How To Do Hard Things: Lessons From Cycling Across America

8 Lessons on How to Do Hard Things: Get Quiet | Anticipate Obstacles | Play the Games | Help | Don’t Fall in Love | Strong Peloton | Your Story | Be Afraid | Final Thoughts

Before starting my Rise 2 Ripple Cycling Challenge across America, I was asked by a well-known self-help author and podcast host, “What makes you think you can do this?”

It was a good question. I was about to ride 3,600 miles over forty-one days at fifty-four and with a new total knee replacement. Crazy, right? 

Our journey started in Astoria, Oregon, and took my wife, dogs, and me through Idaho, Montana, Colorado, Kansas, Missouri, Illinois, Indiana, Ohio, Pennsylvania, and Maryland before finishing at The Lincoln Memorial in Washington, D.C. Each day, I profiled one non-profit rippling goodness into the world. 

Beyond my daily milkshake, yep, that’s right, I enjoyed 43 milkshakes – guilt free – I might add; I revisited some essential life, leadership, and entrepreneurial lessons that can help you know how to do hard things.

8 Lessons on How You Can Do the Hard Things

1. Get Quiet

There’s a requisite hustle that every business leader must have, but it’s essential to find time each day to get quiet. While riding, I noticed that the faster I went, the louder it got, but when I took moments to slow down, it got easier to hear, much like life. 

Mindfulness has been my go-to tool during my executive career, entrepreneurial journey, and ride across America. As a meditation teacher, I’ve seen how life can change when you slow down, get quiet, and mindfully run your business. 

2. Anticipate Obstacles

We, go-getters, tend to be optimistic, abundant, and glass-full folks. They’re awesome sauce qualities, but we all face obstacles. 

To navigate your obstacles, plan for them before going after your hard thing. During our trip, my wife and I would dive into the weather forecast each morning, and if something looked questionable, we created a game plan to keep us safe. With anticipatory planning, you can develop a thoughtful way around your obstacles when you’re calm and focused versus in a moment of reactivity.  

“Obstacles don’t block the path. They are the path.” 

~ Zen Proverb.

3. Play the Short and Long Game 

Too often, we focus on the daily grind, and as a result, we can day trade our lives away.

Don’t get me wrong, focusing on the daily to-do list is essential, but so is creating space to think about what we wish to happen downstream. Before starting my trip, I would visualize myself finishing the ride (long game). I backcasted every stage from that image and saw every day (short game) as a building block to my goal. 

My long-game vision helped me make critical decisions when the conditions became unsafe. Yes, I could have gritted it out, but at what cost? In those moments, I played the long game and got into the RV and out of harm’s way. 

Take the time to set up your day, but don’t forget to focus on where you wish to end up. 

“Every road will take you there if you don’t know where you’re going.” 

4. Ask for Help

A man carrying a placard asking for help on how to do hard things

We romance the idea of pulling ourselves up by the bootstraps and making it on our own, but life doesn’t play out that way. We’ve all received help along the way and will continue to need support as we travel forward. 

Asking for help isn’t a sign of weakness; it’s a statement that says you’re not quitting. We had many moments during our forty-one days when we had to rely on the assistance of others. 

I invite you to take a moment to list where you could use support and go out and ask for it. 

“If you want to go fast, go alone. If you want to go far, go together.”

African Proverb

5. Don’t Fall in Love with Your Plan

When planning our trip, I locked into The Transamerica Trail as my route. Everything went as planned until I met another cyclist heading westbound in Rawlins, WY. I asked him about the infamous dogs of Kentucky, and he shared that they were horrible. 

That evening, we shifted to avoid those dogs and found a route that allowed me to ride on some of the best gravel roads in the country and finish in D.C., where my wife and I met. How cool is that?!?

Here’s my recommendation, plan tight and hang loose as you tackle your hard thing. Make sure you have some slack in your plan to help you adjust when needed. 

6. Select a Strong Peloton

In the cycling world, a group of cyclists is called a peloton. It’s like a moving community, and when they work together, everything goes smoothly. It’s the same for life and business. Finding people who bring out the best in you is one of the best things you can do if you want to have a successful life. I was fortunate to have a fantastic team – starting with my wife – that made our trip much more manageable. 

7. It’s About Your Story

It all comes down to the conversation your having with yourself. If this isn’t healthy, you will leave potential on the table. Each morning, I would start with affirmations and a visualization that framed my day. As a result, there wasn’t a single day that I didn’t want to get on the bike or believed I couldn’t do it. 

You will face a doubter or two when tackling something audacious. It’s natural. Here’s the thing, never doubt yourself. Remember, you’ve survived 100% of your challenges and have the strength to get through anything.

8. Be More Afraid of Not Living Than Dying

As you can imagine, many people were worried about my safety. It was heartfelt and natural, considering how crazy drivers are today, and my ride was celebrating the 21st anniversary of my near-death cycling accident. 

Through my recovery, I came to appreciate and accept my mortality. I’m no longer afraid to die, but what keeps me up at night is not living fully.  

Too many play it safe because they are afraid, and as a result, they never live. Each night before bed, my gratitude practice helps me see all the wonder in my life, and it also helps me appreciate life’s impermanence. Like the Fall foliage, life is beautiful because it doesn’t last forever. 

So there you have it. Eight tips to help you tackle your hard thing. 

Final Thoughts

Now, let’s go back to the question from the author. 

What made me think I could do it? 

The answer is simple. It was already within me from doing hard things all my life, and I bet all the proof you need to tackle something big is also within you. You’ve got this, you can do those hard things too!

I can’t wait to see what you will ripple into the world. 


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