Welcome back from summer, everyone. It’s been great to have a little break, and I hope you enjoyed some of the blogs we shared during July and August. But now it’s September, summer is over, and it’s time to get back at it. I want to start by talking about something that happened over the summer, a lesson around when to let go of the rope.
This idea came from a conversation I had with Danielle Krischik, the host of The Story Effect podcast. I was a guest on her show a few weeks ago; the episode should be out soon. We were talking about my adventures trying to learn how to wakesurf. I’ve shared some of this with you before, and maybe you’ve seen it on social media.
I didn’t grow up on a lake, boating or skiing, so anything on the water feels foreign and doesn’t come naturally to me. But this past year, we got a wakesurf boat, and our family started getting into it.
Of course, the kids picked it up fast. They’re already surfing without the rope and even trying tricks like 360s. My wife, who grew up on the lake and has boated more than I have, is also better at it. But I’m working on it. I’m embracing failure and the wipeouts, and I’m getting better. It’s been really fun to try something new at my age.
Last year, I pulled my hamstring trying to stand up. I wasn’t good at it. But this year, I’ve mastered getting up; I can pop right up and ride behind the boat holding the rope. Now I’ve been working on letting go of the rope and staying up without it.
That’s the hard part. I can surf for short stretches, but I’ve been working all summer to ride that wave without holding on. And finally, toward the end of summer, I nailed it. I let go of the rope and had some of my best runs. I’m not great yet, and some rides are still short, but I’ve gotten way better. And I’ve loved the journey.
While learning, I watched a lot of YouTube videos. One suggested holding the rope with slack for about 30 seconds before letting go. I tried that, but it didn’t feel right. Finally, I just thought, “When I feel ready, I need to go for it.” So I let go. I didn’t know if I was truly ready, and yes, sometimes I wiped out right away. But that’s how I started improving.
Danielle and I talked about this idea in business, leadership and life. There comes a point when you have to let go of the rope. Maybe it’s an old belief, a system that no longer works, a relationship or something that’s holding you back.
Only you can decide when to let go. In my experience, it’s often better to do it sooner than later, but not recklessly. If I had let go right after learning to stand up, I would have wiped out every time and never learned how to really surf. I had to get comfortable first.
Now, when I feel about 70–80% ready, I toss the rope. That’s how I’ve gotten better. Not by clinging to safety, but by letting go.
So, as we come back from summer and head into the last four months of the year, think about what your rope is and when it is time to let go.
It could be in your personal life, your work or your goals. If you’re about 70–80% ready, maybe it’s time. You’ll probably wipe out like I did, but the falls won’t be as dramatic, and you’ll recover faster. And eventually, you’ll get there.
Let me know your thoughts. When did you let go of the rope?
