When Is It Worth Trying Again?

Returning to Mount Whitney forced me to reconsider what failure, persistence, and success actually mean.

In May 2025, I published a post titled, “From Minneapolis to the top of Mount Whitney and back again.” The post detailed my experience traveling to California and back for the sole purpose of hiking Mount Whitney, a 14,505 foot peak in the Sierra Nevadas. The only problem, was that I did not make it to the top. I tried, but the vast amount of snow along the trail made it unsafe and I turned back with about 2.5 miles remaining in the hike. I failed.

Failure can be many things. In its simplest terms, it can be inability to reach a goal—to set out to accomplish something and never accomplish it. But what if the goal was too ambitious? What if the goal was impossible because of circumstances outside of your control? And what about all things you learn along the way? Don’t those things turn failure into success? Why do we measure ourselves by failure and how we do even decide what does or doesn’t count as failure?

As I’ve mentioned here more often than you’d like to know, I had full right hip replacement in December 2024. Because of that, it was probably a little too ambitious of me to try and hike the tallest mountain in the contiguous United States just six months later. Though I didn’t reach the summit in May 2025, it had nothing to do with my surgically repaired hip. Most of you reading this would probably consider my attempt to summit Mount Whitney just a few months removed from surgery a huge success! I didn’t. Call the naivety of being in my forties (not my sixties), or call it just plain hubris, but I set out to reach the summit and I was disappointed that I did not make it. I was so disappointed in fact, that I made a plan to return.

How do we know if our goals are worth it or not?

How do we know when our goals are worth our effort and when they are not? How do we know when what we strive for is making us better, stronger, more resilient and when it is causing us real harm, taking our attention away from things that matter more? When do we listen to that voice in our head that says we are too old, or too weak, or too busy, and when do we listen to that voice that says we can do, we are improving ourselves, and it will all be worth it in the end?

I’m proud to say that on my second attempt, I reached the summit of Mount Whitney. And let me tell you, it wasn’t easy. I began my hike at 3:15am. Over the next six hours I pushed my way through ten miles and 6,145 feet of elevation gain. Then, I had to turn around and come all the way back down, finally arriving back at the trailhead at 5:15pm. I was exhausted. I was hungry. I was thirsty. I could barely stand. But I made it!

Who is actually measuring our success?

In May 2025 I failed to reach the summit of Mount Whitney. If I had never returned to Mount Whitney, no one would have ever noticed. No one would have considered it a failure. But I like to do hard things and I’m determined to reach the goals I set for myself. So, in August 2026, I returned to Mount Whitney and I succeeded. Did I succeed at my own detriment? Was I blinded by hubris? Could my time, energy, and money have been better spent? For those of us pursuing difficult things, we may never know. The cost of our goals cannot be measured, only the results. The things that we learn, the experiences we have, the places we go and the people we meet along the way, the scars we bear—those are the things we can measure, the things we take with us.

Your goals were never meant to be easy

I’m currently reading Dear Writer, You Need to Quit by Becca Syme. It is a remarkably simple, yet remarkably effective book for writers who are struggling to complete a manuscript. By the way, Becca, if you’re reading this, I’d love to be on your podcast or to have you on mine 😀. Anyway, one chapter Becca’s book is titled “Quite Expecting This to be Easy.” The chapter states the obvious: writing a novel was never suppose to be easy. It was never suppose to be fun. It can be fun at times and it can definitely be rewarding, but it isn’t suppose to be easy. Instead, Becca challenges writers to accept the fact that writing is hard and to push through it, every time, until you get used to the feeling.

Maybe that’s why I climb mountains when I really shouldn’t or start businesses when there are much easier things in life to choose. I’ve gotten so used to choosing the hard things that I no longer have a rational sense of self-preservation. Alas.

What goal are you currently striving to achieve? What is preventing you from accomplishing it? How will you decided when it’s time to turn around and go home and how do you know whether or not you should try again? How will you know when to push through the hard things and when to quit?