My Relationship with Money: The Hoarder Mentality That Led to Early Retirement

Growing up, I developed a relationship with money that some might call obsessive, others might call smart, but I see it as a unique blend of hoarding and emotional struggle.
I don’t part with my money easily. In fact, the act of spending—even on things I need—causes me to feel a wave of guilt that’s hard to describe.
While some people feel joy in buying new things or chasing status symbols, I feel the exact opposite. For me, letting go of my dollars feels like losing a part of my future.
This mindset has made it incredibly easy to save and invest over the years, but it’s also a significant part of what shaped my journey to early retirement.
Table of Contents
How It All Started: My Mom’s Influence
My relationship with money started early, largely influenced by my mom. She was adamant about teaching me budgeting, ensuring that I knew the value of every dollar.
It was out of necessity. She and my dad started a business before I was born. So they had my sister and I, and a business, when they were in their early 20s. My two brothers came shortly after that but by then the business was doing ok enough.
So my mom was frugal. We ate cheap meals. She made some of my own clothes. She clipped coupons. The entire time she taught me what she was doing and why. She taught me the value of a dollar. (As I’m writing this, I am almost thinking this is a play on Robert Kiyosaki’s Rich Dad, Poor Dad, except it is “Rich Dad, Frugal Mom”.
One of my earliest and most vivid memories around money involves my first withdrawal from my bank account in either 1st or 2nd grade.
I took out $20 to buy a Transformer toy. My mom, who had been teaching me the value of saving, cried when I spent that money.
It wasn’t the toy itself that brought her to tears. It was the fact that I was spending money I had saved. She was not going to tell me not to spend money. But she made it clear that saving money meant something special.
That moment stuck with me, and it was the beginning of a lifelong struggle to part with money.
Guilt as a Financial Ally
For many, the idea of keeping up with the Joneses is a powerful motivator to spend, upgrade, and accumulate things.
For me, it’s the opposite.
I have no desire to chase after what others have because the very act of spending money, even on things I want, makes me feel guilty. And while guilt is often seen as a negative emotion, in my case, it became one of my biggest financial allies.
It’s not that I’m disciplined. It’s that the emotional difficulty of spending is so strong that it forces me to think twice before making any purchase.
This mindset didn’t just make saving easy; it made investing easy too. Why? Because I didn’t feel like I was losing money when I invested it. Instead, I saw my dollars working for me, growing into more money over time.
I liked the idea of my money making money. And so, rather than sitting on cash or spending frivolously, I poured my savings into investments that would help me retire early—something I accomplished at the age of 42.
Some people (especially on Twitter), think it’s sad that I don’t enjoy spending money. But it’s the opposite. I have found happiness. It doesn’t take spending to make me happy. Instead, it just takes being.
I depend on acquiring things to bring me joy, unlike most of our society. That is freedom!
Obsessive Planning: How I Manage the Emotional Struggle
Despite what sounds like an iron grip on my finances, I’ve had to develop strategies to manage the emotional aspect of my relationship with money. For 24 years, I’ve obsessively tracked my spending and planned meticulously, not because I’m a natural planner, but because it helps me take the emotion out of money.
As I was on my FIRE journey I would get the feeling that I didn’t have enough money or question whether my financial plan would actually work. The only way to quiet that anxiety was to open up my spreadsheets and see the numbers in front of me.
That simple act of reviewing my spreadsheets has been a lifeline. It reassures me that, yes, I do have enough money and that, yes, my plan is working.
I’ve relied on these spreadsheets not just to track spending, but to validate my entire financial strategy. Without them, I’d be consumed by doubt, constantly second-guessing whether I was on track or not.
This isn’t discipline. It’s a coping mechanism that allows me to let go of my dollars in a way that doesn’t feel like loss.
A Hoarder’s Mindset Shaped My Financial Future
What some might see as discipline is really just a deep-seated emotional response I’ve had to money all my life. I hoard it because letting go is too painful. And while this mindset has made it easy to save and invest, it also shaped my early retirement in ways I didn’t anticipate.
By obsessively tracking my spending and planning every dollar’s use, I was able to ensure that my financial goals were always within reach.
I didn’t need the latest gadgets or fancy vacations. In fact, the idea of spending money on anything unnecessary still feels like a betrayal of the values I’ve held since childhood.
And while this might not be a path everyone can take, it’s the path that worked for me. That’s the beauty of personal finance, there are many paths to financial independence
For me, hoarding money wasn’t just about accumulating wealth. It was about securing a future where I could live life on my own terms. It was about making sure that the fear of not having enough wouldn’t control me.
In the end, my relationship with money is what gave me the freedom to retire early, even if it meant relying on a spreadsheet to remind me that I was on the right track.
If you’re someone who struggles emotionally with money, there are ways to take the emotion out of it. The key is finding a system that works for you. For me, it was the spreadsheet.
For you, it might be something else entirely. But in the end, it’s about managing the emotional side of money, not just the financial side.
Final Thoughts
Money is more than numbers. It’s deeply emotional for many of us. And in my case, that emotional struggle turned out to be my greatest financial strength. I didn’t have to rely on discipline because I was so emotionally tied to keeping my money that I naturally gravitated toward saving and investing.
That same hoarding mentality, instilled by my mom from a young age, shaped my financial future and helped me achieve early retirement. While it wasn’t always easy, it’s a path I wouldn’t change, and one that continues to serve me today.
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