It’s Not Failure, It’s Trial and Error

November 6, 2025

You tried. You took the risk. You stepped out over the typical bounds of what you’re comfortable with. You took the chance, and it didn’t work out. You failed… or did you?

Maybe not. In fact, how you respond matters. How you respond can mean that particular flop isn’t a failure; it’s part of a process of trial and error. Sure, sometimes you get it right directly out of the gate. Most times, however, there’s a process involved in testing our ideas in the wild (versus theorizing about it in our controlled spaces). That process involves rolling out our ideas, seeing what does and does not work, making adjustments, and pressing forward with lessons learned. 

The path to success involves twists and turns. Sometimes you start out in one direction, and you find you just need a pivot. A different perspective. A way to keep going instead of stopping in your tracks. Success requires us to move through the messy middle. It requires us to find the small steps that lead to big breakthroughs. And most of all, it comes from refusing to quit on ourselves. Success is the fruit of trial and error.

Strategy vs. Gamble

It can feel like success is highly reliant on luck. Sure, sometimes luck has a part to play. Some luck, however, is something we coax out of the world by doing our due diligence, making informed decisions, and adapting when we need to adapt. We can trick ourselves into thinking we have seized control when in fact, we’re relying on luck – sort of like playing the lottery. 

As a leader, don’t play the lottery. Play chess. There are things out of your control in a good game of chess. You can make an educated guess about what your opponent may do. They might meet those expectations, or they might toss you a curve ball. While you wait for their move, you’re studying the board. You’re weighing your options. You can’t foresee the future, but you can study potential paths and make plans. You can process the data, walk through scenarios, and make an informed decision. When the curve ball comes, you don’t toss the board and call the game a failure. You study what’s changed, you adapt your plans, you try something new that might fit in with this altered landscape of the game. Approach your business like that.

Planning Takes Some Guess Work

Entrepreneurial and leadership gurus like to talk a lot about due diligence. If you’re not careful, you might think that success just relies on doing our homework well. If you hit the market with your very best idea, and you’ve done your homework about who your target audience might be and what they’re willing to pay and what messaging might get them to act, then you’ll be successful. And yes, doing our homework is a big part of differentiating a pure gamble vs a strategic, informed undertaking. Yet, remember, this is chess. 

There are variables we can’t (or at least don’t) anticipate. We make informed guesses about things that we can’t directly control. There are going to be assumptions we make that don’t pan out. There will be data points we assign value to that turn out not to be as valuable as we thought. Someone somewhere is going to toss that curve ball. 

Our planning helped us make informed guesses that may not come to fruition the way we envisioned. And that’s okay. We made informed guesses which means we now add these new data points to the equation and adapt where we need to as we keep moving forward. It’s not a failure. It’s trial, error, adaptation. Rinse and repeat. 

Good Coaching Can Help

When you find yourself in the messy middle, it can be hard to see the success waiting on the other side of all the hurdles. Sometimes you need a trail guide. Having a sherpa who has experience in leading teams and bringing business ideas to life can help you respond to the turns and twists, keep on the path, and make your way to the other side of fear. Having a good coach and mentor can keep you going forward at the point where other people just stop. If that’s the support you’re ready for, let’s talk about how I can help you identify what is keeping you stuck and find the creative shifts that move you forward. Learn more here: Coaching Services.