100 Miles In May Challenge: Tips & Lessons Learned

One thing I did to create the best month ever was take on the 100 Miles in May challenge, which was something I accomplished as part of The Big Ass Calendar Club. The goal was to run or walk 100 miles in May. It was an amazing experience and there were so many lessons learned from it, so I wanted to share some tips & takeaways to help you on your journey.

I created both a video and podcast version so you can deep dive into this if you’d like.

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Tips For Completing The 100 Miles In May Challenge

How do you get 100 miles done in a month (running or walking or a combination)? If you break it down it’s just 3.3 miles a day for an entire month. Here are some lessons learned and tips for completing it.

Work from a position of strength

I knew going into this that I didn’t want to be chasing the miles, so I wanted to work from a position of strength. I got 15 miles done in the first two days to set a good tone. Because of that I was always working from ahead. I wanted this challenge to be something that served me, not something that brought me down or added stress to my life. I always want to be a leader of the pack in everything I do.

Different ways to get miles in

Because I planned on enjoying my 100 mile challenge experience I was always looking for different ways to get my miles in. That way it was fresh and fun. The big victories for me were:

• Going for runs
• Walking & running with my dog
• Basketball
• Golf
• Tennis

The two primary ones were running and doing stuff with my dog Rally. The reason having a dog was such a big victory is I could take her out multiple times a day, and get in anywhere from a quarter of a mile up to a mile each time. So often we don’t realize how much the micro adds up (0.3 miles once a day for 31 days is over 9 miles).

Quantification of your mileage

I tracked all of my mileage on my Apple watch using the Fitness app. When I went for a walk with my dog or went for a run, I tracked it as a workout that way I had some accountability around the structure of my numbers.

I also created a Google Sheet where I tracked my daily mileage by workout. This allowed me to be accountable to my total while having a simple way to quantify my overall progress. That way I knew how many miles I had remaining.

Break it down into managable chunks

When I first thought about doing 100 miles, like a lot of people, what popped into my head was “Wow, that’s a lot.” However, it’s not a lot when you break it down simply. It’s just 3.3 miles every day. Do some activity in the morning, something else around lunch, and something in the evening and you are golden. I found on average that I was doing three to eight activities a day in which I got some form of mileage done (and I did so in a non-taxing way).

I also added one long run a week to my cadence as a way to get ahead of the 3.3 mile per day pace. A long run for me could be between four and seven miles. Doing this allowed me to put in over 37 miles in the first week, and 73 miles in the first two weeks. By day 20 I had already hit my 100 mile goal.

Overcome inconvenient timing

I’m very routine oriented as structure allows me to design my success. I stack the things I know are going to add growth and inspiration to my life. But guess what, every day does not go that way. Often times I would find that I would have a packed schedule in the mornings and my usual workout times were no longer there. What do I do now to get my miles in?

One key to being successful at this challenge is finding those micro moments in your day where you can get some mileage in. Some days it’s only 17 minutes. Other days you’ve got an hour. While on the surface this might not seem like much, taking advantage of those opportunities adds up, especially when you are working towards 100 miles.

Another thing, I don’t believe in having Zero Days where I get in no mileage. Therefore taking advantage of the inconvenient timing is so important (both physically and mentally). It has you walking around with a different energy because you are looking to optimize, not make excuses. This is definitely a skill that you develop, and the more you do it the more it serves you.

Say Yes to things

I’ve found in life the more often I say yes to things, the more good things that happen. A great example of this is when my wife asked if I wanted to go for a walk in the evening. I’d already worked out in the morning so my first inclination was No. However, because I was doing the 100 miles in May challenge I knew it was an opportunity for me to one get in more miles plus spend time with my wife. This mindset and way of living in action has helped me create more stories, memories, and maintain a lifestyle of health, fitness, and fun.

All runs are not created equal

I found that runs can have meanings, and they are all not created equal.

Sometimes I would be doing runs just to get in my mileage. It was more of a goal mindset.

Other times I needed the run. It’s like therapy. It’s refreshing. It’s nice out and I get to get outside and go for a run and get away from the digital world. I would usually run from West Loop down the Riverwalk in Chicago to the Lake, and it would be just me and some music or a podcast. I would make it a point to take pictures and think of it like an adventure. I would be creative and there was a lightness to the runs. Those runs felt amazing.

Other times I was running for excellence. I’d be listening to a podcast with Tim Grover where he’s talking about Michael Jordan and Kobe Bryant and Dwayne Wade, and what they do to be the best in the world. It would inspire me.

Sometimes it’s who you’re running or walking with. I really enjoyed the times in which I would walk with my wife. One Friday night we grabbed an early dinner and then walked two miles back home. I’ll always have that experience in my mind and heart.

Get things accomplished before noon on Saturday

This is one of my recipes for success. The way I win the weekend is by getting things accomplished before noon on Saturday. I want to enjoy the weekend just like everybody else. But at the same time, I know the weekend is a great opportunity to work on my health and fitness. To satisfy both needs I put an emphasis on getting my long runs done on Saturday mornings. That way I can enjoy the rest of the day and/or weekend.

This simple shift in priorities will have you getting more done in all areas of your life before most people even start their day.

Twice a day workouts

One of the challenges I had during the 100 miles in May was getting in strength training workouts. I was putting such an emphasis on running that lifting became less of a priority. So what’s the solution for this? Twice a day workouts.

This is something I initially got accustomed to while doing the 75 Hard mental toughness program (where I was doing two 45 minute workouts a day for 75 straight days). With this challenge I’d get a strength training workout done in the morning, and then in the evening I’d get some miles in (running or walking).

What I like about the twice a day workouts is the mindset of high performance. So often people have a challenge working out once a day and now you are getting in twice that. The momentum it creates bleeds to all areas of your life, and when you get done with an evening run you feel like a million bucks.

Impress Yourself

The last two days of the challenge were over Memorial Day weekend. I had already put in 135 miles and was on vacation in Sarasota, Florida. I started thinking about how I wanted to finish and 150 miles sounded like a nice number. However, I hadn’t mentally committed to putting in 15 miles in the final two days as we were planning on spending it at the beach.

On day 30 I put in six miles. That got me to 141 miles. All through the final evening and the morning of the final day, I wasn’t sure if I wanted to 9 miles that day. What am I going to do? I asked my wife what she thought and she said, “I’m already impressed by what you’ve accomplished.”

And that’s when it hit me. I was not impressed by myself. Others may have been impressed by what I’ve accomplished, but I was not because I knew I could do 150 miles. That’s when I decided that I was going to impress myself.

Even thought it was 90 degrees at the beach I knew how I wanted to complete this challenge. I thought about something Jesse Itzler said, “Winners don’t negotiate their goals.” I brought my running shoes with me to the beach and put in 10 miles (my most mileage of any day).

Finish Strong

As I am doing my 10 mile run on the final day my mindset was to finish strong, because that’s what champions do. Even though I had already completed my original 100 mile goal on Day 20, it was important for me to give it my all. To push myself and shatter any self limiting beliefs. That way I could look back on this accomplishment and be proud of my effort. Because the version of me that could have stopped at 141 miles isn’t as good as the one that found a way to get in 150 miles. This mindset of finishing strong is contagious and helps you become the best version of yourself.

Don’t underestimate the way you can inspire other people

I made it a point every day to take a picture during my runner or walk. This served the purpose of documenting that day, my thoughts, and any nuggets of wisdom that happened. That way I could look back on my journey and relive the moment.

Little did I know that on day three something amazing would happen because of it. My mother in law texted me (unexpectedly) saying “you’ve inspired me and I’m going to do the 100 miles in May challenge. I’m going to do it by walking on Siesta Key beach.”

My mind was officially blown. She mentioned that she saw my Instagram and that’s what inspired her.

Throughout the month she would text me updates saying things like “I’m up to 25 miles, or I’m up to 50 miles.” This put a smile on my face every time.

Fast forward to May 31 and on the very last day my mother in law completed the 100 miles in May challenge by walking on the beach. It was such a proud moment for me to see her take this journey on her own and accomplish this.

You never know who you are inspiring with your actions.


If I can complete the 100 miles in May challenge so can you. All it takes is commitment, intention, and a willingness to live in action. I want to give a shoutout to everyone in The Big Ass Calendar Club who completed this challenge. The stories I’ve seen about people who found a way to finish their 100 miles on the final day as well as the people who absolutely crushed their miles is so inspiring.

I encourage you to take part in a challenge or create your own. Maybe it’s a one 100 miles challenge, maybe it’s the 75 Hard Challenge, or maybe it’s something that’s never been done before. None the less, keep pushing, keep growing, and keep inspiring.

If this post resonated with you then I’d love to hear from you. Drop me a line on Instagram @RobCressy and say what’s up.

If you are a high performer that is looking to become the best version of yourself then I’d love to invite you to be in conversation with me. Let’s jump on a call and talk about how I can support you on your journey. You can schedule a time HERE.

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