Issue #25: The Yes That’s Killing Your Career
Do you remember life before COVID?
Neither do I, really. But I did write some things down. Just in case.
One thing I apparently used to have: gaps in my calendar. Actual white space. Meetings that ended and then… nothing for a while. Time to think. Time to breathe. Time to remember what I was actually supposed to be doing.
Then 2020 happened. Teams happened. Zoom happened. Back-to-back-to-back happened. And look — I get it. We needed it. We built a virtual culture out of necessity, and we made it work. Nobody's blaming the pandemic for our scheduling habits.
Except I kind of am.
Because two years ago, I sat down on a Sunday night and looked at my week ahead. And then the week before. And the week before that. And the week coming up...just to mix things up a bit.
Every minute. Virtually every minute. Gone.
I sat with that for a second. Then I did what any self-aware leader would do and asked myself the obvious question: Why is everyone so desperate to talk to me?
And then I remembered — I'm not that important. I'm also not that fun to talk to. So something else was going on.
The virtual culture had done something sneaky. It hadn't just filled my calendar — it had rewired something. Made saying yes the default. Made being in everything feel like being engaged. Made "no" feel like the wrong answer, or worse, like something I just wasn't allowed to say.
I wasn't booked because the job demanded it. I was busy because I couldn't stop saying yes.
And the reason I couldn't stop saying yes is that, for most of my career, yes was the right answer. Yes to the stretch assignment. Yes to the task force. Yes to the committee nobody else wanted. Yes to the cross-functional project with no clear owner.
That's how you build credibility. That's how you get noticed. That's how I'd earned every seat I'd ever sat in.
What nobody told me — and what I'm about to tell you — is that there's a point where yes stops building your career and starts consuming it.
Most people never feel it coming. Until they look at their calendar from 30,000 feet and realize the view isn't great.
🙋 The Anatomy of a Yes
Not every yes is created equal. There are three versions, and only one is actually working for you.
The Strategic Yes. You said yes because it aligns with where you're going, builds a relationship worth building, or puts you in a room you need to be in. This yes compounds. It creates visibility. It earns the next opportunity. This is the yes that really built your career.
The Reflexive Yes. You said yes because someone asked, you were available, and saying no felt uncomfortable. This yes feels productive. It is not. It's just busy. And busy is not the same as valuable. (I have spent an embarrassing amount of my career being the busiest person in the room and mistaking that for something impressive. It was not impressive. It was a scheduling addiction with excellent intentions.)
The Fear Yes. You said yes because no felt dangerous. What if they think I'm not a team player? What if I get passed over? What if they stop asking? This is the most expensive yes of all. It's not driven by opportunity — it's driven by anxiety dressed up as helpfulness. A type of perverse corporate FOMO.
And be honest: if you sorted your calendar today into those three buckets, which would be the fullest? Probably not the strategic one.
The reason this is so hard to catch is that Reflexive and Fear yeses don't feel wrong in the moment. They feel like being a good person. A team player. The kind of leader who shows up.
But the true high-performers — the elite of the elite — are very comfortable not saying yes.
💸 What Your Yes Is Actually Costing You
Every yes is also a no. (Important: this does not work in reverse.)
When you said yes to the meeting you didn't need to attend, you said no to an hour of clear thinking. When you said yes to the committee, you said no to the project that actually needed your attention. When you said yes to the extra ask because it seemed small — you said no to the margin that lets you do everything else well.
You're not adding things to your plate. You're trading.
And most people are trading strategic capacity for the feeling of being needed — or the comfort of never having to say no — or both. (Always go with both when it’s multiple choice.)
The leaders who've figured yes out tend to have two things in common: they're hard to get on a calendar, and they're considered exceptionally valuable when you do get them.
That's not a coincidence. Their scarcity isn't accidental.
At some point, they made a deliberate — and probably uncomfortable — decision that their attention was a finite resource and they were going to spend it like it was.
Because it is.
🍴 Try a Bite This Week
The goal isn't to become the person who replies to every meeting request with a passive-aggressive "that doesn't fit my priorities this quarter." (Nobody likes that person. Right, Don?!)
The goal is intention. To make every yes a conscious decision rather than a reflexive one.
Three moves that will actually work for you:
Run the Yes Audit. Pull your calendar from the last two weeks. For every meeting, project, or commitment, name it: Strategic Yes, Reflexive Yes, or Fear Yes. Don't judge — just categorize. If the second two columns dwarf the first, that's your data. You don't have a time problem. You have a yes problem.
Practice the Pause. This week, don't say yes to anything in the moment. Not once. For every request — even small ones — buy yourself time: "Let me check and get back to you." You're still allowed to say yes. The point is to make it a decision, not a reflex. Notice how often your answer changes when you've had actual time to think about it.
Name the Trade. For every yes you say this week, write down the corresponding no. "Yes to X → no to Y." Keep the list somewhere visible. Most people have never seen the full cost of their commitments laid out in front of them. It is clarifying. It is occasionally mortifying.
💡 A Final Thought
None of this is about becoming less helpful. It's about becoming more intentional about what kind of helpful you are. The leaders who do this well aren't the ones who stopped showing up. They're the ones who show up only when it counts — and make that mean something.
Here's the part that's easy to miss: the yes problem and the delegation problem are the same problem from two different angles.
Half of what's filling your calendar right now should be on someone else's plate — and the reason it isn't is the same reason your week looks the way it does. Every yes you're holding onto is a no to someone on your team who needed that stretch.
Your overcrowded plate is their empty one.
Which means fixing this isn't just about protecting your time. It's also about adding value to theirs.
We'll talk delegation soon enough. But for now, say yes like you mean it. Say no like your best work depends on it.
Because it does.
🌶️ Add Your Spice
What's the yes you've said most recently that you already know you shouldn't have — and what was the no that came with it?
Drop it in the comments. Let's normalize the deliberate no. (And if this one hit close to home, share it with the person on your team who's clearly drowning in their own helpfulness. They'll thank you. Eventually.)