Hey Reader,

There’s a decision you’ve been meaning to make. Perhaps it’s been sitting with you for months. Maybe longer. You know you need to make it. And you’ve already thought through every angle imaginable. But every time you get close to making a choice, there’s just one more thing you’d like to know first. One more variable you’d like to resolve. One more reason to wait a little longer.

But at work, you could probably make three key decisions before lunch.

There’s a huge gap in how senior leaders approach decisions at work and in their personal lives. At work, we’re used to making calls without having all the facts. A “good enough” decision now is usually better than a perfect decision made too late. When it comes to our personal lives, that logic can go out the window. We can spend days, months, even years hesitating over what we want to do. Every decision feels permanent, as though making the “wrong” one would mean there’s no going back.

From what I’ve seen, two things tend to drive this hesitation.

The first is accountability. When you make a decision at work, there’s a structure around it. There are KPIs, deadlines, colleagues watching, and regular reviews that create natural feedback loops. If something doesn’t work, there’s a clear process. It could mean running a post-mortem, making a pivot, or planning what to do differently next quarter. Course correction is the expected next step.

Personal decisions don’t always come with that structure. Our goals tend to be more vague. Deadlines are “flexible” or nonexistent. There’s no one tracking whether we’re making progress. And if we change course later on, it feels less like an adjustment and more like admitting we’ve got it wrong. For some strange reason, every potential decision feels riskier than it really is. So the safest option (at least in our minds) is to wait a little longer to feel more certain.

The second thing that holds us back is that personal decisions feel… well, personal. When a strategy doesn’t work, it’s the strategy that failed. When a personal decision goes wrong, it can feel like a reflection of who we are as people. We can second-guess our judgment, knowledge, and identity. That can make every decision feel heavier, and the cost of making the “wrong” choice seems much higher than it probably is. The result is a kind of mindset paralysis: “This choice defines me, and if I get it wrong, I’ll carry that alone.” It’s a huge reason why we can be comfortable with ambiguity at work but wait so long to feel certain in the rest of our lives.

These two forces feed into each other. The more a decision feels tied to who we are, the less safe it feels to treat it as an experiment. Without a structure that makes iteration feel safe, the identity stakes feel even higher. We get caught in a cycle of indecision as time keeps passing.

At work, we’re not asked to commit to a strategy forever. We’re asked to commit to it for a quarter, review it, and then decide from there. That time-boxing is what makes it possible to act with uncertainty. We can apply the same logic to our personal decisions.

Think about what’s been sitting with you the longest and reframe it:

• “This is my Q4 experiment, not my final life decision.”

Then write three lines:

• Experiment: “For the next 90 days, I will…”
• What I’m testing: “I want to see if this gives me more energy/alignment/time with my family.”
• Review date: “On [date], I will decide whether to continue, adjust, or stop.”

The review date is a key part of this. It turns a decision into an experiment. You’re giving yourself permission to course-correct in advance, which is exactly what makes it less daunting to start.

Try it with a decision you’ve been putting off. Chances are, taking action will give you more clarity than gathering more information.

What’s the decision you’ve been sitting on? Hit reply. I’d like to hear about it.

From one human to another,

The human side of leadership is something I've built my keynote around. If that's a conversation you'd like to bring to your organization, you can find out more by clicking the banner below.

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