You’re looking at me this week because the rest of the crew got squeamish about answering questions on perception. Jeff would’ve turned it into a therapy session. Marcus would’ve given you a twelve-point framework. Maya would’ve written poetry about authenticity. And Riley? Riley would’ve told you perception doesn’t matter, which is exactly what someone says when they’ve never had to manage it.
I live in the space between who people think I am and who I actually am. That gap? That’s where the work happens. So yeah, I’m taking these questions. Let’s talk about what it actually costs to control how you’re seen.
Question One: The Image Tax
Reader asks: “I work in tech sales and everyone at my company goes hard on the ‘work hard play hard’ thing. Expensive dinners, bottle service, the whole performance. I can’t really afford it but I also can’t afford to be the guy who doesn’t show up. How do you keep up the image without going broke?”
You’re paying what I call the image tax. It’s real, it’s expensive, and pretending it doesn’t exist won’t make your career easier.
Here’s what nobody tells you: the trick isn’t keeping up. The trick is being selective about which nights you show up for. I don’t go to everything. I go to the nights that matter, and when I’m there, I make sure people remember I was there. One good night where you’re fully present beats five nights where you’re nursing the same drink and checking your phone.
When I do show, I’m in the suit. I’m buying a round for the right people. I’m the one who knows the bartender’s name and gets everyone moved to the better table. That costs money, yes. But it costs less than showing up to everything and doing it halfway.
The other part? I’m honest about the nights I skip. “I’m tapped this week” works better than a fake excuse. People respect the honesty more than you think. Marcus would tell you to budget for this like any other business expense, and he’s not wrong. But I’ll add this: budget for impact, not frequency.
And look, if your company culture requires you to spend money you don’t have just to be considered a team player, that’s not a culture problem. That’s a you-picked-the-wrong-company problem. The image tax should open doors, not drain your account to stay in a room that doesn’t actually value you.
Question Two: The Authenticity Trap
Reader asks: “Everyone’s always saying ‘just be yourself’ but that’s bullshit, right? The version of me that gets ahead isn’t the real me. It’s the version that laughs at unfunny jokes and pretends to care about golf. Am I supposed to feel bad about that?”
No. You’re not supposed to feel bad about it. You’re supposed to feel something about it, though.
The “just be yourself” crowd—and Maya would be leading that parade—acts like there’s some pure, unfiltered version of you that should work everywhere. That’s not how the world works. We all code-switch. We all adjust. The person I am at a client dinner isn’t the same person I am at 3am when the night’s actually gotten interesting. That’s not fake. That’s called reading the room.
But here’s the part that costs you: if the gap between performance-you and actual-you gets too wide, you’ll wake up one day and realize you’ve built a whole life for someone who doesn’t exist. I’ve watched it happen. Guy spends ten years pretending to give a shit about things he hates, makes a fortune, buys the house, gets the title. Then he’s sitting in that house wondering why none of it feels like his.
The real question isn’t whether you should perform. It’s whether the performance is moving you toward something you actually want, or just toward what you think you’re supposed to want.
I fake caring about golf. I don’t fake caring about the people I’m playing golf with. That’s the line. If you’re performing interests, fine. If you’re performing values, you’re going to pay for that in ways money can’t fix.
Riley would tell you this is exactly why she doesn’t play the game, and good for her. But she pays a different price—she gets less access, fewer opportunities, more friction. That’s her tradeoff. You don’t get to make no tradeoff. You just get to pick which one you’re making.
Question Three: The Visibility Problem
Reader asks: “My boss keeps telling me I need to be more visible—speak up in meetings, network more, ‘put myself out there.’ But I do good work. Why isn’t that enough? This feels like extrovert propaganda.”
Jeff would tell you this one. He’d say your boss is asking you to be someone you’re not, and that you should find an environment that values your natural strengths. He’d make it sound very reasonable and very supportive.
I’m going to tell you something different: your boss is right.
Good work that nobody sees is a hobby. I don’t make the rules. You want the work to speak for itself, but work doesn’t speak. You speak. And if you’re not speaking, someone else is speaking for you, and they’re probably getting it wrong.
Here’s what visibility actually is: it’s making sure the people who make decisions about your career know what you’re doing and why it matters. That’s it. It’s not about being loud. It’s not about being fake-extroverted. It’s about making your work legible to the people who control your opportunities.
You don’t have to work the room at every happy hour. But you do have to make sure your boss’s boss knows your name and can list two things you’re good at. You don’t have to speak in every meeting. But when you speak, it better be worth listening to.
The price of invisibility is that you get overlooked. Not because you’re not good. Because humans are bad at valuing what they can’t see. Marcus knows this—that’s why he tracks everything, makes sure his results are visible and quantified. He doesn’t wait for people to notice. He makes them notice.
You can call it extrovert propaganda if you want. Or you can call it the actual terms of employment in a world where perception drives decisions. Your call. But if you’re choosing invisibility, own what that choice costs you.