Stoicism, Wilderness Survival, and the Power of Habit

Hello, fellow experiment-preneurs, leaders of play, and failure fanatics! 

It’s the fifth issue of The Leader’s Playground, and I have more fun with each one. Thanks for coming with me on this adventure. 

I’ve been watching “Alone.” It’s that reality show on the History Channel which drops 10 experienced (some more than others…) outdoor survival enthusiasts completely alone in some remote landscape where they try to survive for 100 days—with nothing but a few selected tools and the clothes on their backs. 

The winner, of course, gets a big money prize but all contestants learn a lot about themselves, the wild, and survival, often by way of experimentation when all else fails. 

Please forgive me for likening that intrepid experience to being a leader in today’s world, but I’ve got to say: There is some overlap. 

How often have you felt as if you’re completely alone in the middle of nowhere, have lost your fire starter (or team morale), and are staring utter failure in the face? What do you do when your tried and true methods fail you? 

That’s when we experiment. And, if we’re lucky—and willing—we learn. 

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Welcome back to The Leader’s Playground. I’m delighted you’re here. 

(And I’m very glad to be writing this from the comfort of my home, rather than scribbling my thoughts into a piece of driftwood, alone somewhere on the coast of Alaska!).  

Okay, enough pretending I’m Bear Grylls. Let’s dive in—are you coming?

What I'm Curious About This Week

Ever curious about personal development, I’m drawn to material—podcasts, books, shows, anything at all—that can help me understand myself and, relatedly, the world a bit better. 

Ryan Holiday (author and philosopher behind The Daily Stoic) is one of my favorite thinkers. He was the guest on a recent episode of the High Performance Podcast, and the conversation is full of classic Stoic wisdom for the modern-day human. 

I especially love Ryan’s reminder to us all (which happens to be the title of his newest book), “Discipline is Destiny.” Talk about a splash of cold water to get you going! 

While perhaps a bit shocking, it’s a classic wisdom and one which I aim to incorporate in my life. Things get hectic while traveling and habits fall away (as I’ve recently shared!), but as often as I’m able, I practice habits that make me feel my best. 

Check out Ryan's episode, and let me know what you think!

From the Lab at P2

Speaking of building habits and practicing discipline…

You probably know by now (unless you’re new here, in which case, hello!) that the P2 Lab is all about experimentation in order to better ourselves as leaders, coaches, and people. 

And one thing I’ve learned is that building new habits is a lot like experimenting. We may have an idea about how to change our life for the better—whether it’s something as “small” as 5 mins of quiet time each morning, or as all-encompassing as quitting alcohol or sugar. 

(The new habit I am adopting at the moment is reading the daily message from Ryan Holliday’s book The Daily Stoic, which I do before my morning Headspace meditation. Today’s was about not judging events as good or bad and just seeing them as they are.)

But the reality is that implementing a new habit involves a lot of unknowns: How will I incorporate this into my routine? How will it impact my day-to-day flow? Will it have the effect I expect or want it to? How long will it take for it to become normal? 

Experimenting with habits looks different for everyone, but one key tip I have to offer is this: 

Decide in advance the timeline you want to stick to while you try this thing out, and have a purpose linked to your experiment that you can measure as you go. 

I just joined a cancer charity challenge that requires me to do 100 press-ups and 100 sit-ups every day in November. I’m passionate about the purpose behind it, and the month-long timeline gives me parameters to focus on. 

Then, when the challenge has ended, I can decide whether or not I want to continue the habit indefinitely—based on how it makes me feel and how it adds to, or detracts from, the rest of my life. 

Is there a habit or practice you’d like to implement in your life? Have you started, or how’s it going so far? Reply to this email and tell me your experience with experimenting. I’d love to know.

The Leadership Tales Podcast

Indigenous recruitment leader Jennifer Ménard-Shand has a long and fruitful career in the hospitality recruitment industry. After a difficult childhood, she dealt with anxiety and imposter syndrome for the first phase of her professional life. 

In spite of those hardships, however, Jennifer has gone on to become a mentor to many culturally oppressed communities via her work in the corporate space. I loved talking with her and learning from her about equity and inclusion, and how we can all overcome imposter syndrome in our own lives. 

Give the episode a listen! And if you feel like leaving a review (or tips for me on how to become a better host), I invite you with gratitude for sharing. 

Thanks for joining me again. 

Thanks for joining me for another winding issue of The Leader’s Playground. I appreciate each and every one of you—and especially the responses and questions you send my way.

This week, remember discipline is destiny. How are you setting yourself up for success with new habits?

If you have questions or thoughts to share, please don’t hesitate to respond to this email. I’d love to chat with you. And if you like what I’m doing and have someone who might enjoy it too, please forward them this email or invite them to subscribe below. 

See you next time. Be well!

Cheers,Colin

To learn more about my book, Be More Wrong: How Failure Makes You an Outstanding Leader, click here.