition:

“Oh you don’t have to do that!”

“Oh that’s so kind.”

“You’re such a Giver. Thank you so much!”

However, the praise that I was chasing never even stuck. They were praising this facade that I’d constructed, while meanwhile, I knew the truth. I wasn’t paying for this… my company was. Our LPs were. The people who entrusted me with their money to help them make returns. The firm that gave me every opportunity to build the career I couldn’t even dream of as a kid. And here I was, pocketing more for my own gain.

“Embezzlement” became one of those words that, whenever I heard it, would cut me like a dagger to the soul.

The silly part is that I wasn’t even buying what I wanted. I love a great conversation over dinner but I care so marginally about the food that’s in front of me. I’m just as happy with a Sweetgreen salad or Chipotle bowl as an expensive steak. And most of the time I just want some cottage cheese or a protein shake.

If I really listened to myself and the food didn’t matter, then why did I do it?

1) I wanted to impress who I was with. My hope was that in buying them food, they would be more likely to love me. I wanted the identity of being “generous.” (The sad side effect was that when I genuinely gave from my own pocket, the joy of giving had already been diluted for me. Giving at meal time became an implicit reminder of all the instances that it wasn’t truly “on me.”)

2) I harbor a deep insecurity about having enough money. Don’t get me wrong - I had plenty growing up. My parents gave us everything we needed to have a thoroughly enjoyable childhood. However, when I got to college, I realized I had far less than those who came from more means. I felt left out of some groups and opportunities because of my lack of funds. So, I did everything I could to ensure that I’d never go back to that place. I wanted to fit in so badly. I wanted to be a part of the cool crowd, but I didn’t have the money that the cool kids did. And I didn’t see a way to get it in any reasonable amount of time.

So, I saved like crazy in any way I could - saving food from the dining hall so that I didn’t have to buy dinner on the weekend, graciously accepting when friends would buy me drinks at the bar, and always looking for the “best deal possible.” I justified it as being “scrappy.” And it was. But there was also definitely times when it crossed the line. I know it did because I felt it. That same queasy feeling in my stomach. The food didn’t taste as good and the beer smelled just a bit off.

I also worked my a** off to get a high-paying job so that I could afford the stuff that would win me membership to the group. I wanted the freedom to do what I wanted. I was lucky enough to land at a place that took care of me… and then some. I had more than I needed straight from the start. But at this point, the “scrappy” habits were already so engrained that they were hard to let go. I’d take a $3 sparkling water home from the office. Why? Because I could justify it as a small thing in the grand scheme. And yet, to me, it felt like an incremental dollar I didn’t have to spend. So, it was worth it.

Once again, my justifications always felt sound, “Why would my company care whether I drink it at the office or at home? Same difference to them.”

And yet, I always knew where the line was. Because I could feel it in my stomach.

As I made it a habit of ignoring that feeling during these little acts, it became easier to push it to the side for the big stuff. A $3 sparkling water quickly cascaded into a $100 dinner. It started to all feel the same to me. And over time, that feeling became progressively more numb.

Time to face it - I’ve become addicted to making & saving money. I don’t use that word lightly - it’s become an unhealthy addiction of trying to stockpile no matter the cost (pun intended - gimme 1 single joke… comedic relief… as I’m still swimming in this feeling of being a scumbag).

It’s funny how easy it is to believe that we’re “not that person.” I’d fancy myself a pretty stand-up guy in most of my life. I genuinely enjoy giving to other people and making their day. I have a core value of “I tell the truth to others and myself” (and clearly this remains an aspirational value). However, “I’m trying” is no excuse for how many times I blatantly lied on my expense reports after knowing it was the wrong thing to do.

It just truly became an addiction. I never thought it’d be me. I never thought I’d be like those guys who commit financial crimes walking with their white collars & cuffs into the courthouse. I would judge them, saying, “How could you be so stupid as to throw away your whole career over a little extra?”

But, who was I to judge their greed? Because what did I do when given the opportunity?

Money corrupted me. It made me blind to my most basic, core values of honesty & modesty.

I failed to heed Warren Buffett’s advice:

$13,760 over 4 years vs my far larger salary…

So, I’ll offer up my own admission:

“Hi, I’m Trent. And I’m an addict.”

I also never used to understand the criminals who turned themselves in on TV. It always felt fake to me - the perp just walking into the precinct and letting the cops slap the cuffs on him. But now I get it. Now I see…

Guilt is its own punishment.

And honesty is its own reward.

A Living Hell.

A Living Heaven.

I realize that I might have destroyed my reputation for what I just did. I could’ve just left the firm without anybody knowing. Instead, now, my company will most certainly fire me (and I don’t blame them, I’ve tried to make it easier on them by offering my own resignation). Companies might never hire me. I might never be entrusted to manage money. Most importantly, colleagues, partners, and friends might never trust me. But the reputation-destroying acts were already done. That hand was already played.

So, today, my only choice was how to play the next hand. And what I just did was one of the realest moments of my life. I was able to silence my fear and sidestep my self-protective ego. I was able to listen to that inner voice that led me to doing what I knew was the right thing.

James Clear has this great line:

Today’s action was 1 single vote in the “honest” category after the opposition got out to a commanding 131-0 lead.

Once again, don’t get me wrong - I don’t see myself as a hero. What I did consistently was unequivocally wrong. So, to turn myself in was inevitable. It was just a matter of when.

Also, to be clear, my company was not aware and did absolutely nothing wrong here. The blame rests entirely on my shoulders.

I’ve realized that our insecurities, left unaddressed, follow us.

No matter how far we run or how high we climb, our insecurities will follow close behind. And they’ll lead us to take actions that are grossly misaligned. Even as I amassed more than I ever could’ve imagined, my fear of being broke never truly left me. It still hasn’t… so, I have to confront it everyday.

But, now, when I do something wrong, I know there’s no running from it. Because eventually, it will catch me. And when it does, I’ll have wasted so much energy trying to escape it that I’ll be distracted from the life in front of me.

So, step 1 has been to turn & see what’s been lurking behind me.

To turn around & face it.

To turn myself in & accept it.

Now, I feel empowered to move forward towards this new place of serenity.

Living honestly is the only path forward.

Because living honestly breeds alignment.

And living in alignment is its own reward.

In fact, alignment is the only reward.

You might be left asking, “What inspired this? Why now?”

As I listened to this podcast, turns out Martha Beck’s Source also spoke to me, as it said: