For years, I could tell you exactly how it felt to have the Chairman of the largest music company in the world wave us off dismissively. The preparation. The nerves. The moment I realized he was done listening. Was I naive to think I belonged in the room anyway? Yes.

Was I still crushed by that wave of the hand? Yes.

I even made myself a promise: if I ever sat on the other side of that desk, I would handle it differently.

Then Cassandra brought me something I didn’t understand, and I did essentially the same damn thing.

Apparently, remembering how someone made you feel doesn’t automatically change how you treat people when you get their job.

A few things I see more clearly now:

My ambition was doing some of the planning. We wanted the company to understand what was coming. We also wanted the chairman to see how smart we were. Those two desires got mixed together, and we chose our audience accordingly.

We rehearsed the words more carefully than we considered the decision. We knew who would speak and when. We were much less clear about what, specifically, we wanted someone to do after listening.

His success helped explain his reaction. The business he understood was working beautifully. We were asking him to take seriously something we couldn’t fully explain, while he had years of results supporting his view.

Being dismissed made me quieter. That part matters if you’re the boss. You may think you’ve finished one conversation. The person across from you may decide against bringing you the next one.

What I’d do differently:

Before pitching: find someone who understands the issue, has credibility with the decision-maker, and can help define a useful next step.

Before dismissing: ask one more question. Or at least take a beat. Especially when the person bringing the idea has already earned my respect.

The question I’m left with:
Who gets the version of me I once promised I’d never become?

It feels good to be the person who can sort things out.

Especially when you’re young. Somebody hands you a problem, you figure it out, and people start trusting you with more. That can be how you build a career. It can also be how you end up being the mule. Another word for mule is Donkey.

I once put forty thousand dollars of my own money into a company to make payroll after my “partner” emptied the account so he could go have a ‘big weekend’. He paid me back. A few months later, he asked me to do it again.

I had treated the first time as an emergency. By the second time, he seemed to regard me as the arrangement. Also known as the sucker.

That’s the part I’d pay attention to. When you get everyone through a crisis, it can look as though the problem has been solved. Payroll goes out. The angry phone call ends. Everybody gets back to work. But what changed that would keep it from happening again?

If the answer is nothing, your ability to cope may be the only thing holding the arrangement together. Ask yourself: Are you solving problems or are you setting precedents you might regret down the road?

And you can be proud of solving problems. I understand. I thought being able to handle things meant I was getting good at the job. Sometimes I was. Other times, I was getting good at making somebody else’s failure less inconvenient for them.

You don’t have to decide the person is a villain before you notice that.

The music manager who left me alone in a different crisis was somebody I respected, and still do. I felt very differently about the “partner” who kept taking the money. But in both cases, I needed help that I wasn’t getting. Their other qualities didn’t change that.

Ask what happens after the emergency

There’s a difference between learning to handle a hard situation and being left alone with one. Somebody can give you responsibility and still stay available. They can let you make the call, help you prepare, and step in when it goes beyond what you can decide. That’s how I’d want a junior person to learn.

When you’re the junior person, though, it can be hard to tell which situation you’re in. You’re busy trying to prove you can do it. You may not want to ask whether you should be doing all of it.

That’s one reason your boss shouldn’t be your only source of advice. They have a stake in keeping the work moving. A good mentor has room to ask what this arrangement is doing to you.

Find somebody experienced who isn’t depending on you to make the problem disappear. Tell them what happened, what you were asked to do, and what you were actually able to decide. Ask, “Does this sound like a reasonable thing to keep expecting of me?”

Then get specific about the next time. Who will be available? Who can make the decision? What help can you offer, and where does that help stop?

Saying no can have a cost. My partner found the money when I refused the second time, but our relationship declined from there. I’m not going to pretend a boundary makes everybody happy. It did mean that particular solution no longer came out of my bank account.

Before you volunteer to fix the next crisis, ask yourself one question.

Am I helping with an exception, or agreeing to become ‘Plan A’?

Have you ever been so good at helping that people stopped asking whether it was your responsibility?

I knew my High School Best Friend was right. That was the embarrassing part.

When he told me I’d stopped calling, and that I had ‘sold out’ my high school friends, I didn’t need time to think about it. Even though I was having a crazy rocket ride career-wise, I knew I was ignoring my friends. So, I reached out, we started talking again, and we made dinner plans. Then an invitation to Sinatra’s birthday came along for the same night, and I canceled on my friend.

I understood the problem perfectly. My next decision was still the same.

That’s easy to miss when you’re trying to repair a friendship. You feel bad. You have the conversation. You make a plan. There’s some relief in that, and you can mistake the relief for having fixed something.

But the other person still has to find out whether you’re going to show up.

I think I was counting on our history to do work I wasn’t doing anymore. We’d been close since high school. His mother had been like a second mother to me. Surely a friendship like that could survive one more change of plans.

Except he wasn’t living through one change of plans. He was living through the whole pattern. I was judging my latest excuse. He had all the earlier ones to consider.

And this was a hell of an excuse. Sinatra. I went. Don Rickles insulted my hair, and it made my month. I’m not going to pretend the party was disappointing just to make the lesson easier.

The Sinatra thing was a great night. I still wish I’d kept the dinner.

The dinner has to be allowed to win

There will always be something you can make a case for. A work thing. An invitation you’re afraid you won’t get again. You don’t need my job, or Sinatra, to keep moving the same people to next week.

And sometimes you really do have to cancel. People understand that. But if a friendship matters, there have to be occasions when you turn down the other thing. Even when it’s good. Even when keeping your word costs you something you wanted.

Otherwise, what have you actually promised?

The people who knew you before your career took off remember a version of you that your new world may never see. You can make wonderful friends at work. I did. But being welcomed into a room doesn’t take care of the people you’ve stopped calling.

If somebody has already told you they miss you, take that seriously. Look at the last few plans you made with them. How many did you keep? How many became “soon”?

Pick one you can keep. Make it specific. And before the next invitation arrives, decide that this time the dinner stays on the calendar.

You can’t require somebody to feel close to you again because you’ve finally made an effort. I didn’t get those relationships back the way they were. But you can stop asking them to trust an intention and give them an evening you actually show up for.

I knew he was right. What I needed to learn was how to let that change my next decision.

There is a strange punishment that comes with being good at solving problems: eventually, people stop bringing you problems and start giving you ownership of them. Regardless of where the problem came from.

When you’re starting out, this feels great. You become the person who can handle things. The boss trusts you. Coworkers call you when something goes sideways. You get access, responsibility and probably a little ego boost from being the one who can walk into a mess and walk out with a solution.

Then things shift.

You stop asking whether the problem is actually yours. And people begin to take you and your skills for granted.

I learned this in a fairly spectacular way when I rented a car in my own name for someone who had no business driving it. At the time, it didn’t feel like I was making some enormous ethical or professional decision. It felt like Tuesday. There was a problem. I was the problem solver. So I solved it.

A few hours later, I was sitting behind the locked doors of a police station while a detective looked at my driver’s license and asked why my name was on the rental agreement.

There is an age old adage: The ‘Curse of Competence’. I learned about that the hard way and in this case, it nearly ended in me getting criminal charges.

If you solve enough emergencies, you can start confusing capability with obligation. I can fix this becomes I should fix this. Then I should fix this becomes I’m responsible if this isn’t fixed. Even if I had nothing to do with creating the problem.

That progression is how good employees end up carrying risks that properly belong to the company, the boss, the client or the person who created the mess in the first place.

And there is another trap. When your improvised solutions keep working, you start believing the improvisation itself is smart. You forget how much luck was involved. We had escaped so many ridiculous situations that I started to think we were bulletproof. In reality, we had just been lucky enough not to hit the wall yet.

The useful question isn’t only, “Can I solve this?”

It’s, “What am I personally agreeing to own if I do?”

That might mean your name on a contract. It might mean promising a deadline you don’t control. It might mean covering for somebody repeatedly until their job quietly becomes yours. It might simply mean teaching everyone around you that whenever they create a disaster, you will absorb it.

Sometimes the most professional answer is not a clever solution. It’s a boring boundary.

In my case: “Take the limo or leave it.”

He would have been furious. I would have had an unpleasant ten minutes. Then everybody would have moved on.

Instead, I avoided ten minutes of conflict and bought myself an hour and a half wondering whether I was about to become an orange jumpsuit guy.

That was a terrible trade.

Being dependable is valuable. Being endlessly available for other people’s consequences is not the same thing.

The best fixers eventually learn one last skill: when to say NO.

That’s the part of the story I don’t want to lose. He forgot a meet and greet with the DEA at a spectacularly bad moment. His character was impeccable. Both things were true.

When somebody lets us down, it’s tempting to go back and reconsider the whole person. Were they ever any good? Was I wrong about them? Sometimes you do need to reconsider. But sometimes a good person has a weakness you already knew about, and you stopped accounting for it.

We knew this guy wasn’t great with details. We were excited to get on with the evening, and for a few minutes we acted as though he was.

That’s worth looking at in your own life. Think of somebody you trust. Now finish the sentence: “I trust them to…”

You might trust someone to tell you an uncomfortable truth. You might trust them to handle an angry client. That doesn’t automatically mean you should trust them to remember a deadline without writing it down.

It’s unfair to expect somebody’s good intentions to cover a weakness you both know is there. And it doesn’t help the relationship when you quietly cover for it, get tired of doing that, and eventually blow up.

So talk about the actual job.

“Walk me through what’s left before we send this.” That gives you something useful to discuss. “Are we good?” mostly gives the other person a chance to reassure you.

I liked asking “Are we good?” I wanted the answer to be yes. In that sense, I was helping make the question less useful. If I’m already halfway out the door, how much room am I leaving for an answer I don’t want?

An open question won’t make anyone infallible. They can still forget something. But you can ask them to pull up the schedule and go through it with you. Then you’re both looking at what needs to happen, instead of trying to decide how confident to feel.

That’s also where you can agree on a little help. Put the deadline in the calendar. Have somebody else check the details. Say who’s doing what. You don’t have to turn it into a trial of somebody’s character.

We ended that particular night staring at a blank blue television screen. The tour manager asked if we were watching the blue channel again. Apparently, we were all quite satisfied with what we were seeing.

Before your next handoff, try one question: “What’s still left to do, and who’s doing it?” Then give the person time to answer.

Who would you trust with your last dollar, but never put in charge of the calendar?

A young employee can receive every official piece of information and still have no idea how the place works. The handbook explains policy. The meeting explains the decision. Neither explains the people, the history or what everyone is too careful or scared to say.

That missing layer used to arrive informally. Someone older would catch you in a hallway, take you to lunch or walk you around the block. You could ask a question before you knew how to phrase it, and they could answer with context.

Those exchanges built judgment. A mentor did more than tell you what happened. They helped you see why it happened, which part mattered and what you were failing to notice.

Recorded work makes that relationship harder. Slack pushes every word to the cloud. Email can be forwarded. A video call may be recorded and transcribed. A naive question can become a permanent sentence with the employee’s name on it. A candid answer can travel without the mentor’s tone or context.

So both people become careful. The employee asks the polished question. The senior person gives the defensible answer. The exchange stays professional, but little mentoring occurs.

Older workers can often work around this because they already have relationships. A young remote employee may not know who is safe, who is generous or how to ask for ten honest minutes without turning it into a formal meeting.

We sometimes describe that gap as a lack of initiative or judgment. But judgment is learned through small corrections. Somebody tells you that you are reading the room wrong, that the visible problem is not the real problem or that the impressive title belongs to the wrong person.

If I were starting at a remote company today, anytime I was able to go to the head office, I would find the salty veteran outside my reporting line, someone who does not control my compensation. I would ask for a walk, a coffee or an unrecorded phone call, then ask one question: What am I missing?

Privacy is not permission to hide misconduct or avoid accountability. Decisions and commitments still belong in writing. Mentorship needs a smaller protected space: one relationship where a beginner can sound like a beginner and an experienced person can tell the truth with the context intact.

Younger workers do not need another information channel. They need someone they trust enough to ask, What am I missing? That is where good judgment begins.

— JC

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Most career advice is written for people who leave.

Take the better offer.

Get the bigger title.

If they won’t promote you, promote yourself somewhere else.

Leaving is active. It photographs well. You get to announce a new chapter and thank everyone who was part of your incredible journey.

Nobody opens up LinkedIN and posts:

Most career advice is written for people who leave.

Take the better offer.

Get the bigger title.

If they won’t promote you, promote yourself somewhere else.

Leaving is active. It photographs well. You get to announce a new chapter and thank everyone who was part of your incredible journey.

Nobody opens up LinkedIN and posts:

‘Thrilled to announce I still work here and have no intent of leaving.’

But staying can be a strategy too.

My friend Franklin has spent 35 years at the same television network. Not a sleepy television network, either. A famously chaotic one in an industry that has spent the last three decades being set on fire by technology.

He didn’t survive by hiding under his desk.

He became useful in ways that compound.

First, no task was beneath him. If something needed to get done, he would help get it done.

That doesn’t mean doing everybody else’s job.

There’s a difference between being willing to carry the bag and becoming the company mule. If you constantly rescue people, eventually they stop learning how to swim.

The skill is knowing when your involvement saves the outcome and when it merely saves someone from responsibility.

Franklin also accumulated something companies claim to value right before they lay off everyone who has it:

Institutional knowledge.

Institutional knowledge isn’t remembering where the old files are stored.

It’s knowing how decisions actually get made.

The org chart tells you who is in charge.

Institutional knowledge tells you who needs to agree, who only needs to feel consulted and which objection means no even when the person saying it uses the word “maybe.”

It also tells you people’s tendencies. Being able to (correctly) predict how people will react to a certain thing is invaluable in life and in business.

That knowledge makes you particularly valuable when a new boss arrives.

The new boss has authority.

You have the map.

Used badly, that becomes corporate politics: hoarding information, protecting territory and watching somebody step on the land mine because they didn’t ask your permission.

Used well, it becomes judgment.

You can tell someone which battles matter, which battles are winnable and which battles will leave them bleeding on a hill nobody remembers asking them to take.

Thirty-five years also puts a lot of chips in the bank.

Make a mistake after six months and people wonder if hiring you was the mistake.

Make one after 25 years of being dependable and it’s Tuesday.

Of course, staying isn’t automatically noble.

You can remain somewhere because you’re growing, accumulating trust and becoming more valuable.

You can also remain because updating LinkedIn sounds exhausting.

Leaving isn’t automatically brave, either. Sometimes it’s just restarting before anyone notices you never learned the last place.

The better question is not:

Should I stay or should I go?

It’s:

What is compounding?

If the answer is your judgment, relationships, knowledge and influence, staying may be producing something another salary bump can’t replace.

If only your years of service are increasing, you may just be getting older in the same chair.

Some people build careers by repeatedly opening new doors.

People like me.

Franklin built his by learning everything about the room he was already in.

Neither choice is automatically right.

But don’t confuse movement with progress.

Sometimes the longest way forward is staying exactly where you are.

But staying can be a strategy too.

My friend Franklin has spent 35 years at the same television network. Not a sleepy television network, either. A famously chaotic one in an industry that has spent the last three decades being set on fire by technology.

He didn’t survive by hiding under his desk.

He became useful in ways that compound.

First, no task was beneath him. If something needed to get done, he would help get it done.

That doesn’t mean doing everybody else’s job.

There’s a difference between being willing to carry the bag and becoming the company mule. If you constantly rescue people, eventually they stop learning how to swim.

The skill is knowing when your involvement saves the outcome and when it merely saves someone from responsibility.

Franklin also accumulated something companies claim to value right before they lay off everyone who has it:

Institutional knowledge.

Institutional knowledge isn’t remembering where the old files are stored.

It’s knowing how decisions actually get made.

The org chart tells you who is in charge.

Institutional knowledge tells you who needs to agree, who only needs to feel consulted and which objection means no even when the person saying it uses the word “maybe.”

It also tells you people’s tendencies. Being able to (correctly) predict how people will react to a certain thing is invaluable in life and in business.

That knowledge makes you particularly valuable when a new boss arrives.

The new boss has authority.

You have the map.

Used badly, that becomes corporate politics: hoarding information, protecting territory and watching somebody step on the land mine because they didn’t ask your permission.

Used well, it becomes judgment.

You can tell someone which battles matter, which battles are winnable and which battles will leave them bleeding on a hill nobody remembers asking them to take.

Thirty-five years also puts a lot of chips in the bank.

Make a mistake after six months and people wonder if hiring you was the mistake.

Make one after 25 years of being dependable and it’s Tuesday.

Of course, staying isn’t automatically noble.

You can remain somewhere because you’re growing, accumulating trust and becoming more valuable.

You can also remain because updating LinkedIn sounds exhausting.

Leaving isn’t automatically brave, either. Sometimes it’s just restarting before anyone notices you never learned the last place.

The better question is not:

Should I stay or should I go?

It’s:

What is compounding?

If the answer is your judgment, relationships, knowledge and influence, staying may be producing something another salary bump can’t replace.

If only your years of service are increasing, you may just be getting older in the same chair.

Some people build careers by repeatedly opening new doors.

People like me.

Franklin built his by learning everything about the room he was already in.

Neither choice is automatically right.

But don’t confuse movement with progress.

Sometimes the longest way forward is staying exactly where you are.

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There was a moment in that elevator when the entire situation changed.

Edward’s first reaction to being fired was basically, “Fuck him, I’m leaving.” His second reaction was that he could talk the owner out of it.

Both made perfect sense.

He was hurt. He was pissed. And he was a salesman who had spent years believing he could talk his way into, or out of, almost anything.

The problem was that neither of those reactions had anything to do with the situation he was actually in.

He was getting fired.

Fair or unfair, the decision had been made. I had already fought the battle and lost. There was no version of the next twenty minutes where we walked into that room and everybody suddenly said, “You know what? Never mind.”

Once that became clear, the objective had to change.

The objective was no longer to keep the job.

It was to leave with his reputation intact, avoid saying something he would regret (this is the part I’ve gotten better at), preserve whatever relationships were worth preserving, and get paid as much as possible on the way out.

That sounds obvious when you’re reading it calmly.

It is incredibly difficult when you are the one whose career just got punched in the face.

I think we waste a lot of energy trying to win battles that have already ended. We keep arguing the case. We try one more pitch. We send the angry email. We demand that somebody admit they were wrong.

Sometimes they were wrong.

That doesn’t mean they’re going to change the decision.

There’s a point where continuing to fight for the old outcome actually makes the new situation worse.

Edward eventually got there somewhere in the mid-30s of that elevator ride. You could almost see the switch flip. He was still angry. Still hurt. His face was still a mess.

But now he understood the assignment.

This wasn’t about saving his job anymore. It was a negotiation.

And he was really good at negotiations.

He walked into the room, kept himself together, made his case and got a very good exit package. That package eventually helped him start another company.

None of that makes the firing fair. It doesn’t retroactively make the owner right.

It just means Edward stopped needing the situation to be fair before he started dealing with the situation as it actually was.

That’s the thing I’ve tried to remember ever since:

When you can’t change the outcome, change the objective.

Be pissed. Be disappointed. Fight like hell while there is still something to fight for.

But learn to recognize the moment when the fight is over.

Because once it is, your job isn’t to win the last battle.

It’s to put yourself in the best possible position for whatever comes next.

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The new Wise Uncle episode is out now: https://www.wiseuncle.fm/p/the-boy-genius-gets-fired

If you like this, or it spoke to you, please Restack this.

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