At nineteen, I was commuting from my parents’ house to architecture classes I’d stopped caring about, and it felt like a fifth year of high school.
Architecture had been the dream my whole life — designing spaces where people could live better lives. But once I was actually in the program, driving the same roads every day, sleeping in the same basement bedroom, watching my parents barely speak to each other, the dream didn’t fit anymore. Or maybe I just couldn’t dream properly in that house. All my friends had escaped to real college experiences. I was drowning in place.
Here’s what I was actually doing, though I couldn’t have named it at the time: I was sitting in a waiting room. Waiting for the degree to make me legitimate. Waiting for the right moment. Waiting for my real life to be called.
If you’re somewhere in your twenties feeling some version of that — lost, behind, unsure whether you picked the wrong major, the wrong city, the wrong everything — I want to hand you the thing I wish someone had handed me. Not comfort. A door.
The Waiting Room Trap
Most people treat their twenties like a dress rehearsal. Like these are the practice rounds, and the real game — the one where choices actually count — starts later. After the degree. After the entry-level years. After you figure yourself out.
But life has no practice rounds. It’s already real. It’s been real the whole time. Every year you spend “getting ready” is a year of the actual thing, spent in a chair.
I’ve watched people run this pattern for decades: perpetually one more credential, one more promotion, one more year of experience away from being qualified for the life they really want. They spend their whole lives getting ready for a life they never actually live.
And here’s the part that matters if you feel lost right now: feeling lost is not the problem. Lost means you’re out in the terrain, comparing the map to the ground, discovering the map is wrong. That’s called navigation. The problem is parked — staying put in something you already know doesn’t fit because moving feels premature. I wasn’t lost at nineteen. I was parked. There’s a difference, and only one of them is fixable by thinking harder.
“Find Your Passion” Is Terrible Advice
The waiting room has a soundtrack, and it goes: don’t commit to anything until you find your passion.
Wrong. Passion follows competence. Master something valuable first — then the passion develops. Telling a 23-year-old to find their passion before they’ve built any real skills is how you get broke people who are great at describing the life they’d love and terrible at building it.
I learned this before I could drive. At ten, I was hand-sewing little bean-filled toys called Mooshi’s at my parents’ kitchen table — fabric from the JoAnn’s remnant table, rice or beads inside, every one unique. Kids at school started paying five bucks apiece. Custom orders. Hundreds of dollars in a shoebox under my bed. Was sewing my passion? Of course not. But making something people wanted lit me up in a way nothing else did — and I only discovered that by making things, not by contemplating what I might enjoy making someday.
That pattern — get good at something, make it better than anyone expects, turn it into value people will pay for — became the blueprint for everything I built later. But let me be honest about the sequel, because it carries the second half of the lesson. In college I ran a t-shirt business for fraternity and sorority events. Made almost enough to pay for a year of school. Then bad decisions, a falling out, a lawsuit — and I graduated with $25,000 in credit card debt. The skill was there. The interest was there. The market was there. What was missing was discipline, and passion without discipline creates debt. Every time.
So instead of hunting for passion, run the three-part test on whatever’s in front of you: Are you good at it — or do you have the raw aptitude to become excellent with practice? Do you care about it — would you read about it, think about it, work on it unpaid? And will someone pay for it — because if not, you’ve found a hobby, which is fine, but call it what it is. Where all three overlap is where passion becomes sustainable. You find that overlap by working, not by waiting.
Direction Beats a Plan
The other thing keeping you in the chairs is the belief that you need the whole map before you move. You don’t. You need a direction and a first step.
My own direction changed on a barstool. My best friend Brian came home from Bowling Green with stories that made my commuter life feel like a prison sentence, and talked me into transferring. His sales pitch was not sophisticated — it involved the male-to-female ratio. But that unglamorous conversation rerouted my entire life. Because I transferred, I met Jodi at a fraternity party junior year. Because of Jodi, I eventually moved to Cleveland at twenty-two — in debt, no savings, no guarantee — for a job and a woman and a chance to find out who I could become when I wasn’t managing everyone else’s crisis.
Was any of that The Plan? There was no plan. There was a direction — away from the life that was shrinking me, toward one I’d have to build — and a willingness to take steps before the variables lined up. They never line up. Nobody is ever really ready. The people who look like they had it together when they made their big move were just as uncertain as you are. They moved anyway, and competence caught up with them on the road.
Waiting for certainty is just procrastination with better excuses.
What to Do in Your Twenties: Five Choices That Compound
Not tips. Choices. Each one is cheap to make at twenty-five and brutally expensive to make for the first time at forty, because everything on this list compounds — which means the earlier you start, the more decades the interest works for you.
1. Build one skill past the point of impressive. Not five skills to “keep options open” — that’s the waiting room with extra steps. One skill, driven deep enough that people seek you out for it. Depth is what converts to money, confidence, and options. Options come from being excellent, not from staying uncommitted.
2. Get financially boring. Track your net worth, not your income. Income is vanity; net worth is sanity. I know people earning over $500K with negative net worth — high-earning prisoners. Meanwhile someone making $70K with zero debt and six months of savings has more actual freedom than the guy with the BMW and the anxiety. Boring money is what lets you say no to soul-killing work and survive the early years when the thing you care about doesn’t pay yet. I financed a lifestyle before I’d earned one, and spent years buying my freedom back.
3. Choose your people like your life depends on it. Who you spend your twenties with quietly writes the defaults for the rest of your life — especially who you build a life with. Jodi believed in my potential more than I did, and that single relationship made every risk after it survivable. Meanwhile, the wrong crowd doesn’t announce itself; it just normalizes small compromises until they’re your personality.
4. Do the hard reps while recovery is cheap. Your twenties aren’t low-stakes — no years are. But they are the years when you recover fastest and when a hard rep pays interest the longest. The difficult conversation, the intimidating project, the risk that might publicly fail: every one you take now builds evidence. Every one you dodge builds a dodging habit, and that compounds too.
5. Decide what you’re not carrying forward. Some of what’s in your bags was packed by other people — your family’s patterns around money, conflict, silence, drink. Your twenties are the cheapest decade to put those down, before they’ve soaked into a marriage, a career, kids. I’ve written a whole post on this one: The Cycle Ends With You.
What Thirty Actually Rewards
Here’s what nobody tells you about the far side of this decade: thirty doesn’t reward the person with the tidiest plan. It rewards the person with the most evidence.
Earned confidence — the real kind, not fake-it-till-you-make-it anxiety in a power suit — comes from one source only: a stack of hard choices you actually made, failures you actually survived, and proof that you can handle whatever comes. Decisions stop being agonizing, not because they get easier, but because you’ve built the ability to handle their consequences. Problems stop being crises and start being puzzles.
You cannot build that stack in a chair. Every piece of it is out past the waiting room door.
So: you’re not behind. There is no schedule, and the people who look ahead of you are mostly just better at posting. But you are, possibly, parked — and that part is yours to fix, today, with something as small as one honest conversation, one application, one rep.
The receptionist is never going to call your name. Get up anyway.
This is the terrain my book covers start to finish — Brave & Boundless: 15 Rules for Breaking the Cycle and Building What’s Next was written for exactly the decade you’re standing in.