Playing It Safe Has Never Been Riskier

The conventional path is the riskiest bet you can make

You are doing everything you were told. You got the degree, got the job, contribute to the 401(k), save a little on top. On paper, it all looks fine, you are doing what you are supposed to, pursuing the stable job and climbing the ladder.

But when you look around, you start to get discouraged. The cost to just be alive is crazy. Everything you need - a home, food, insurance, utilities, a car - costs more every year. And what you want? A family, an occasional vacation, time with friends? That’s increasingly out of reach too. You start to look around and something doesn’t add up.

Maybe you’ve seen those TikTok videos, often a younger girl in the car, maybe early to mid 20s, visibly distraught, realizing the path is not working.

You’re not having a breakdown on camera, but you may be at the point where you get where she is coming from. That discouragement in the back of your head? That feeling that everything you want is just out of reach, or will take decades longer than it should? That’s the signal.

The question nobody’s asking: What if the path itself is the problem?

The Rules Changed

The “safe” playbook you inherited was built for a different era. The times were different. The workforce was less competitive. Institutions were more accountable. The dollar actually held value.

But the most important difference? The money itself broke. Since 1971, the dollar isn’t backed by gold anymore. The Federal Reserve can create trillions at will, and the government runs on unsustainable debt. More dollars get created every year, which means everything gets more expensive - not because you’re failing, but because the currency is failing.

Everything is more expensive, both consumable goods like food and whatever else and also assets like a home or a share of the S&P500. The goalposts move every year, and nobody told you the game changed.

The “safe” path you’re on now exposes you to systemic risks that only grow every year.

The Illusion of Safety

Here’s the truth: you’re already taking massive risk. You just don’t see it.

You’re working a job that gives you a 3% annual raise while real inflation runs 5-10% each year. Every few years you might get a promotion 10-15%, maybe 20% if you’re lucky. Meanwhile, food prices and house prices are climbing higher.

The math doesn’t work. You know it deep down, but it feels “safe” because it’s what you think you are supposed to do. You see it has worked for your parents, grandparents, or others in your life, and you think it will work for you.

But the path you’re on is within a system itself that is unsustainable. The US Government is now $38 trillion in debt, which is only growing.

Bonds, savings accounts, stable employment, all denominated in and dependent on a monetary system that’s structurally broken. You’re not building on solid ground. You’re building on quicksand.

Even if your 401(k) grows 15% by investing in the S&P500 and you feel like you’re winning, when you account for inflation, your growth may be closer to 5%. And the bigger problem is that your wages aren’t keeping pace with asset prices, meaning if homes and stocks are going up, but your wages only increase by 3% most years, you can afford less and less over time.

Your net worth might look like its growing on paper, but your purchasing power is eroding. The S&P might be up, but you’re still losing ground in real terms.

And then there’s AI. Marc Andreessen calls it the biggest technical revolution of his career, bigger than the internet.

In October 2025, over 100,000 jobs were cut, the most in 22 years. The labor market is softening. The median new hire is now 42 years old. Entry-level positions are vanishing. Junior roles are being automated.

The ladder you’re trying to climb is disappearing beneath you. The disruption isn’t coming, it’s here and it is accelerating. The “stable” path is getting exponentially riskier by the year.

The Liberation

You’re already taking risk, so instead take intentional risk.

You’re on the conventional path right now, and the conventional path doesn’t work anymore. So if you’re going to take risk anyway - and you are - take it toward something that actually works. Take control instead of hoping the broken system carries you through.

Stop dooming. Start building.

Every generation has its challenges. Your parents had theirs. Your grandparents had theirs. Back in 2020, I found myself unsure of what the future held, discouraged in the wake of all the chaos around COVID, lockdowns, etc.

My dad told me: “Jackson, every generation has their challenges.” That stuck with me. Because it’s true. Our situation is not unique and our challenges are arguably easier than previous generations.

That said, the dooming culture is getting worse. Doomscrolling and gambling on prediction markets won’t save you. The future belongs to people who lean in, learn, and build, not people who check out.

Here’s what I mean by calculated risk:

Learn emerging technologies. You have a supercomputer in your pocket and AI to turbocharge it. Think about this: when the internet was emerging, you had to learn it with books and trial and error. The internet didn’t exist yet, so you couldn’t look things up on the internet. Now? You have infinite knowledge at your fingertips. Find what excites you and start learning. Most people won’t do this. That’s your edge.

Pursue your calling. You’re already on a path that isn’t working. Stop and reflect. Pray on it, meditate on it, take long walks - whatever works for you. Figure out where your mind drifts to, what interests you, and start pursuing it, even a little each day. A little each day compounds. You’ll get closer to where you need to be faster than you think. Your parents, friends, whoever may question you, but you need to listen to yourself. If I’d listened to other people’s advice, I’d still be on the “safe path.” You have to trust yourself. That discomfort of going against the grain? That’s not a warning sign. That’s the signal you’re on the right track.

Save in assets that can’t be diluted. If you’re saving in dollars, you’re destroying your wealth. Store your wealth in assets that can’t be debased and that grow against the real rate of inflation - the one you live every day in groceries, utilities, insurance, and housing costs. Personally, I use Bitcoin as my main savings account, with investments still in equities and precious metals.

Stay ahead of the curve. Most people will doom. That’s the reality. You don’t have to be most people. If you spend time each day to better yourself, learn new skills, pursue your interests, you’ll be in a totally different place before you know it.

You don’t know exactly what the future holds. Nobody does. But you know there’s a path that works and you are starting to realize it’s not the conventional one.

The Best Time to Be Alive

This is still the best time to be alive. Not in spite of the disruption, but because of it.

Everything is changing. You have infinite leverage in your pocket if you can figure it out. The people who see this early and move will build the future.

Yeah, it’s going to take effort and “risky” choices. It’s going to require lots of time and sacrifice. Picking up your bootstraps and staying ahead of the curve. But that’s always been true for people who actually win. The difference now is the upside is bigger and the gap with those who don’t is wider.

You’re already on the risky path. You just don’t realize it yet. The conventional playbook is the high-risk bet. Don’t doom. Take control. Take agency. Build something real. And if I can be helpful along the way, reach out.

If this resonated with you, share it with someone on the conventional path who needs to hear it. I send one of these each week, so make sure to get on the list. And if you reply or comment below with what you thought about this piece, that helps me keep improving.

Signals Worth Your Time

Ideas, conversations, and work that shaped how I’m thinking this week.

1. 1. The Great Rebalancing by Jeroen Blokland
   Started this book, which explains the underpinnings of our debt-driven global economy and why scarce assets have become the ultimate investment. Blokland is a portfolio manager with 20+ years of experience who no longer owns bonds - not personally, not for clients. Recorded a podcast to discuss. Link here.

   2. Claude Code
   Claude Code has been all over my feed, so I’ve been spending more time in it. Still early, but I’m finding real efficiencies in automating work. Worth exploring if you’re looking to stay ahead of the curve.

   3. Bitcoin’s Silent IPO: Why This Consolidation Isn’t What You Think
   For anyone confused by Bitcoin’s price action, Jordi Visser’s piece from November explains the dynamics well. I continue to have a positive outlook for 2026 - more Wall Street firms are enabling access, significant rate cuts are expected, and we’re in an election year that may see major stimulus.