So check this out. There was a guy who spent years teaching other people how to build wealth, giving totally solid financial advice. He would watch his clients crush it. But ya know what? The whole time he was quietly drowning. This guy couldn’t afford gas. Literally, searching under his car seats for loose change. In today’s dollars, he was pulling in around $180,000 a year as a financial planner and somehow spending $200,000!
That guy is Joe Saul-Sehy, host of the Stacking Benjamins podcast, and he dropped this story at the 1% Better Conference in a keynote that took place last weekend. And honestly should be required listening for anyone who’s ever said something like,”if I just made a little more money, everything would be fine.”
Spoiler alert: it wouldn’t.

I’ve been thinking about this talk ever since, because so many of the things Joe unpacked are the same traps I see people fall into all the time. And honestly, some of it also hit close to home. So let’s break it down, because there is some stuff here that go way beyond typical financial advice.
The Real Problem Isn’t Your Income
Here’s the thing about Joe’s story that makes it so uncomfortable and yet so relatable at the same time. He wasn’t broke because he didn’t earn enough. He was broke because he had zero financial controls, and he believed with complete conviction that earning more would fix everything.
“If I made $200,000, I’d have spent $230,000,” he said. And that’s not some punchline, that’s a pattern. A pattern so many of us know intimately.
It’s the lie he bought into, and that I see people buy into constantly, is that working harder and making more money is the magic lever. Pull the lever hard enough and everything sorts itself out. The debt suddenly disappears. The stress just melts away. You finally feel like you finally have it together.
But here’s what actually happens. When you have no financial framework and no real understanding of where your money goes or why, a bigger paycheck just means bigger spending. The proportions typically stay the same, right? The anxiety stays the same. You just do it at a totally higher altitude. More money without more intention is just a faster treadmill.
The Embarrassment Trap
Before Joe got into the financial stuff, he told this incredible story about a weekend trip to Chicago he took in his mid-twenties with the woman who would eventually become his wife. He was completely broke, busting ass at three jobs, trying to impress her, and absolutely not telling her any of that.
He booked a awesome jazz club. Nice restaurants. A charming boutique hotel downtown Chicago. All on a f’n prayer and a credit card he wasn’t sure would even go through.
This is wild. We’ve all been there. We don’t know what we don’t know. Well, he didn’t know the minibar cost money. Genuinely did not know. He was cracking open Bud Lights and eating M&Ms like it was a free snack bar, and by checkout, the bill was a disaster.
Standing at the front desk at checkout, with a suitcase packed full of stuff he’d swiped from the fridge that morning, and a line of impatient people behind him. Joe had to look the front desk woman in the eye and say “I had all of it.”
So here’s why Joe tells this story. Because in that moment, facing that embarrassment, his life didn’t end. He survived it. His girlfriend didn’t leave. They laughed about it the whole drive home. And 33 years later, she’s still his wife!
The point of the story isn’t the minibar. The point is that we build failure up in our heads into something catastrophic and something that will ruin us socially, financially, and permanently. But Then when we actually fail, or get embarrassed, or make the dumb decision, it turns out to be survivable. Usually even teaches a lesson.
We stay stuck because we’re terrified of looking stupid. But looking stupid, it turns out, is just the tuition.
Bad Data Is Good Data
One of the most useful ideas I’ve heard in a long time (and we kept saying it over and over at the conference) came from a clip Joe shared from a financial planner named Benjamin Brandt. The idea is to treat your life like a series of science experiments.
If you tried something and it didn’t work? Great. That’s data. Did you hate it? Cross it off. Now you know. Did you tried something and it just clicked? This is also data. Now you know what to chase more of.
We tend to treat failure like a final verdict. Like it means something definitive about who we are as a person, and what we’re capable of. But as it turns out, failures are just experiments that didn’t go the way you hoped. And every scientist will tell you that a failed experiment still teaches you something.
Joe actually lived this. After years in financial planning, inspired by a mentor who quit his job and went to literally climb actual mountains! WTH! Joe decided leave financial planning and to go back to school to become a high school teacher. He thought he loved teaching. He did love teaching. But teaching in a high school? This was not for him. Too much bureaucracy, and too little creative freedom.
A lot of people would call that a failure and use it as evidence that they shouldn’t try anything new at all! But Joe looked at it and said, “Ah-ha! This is good data.” He knew he loved teaching but needed like a different format. So he started a financial blog. The blog became a podcast. The podcast became one of the most celebrated personal finance shows in the country. Kiplinger and Bankrate both eventually called it the best personal finance podcast in America. Whoop Whoop!
None of that happens if he doesn’t take the teaching risk. And none of it happens if he treats that “failed” experiment as a dead end instead of a data point.
Ask Who, Not How
This key takeaway is one that I kinda wanna tattoo on my brain, because it completely changes how we approach getting better at anything.
Most of us, when we’re stuck, we ask. “How do I do this?” We google it. We watch YouTube videos. We buy another book. We consume more and more information trying to figure out the actual mechanics of a thing we don’t know how to do.
Joe says the better question to ask is, “Who do I ask?”
Who already knows this? Who knows me well enough to cut through the AI slop and noise and point me toward exactly what I need? Who can shorthand the learning curve because they understand my situation?
For Joe, when his financial life hit rock bottom, that person was a CPA named Sue. He came clean with her about the full scope of the financial mess he was in. It felt horrible. He was embarrassed. But sitting with her over a few lunch meetings, he suddenly had a payoff plan, a negotiation strategy, and for the first time, a real sense of power over his own finances.
So you see. The same brain that got Joe into the mess couldn’t get him out of it alone. He needed another brain in his corner.
So I started thinking. Right? Where am I just spinning your wheels right now. Financially, professionally, personally. Am I just grinding on the “how” when there’s a “who” who could cut that learning curve in half? This is why mentors matter. This is why community matters. This is why, frankly, surrounding yourself with people who have already solved the problems you’re dealing with is worth more than the cramming or productivity hacks.
Find your who. It’s worth more than any amount of “how.”
The 85% Problem
Joe said something that stuck with me in a way I wasn’t expecting and kinda funny. He called 85% “the bitch.” And I think he’s right.
Here’s what he meant by that. When life is genuinely bad, you change it. When life is great, you lean in. But when life is 85%? You just kind of… keep going. See, it’s not bad enough to leave and not good enough to be truly energized. You’re comfortable enough to stay stuck.
His mentor at work embodied what it looks like to refuse that 85% Life. The guy wrote his resignation email, and said he didn’t love financial planning even though he liked it. He had other mountains to climb. Then he literally climbed Mount Everest and a lot of the world’s major peaks and now runs an adventure travel company. So rad!
That email was the just nudge Joe needed. He looked at his own 85% life and decided he wasn’t willing to stay in it.
So, here’s the question to think about. Where in your life are you just accepting 85%? Where are you staying comfortable enough in something that isn’t bad enough to leave but isn’t close to what you actually want? Just think about that.
Define What You Actually Want First
Joe then walked the audience through an exercise, and it’s one of those things that sounds maybe a little morbid but lands like hard.
Imagine the year before you die. You’re in relatively good health. Things have gone well. Who are you in that version of your life?
We wrote down things like being surrounded by family, staying active and mobile, being engaged in their community, having less stuff and more focus, and of course, not worrying about money.
So then we were to look at your calendar for this week. Like currently. Right now. This week. What are your goals for the year. Now ask yourself why you aren’t already living for, or towards those things? Life life now!
Because here’s what happens when you get clear on that end-of-life vision. Decisions get easier. You know what to say yes to. You know what to cut. The clutter, the obligations, the shiny objects, all of it gets filtered through one clear question of does this actually move me toward that future self or away from it?
For Joe, the answer to that question is what gave him the courage to leave financial planning, to try something new. To try teaching, to start the blog, to keep opening the next door even when he couldn’t see what was behind it.
You don’t have to have a perfect 30-year plan. You just have to know where you’re going well enough to take the next honest step.
The Courage Flywheel
Joe then laid out what he calls the courage flywheel, and it’s simple enough to actually use.
Courage is what gets you to try something. And trying gives you data. Data, whether it’s a win or a loss. (remember bad data is good data) This builds confidence. Confidence then creates commitment. Commitment gives you the courage to open the next door!
Courage leads to confidence, which leads to commitment. Then you do it again.
The key thing he pointed out is that you can’t see the next door until you open the one in front of you. You can’t plan your way to a path you haven’t walked yet. You have to move first, and the path reveals itself.
I know, Man! That kinda sounds terrifying to a lot of people. It also sounds somewhat irresponsible. But think about every meaningful thing you’ve done in your life. Did you have a perfect roadmap before you started? Most likely not. You took one uncertain step, survived it, and then you get to see a little more clearly what was next?
One percent better isn’t about a massive transformation. It’s about opening one door today. And then another one tomorrow.
The Part About Money That Actually Matters
I know what you are thinking. Chris, So where does all of this connect back to Heavy Metal Money and personal finance? Because this isn’t just a motivational talk. There’s real, practical money shit in Joe’s story.
Think of the financial controls piece is the foundation. It doesn’t matter what you earn if you have no system for where it goes. This is budgeting, yes, but more than that it’s intentionality. It’s knowing why you’re spending money, not just how much.
The “who not how” principle applies directly to your finances. If you’re spinning your wheels trying to figure out investing, debt payoff, tax strategy, or retirement planning on your own, the answer isn’t just more YouTube videos. It’s finding the right person who can see your full picture and help you make sense of it.
The vision exercise is arguably the most important financial planning tool most people never use. If you don’t know what you’re building toward, what a life that feels genuinely good actually looks like, you’ll keep chasing income without any idea of when you’ve arrived. You’ll make $180K and spend $200K because “more” doesn’t have a ceiling when it’s not connected to anything real.
The goal isn’t a number in an account. I mean it could be, but the goal is the life you just described when you imagined yourself a year before the end, healthy, happy, surrounded by people you love, doing things that matter to you.
Horns Up
Joe’s talk wasn’t some 30-step financial system. It wasn’t a formula. It was an honest look at the gap between where most of us are and where we actually want to be. And a reminder that the gap closes one imperfect, embarrassing, courageous step at a time.
You’re gonna make mistakes. We all do! You’re gonna open doors that go nowhere. We all have done it! You’re gonna raid the minibar without knowing it costs money and then have to come clean at the checkout counter. lol!
That’s not failure. That’s data.
Get honest about what you actually want from your life. And then start doing those things now to help get you there, not when you hit some income milestone or pay off the last card or finally feel “ready.” You’ll never feel ready. Open the door anyway!
Horns up. \m/ \m/
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