If you love this content (please share it), but also check out my Podcast & connect with me on YouTube / Twitter.
We turn your favorite newsletters into podcasts at 10minmindset.org
Sponsored by MyFitnessPal: I've been using MyFitnessPal for years and it's one of the most useful apps on my phone. You can optimize your sleep, your schedule, your workflow, but if your nutrition is off, none of it performs the way it should. MFP is how I keep that piece dialed in. I log a meal in about 10 seconds, the database has everything in it, and it connects with whatever wearables or health apps you're already using. If you want one tool that quietly makes everything else work better, this is the one I'd start with. Go to podcast.myfitnesspal.com and use code SCOTT for 15% off Premium.
The gap between the path that works for you and the path you chose because it sounds better when someone asks what you do.
You’re paying a tax you’ve never heard of. It doesn’t show up on any balance sheet and no accountant will flag it.
I call it the Prestige Tax.
It’s the premium you pay, in years, in money, in energy, to stay on a path that sounds impressive instead of a path that works. And almost every ambitious person I know is paying it.
You didn’t choose your ambition. You absorbed it.
Think about how you ended up where you are. The career. The business model. The version of success you’re chasing.
Did you sit down, look at every option available to you, and choose the one that fit best? Or did you look at the people you admired, notice what they were doing, and follow a version of their path?
Be honest.
You absorb your ambitions from your environment the way you absorb an accent. You scroll past enough “quit your 9-to-5 and build a startup” content, and eventually that becomes the only version of ambition you can see. You’re living inside someone else’s definition of impressive and you picked it up so gradually that it feels like your own.
The path you’re on right now probably isn’t the result of clear thinking. It’s what you were exposed to. A specific narrative about what success looks like, and you adopted it before you realized the menu had other pages.
You confused difficulty with value
Somewhere along the way, you decided that the harder something is, the more valuable it must be. If you’re struggling, you must be doing something important. If it feels easy, you must be cutting corners.
A surgeon who performs a routine procedure that saves your life created enormous value. The fact that she’s done it a thousand times and it felt easy doesn’t reduce what it’s worth. You’d actually prefer a pilot who follows the proven system over one who improvises. But in business, we’ve built an entire culture around rejecting proven systems and figuring it out yourself. We celebrate the founder sleeping on the office floor as if suffering is a prerequisite for building something that matters.
That’s the version of the story that gets engagement. It’s not the version that builds wealth.
The menu you’ve never seen
I’ve recorded over a thousand podcast episodes with founders, executives, investors, and operators. And one thing keeps coming up.
The ones who built real, lasting wealth almost always did something that surprised me. At some point, they chose a path that nobody around them was talking about. A path that didn’t match the dominant narrative. Some bought businesses instead of building them from scratch. Others invested in industries nobody finds glamorous: property services, B2B maintenance, logistics.
I had Jon Ostenson on the show recently. Jon runs FranBridge Consulting and wrote Non-Food Franchising. Former Accenture consultant, former VP at Carter’s overseeing $350 million in annual revenue, former franchise president. He told me something that stuck: 80 to 90 percent of his clients end up investing in industries they didn’t know existed before their first conversation with him. They walked in thinking business ownership meant restaurants or tech startups because those are the only options the culture puts in front of you. (Full conversation here.)
The menu of options for building wealth and freedom is enormous. You’ve only seen the first page because that page has the best marketing.
Where the tax shows up
Try this. Next time you’re at dinner with friends, tell them you’re buying a home services franchise in a mid-tier city. Watch their faces.
Now imagine telling the same group you’re launching an AI startup.
One path might generate better returns with lower risk. The other generates better dinner conversation. That’s the Prestige Tax. It’s the premium you pay to stay on a path that other people understand and admire, even when a less impressive path would get you where you want to go faster and with less damage.
I’ve watched people turn down opportunities that would have made them real money because they couldn’t figure out how to describe them on LinkedIn. I’ve watched people spend five years building something from scratch that they could have owned in six months because “I built this from zero” carries more weight at a conference than “I focused on growth instead of reinventing the wheel.”
The tax doesn’t look like a tax. It looks like ambition. And that’s why it’s so expensive. You can’t fix a problem you think is a virtue.
Two questions to find your tax
You can figure out your own Prestige Tax right now.
First: if nobody could ever see, judge, or comment on your career, what would you do differently? If your LinkedIn went dark tomorrow and you never attended another networking event, would you still be on this path?
Second: what opportunities have you dismissed without serious analysis because they didn’t fit your image of what success should look like?
The gap between those answers and your current reality is your Prestige Tax. Measured in years, money, and the particular kind of exhaustion that comes from optimizing for the wrong audience.
The guests I’ve interviewed who seem the most free share one thing. At some point, they stopped choosing the path that sounded best and started choosing the path that worked best. Even when their friends didn’t get it. Even when they had to sit through a few dinners where their path didn’t generate the same excitement as someone else’s startup story.
You can optimize for prestige or you can optimize for freedom. Sometimes they overlap. When they don’t, which one you choose tells you everything about what you actually value.
You’ve been paying the Prestige Tax your entire career. You just didn’t know it had a name.
Follow Jon Ostenson: Twitter/X | LinkedIn | FranBridge Consulting | Non-Food Franchising
Thank you for reading,
Scott