Challenging Myself

Taylor Roark
5 min readMar 13, 2021
Image credit: Jukan Tateisi (Unsplash)

Over the past few months, I’ve been experimenting with the structure of challenge as a new form of learning and understanding for myself.

I’ve never been much interested in challenges. Maybe it’s because I grew up as an only child and spent a lot of time entertaining myself. I was not particularly athletic growing up and don’t have memories of locker room talk where the boys challenged each other to do things beyond what was assumed possible.

Over the past several years, I have seen lots of social media posts from people about various challenges going around. I had a lot of judgment against people posting their participation in these challenges, assuming that it was all about vanity. I have had a huge shift in recent months.

Last summer, there were a lot of posts going around of people doing 25 push-ups per day for 25 days. I was nominated at least twice to join in but I didn’t publicly respond because I didn’t want to “show off.” And I think I knew that I would be able to accomplish it — not necessarily complete all 25 in one go from Day One. But I knew that, if I put my mind to it, I would finish the challenge.

After the second nomination, I decided to take the challenge but to do it privately. I quickly noticed my progress from repeating a physical practice on a daily basis. For the first few days, I could only do 10 or 12 push-ups in one set and so would take a couple sets to complete all 25. Within a few days I was up to 15 or so in my first set and then 20 and then 25.

At some point, I started watching videos providing pointers on form and technique. I particularly enjoyed Adam Frater from Shredded Academy and this video for beginners. I became less concerned with how many push-ups I was doing and focused on how well I was doing them.

At the end of last year I undertook a Completion Exercise, which is an intuitive practice I use to help me understand and appreciate what I’ve created and learned for the year and, most importantly, what I want to focus on next.

One of the things that I want to focus on for 2021 is 30-day challenges. I was surprised that this desire came through. When I did this exercise in December, I hadn’t been focused on the push-up challenge for months and I hadn’t engaged in any other challenges. But clearly, my intuition was nudging me to experiment with this as a structure.

I started January with 30 days of Wim Hof breathing, which I wrote about here. I liked the practice so much that I still start every morning with it and now routinely hold my breath for upwards of 3 minutes, which gives me subtle but powerful focus, calm and determination throughout my day.

In February, I decided to write every day — 500 words. It was definitely a different challenge. I have wanted to create a regular writing practice for years and I have avoided it like the plague! As much as I have wanted to express myself, before I sit down and start the process I think of a million reasons not to write anything. I can convince myself that I have nothing to say or that a mob with pitchforks and torches will come to my home to lynch me for whatever I do write. It is all some form of resistance. For a better understanding of resistance in writing or any creative endeavour, I strongly recommend The War of Art by Stephen Pressfield.

I got through February — just! It was a really tough structure for me, much harder than the push-ups or breathing practice. Most days, I was just writing words about what happened or hadn’t happened during the day as a sort of processing tool. I usually busied myself with a million other tasks and would often sit down to write only a few minutes before midnight. I thought that my writing was awful and that I truly had nothing to say.

My saving grace came from a friend who was holding me to account for this challenge. I complained about how unhappy and unsatisfied I was with my writing. He listened and then reflected back to me that I had not set a challenge for myself to be happy or satisfied with my writing but that I had only challenged myself to write 500 words per day. By that measurement, the only standard of “success” was whether I was writing 500 words or not!

That lesson had a profound impact on me. When I finished the 30 days, I reflected on what the practice had taught me. Unlike the Wim Hof breathing, I did not feel that it was necessary to continue writing 500 words a day. But a lot of my anxiety and fears and resistance had been addressed and alleviated, even by just processing the days’ events.

And I am left with a desire to focus on intentional writing, like this article. I enjoy gathering my learning and sharing it, first and foremost for my own learning and craft. I would be doubly happy and satisfied if it provides entertainment or assistance to anyone else along their journey but that is not my focus.

And that brings me to a final understanding and appreciation of challenges, and a reflection on my earlier assumptions about others. I am learning that a challenge made public may not have anything to do with vanity and may be motivated by any number of other reasons.

It may be to overcome resistance and keep oneself to account. Or to inspire and support others. Or just to connect with the world, each to his or her own. It may be for any reason at all!

And now I am challenging myself to suspend judgment of others and to focus on my own challenges….

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Taylor Roark

Spiritual Alchemist | Mythicist | Reincarnated Honey Badger. Owner, Galliant Trainings — “The adventure you seek in life is yourself!”