The first time I robbed Peter to pay Paul was at fifteen. I was determined to get myself to a family reunion in Southern California, something Dad had no interest in attending or paying for, which meant I had to figure it out on my own.
So I did what any financially strapped teenager with no job would do: I did the math in my head and decided to skip school lunches. Not in a noble, hunger-strike-for-justice kind of way—more like a “Sorry, pizza-day, but you’re standing between me and the Pacific Ocean” kind of way.
Every day, for months, unbeknownst to Dad, I funneled my lunch money into what I considered my offshore account. In reality, it was an envelope tucked under the mattress of my captain’s bed. I called it my “secret savings account.” I won’t call it exactly embezzlement. You call it what you want. Forensic accountants might call it “asset misappropriation”; fifteen-year-olds call it “good planning.”
There was something thrilling about watching the cash pile up. While my friends chowed down on chicken fingers and French fries, I was tasting the intoxicating flavor of liquidity. Sure, I was hungry, but hunger felt like an acceptable handling fee. Every dollar brought me one mile closer to palm trees, family I hadn’t seen in years, and the Los Angeles Dodgers.
And when I got home each day, I made up for it by inhaling two peanut butter and jelly sandwiches like a bear preparing for winter.
By the time I had enough saved to be taken seriously—around four hundred dollars, I realized two things: one, money is freedom, and two, freedom comes with a growling stomach around fourth period.
At last, the day had finally arrived for me to put my money to work. I did the only logical thing a fifteen-year-old in 1994 could do: I hopped on my bicycle and rode myself downtown to the travel agency. This was the pre-Internet age, when booking a plane ticket required human interaction.
The agency was tucked on the ground floor of the Broadway Tower, a skyscraper by Enid, Oklahoma, standards. Fifteen stories. I think the FBI was on the seventh floor or the thirteenth floor. I locked up my bike, marched in as if I belonged in an Esquire magazine profile, and plopped my envelope of cash on the agent’s desk. I wanted a ticket from Oklahoma City to Los Angeles, and I wanted it yesterday.
The agent looked at me. I looked at the agent. Somewhere in that moment, a line of logic must have broken in the travel industry: “This kid is fifteen. He has cash. He seems determined. Let’s just do it.”
And just like that, this woman made the executive decision to sell me a plane ticket. How did she not call my dad? How did she not call the authorities? Maybe the universe was amused. Maybe it had a soft spot for persistent teenagers. Or maybe the rules were written in pencil. Today, I couldn’t find any US law that required an airline to demand written parental consent.
“Have you ever flown alone before?” she asked.
“Oh, absolutely,” I said. “I’ve flown a number of times.”
It was mostly true. Over the years, responsible adults made sure I was securely deposited at gates and reclaimed on the other end. This was the golden era of the Unaccompanied Minor Program. Airline staff would escort you through the airport with a level of formality normally reserved for diplomats. They’d walk you right up to the gate, hand you off like a baton in the 4×400 relay, and then repeat the process in reverse when you landed. Sometimes, snack boxes were even involved. I felt like I was part of aviation’s most exclusive club.
“Do you need an escort?”
“Nope,” I smiled.
The travel agent studied me for a moment as if assessing my survival odds: Could he find his gate? Could he board the correct plane? Would he accidentally join a connecting flight to Milwaukee? These were important questions.
“Are you sure?”
“Yep.”
I was now older, which I thought graduated me out of the escorted-snack-box class and into a new category: Good luck out there, kid. No handlers, no lanyards, no official transfer of custody—just me, my backpack, and a belief that airports were navigable if you followed signs and pretended to know what you were doing.
At this stage of my life, I thought I was practically an adult. Seeing my dad go to prison when I was twelve had a way of accelerating the timeline on adolescence. There’s nothing quite like visiting a parent behind bars to make math homework and ballcourt squabbles feel small. You learn to make decisions, manage logistics, and generally fend for yourself. By this point, I had already opened up a safe deposit box account for my baseball cards by myself. I didn’t trust the kids in my neighborhood. And I did other adult stuff when I got back from California. On my own, I applied for my Social Security card downtown so I could get a job at Braum’s Ice Cream & Dairy. Getting the card was a two-step process that required me to first request a copy of my birth certificate from Wyoming Vital Statistics Services. As I said, I thought I was an adult, and I acted like one.
“Almost done,” the travel agent said, fingers flying across the keyboard that made a satisfying clack-clack-clack with every keystroke. A green cursor blinked on her screen like it was thinking through the logistics of my entire future.
Behind her, the dot-matrix printer sputtered to life—eeeerrrrrrr-chkk-chkk-chkk. The computer spat out my ticket. She tore the perforations with a practiced wrist flick and stacked the layers into a little booklet. Then, almost ceremonially, she slid it across her desk toward me with two fingers.
“Alright,” she said. “OKC to LAX, one stop in Dallas. Have fun out in sunny California.”
“Thank you. I will.”
When I walked out with that ticket clutched in my hand, I felt like a cross between a secret agent and a magician who had just pulled a 747 out of a hat. A ticket to the West Coast. Somehow, I had pulled it off.
Getting that ticket taught me two principles that surely help bend the universe in my favor from time to time.
Number one: I have to take shots to get what I want. My shot at that ticket wasn’t guaranteed, but if I hadn’t put a plan in motion and aimed, I would have missed the opportunity entirely. And that, I realized, is what makes life happen: some planning and taking shots.
Number two: ask and ye shall receive. The kid version of that principle is blunt: if I don’t open my mouth, the world assumes I don’t want anything. So I ask. I ask politely, nervously, shamelessly. I ask with cash if I have it, or with charm if I don’t. And sometimes I get handed what seems impossible. Sometimes I even get a little grin from the universe, as if it’s saying, “Well, because you asked, here you go. Now don’t mess it up.”
As I pedaled home with my ticket, it dawned on me that I had a playbook for life. One part courage, one part nerve, one part sheer boldness, and suddenly, the world seemed less like a place of “rules” and more like a place of possibilities.
Another time I made my money work was when I bought Cal Ripken’s 1982 Topps rookie card. This was several years before he broke Lou Gehrig’s record, back when he was showing up every day, never sitting out a game due to injury or personal reasons, and somehow he made it look easy. I admired that. There was something about Ripken—steady, relentless, reliable—that made the rest of the world seem like it was taking the day off while he kept pressing forward. The kind of guy you wanted on your team, on your street, or, in my case, in my card collection.
Getting the money for it, however, required a different kind of stamina than the plane ticket. I helped Dad on a big roofing job, which meant I hauled away old shingles in the sweltering Oklahoma sun while his crew stripped off the roof above me. The work was exhausting, filthy, and hot enough that you could fry an egg on the shingles if you were that desperate. Every sweaty, back-breaking hour I clocked got me closer to my goal. By the end of the day, I had enough. The card was waiting for me at Don’s Dugout, gleaming behind the counter like it had been waiting for a scrappy kid who had learned that ambition wins every time.
When I finally held it in my hands, I felt the same thrill I’d felt with the plane ticket. Here was proof of my resourcefulness, my grit. Owning that card was a small, tangible victory, and it seemed to whisper: You can make your money work. You can make yourself work. And if you do it long enough, the universe will let you hold something cool in your hands.
Working for Dad also taught me a couple of rules that stick to this day.
Rule one: persistence pays off. Literally. I haul shingles in triple-digit heat, and eventually I’m rewarded. I get the rookie card. I get the result. It’s tedious work, yes, but that’s exactly the point. Cal Ripken didn’t break Lou Gehrig’s record by sitting on the couch at home; he did it by showing up, game after game. Same principle. Show up. Keep at it. The universe rewards people who put in the work.
Rule two: Pride in ownership is a powerful motivator. It’s one thing to save money. It’s another to spend it on something I genuinely value, something that makes me feel smart and capable. Holding that card was proof I had done more than just scrape together coins; I earned my way and made something mine. There’s a freedom in that, a joy that no allowance, gift, or handout can replicate. And it stuck with me, long after the roof job was done and Ripken’s rookie card sat in my safe deposit box.
Another time I made my money work was the summer before my first semester of college, when I made the fiscally conservative, aesthetically questionable decision to invest in a Flowbee. For the uninitiated, the Flowbee is a revolutionary haircutting system that promises “professional results in the comfort of your home,” which is a polite way of saying “prepare to vacuum your head.”
At eighteen, though, it was a revelation. A good haircut in those days cost real money, money that could be better spent on gas for my Ford Tempo, fast food, or video rentals. The Flowbee, on the other hand, was a one-time purchase. Thirty minutes of studying the instruction manual and attaching plastic spacers to the head that comes attached to a hose, and suddenly, I was my own barber, stylist, and custodial staff. It sounded like a Shop-Vac and looked like a failed NASA prototype.
To call it a perfect haircutting solution would be somewhat misleading. I found that the Flowbee did not sculpt, shape, or style like a barber or hair stylist; it simply removed my hair in a generally consistent pattern, the way a lawnmower “styles” grass. But consistency has value, and for years it got the job done. I used that thing through my twenties, my early thirties, and right up until the great irony arrived: I went bald. The Flowbee, having bravely fought the good fight, was retired not because it failed, but because my scalp declared independence.
Before it bowed out, though, it served a second career cutting my boys’ hair—because nothing says fatherly love like telling your children to sit still while you vacuum their heads. The results were… acceptable. Not fantastic, not tragic. Mostly uniform. “You look fine,” I’d tell them, which is Flowbee code for “No one will laugh out loud.”
In purely financial terms, the Flowbee was a monster win: hundreds of haircuts over two decades for a measly hundred bucks. Making my money work? Absolutely. Did I look like I belonged on the cover of GQ? Absolutely not. But I do know one Flowebee user who has appeared on the magazine’s cover several times.
That honor belongs to actor George Clooney. He’s been using the haircutting machine for years. Correspondent Tracy Smith asked him on CBS This Morning if he’d been cutting his hair at home due to the pandemic, to which the actor answered, “I’ve been cutting my own hair for 25 years. Look, my hair is really like straw, and so it’s easy to cut. You can’t really make too many mistakes.” Clooney further explained, “Years ago, I bought a thing called a Flowbee. It comes with a vacuum cleaner and clippers. I still have it. My haircuts take literally two minutes.”
Imagine it: Clooney—global icon, Oscar winner, coffee pitchman, “Sexiest Man Alive” alumnus—standing in his bathroom giving himself a Flowbro like it’s the most natural thing in Hollywood. He gives a single pass, checks the mirror, and walks out red-carpet ready. Not even a pause to question the physics. “Two minutes.”
So like Clooney, using the Flowbee, I was always trimmed and solvent, two metrics that serve a man surprisingly well in life.
Eventually, my strategy for making money work graduated from siphoning lunch money and vacuum haircuts to something with a bit more gravitas: the 401(k). This was adulthood’s version of the envelope under the mattress, except with quarterly statements, mutual funds, and stern language about risk tolerance.
I started socking money away early, not because I was a financial genius, but because my first real employer said the magic words: “The company matches a percentage.” Free money is free money, and I’ve never been too proud to take it. So I signed up and let compounding interest do for me what the Flowbee never could: make me more attractive on paper.
The beauty of a 401(k) is that other people do most of the work. You contribute, the market goes up and down, and somewhere in the background, your money quietly multiplies. Today, I look at the balance once or twice a year, just long enough to reassure myself that civilization hasn’t collapsed, then go back to living my life. There is a certain peace in not staring at your retirement account every month; it’s like seasoning a steak and then leaving it alone on the grill instead of flipping it every 12 seconds. The less you meddle, the better things tend to go.
Of course, money has a way of teaching lessons at the most inconvenient intervals. During my divorce, my 401(k) was split fifty-fifty, a reminder that sometimes other people get to “work” your money too, whether you planned for it or not. It was called a qualified domestic relations order, a decree for my retirement plan to pay marital property to my ex-wife. There was no market index fund that could hedge against that. But even then, with the balance effectively cut in half, the principle remained the same: keep contributing. Keep compounding. Keep showing up. Slow and steady.
And that’s the thing, most wealth isn’t built by heroic stock picks or whispering “Buy!” into a Bloomberg terminal at midnight. No gimmicks. No magical thinking. Just financial common sense that’s guaranteed to work. It’s built by making reasonable decisions consistently, over a long period of time. I drip contributions into a tax-advantaged account, don’t panic when the market throws a tantrum, and one day I’ll look at the numbers and say, “Well, would you look at that—time was my friend.”
Word Count: 2,634
Here are six “writing” takeaways from this chapter:
The Beginning
1. Start With Motion
Good memoirs don’t sit around clearing their throat. They push the reader into a moment already happening. Notice how the chapter doesn’t start with a biography of adolescence, or a thesis about money; it starts with a kid secretly funding a trip to California. Motion is sticky.
Try This: Drop the reader into an action from your life, no warm-ups, no prefaces.
2. Use details to earn clarity, not clutter
The captain’s bed, the Broadway Tower, the envelope under the mattress. These are specifics that do work. They reinforce time, place, and stakes without drowning the reader. Precision. Concrete nouns make abstract ideas understandable.
Try This: Replace generalities (“I saved money”) with one vivid detail (“an envelope stuffed under my captain’s bed”).
The Middle
3. Raise stakes by raising responsibility
Good middles are where the reader sees a person become accountable. Here, the middle isn’t a lull; it’s where the narrator gets his plane ticket and baseball card through strategy, nerve, and labor. Responsibility creates tension, and tension keeps pages turning.
Try This: Write a scene where you had to assume responsibility: financial, emotional, or logistical.
4. Show consequence, not commentary
I don’t tell readers “I matured early.” I show it: opening a safe deposit box, buying a ticket, working a roofing job in triple-digit heat. The reader draws the conclusion. Memoir works best when the writer trusts the reader to get it.
Try This: Cut the preaching. Replace judgment with behavior. Let the reader decide what it means.
The End
5. End by widening the lens, just a little
Instead of a sentimental bow, the chapter zooms forward into adulthood: matching contributions, compounding interest, and QDRO splits. It’s a memoir doing what a memoir should, pulling meaning from the ordinary without melodrama. The teen who saved lunch money becomes the adult who invests steadily.
Try This: Write a closing paragraph that links an adolescent trait to an adult behavior.
6. Extract insight, not sermons
The final idea—“time is my friend”—lands because it’s modest, earned, and universal. I don’t lecture about finance. I demonstrate the passage of time, the discipline of contribution, and the simplicity of compounding. Clarity, restraint, and respect for the reader’s intelligence.
Try This: State one clean insight your reader can pocket, without flair or preaching.
