The other day, someone asked me to share a time when I achieved a challenging goal. Their question came during a deeper conversation about goal-setting and the power of pushing ourselves through discomfort—stretching beyond what feels safe to achieve truly challenging goals in life.
Before I dive into my own story of achieving one of those goals, let me set the stage…
When you’re setting your goals, it’s easy to fall into the trap of lowering the bar, consciously or unconsciously. Instead of embracing a “sky’s the limit” mindset, we often impose ceilings on our potential, shaped by limiting beliefs and old paradigms we carry. And when that happens, we shift away from setting challenging goals—ones that stretch us—to aiming for what feels safe and attainable.
I’m writing today about setting challenging goals – the ones that scare you just a little bit – and my own experience on achieving goals like that.
Rewind about five years…
A group of friends were in their third year of taking annual trekking trips to Nepal. Each time they would come back, sharing stories and pictures from the trip, I would tell myself, “Next time.” The invitation to join them was always open; truth be told, I had dreamed of going to Nepal since I was a teenager. My level of desire was high…
At the same time, in my mid-forties, my fears and insecurities were just as high. Maybe I was too old? Could I keep up?
At the same time, my excuses were equally high. I was too busy. My wife and kids needed me at home. It was too expensive to go. My company couldn’t run without me there.
The result? I kept kicking the can down the road. Every year, my friends would go, and every year, when they came back, I wished I had been with them. Every year, I said, “Next time.”
If there’s one thing I have learned by listening to Jesse Itzler, it is that time waits for no one. Paraphrasing, I have heard Jesse talking about his mountain adventures. “There are no seventy-year-olds up there.”
LESSON ONE: Don’t wait. Do it now.
I knew that every time I said “next time,” my window of opportunity was closing. So, four years ago in January, I set my challenging goal. I was going to trek through Nepal in 2022. I had always set goals for myself at the beginning of the year. This time, though, I was setting a goal that scared me. I knew this was going to be a stretch as most of the guys I’d be traveling with were younger than me.
LESSON TWO: Set big goals that stretch you.
Accepting the challenge of this goal, I got to work. I trained with the guys I’d be traveling with. I trained alone. I trained early in the morning and late at night. I trained on hot days, and I trained in the rain. When the training began, I was not in the proper shape for a mountain trek. Over time, through consistent effort, I got there.
LESSON THREE: Consistency is key. Be prepared to do the work no matter what.
At the same time, I was studying my goal and the challenges it would bring me. I researched the terrain and the time of year. I dug into the travel requirements. I watched YouTube videos where people documented their own experiences in the country and on the trekking trails, and I studied their gear lists. I listened intently for what worked and what they would have done differently.
LESSON FOUR: Invest time studying your goal and learning all you can about success.
All of that studying put me in a position where I could picture parts of the trip. I began visualizing the experience we were about to have, literally closing my eyes and imagining my time in Nepal, spending time there in my mind before I ever left the house. This included thinking through what could go wrong and trying to make friends with the challenges before they happened so that if they did occur, I would not be thrown off by them.
LESSON FIVE: Visualize your goal, what success looks like, and the challenges.
Finally, I was in Nepal, trekking through the backcountry. This leads me to my last piece of advice for achieving challenging goals. Before I left, I had decided what my purpose was for this trip. It is very personal to me, and I am going to keep it that way, but my point is this. When the trip got hard, and there were many times that it did, knowing my “why” allowed me to push through the challenges. Without my “why,” there is a good chance I would have considered quitting. With my purpose in hand and clarity about what I was in Nepal to accomplish, I had the additional strength I needed to keep going.
LESSON SIX: Connect your why/purpose to your goal.
Nepal was a time when I achieved a challenging goal. I have other examples I could share, but this one comes with so many examples of how I addressed each challenge. The best news? As I write this today, it is just a couple of months after completing my third annual trip into Nepal. Each year, I learn more about myself and achieve new goals that challenge me in new ways.
The Takeaway
Set a goal that challenges you, consider the lessons I shared above, and achieve your own challenging goal this year. There’s nothing special about me or my story other than the fact that I decided to quit kicking the can down the road. You can do the same, and the time is now… Apply this to your own life – to your own Nepal – and see where it takes you.
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Ready for more?
If you liked this, then you might be interested in my new book, Living Life Daily. Designed to motivate and challenge you every day, this book offers 365 thought-provoking prompts that will push you to reflect, take action, and embrace meaningful change. Whether you’re striving to set clearer goals, build resilient habits, or cultivate a winning mindset, each daily entry is packed with wisdom and practical advice to help you take small steps toward big results. Find it here!
You’ll also get massive value out of the Grit Meets Growth podcast that I share with Chris Cathers. It’s for people who want more out of life… at work, at home, in their relationships, and in their health and wellness. Find it here or on your favorite podcast platform! – John
