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The Test Summer Gives Every Leader
Unstuck Monthly | June 2026
Our leadership identity rests on what we can control. Summer quietly proves otherwise.
Every summer I watch the same thing happen to people who lead. The calendar starts to thin out. One direct report is in Europe, another is at camp visiting days, the client who needed everything yesterday has gone quiet until after the Fourth. And somewhere around the end of June, a particular kind of leader starts to grip.
You know the grip. The Slack messages sent at 9pm to confirm a thing that didn’t need confirming. The “just looping back” on a decision that was already made. The quiet, gnawing sense that if you take your hands off the wheel for ten days, the whole machine will drift into a ditch.
Wouldn’t you know it, the machine almost never drifts into the ditch. You come back tan and slightly anxious, and the thing ran fine. Which raises a question most senior leaders work very hard not to ask: if it runs fine without me, what exactly was I holding?
The optimists died first
That question is one most leaders avoid, because the honest answer might cost them something. Facing a hard truth about yourself takes discipline. The Stockdale Paradox is the best description of that discipline I know. Maybe that’s why it came up three times this month, in separate conversations among people who’d never met.
If you don’t know it: Vice Admiral James Stockdale survived seven years as a prisoner of war in the infamous Hanoi Hilton. When Jim Collins asked him who didn’t make it out, the answer surprised everyone. The optimists — the ones who said “we’ll be home by Christmas,” and then Christmas came, and then it came again. They died of broken faith. Meanwhile, the survivors held two things at once: first, unflinching honesty about how brutal the facts were, and, second, unshakable faith that they’d prevail in the end.
Most people remember the faith half and forget the brutal-facts half, and that’s the misread on Stockdale’s story. Positive thinking does nothing. The discipline of the survivors was the refusal to lie to yourself about your situation while still refusing to give up.
You built a dependency and called it leadership
Here’s the brutal fact for the summer gripper, and I’ll say it plainly because it deserves no cushion: if your organization cannot breathe without you for two weeks in July, you have not built an organization. You’ve built a dependency, and you’ve been calling it leadership.
It stings because the busy months hide it. When the machine is humming, you can’t tell how much of the hum is you and how much would happen without you. When it’s all running, the hum sounds a lot like competence. Yours.
The lights stay on either way
Most of us conflate two things that could not be more different. There’s they need me to keep the lights on, and there’s they’re better because I’m here. We chase the first because it feels like the second, but it isn’t.
Indispensability is fragile. It means you’ve built a single point of failure and named it after yourself. Real value is the opposite. You build something that runs without you, and then your contribution becomes the higher-order work only you can do: judgment, vision, developing the next layer of leaders. You stop being the engine and start building better ones.
The leader who can be gone in July and watch the lights stay on has earned the right to do the work that actually requires a leader. Think of it as a promotion in altitude.
Before you decide it’s fine
Four questions to sit with before you do anything about it:
What is the one thing you grip hardest, and what are you afraid will happen if you let it go?
What’s the brutal truth about your leadership style you’ve been too busy to face, and do you actually believe you can build past it?
If your organization ran for two weeks without you and ran well, what would that tell you about the work you should actually be doing?
Where have you been confusing they need me with they're better because I’m here — and what would it take to move from the first to the second?
An experiment for the next eight weeks
This summer, I want to hand you something to do, not just something to think about.
Pick one thing you currently grip — a decision you always weigh in on, an approval that routes through you, a meeting that doesn’t happen without you in the room — and decide to take your hands off it. Tell the relevant people you’re stepping back from it deliberately, set a time and place to review, and then do the genuinely hard thing: leave it alone and watch.
You’ll learn one of two things. Either it holds, which means you just freed yourself for higher-order work and proved your bench is deeper than your fear told you. Or it wobbles, which means you’ve found the exact spot where you’ve been substituting your “leadership” presence for an actual system, and now you know to build something else before the September blitz arrives.
Both outcomes are wins. The only losing move is to grip all summer, learn nothing, and arrive at Labor Day having confirmed only that you’re tired.
It takes more nerve to leave the work machine alone than to keep your hands on all the wheels and levers. The grip feels like leadership; usually it's just fear in disguise. So spend the season finding out what you actually built. Be honest about what you find, and trust that you can fix the rest.
“Alex was an excellent thought partner... He shed new light on issues and provided tools to assist in workplace challenges that will pay dividends for years to come.”
— Michael, Chief of Staff, U.S. Government
Letting go is hard to do alone. A thought partner makes it clearer and keeps you honest about what you find.
I upgraded my ICF coaching credential this summer, from ACC to PCC. The certification changed; the practice didn’t.
If you’re heading into the summer gripping something you suspect you should release, let's talk about it before September turns it back into noise.
Great conversations start with shared insights. My coaching practice, like this newsletter, thrives on connections. If you know someone who's navigating their own sticking points, I’d love for you to share this with them.
