Remember when they told you to be careful? Don’t rock the boat. Don’t challenge the wrong person. Don’t take that risky project. One wrong move and you’re done, buddy. Toast. Blackballed. Your career over before it started.
Well, congratulations. You listened. You played it safe. You meticulously avoided every potential landmine, navigated every political minefield with the precision of a bomb disposal expert, and kept your head down for years. And you know what you got for it? A 3% raise and a promotion to Senior Individual Contributor IV, Level 2, Tier B.
Meanwhile, Silicon Valley’s finest are out here failing upwards like it’s an Olympic sport they invented.
You know who I’m talking about. The guy who burned through $400 million on an office-sharing company that was just subletting with extra steps and a beer tap. The executive who shipped a product so broken it became a verb for failure. The founder who raised nine rounds of funding for a company that never actually figured out how to make money before selling it to some other sucker for “future potential.”
These people don’t have careers. They have highlight reels. They don’t make “career limiting moves” – they make “bold bets that didn’t quite pan out but taught us valuable lessons about the market.” When they get fired, they don’t update their LinkedIn status to “seeking opportunities.” They announce they’re “taking time to explore the next frontier” and immediately get ten offers to join boards and three podcast invitations.
You know what happens when you or I screw up? We get a talking-to from HR. A note in our file. A quiet suggestion that maybe we’re “not the right culture fit” anymore. We don’t get to write a Medium post about our “journey through failure” that gets 50,000 claps. We don’t get invited to speak at conferences about “resilience” and “pivoting.”
The rest of us are playing chess while they’re playing Calvinball, except they’re also writing the rules and we just found out the board was always on fire anyway.
You missed one deadline? Career limiting. You pushed back on a bad idea from someone two levels up? Career limiting. You refused to put your name on something you knew was wrong? Definitely career limiting.
But launch a cryptocurrency that immediately tanked and took a bunch of retail investors’ money with it? That’s just “being early to an emerging space.” Get caught massively overstating your product’s capabilities to investors? That’s “evangelical product vision.” Burn through your entire runway in eighteen months with nothing to show for it? That’s “learning what doesn’t work.”
The truth is, there are two completely different rule books. There’s the one they gave us – the one about being a “team player” and “managing stakeholder expectations” and “demonstrating consistent delivery.” That one’s real. It applies to you. Follow it carefully. Your annual review depends on it.
And then there’s the one for people who’ve already made it into the club. That one’s more like guidelines. Suggestions. A vibe. And the main rule is: if you’re already in, you’re probably staying in. Your network is your net worth, and your failures are just proof you’re willing to take risks.
You know what’s really wild? We all know it’s a scam, and we still play by the rules. We still nervously laugh at our boss’s bad jokes. We still say “let me circle back on that” instead of “that’s a terrible idea.” We still work weekends to hit arbitrary deadlines while watching people who couldn’t code their way out of a paper bag raise Series C funding for an app that’s basically just email with AI slapped on it.
So here’s to all of us who still believe in career limiting moves. Who carefully craft our LinkedIn profiles to hide the gaps. Who practice our elevator pitches. Who actually try to deliver value instead of just talking about disruption and synergy.
We’ll be fine. We’ll hit that median, maybe break above it if we’re lucky. We’ll get our cost-of-living adjustments and our occasional promotions. We’ll be employable.
And they’ll be on their third failed unicorn, sitting on four boards, and somehow still richer than we’ll ever be.
But at least we’ll have our dignity. And our complete lack of career limiting moves on our permanent record.
That’s worth something, right?
…Right?