A Letter: Gen X to Millennials - One Lost Generation to Another - You Ain't That Lost
I need to tell you something, and I'm not sure how you're going to take it.
You're not lost.
I know it feels that way. I know the economy handed you 2008 right when you were supposed to be starting out. I know student debt is a weight my generation never carried at your scale. I know housing prices look like a sick joke. I know you did everything "right" and the math still didn't work.
I'm not here to minimize any of that.
But I need you to know: they called us the lost generation too.
Gen X Got Written Off
I grew up in the '80s. We were the latchkey kids — the ones who came home to empty houses because both parents worked, or because there was only one parent and they were doing everything. We were raised by television, Trapper Keepers, and benign neglect.
The headlines called us slackers. Directionless. Cynical. A generation with no future, squeezed between the Boomers who had all the jobs and the world that didn't seem to want us.
Sound familiar?
We came up during recessions, the AIDS crisis, the crack epidemic, and the constant low hum of Cold War anxiety. There was no internet to tell us what to do. No influencers. No roadmaps. Just us, figuring it out in real time.
And here's the thing: that figuring it out? That was the training.
Boredom Was a Superpower
There's something I don't think younger generations fully understand, and it's not your fault — you never experienced it.
We were bored. Legitimately, profoundly, nothing-to-do bored.
No smartphones. No streaming. No endless scroll. Just long summer afternoons with nothing but time and whatever you could invent to fill it.
And so we invented.
We built ramps for bikes out of plywood and cinder blocks. We figured out how to make $20 last a whole weekend. We started businesses without knowing that's what we were doing.
I got my first real job at 14. The house next door was empty — up for sale — and one day the real estate agent was there while I was mowing our lawn. He asked if I wanted to make a few extra bucks keeping the yard clean on the house he was trying to sell. I said sure.
That turned into mowing several houses in the neighborhood. No business plan. No LinkedIn. Just a kid who saw a gap and filled it.
Boredom taught me that nothing comes to you. You go to it.
Two Jobs, One Crappy Car
By the time I was 16, I was working two jobs. Not because I was ambitious. Because I wanted a car.
Not a nice car. A piece of crap car that would get me to my friends, to dates, to concerts. We'd stand in line for hours to buy tickets — actual paper tickets — because that's how it worked. There was no app. There was just showing up.
The car cost maybe $1,500. I don't remember exactly. What I remember is earning it. Dollar by dollar, shift by shift, until I could hand over cash and drive away in something that was mine.
That car wasn't about transportation. It was about freedom. And freedom had a price, and I paid it.
Nobody told me I deserved a car. Nobody said the system was broken because I couldn't afford one. I just worked until I could.
Rejection Was the Curriculum
You want to know the most useful skill I built in high school?
Getting rejected.
If you wanted to ask someone out, you had to actually ask them out. Face to face. No DMs. No swiping. You walked up to someone, heart pounding, and said the words. And most of the time, they said no.
Not "no response." Not "left on read." Actual, spoken, in-person no.
It was brutal. And it was the best training I ever got.
Because eventually, someone said yes. And I learned something that took years to fully understand: the rejection wasn't the obstacle. It was the price of admission. You paid it in reps. In volume. In discomfort.
I had girlfriends throughout high school — not because I was special, but because I kept asking. The effort was born out of necessity. There was no other way.
What I'm Not Saying
I'm not saying we had it harder. We didn't have your student debt. We didn't graduate into a financial crisis. We didn't have a pandemic shut down our early careers.
And I'm not saying "just work harder." That's Boomer advice, and it's lazy.
What I'm saying is this:
The skills that saved us — the ability to sit with boredom, to tolerate rejection, to build something from nothing without a playbook — those aren't generational traits. They're human traits. You have them too.
They just got buried.
Buried under algorithms designed to keep you comfortable. Buried under a culture that said "follow your passion" instead of "get useful." Buried under student loans that made risk feel impossible.
But they're still there.
The Practical Part
If you're a Millennial reading this and feeling stuck, here's what I'd offer:
1. Manufacture your own boredom. Put the phone down. Sit with nothing for an hour. See what your brain does when it's not being fed. That's where the ideas live.
2. Collect rejections on purpose. Apply for jobs you think you won't get. Ask for things you think you can't have. The word "no" loses its power when you've heard it enough times.
3. Work for something specific. Not "financial freedom." Not "passive income." Something real. A crappy car. A trip. A number in your account that means you can breathe. Abstraction doesn't motivate. Specifics do.
4. Find the gap and fill it. Stop waiting for someone to hand you the playbook. Look around. See what's missing. Say "sure thing" and figure it out as you go.
5. Understand that discomfort is the raw material. Not the obstacle. The material. The thing you build with. If it feels hard – do it hard, you're probably on the right track.
When It Started to Take Shape
I was 18 when things shifted for me.
I'd graduated high school with a 1.6 GPA. Not because I couldn't do the work — I just didn't see the point. Nobody in my family had money. Nobody talked about careers. We were on food stamps, and that felt like the ceiling.
I got a job at The Price Club stocking shelves for $5 an hour. I figured that was the trajectory — work, pay rent, repeat.
Then I met a girl. Got her pregnant. Had a daughter.
That changed everything.
I looked at this kid and realized I had nothing to offer her. No skills. No credentials. No path. Just a name tag and a time clock.
I didn't have a plan. I had panic. But panic, properly aimed, is fuel.
Back then I was reading Brian Tracy and Tony Robbins — the self-help stuff people mock but that actually works if you do what it says. One piece of advice stuck: ask someone who's done what you want to do.
Sol Price — the founder of Price Club — used to walk every warehouse once a year. When he came through ours, I introduced myself and asked him for his best advice.
He said: "Learn everything you can about money and business."
That was it. Nine words. I didn't fully understand them for another 20 years.
But I started. Enrolled in college while working full-time. Moved from the warehouse floor into audit. Made manager. Got pulled into the Price Club / Costco merger. Spent 12 years there, then jumped to EchoStar. Kept stacking credentials — Six Sigma, LEAN, PMP, Executive MBA.
Eventually landed in the CFO's office. From $5 an hour stocking shelves to the executive floor.
No connections. No inheritance. No special talent. Just a decision, followed by two decades of showing up.
The Scot Free Take
Here's the truth nobody told either of our generations:
"Lost" is a story, not a sentence.
Gen X was written off as slackers with no future. We built careers, families, and lives anyway — not because we were special, but because we didn't have the option to wait for permission. We just started.
You have the same option. It's just harder to see because there's so much noise telling you what you can't do, what's broken, what's unfair.
Some of that noise is true. The system is rigged in a lot of ways. Housing is absurd. Wages have stagnated. I'm not here to tell you it's all in your head.
But I am here to tell you that generations before you have started from worse positions and figured it out. Not because the world was easier — it wasn't — but because they didn't have a choice.
And neither do you. Not really.
You can wait for the world to get fair, or you can start building with the world you've got.
I know which one works.
You ain't lost. You're just early in a longer game than anyone told you about. And the skills you need — the tolerance for boredom, the resilience to rejection, the ability to spot a gap and fill it — those aren't gone.
They're just waiting for you to use them.
— Scot Free
If you're ready to stop feeling lost and start building – I escaped the paycheck to paycheck trap – now I share the Blueprints.
