Every setback arrives twice
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The CEO’s assistant opened the door and said, ‘Phil is here.’ She closed it behind me.
I said hello and sat down. The room felt different from our other meetings. There was a long pause. Then he looked at me and said, ‘I’m overwhelmed.’
Two words and they were all he could manage and a thousand words and feelings sat behind them.
There is little to say in a moment like that. Fixing, explaining and planning the next move can all wait. The job in that moment is to stay in the room with someone who is hurting and let them know two things. They can say how they feel without being judged. And they don’t have to be alone when they say it.
I said very little in that meeting and it proved to be a circuit breaker for him.
I’m writing this in late September 2026, and there are many reasons to feel overwhelmed. Rising interest rates, cashflow, sales targets, customers, board pressure and AI anxiety in the team are all landing at once.
And it would be untrue if I said I was immune to that feeling. I’ve carried my own version of what that CEO was carrying. I knew I needed to remove a senior leader, and I knew what that would do to the stability of the company. That situation arrived while we were raising capital and negotiating complex deals. My team needed support. And through all of it, I was trying to be a present father and husband.
Any one of those would have been a full load. The hard part was that they arrived together, and each one made the others more difficult.
So how do you keep leading when the odds feel stacked against you? In my experience, three things help.
1. Say it out loud
The hardest decision a leader makes is asking for help. It runs against the persona most of us were taught to aspire to: be the leader who arrives with the answers.
Asking for help well takes language. You describe the problem clearly enough that your team and advisors can triangulate it with you, test it from angles you can’t see, and map the scenarios in which it gets solved. A simple version sounds like this: here’s what I’m seeing, here’s what I think it means, here’s where I’m unsure, and here’s what I need from you.
That language is a muscle. It builds with repetition, and most leaders start with very little of it.
The CEO in that room started with two words. That was enough to begin. Once overwhelm is said out loud, it becomes something two people can look at together, and that’s when you can take the next step.
2. Write the second event
Every setback arrives twice. First as the event, then as the meaning you give it. You get no say in which setback arrives, or when. However, the meaning is yours to write.
Two CEOs can lose a major customer on the same day. One decides it proves the business is failing. The other decides it shows where the product needs work. Same event, different meaning, and two very different Tuesday afternoons.
The emotion follows the meaning. So, when overwhelm arrives, a useful question is this: what have I decided this means? Often the answer is a story written in a hurry, at 10pm, on your own. You’re allowed to write it again in daylight, preferably with someone else in the room.
3. Find the door
Every decision, by definition, offers a choice. Yet many of us talk ourselves into believing we have none. We’ve put in the years, the capital and our reputation, and sunk cost tells us the only option left is to keep going.
In my experience, that is almost never true. There is always a choice. Sometimes it’s to push on with new terms. Sometimes it’s to change the shape of the thing. And sometimes it’s to walk away and start again, which is its own act of leadership.
Think about that partnership that could change the trajectory of your business. There are six decisions you need to make to ensure it’s worth your time and guess what the last one is? The IDEAL framework walks through all six.
Seeing the door changes how the room feels, even if you never walk through it.
It’s about making the weight manageable
None of this makes the weight fully disappear. Some weeks, saying it out loud, rewriting the meaning and finding the door will lighten the load a little and no more. If the overwhelm hasn’t lifted after a few weeks, that’s a conversation for your doctor or a psychologist. Booking that appointment is a leadership decision too.
The steps are simple. Doing them in a hard week is the work.
The CEO in that room didn’t need a plan that afternoon. He needed to say two words and have someone hear them. Everything else could come after that.
So here’s my question for you this week. What words have you been carrying that nobody has heard yet, and who could you say them to?
See you next Wednesday.
Phil Hayes-St Clair
CEO Coach
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