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I often get asked how I come up with my content ideas, and candidly, I don’t really know. Each morning I genuinely have 0 idea what I’m posting. This one was a straight one take, no script, and really just a nostalgic rant in my opinion.

But apparently half a million people resonated with it. You can also view it on Tiktok here.

About a month ago, I got a text on a Sunday from one of my oldest friends. It was the standard "Hey, do you have a minute? I’ve got something I need to talk about" message. If you read my post from last week, you know my stance on this. Just call. We’re adults; we don’t need a written warning that a friend wants to chat. Because of that preface, my heart immediately dropped. My brain went to the worst-case scenarios. Did his mom pass? Are he and his fiancée calling it off? Was there an accident? This isn’t a guy I talk to every Tuesday. He’s one of those friends I’ve known for over 25 years (we went to preschool together) but we probably only see each other once or twice a year.

We ended up chatting for an hour. At the very end, he finally asked me to stand in his wedding. I’d known it was coming, but he isn’t exactly the "Type A" planner of the group, so getting the official ask at the 9th or 10th hour wasn't a shock. Of course, I said yes. There’s that awkward moment on the phone where two men are trying to communicate 2 decades of history and brotherhood, but all you can manage to say is, "You’re the man." In your head, you’re thinking, Dude, I still remember your childhood home phone number. I love you. You’re my guy. No matter what I’m with you forever. But out loud, it’s just casual. Then he dropped the logistical bomb: the bachelor party was in Nashville. In 3 weeks.

I’m fortunate to be in a position where I can afford small luxuries, like refusing to do layovers for any flight under 2 hours. But even so, a last-minute round trip to Nashville was $600. As we were talking, I could feel the mental calculator in the back of my brain starting to whir. I started doing the math on the tux rental, the Lyfts, the registry gift, the Airbnb, and the hotel for the out-of-state wedding. I blinked and realized that standing in this wedding was a casual $1,500 investment. It makes you feel like a jerk for even thinking about money when it comes to your oldest friend, but we all do it.

We want to believe our loyalty is priceless, but in your 30s, every 'Yes' comes with a line-item invoice.

The tension between living for today and preparing for tomorrow gets even heavier when you look at the other end of the spectrum. Last year, we lost my Nannie (grandmother). It was my first time experiencing hospice as an adult with a fully developed frontal lobe. There is something both terrifying and beautiful about watching a loved one slowly drift away, but I also recognized the immense privilege of her passing in her own bed. Having family around 24/7 and hiring night and weekend nurses to ensure she was comfortable is a blessing, but it is a staggeringly expensive one.

Many families are out here struggling with aging parents while simultaneously white-knuckling a mortgage, student loans, and the pressure to save for a retirement that feels 100 years away. You want to take the trip to Italy or the Pacific Northwest, but you know it’s going to require a credit card swipe—or several. We all wish money wasn't an object in these moments. We want to say yes to the care, the trip, and the experience without thinking about how that $2,000 could have gone toward a wedding ring or an emergency buffer.

The real goal of financial independence isn't the ability to buy things, but the ability to provide dignity and presence when life gets heavy.

On Thursday night, the theory became reality as I landed in Nashville. I stayed with a friend and his fiancée, who happens to be my best friend from college and my former roommate. Their own wedding is in Cabo later this year, where I’m the best man. That’s another flight, another tux, another "investment." But that night, we just ordered curry, enjoyed some herbal remedies on their porch, and caught up on work and life. We watched some trash reality TV, laughed our asses off, and were in bed by 1030pm. Friday morning, I spent my time working from various coffee shops, waiting for the other 4 guys to arrive.

Once the crew was together, we checked into an Airbnb in Germantown, the best spot in the city if you ask me. We hit a couple of bars, grabbed some BBQ, and I immediately leaned into my love language: being extremely competitive over cornhole and pool. Saturday started at Helen’s near Vandy for some hot chicken and waffles, followed by axe throwing where I managed to win cricket. We moved on to a bizarre soccer and curling bar, where I proceeded to talk a healthy amount of playful shit during a round-robin tournament.

Eventually, we ended up on Broadway. We were the quintessential group of 5 guys in their 30s, mostly married or in long-term relationships, standing around a table with overpriced drinks playing "Heads Up" on an iPhone because the music was too loud to talk. We lasted about an hour before we retreated to Pinkerton’s for more BBQ and 2 hours of darts. We played the game the Puma crew taught me in Vietnam, you have to hit every number and then the red bullseye in order. It was electric. We hit the hay early, and I flew home the next morning feeling the post-trip slump. My dopamine was low and my diet was 80% fried food, but it wasn't regret I was feeling. It was just the reality of the trade-off.

I never regret the $500 spent on a memory, but I always feel the weight of the $500 I didn't plan for.

Flying home, I kept thinking about why we struggle so much with the mental side of money. I don't think "I should have bought those new running shoes instead of going to Nashville." But I do think about the balance. This is why I tell people they shouldn't even talk to a financial advisor until they’ve figured out their "Number." It’s not a net worth goal. It’s a baseline. It’s the amount of money you need to save or invest every single month, consistently, for 12 months straight.

Maybe it’s $500 toward student loans, $100 into a savings account, or 15% into your 401k. Whatever it is, you have to hit it. For me, I like having at least $20k in cash at all times. It’s an arbitrary amount, but it’s the number that gives me peace. Everything beyond that goes into aggressive index funds or startup investments. I’m not a multi-millionaire, but I’m trying to solve the puzzle of living for today while building for tomorrow.

The secret to enjoying your life is finding the specific 'Number' that allows your brain to stop calculating and start participating.

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