My Money Story (Part 2)
Always Bet on My Self
Freedom from financial stress followed me through my teens and into college. I was fortunate that my only real job was doing well in school and chasing my basketball dream. A couple of summer jobs came and went. Security at local events. A summer at Family Video. Nothing demanding, but nothing that paid much, either. It was ok though, because I didn't need much. I was free to be young, and money still felt like it always had somewhere in the background, quietly okay.
What I didn't know was that the background wasn't as quiet as I thought.
It wasn't until I graduated and became my parents' financial advisor that I learned what had actually been happening during my college years. While I was attending a small, expensive Division III school to play basketball, going out to dinners with friends, traveling for spring break trips, and making unnecessary Walmart runs, I was spending money we didn't really have to spend. I was living without thinking twice, and my parents were quietly tapping into resources meant for their future.
I remember sitting with my dad's Social Security statement and seeing the lean years marked by low reported income that perfectly coincided with my time in college. During those years, he had been consulting and building something he'd always wanted to build—his own company, J&K Group. I knew he was enjoying the work. I knew he believed in what he was doing. I didn't know that he wasn't being paid, that his trust in others had cost him more than I realized, and that he had chosen to carry that quietly so my sister and I wouldn't have to.
We’ve talked about those years and his decisions, and I know he would do it again. He's told me as much. And I understand that kind of love doesn't calculate, it just protects.
But his experience wrote a script in me that I wouldn't even know was running for years: “I will never let someone else determine my financial security and freedom. I will always bet on my Self.”
The script stayed dormant for a while. Then 2008 arrived.
I was four years into my career, working for a large retirement-planning company owned by AIG. I was building relationships with teachers across Indianapolis, slowly laying the foundation for what would one day become my own firm, although I didn’t know it in the early days. When AIG received its government bailout during the Great Financial Crisis, the comments in the teachers’ lounges started. Most of them were jokes, but some weren't. A few teachers even moved their accounts to other companies. It was then that I felt something shift in me. It wasn’t panic, but recognition.
Someone else's decisions were impacting my business. Decisions made in New York City were creating friction in something I had worked to build. Thankfully, the money wasn't significantly affected. But the feeling was clear.
I knew, sitting in those teachers’ lounges listening to the questions and the frustration, that I would one day work for no one but my Self. The only person I would allow to disrupt my financial security would be me. I wasn't worried about that. I'd bet on my Self eleven times out of ten.
So I made a plan. I would spend my remaining time at the company building relationships that belonged to me, not the firm. I would save carefully, build a runway, and launch when the number felt right. I knew exactly what I was doing and why.
Then I deviated from the plan.
At a local Financial Planning Association meeting, I met an advisor looking for someone to be part of her succession plan. The conversations were good. The opportunity seemed ideal. And at the last moment, I made a decision I would later recognize as one made with my mind instead of my heart.
I joined her firm.
I took a significant pay cut. $250,000 down to $50,000 in year one, $75,000 in year two. I told myself the long-term reward would justify the short-term sacrifice. What I miscalculated was how slowly the growth would come, not from lack of effort, but from circumstances outside my control. And as the salary ran low, the savings I had set aside to launch my own firm quietly disappeared to cover the gap.
I had trusted that someone else would have my best interests at heart.
And in doing that, I had put my Self in exactly the position my subconscious had spent years trying to avoid.
I was stuck. Savings dwindling. Income capped. No clear path forward.
The irony was almost too clean to miss. The script I had written, watching my father, never let someone else hold your financial future, had been willingly handed over, convinced I was making a smart move. I had made a decision from my head and left my heart out of it entirely, and the result was two years of sitting with what that felt like.
I don't say this to assign blame. The opportunity wasn't malicious. But it was misaligned. And misalignment, I've come to understand, has a way of making itself known.
Two years in, almost to the day, I launched my firm.
And I haven't looked back.
There's something clarifying about arriving at a place you always knew you were heading, even when the path surprised you. The detour cost me money, time, and a fair amount of peace. But it also deepened the script in a way that comfort never could have. I needed to feel what it was like to hand the wheel to someone else. To sit in the passenger seat of my own financial life and recognize, clearly and without question, that it wasn't where I belonged.
The script, “always bet on your Self,” might come across as arrogant, but it’s not. It's the recognition that my financial security and freedom are mine to steward. That no one else will protect them the way I will. That the deepest form of alignment is showing up fully for the life only I can live.
My father taught me that, even though he never said it quite that way.
The Universe reinforced it, even though it took a detour to do it.
The story isn't over.
But I know whose hands I want holding it.
Keep pursuing,
JC
Note: This was inspired by my recent work in the Anya Institute for Human (R)evolution Integrated Wealth Advisor program, focused on defining my wealth narrative and conditioning. This is the second in a series of posts inspired by my answers to the course exercises. I don’t know how many posts there will be, but they will help me tell my wealth narrative.