The Best Leaders are Drowning

Adapted from the forthcoming Time Boss book “Your Best Leaders are Drowning,” coming early 2027.

Let me tell you a story that might sound familiar.

Sarah is a VP of Operations. Person for person, she's the primary reason her company has had the success it’s had the past few years. She's the one who got the rebuild across the finish line when the first attempt stalled. She's the one the team trusts. She's the one her CEO would promote again tomorrow in a heartbeat.

It's 7:12 on Monday morning and Sarah’s at her desk. She got here at 6:45 because she didn't want to walk in unprepared to her first meeting at 8am. She’s actually been awake since 5:41am because she couldn't get back to sleep, thinking about the thing she said she'd handle last week and didn't. She has a weekly leadership sync at 9. A one-on-one at 10. An interview she can't skip at 11. Lunch is a bar she'll eat at her desk between emails because she feels behind. Three more meetings fill the afternoon, one of which she added Friday when she realized she hadn't actually talked to her new hire in three weeks.

Her day feels reactive, pulled in a million directions, when what her CEO really needs from her is strategic impact.

To her credit, she has a calendar block from 3:00 to 4:30 today to work on the strategic rollout plan (the one her CEO asked for six weeks ago). It's the most important thing on her calendar today. She has moved that calendar block seven times, and it’s going to get moved again today, because another fire came up, and who could blame her for putting out fires?

It always feels like fires these days.

It Hasn’t Always Been This Way

When Sarah came in three years ago, she was the hire who made everything else click into place. She read the strategy in her first week and came back with three improvements nobody had thought of. She built her team in ninety days. She shipped the rebuild the previous VP had been promising for two years. At the first board dinner she went to, three people pulled her CEO aside and asked where they'd found her.

She cared. Everyone could see it. She cared about the work. She cared about her people. She cared about being the person she'd been hired to be.

What happened to that Sarah? Did she stop caring?

Of course not. And that’s the problem.

The Problem: Caring Out of Control

Do you see yourself in Sarah? If you’re a leader who cares, I bet you do.

Like Sarah, you’re not drowning because you stopped caring. You’re drowning because somewhere in the last year, the volume of things you care about exceeded the cognitive space you have available.

You didn't stop caring. You didn't get lazy. You didn't lose your edge.

You’re simply overloaded, with more to do than time to do it. This isn’t an emotional problem. It’s a math problem.

Your caring has caused you to say “yes” to more than you can handle. It was caring out of control, and now you are over capacity.

And because you care deeply, you’re afraid that if you don’t keep grinding, it’s going to hurt you or someone you care about.

Put simply: you’re overwhelmed.

What Overwhelm Looks Like

I want to give you language for what you're experiencing. You know something is wrong. You can feel it. You don't have a name for it yet, so it's easy to tell yourself a story. “It’s just a hard quarter. I took on a lot, but I’ll bounce back.” And you will, for a while. That's part of the problem.

Overwhelm has specific symptoms, not vague ones. Not “stressed.” Not “burning out.” Specific, observable tells. And if you see them in yourself, you can do something about it before it’s too late.

Constant Firefighting

Your week is wall-to-wall meetings, emails, messages, and “have you got a minute?” Nearly every one of those items is someone else's request. If you opened your calendar right now, you'd struggle to find a one-hour block that belongs to you. You'd find plenty that belong to your team, your peers, your vendors, and your boss.

No Strategic Work

Quarterly goals. The rollout plan. The hiring framework. The product launch. The things only you can do. They keep not getting done. Every Friday you tell yourself you’ll get to it next week, and you mean it every time. It’s not because you don’t care. Care alone doesn't create space on a calendar that's already full.

The “I’ll Get To It Next Quarter” Trap

Same pattern, longer time horizon. The leadership development program you pitched in January. The process redesign you’ve been talking about for eighteen months. You’ve been meaning to, and you’ve been meaning to, and you’ve been meaning to, as if next quarter will suddenly spawn available time. It won’t, and that thing won’t get done next quarter, or the quarter after that.

Short on Patience

Your fuse is an inch shorter than it was six months ago. You feel it when your boss calls or walks into your office with a new idea. Tension. Every new request lands on top of an already infinite to-do list, and you’re beginning to resent people for it. Your team and your boss let it slide because they know you’re carrying a lot, but you know it’s not sustainable.

Quiet Withdrawal

You stopped volunteering ideas in the leadership meeting a few months ago. You used to be the one who saw around corners, anticipated needs, raised your hand and said “yes.” Now you keep your head down and hope nobody adds to your plate.

Your Team is Copying the Pattern

This one is harder to see, because it shows up in your team. Your direct reports are staying late. They’re canceling their one-on-ones with you because they’re too slammed. They’re answering email at 10pm and 6am. They learned from you that this is how the job works.

If you're nodding along to at least three of these, keep reading.

If it feels like I'm reading your mail, it's because I was that leader from 2006 to 2016. A senior leader in growing companies. Incredibly capable, and incredibly overwhelmed, and it cost me dearly.

You Unintentionally Chose This

Here’s the hard part: you unintentionally chose all of this.

Every “yes.” Every meeting you accepted. Every commitment you took on. At no point were you an indentured servant. You had the option to push back, to set a boundary, to say “no,” to communicate the trade-offs and let your boss decide, and you didn't. You were doing what you thought the things you care about required.

You didn’t think you had a choice.

And you were wrong.

Even worse, you haven’t told anyone you’re overwhelmed, and you haven’t asked for help.

Why You Haven’t Asked for Help

So if you’re overwhelmed, why haven’t you asked for help?

Here is the thing most leaders won’t admit: the best leaders are the best at hiding overwhelm.

You became a top leader because you could carry more, and the first thing you learned about working for your boss was to carry more. The better you got at carrying, the more you were given. That isn't a criticism of you or your boss. It’s simply how things work. We follow the path of least resistance, and you made things easy by continuing to say “yes.” That is how every leader I've ever worked with got promoted in the first place, and that’s how I ended up the COO of early-stage, venture-backed software companies.

But the thing about leaders who can carry more is they keep carrying. Past capacity. Past sustainability. Past the point where it costs them something real. So you won't tell your boss. You won't raise a flag. Because you’re afraid that telling them will cost you something: the role, the authority, or the responsibility you earned by saying “yes.”

You’re afraid that if you raise a hand and say “I am at capacity,” or more bluntly, “I am overwhelmed,” your boss will hear “I don’t have what it takes.” You’re afraid that the moment you admit it, your role goes to someone else. You stop being the person they call.

So you don't tell them.

Of course you could go to your boss, and a good boss would be there for you. You could say “I'm at capacity.” You don’t. That choice is yours. No one is forcing you to hide. Whether valid or not, the fear is real. It creates silence, and that silence is still a choice you make.

That choice to not ask for help keeps you overwhelmed. Eventually it hits your health and your relationships, and you keep hiding it. Then it hits your performance, and suddenly everyone can see it. You can’t hide it anymore. At best, you’re browning out by then.

And if you wait too long, you’ll burn out.

Reality is Your Friend

Here is the mindset I need you to embrace:

Reality is your friend.

The overwhelm you’re facing is not a thing to be ashamed of or to hide from. It’s also not going to resolve itself with time. In fact, if your company is growing, it’s only going to get worse. Overwhelm is simply a thing to name, to accept as what is. The quicker you catch up to that reality, the quicker you can fix it. Step one is accepting it.

And the reality is you’ve chosen to say “yes” every step of the way. It’s tempting to blame your boss, your company, or your workload. Don’t. You made the choices that brought you here, right or wrong, and it’s your responsibility to change. That’s good news. It means you can.

You Need a New Approach to Time

What you’re experiencing is not a personal failing. You’re not lazy. You’re not disorganized. You’re not missing some trick the productivity people have figured out. You’re not fragile.

You’re loyal.

You carry the weight because you care.

You care about the work.

You care about your team.

You care about what your boss thinks of you.

And that caring drives you to keep saying “yes” until you’re utterly overwhelmed.

Whatever approach to time got you here can no longer contend with the complexity of your environment and the chaos that comes with a growing company. Effort alone won't close that gap. You’re already working harder than ever.

What you need is a new approach to time. One that contends with the complexity and chaos around you. One that is simple and repeatable. One that restores peace of mind and delivers meaningful results. A new approach that can help you get the results you want, with an experience of life you actually want.

And I have a very simple next step for you.

We can help you. You unintentionally chose your way into this situation.

You can intentionally choose your way out.