September 28, 2026

Why Founders Stop Trusting Their Gut | Full Send Management

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A founder asked me for the answer four, maybe five times on one call. They got on wanting to fix how they come across to their team, and the conversation kept coming back around to some version of give me the sentence to say. At one point they asked me, "Am I supposed to find the answer?"

This is somebody who walked away from a big job and went on to build their own company. They made those decisions on their gut, with nobody handing them a tool, and that's how they got where they are.

So I asked what they could borrow from someone close to them who is great at the exact thing they struggle with. "I don't think I can be like that." Then, "I kind of don't want to be." Then, "I don't know, actually."

Marinate in that for a sec. One question got three different answers back to back, and my read is the person giving them didn't know which one was theirs.

I've been talking about this a lot lately. When people ask for the tool, or they say "I don't know," it often goes back to they don't trust their gut, or they just can't hear what their gut is saying. It can also be somebody who is just, stuck. We say we don't know where to start, or we don't know what to do. It's not that we don't know, it's we can't hear.

Or we are so afraid of making the wrong choice. If I'm working from somebody else's tools and opinions and it doesn't work out, it's not entirely my fault, and that is more comfortable than being wrong with my own idea. No one says this out loud to themselves, and most of the time it's subconscious.

Founders have a lot of noise around them and no one around to challenge their gut, because everybody just says yes. Many of them have reached a level higher than they ever thought they would when they started the company, and so they second-guess so many decisions. They end up doing what other people want and taking it as their own.

Learning from other people's mistakes is a valuable tool. I could have sat there and said here's what I would do, and that doesn't mean it's going to work for you. If I tell you what to do, it's 50-50 whether you do it and another 50-50 whether it works. You hang up the phone and either you forget it or it never sat right with you, and the next time we talk we're spinning our wheels. So before you waste anyone's time asking them what you should do, think about the fact that your answer is probably the best one for you because it's yours. And when you commit to something that was your idea, it gets done.

Nerves around a decision are fine, but if you have clarity your gut will sound the alarm when it's wrong. When someone makes a decision it is the right decision at the time, it may pan out to be wrong, and that's where pressure testing the strategy comes in. That's why having an advocate who has no stake in the outcome is so key to getting off Executive Island, somebody who will challenge what you just said and ask the right questions at the right time so you can feel confident in your decision.

What's one question you've been handing to other people lately under the label "I don't know"?

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