Sometimes You Have to Step Back to Step Forward

When I pivoted careers, first from real estate into cycling coaching, and later from coaching athletes to coaching leaders, I made a choice that didn’t make sense on paper.

I worked more hours.

I earned less money.

And I took on every client I possibly could.

Why? Because I needed the repetitions.

When I became a cycling coach, I didn’t pretend I already knew everything. I coached as many athletes as possible, any level, any goals, because I knew that to become great, I had to get my reps in and see who I worked best with. I needed to fail, learn, adjust, and repeat until coaching wasn’t theory; it was instinct.

I did the same when I started leadership coaching. For the first two years, I lowered my fees and worked with as many leaders as I could. Every session was a chance to refine my craft, discover patterns, and learn who I could help most.

Now, I’m highly sought after and work with founders and executives who are scaling companies into the hundreds of millions. And here’s the paradox: I only got here by being willing to go “backwards” first.

So if you’re in a season where you’re making less, working harder, or doing things that feel beneath you, don’t panic. You might just be in your apprenticeship phase. The phase where you’re building the skills and wisdom that no shortcut can give you.

The step back is often the launchpad for the leap forward.

Reflection for you:

Where in your life or business are you avoiding a step back because it feels like failure when it might actually be your best investment?