Managing A Career

Two friends are hiking when a bear comes over the ridge. One of them drops their pack and starts lacing up a pair of running shoes. The other one stares and says, "What are you doing? You can't outrun a bear." And the first one says, "I don't have to outrun the bear. I just have to outrun you." I think most of us have that joke backwards. We spend our careers trying to outrun the bear, and the bea...

When people called Terry Rice lucky, he had an answer: luck is when preparation and opportunity are met with action. In Luck When Preparation and Opportunity Meet Action (MAC-162) we covered the action. Five words, Hey, I like your podcast , said at a free kids' gymnastics class in Brooklyn, turned a chance meeting with Jason Feifer, the editor in chief of Entrepreneur, into a working relationship...

You've written the post. It's good. It's a real lesson from a real project, and you know it would help somebody. Your thumb is over the button, and a second voice shows up that has nothing to do with whether the post is any good: what if my boss sees this? I've spent a run of episodes on public posting. In You Need to Be Posting Publicly (MAC-144) I made the case for why. In What to Post When You...

You have fifteen minutes on the calendar with a vice president who oversees two hundred people. She's been friendly from the first second. She leans forward, smiles, and asks the easiest question in the world: "So, what's your team working on right now?" And you answer it. Of course you do. The vendor migration. The new intake form. The quarter-end reconciliation. About three projects in, you noti...

Five words. Hey, I like your podcast. That's what a man said to a stranger at a free kids' gymnastics class in Brooklyn. A few years later those five words were worth, in his own estimate, hundreds of thousands of dollars. And when people hear that story, almost all of them reach for the same explanation: he got lucky. This week on Managing A Career I want to fix something I've been saying on the...

It's Friday afternoon, and you've just sent the weekly update. Eleven bullet points, every one of them true. Met with the vendor. Reviewed the draft. Followed up on open items. Closed out the quarter-end checklist. Eleven bullets that cost you something like fifty hours. Your manager skims them on the way to another meeting. Your manager's boss never sees them at all. By Monday morning, the most i...

Nobody has ever been written up for doing too much research. That's what makes it such a good place to hide. In the biggest calls a career throws at you — the job, the promotion ask, the pivot you've been circling for two years. Research looks like diligence, and it feels like diligence the whole time. But past a certain point, it stops being research and starts being a well-dressed way of not dec...

It's 11:40 on a Tuesday night, and you are not asleep. You're replaying a sentence. Your skip-level said it around two-fifteen that afternoon, in a meeting with five other people in it: "Let's make sure we're being realistic about that timeline." You've run it back maybe forty times since. Tried it with the emphasis on realistic . Tried it on that . Drafted three replies you're never going to send...

Two people walk out of two different meetings having heard the same sentence: it didn't work . One of them skipped a step in a process the company has run four hundred times. The other tried something the company has never tried. Same sentence, same tone in the room, same quiet adjustment in how each of them gets described in the next talent review. That's the problem underneath this whole piece:...

Two things went on your calendar this quarter. The first was a commitment to someone else. That meeting, you have never moved it once. When it landed on top of your own doctor's appointment, the doctor got rescheduled. The second was an hour you blocked for yourself — the certification, the analysis you keep meaning to start, the conversation you keep meaning to have. You have quietly moved it fou...

here is a specific moment this episode is built around, and you have almost certainly lived it. You are writing up your contribution — for a review, a self-assessment, a conversation you are trying to prepare for. You know what happened. You know it mattered. You get to the word saved — "which saved us about" — and you stop. Because the next word is supposed to be a figure, and you do not have one...

It's four-forty on a Thursday, and a message lands that starts with two words. Quick question. It is not a quick question. It never is. Forty minutes later you've untangled why two teams were working from different numbers, gotten the right person on a call, and the thing that was going to blow up on Monday is now just a thing that got handled on Thursday. Nobody will ever know it was going to blo...

Somewhere in the last ninety days, someone typed your name into a search bar. You weren't job hunting. You hadn't applied for anything, hadn't touched a single profile, hadn't done a thing to invite the attention. You were having an ordinary Tuesday. But somewhere else, in a room you weren't in, a person was about to say your name out loud — for a project, a panel, a role, an introduction — and be...

Agreement is the cheapest thing you will ever get from an audience. A few weeks ago I made the case that you need to be posting publicly — building a searchable body of work outside your company's walls, before the day you actually need it. You Need to Be Posting Publicly (MAC-144) laid out why. What came back, over and over, was people telling me they agreed. Completely. And then posting nothing....

A while back I walked an entire arc, start to finish. Rock to star. How influence accumulates inside an organization, how far it reaches, and exactly where it stops reaching. And I never once told anyone where they were standing on it. That is the unfinished business here. But I want to close it in a way that survives contact with the one thing that wrecks every self-assessment ever written — the...

Picture the room a few seconds after the meeting starts. The projector is still warm from a slide deck someone spent the entire weekend building — right numbers, right format, delivered clean, exactly as promised. Heads nod. And then, ninety seconds later, someone who has said almost nothing so far leans forward and asks one quiet question that turns the meeting everyone thought they were in into...

There is a specific moment that happens in almost every meeting, and if you pay attention you can feel it in your body. Someone is presenting. The room is nodding along. And a question starts forming in the back of your mind — something that doesn't quite add up, a number that seems off, an assumption nobody has said out loud. You glance around the table, and everyone else looks fine with it. So y...

There is a moment in every professional's career — usually a Thursday afternoon, usually too late to fix quietly — when the mistake surfaces. A wrong number in a quarterly summary. A miscommunicated timeline. A judgment call that turned out wrong. And in that moment, the professional makes a second decision that matters far more than the first: whether to move or to freeze. This is the fulcrum tha...

Someone reads something you wrote — an email, a proposal, a post you were a little proud of — and they tell you it sounds like a machine wrote it. Not "this could be tighter." Not "strong draft, a few notes." They say it sounds AI-generated . And every instinct in your body fires the same four words: but I wrote it. That reaction is universal. It is also, without exception, the wrong move. Not bec...

The watercooler was never random. That single line is where this whole argument begins, and it's worth sitting with — because almost everything professionals believe about remote work and lost connection rests on the opposite assumption. The story we tell ourselves is that the office was a place of happy accidents. The best career-building moments happened by chance: the hallway run-in, the coffee...

You left a job once because you were exhausted. Maybe more than once. You were drained, you couldn't recover, Sunday nights felt like dread, and eventually you decided this place is burning me out — so you left. Then, six months or a year later, you found yourself at a different desk, in a different company, with a different manager, and it felt exactly the same. That repetition is the most import...

There's a career trap that rewards you for walking into it. It doesn't announce itself. It builds quietly, one undocumented process at a time, one knowledge-transfer conversation that never happened, one person who came to you instead of figuring it out themselves because it was easier and faster and that's just how things work here. By the time you recognize it, you've been in it for a while. Thi...

The day you find out your role is being eliminated is a terrible day to start building your reputation. So is the morning you finally decide you've earned a promotion — and you realize the only people who can speak to what you've actually done all sit inside the same building you're now trying to leave. I want to talk about something almost nobody does until they're in crisis, which is exactly why...

Picture this. You've just been promoted. You earned it — you were the best at what you did, and everyone knew it. The first few weeks feel like validation. Then, slowly, things start to feel wrong. Not catastrophically wrong. Just off. You're working as hard as you ever have, maybe harder, and somehow getting less done. The decisions that used to feel clean are murky. The problems that used to res...

AI is Eroding the Signals Employers Use to Judge Talent — And Nothing Has Replaced Them There is a problem developing in the professional world that most career advice hasn't caught up to yet. It's not the job-loss story — that one is getting plenty of airtime. It's something quieter, and in a lot of ways more corrosive: the collapse of the signals the entire career ladder was built on. To underst...