What Sailing With a Cat Can Teach You About the American Economy
Plus How the Federal Reserve Stole your Future
We’re not just behind on rent. We’re 13 years behind on wealth.
Because your salary didn’t inflate with the economy, but everything else did.
But I’ll get to that in a little bit…..
A lot of you really loved the last Substack on tech employees burning out, some to the point of flocking to unexpected career switches like hobby farming or becoming baristas.
Although, I got some pushback on LinkedIn (not surprised as people love to complain over there, lmao). Some folks said the post came off as privileged.
Let’s clear the air: I left my tech job while I was in debt. My job didn’t have any salary raises available and I’d already been there a year and a half. At the same time, Denver was getting annihilated by inflation. The cost of living skyrocketed. So while my paycheck was stagnant, I had just started to make some money on my own from social media. I decided to take the leap with no emergency fund. No safety net at all. Which, to be honest, was the story of my entire upbringing. I don’t come from money or connections. Just pure delusional confidence.
I wound up turning out more than fine.
But I know that’s hard for some people to process. Because if they let themselves admit that their go-to excuse—“easy for them, they’re more privileged than me”—might not be true, then they have to face something else. That the only thing between them and what they want is the story they’re telling themselves to avoid doing it.
So let’s talk about an even wilder story of someone with no financial privilege who also quit his job.
Sailing Away From Jobs
Meet Oliver Widger, also known on TikTok as saling_with_phoenix
He’s a new TikTok star documenting his sailing voyage with his cat, Phoenix. He left his job with $10K in debt, liquidated his 401K, and taught himself how to sail by watching YouTube videos!
He’s made a splash in the media; literally and figuratively. He’s had many articles written about him, got a personal welcome from the mayor of Hawaii when he docked there, and yes, you can track his location in real time.
Here’s my take: I approve.
But let’s get this out of the way, he’s now making bank and he is a content creator/influencer. He found an interesting niche: sailing and unemployument, started making content about this nich, and he got really good at story telling. Across his TikTok, Instagram, and Youtube he has 3.4 million followers.
His TikTok views are solid, which means the creator fund is paying. Same with his YouTube. He’s selling merch, linking his Venmo, and building a community of loyal fans who will probably fund whatever he does next like podcasts, a Substack, brand deals, a book, speaking gigs. He’s no longer some broke dude on a boat. He’s building a business.
The media still treats these stories like some “poor kid throwing away his career” situation. Meanwhile, he’s making five figures a month. And it’s not a step down. If he plays his financial cards right, it’s a glow-up.
And what I lot of people don’t understand is even if his account fails, he gained so many skills through his journey growing this account that these skills will transfer into something else amazing.
He’s getting paid to exist. That’s the wealth code social media can unlock. My goal here isn’t to pitch you on becoming a creator. This is a reminder that there’s joy here. That’s why people like me don’t go back. That’s why we’re okay with being cringe online and letting strangers perceive us.
Jobs will always be there. He can go back if he wants. The fear of career gaps is culty, honestly. If you didn’t know, I was in a cult briefly. They called the desire to leave “the drift.” They didn’t stop you from leaving, they just warned that the drift would get you. That you’d slowly lose your spark and fall behind.
Speaking in my own experience, I have been offered several jobs this year. I do not have a resume handy nor actively apply to jobs. These positions include:
Director of Content at an HR start up (they also offered to buy my business)
Head of Marketing at a very large social media platform you all use (they just emailed me this morning)
Digital marketing companies regularly ask me to consult
This is all from creating something that adds value and shows that I can execute on something. While I normally politely decline, it is always a huge compliment. He will have his own opportunities like this, if not better. So if his account flops one day, who cares. Your organization can get laid off tomorrow. That doesn’t mean you don’t have skills to leverage for a new opportunity later.
Jobs come and go. And I’m sure since you all are similar to me, you understand that. Every time you have no idea what to do next, the second you relax and remember your worth, the opportunities are flowing.
So the “you’re just throwing everything away when you leave corporate and start creating content” trope is manipulation. There is no “drift.” There’s no version of you that you’re ruining or missing out on by choosing an unconventional path. Whether that’s monetizing your weirdest interests or taking a year off to just chill. You’re not falling behind.
And calling this stuff “privileged” misses the point. Everything is privileged. At the same time, there’s always someone who will have something you want but don’t have yet. This guy sold his retirement fund to do this. That’s a good indicator that he didn’t have a safety net. And honestly, money has been worthless for a while. I think we’re finally starting to feel that in how we assign meaning to our lives.
Existential Dread from 2020
Here’s a little thought experiment.
If you had a crumpled $1 bill in your pocket, you probably wouldn’t care much about it. You might forget it’s there, wash your pants with it inside, or drop it between the driver seat and armrest and never look back.
But if you had a $100 bill? You’d know exactly where it is. You’d keep it safe.
That’s what I see happening in our economy right now.
When money is cheap to borrow, inflation is out of control, and your paycheck doesn’t reflect any of that, you start asking questions. Like:
Why am I working this hard?
Why are we building dumb companies that don’t improve the world?
What even is Airbnb? They don’t own anything. They just arbitraged housing and somehow became worth $100 billion.
My take? When money loses its value, so does the motivation to chase it. That’s what’s happening now. And it’s why so many of us feel weirdly aimless. Because 40% of the US money supply was printed in 2020. That’s not a conspiracy. That’s a fact. And it changed everything.
We all felt the short-term impact. But let me show you how this will affect your long-term ability to build wealth, not just your salary.
Because your wages didn’t rise with the money supply, you missed the biggest wealth expansion in modern history. Stocks soared. Housing prices exploded. Groceries, healthcare, everything inflated. Meanwhile, your salary crawled up by 3% a year, if that.
Over time, that compounds into a massive gap. Just from the changes since 2020, the average salaried worker is now 13 years behind in wealth creation. That’s not 13 years to get rich. That’s 13 years just to break even with where you’d be if the economy hadn’t been rigged.
Here’s a breakdown:
Scenario 1: Normal salaried worker
Starts at $68,000 in 2020
Gets 3.5% raises annually
Saves 10% of income
Invests savings at 7% market return
→ Ends up with $340,123 after 20 years
Scenario 2: Worker whose salary tracked asset inflation
Starts at $68,000
Gets 20% raises for the first 2 years
Then 7% raises annually
Same 10% savings and 7% returns
→ Ends up with $620,443 after 20 years
Wealth gap after 20 years = $280,320
This is what happens when your wages don’t keep up. And to catch up?
Scenario 1 would have to work 13 more years—saving and investing the whole time—just to reach the same outcome.
So yeah, sorry for the econ detour, but this matters. This is why so many people feel stuck and tired and vaguely hopeless. It’s not laziness. It’s math.
How are we supposed to get hyped about climbing the ladder at work when we’re 13 years behind because of political incompetence from 2020 to 2022?
Thirteen years is not a minor delay. That’s the difference between:
Renting forever vs owning a home
Working until 70 vs retiring early
Surviving vs building generational wealth
And the media won’t talk about it. They’d rather churn out hot takes on Tesla or tell you to be mad about whatever’s trending this week.
In reality, he lost 13 years of progress. So yeah, some of us are saying screw it. Let’s sail. Let’s film it. Let’s see what happens.
Oliver on a sailboat isn’t irresponsible. He’s what it looks like when someone realizes their paycheck is just a bunch of crinkled $1 bills now. And decides to spend his time doing something that actually makes him feel alive.
The Take Aways
The new dream job is no job. Just vibes and Wi-Fi.
Cringe is the currency of freedom.
13 years behind. No wonder we feel exhausted.