Money came fast. Nine months after law school, I was a millionaire, and by 32 a multi-millionaire. As Chairman of the Napoleon Hill Institute and former CEO of Leigh Steinberg Sports & Entertainment, I had access to anything. My view then was simple: more cash, more joy. That belief was wrong.
My opinion is clear: wealth is a tool, not a scorecard. When money becomes your identity, it drains meaning. The real game is to shop for the right things—health, love, purpose, and service—before the bill for ego and excess comes due.
The central truth I learned the hard way
Money only amplifies who you are. If you buy the wrong things, it multiplies emptiness. If you invest in the right things, it multiplies fulfillment.
“I really believed that I could buy happiness.”
“Pretty soon I got to a point where I owned every single thing or could do anything I wanted. The problem was it left me empty.”
That was my life while married to an unbelievable woman and raising three daughters. I chased stuff, status, and the next high. I spent time with the wrong people, in the wrong places, doing the wrong things—alcohol included. The more I shopped, the more guilt piled up, and the bigger my ego grew to cover it.
“I used my money to shop for the wrong things… I literally had no worth cuz I was shopping for the wrong things.”
Why the scoreboard can’t be your soul
Ownership without inner worth is a hollow victory. You can hit your numbers, crush deals, and still feel nothing. I did. The rush fades. The void does not.
Does money matter? Yes. It buys options, safety, and time. It funds causes. But there is a line where cash stops helping and starts hiding the real problem—self-worth tied to possessions and attention. The counterargument says, “More money will fix it.” It won’t. It only adds volume to the noise inside.
What to shop for instead
Switch the cart. Change what you buy with your time, energy, and money.
- Buy time with family. Schedule it first. Guard it.
- Buy health. Sleep, movement, and sobriety beat any luxury.
- Buy service. Give daily. Start small and be consistent.
- Buy growth. Read, coach, mentor, and learn.
- Buy accountability. Friends who tell you the truth, not what you want.
- Buy alignment. Spend where values and calendar match.
Ego loves shiny things; purpose loves simple things. One numbs you. The other fills you.
Signals you’re shopping for the wrong things
There are tells that your cart is off track. Notice them early and pivot.
- High net worth, low self-worth feelings.
- Escaping with alcohol or constant distractions.
- Buying to impress people who do not care about you.
- Guilt after purchases or nights out.
- Endless chasing without clear values.
These signs do not make you a bad person. They are a wake-up call. Answer it.
The turn that saved me
I stopped shopping for status and started investing in worth. I chose honesty, service, and presence. I rebuilt trust at home. I re-anchored my identity to values, not things. That is where real wealth lives.
You can do the same. Audit your spending of time and money this week. If it does not align with your values, cut it. Then add one daily act of service, 20 minutes of learning, and one hard conversation with someone who will tell you the truth.
Happiness is not bought. It is practiced. The receipts are your habits. The dividend is peace.
Call to action
Make your next purchase a decision to live by values. Pick one change today—less ego, more service; less escape, more presence. You will feel the return fast. Your family will feel it faster. Choose worth over things, and let your money serve your life, not replace it.
Frequently Asked Questions
Q: How do I know if I’m tying my identity to money?
Watch your mood after wins and losses. If your self-respect swings with your bank balance or praise, your identity is stuck to the scoreboard.
Q: What is a first step to rebuild self-worth?
Start with daily non-negotiables: gratitude, exercise, learning, and service. Keep them for 30 days. Small, steady actions repair trust with yourself.
Q: Can I still chase big financial goals without losing myself?
Yes—tie goals to values. Define who benefits, how you will serve, and what boundaries protect health and family. Ambition needs guardrails.
Q: What if my friends enable the wrong habits?
Change your circle or change the rules. Set clear limits on time, spending, and substances. Find mentors who prize honesty over hype.
Q: Does money buy happiness at all?
It buys comfort and choices. Happiness comes from meaning, relationships, and contribution. Use money to support those, not replace them.
