Have you had that feeling of knowing, deep down, that something just isn’t working?

Recently, I had an unproductive conversation with one of my children where I kept using the same approach, expecting a different result. Or I think about a client who told me his morning routine of rushing straight to the inbox was setting him up for a bad day, yet he continued the habit. Often, I hear the same pattern show up in weekly staff meetings that consistently drain energy, or in the recurring, frustrating conversations my clients keep having with a team member.

We see the invitation to change, but instead of stepping toward it, we try to squeeze one more drop of juice out of the old way of doing things. I watch myself and my clients tweak the meeting agenda, rephrase the same passive-aggressive feedback, or try to move faster through the rush.

Why do we do this? We tell ourselves it’s because we don’t know how else to do it, but I suspect it’s often an unconscious calculation of risk.

The fear of doing something different

For years I’ve heard that change only happens when the pain of staying put becomes unbearable. But recently I’ve been thinking: What if we stop waiting for the pain to get bigger? Instead, we could reduce the fear of trying something new.

The rewards for stepping into uncertainty are so much greater than we realize, precisely because the learning is immediate and valuable. When we resist change, we protect ourselves from the possibility of looking foolish, but we sacrifice the opportunity to learn new skills and delay the benefits that come from finding new options.

Failure as an apprenticeship

I know that real-world conversations aren’t cheap experiments, and the stakes can be high. But the real risk isn’t in trying something new—it’s in the quiet corrosion of staying small.

As George Leonard reminds us in his book Mastery, we need to see this through a different lens:

Think of it this way: There are two kinds of failure. The first comes from never trying out your ideas because you are afraid or because you are waiting for the perfect time. This kind of failure you can never learn from, and such timidity will destroy you. The second kind comes from a bold and venturesome spirit. If you fail in this way, the hit that you take to your reputation is greatly outweighed by what you learn…

The goal here isn’t to be reckless; it’s to embrace the second kind of failure—the one that serves as an apprenticeship.

When you look at that frustrating meeting or that recurring conversation, I invite you to see it not as a risk, but as a tiny laboratory for learning. You don’t have to overhaul everything.

Your tiny, venturesome experiment

What if you chose one small step toward a new way?

• Instead of getting stuck in this recurring conversation with my child, I could start by saying, “Before we dive in, I want to share my intention for this discussion.” That at least creates a new pattern!
• Instead of letting our inbox pull us, we could spend the first five minutes of our day clarifying three things we must attend to today and booking time on our calendar to do them. 

These small actions might feel weird, maybe even a bit like failure if the conversation stumbles. But that little stumble is how you learn where the friction is. It points you toward a different option next time. It’s an irreplaceable reward that you can only earn through action.

Remember, the way to apprentice as a leader is to act on your ideas as early as possible. You have everything to gain.

So, where are you holding on to the old way, trying to squeeze one last drop of juice? Pick one recurring, frustrating scenario and design your tiny, venturesome experiment for this week.

Hit reply and let me know how it goes. I’d love to hear about it.