Photo by Kelly Sikkema on Unsplash

For so many of us, 2020 has been a year of unexpected challenges and opportunities, sorrows and delights, and a whole lot to process going forward.

I always enjoy the process of journaling and reflecting at the end of each year, but this year, it feels non-negotiable. As though the lessons and experiences of this year need to be written out of my system in order to be fully processed and embodied.

And so with that in mind, here are some of the lessons that most stood out to me from a year full of growth, experimentation, small steps backward…


We all have a feeling that drives the work we do. The better we can identify and lean into the feeling, the more truly “us” our work will be.

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I always wanted to be a rock star.

As far as creative dreams go, this is my oldest and purest.

In High School, my best friends and I had a band that played Weezer, Blink-182, and Metallica covers. Once I graduated, I started a hardcore band that wrote our own stuff and played shows around town.

Most shows we played were to small audiences of 30 people or so, the biggest had an audience of maybe 100. We were about as far from famous as we could get, but that didn’t matter. …


I mean, let’s not beat around the bush.

It’s an awkward, uncomfortable, turbulent time of growth and exploration where we experiment, rebel, and push the boundaries as we decide who we’ll become. We make our share of mistakes and execute horrendously poor judgment along the way. With each mistake, our view of the world and our place within it becomes a little more nuanced and self-aware, but it’s a slow, painful, often embarrassing process that most of us are glad to have put behind us.

Except… We haven’t.

Sure, our bodies may have developed past the gangly, acned teenagers we…


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It would be something of an understatement to say I’m a fan of walking.

Aside from taking at least one long walk every day, I take many of my calls while walking, read books about walking, generate all my best ideas while walking, and–as you may have noticed–like to write about walking as well.

No, I’m not a fan. I’m obsessed.

Kelly, on the other hand, isn’t quite as keen. Despite this, every so often I manage to convince her to go for a long walk together, such as the one we took last weekend.

The destination was a section…


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In 1988, Andre Agassi and Boris Becker faced off for the first time, kicking off what would become one of tennis’s great rivalries.

Agassi and Becker were two of the top players in the world, finishing the year ranked №3 and 4 in the world respectively. But despite Agassi’s superior ranking, in this first meeting between the two stars, it was Becker coming out on top.

“His serve was something the game had never seen before,” Agassi later recalled. …


Image by Gaetan Werp

I lifted my gaze for only a second, but that was all it took.

My foot slipped on the rain-slick rock and the next thing I knew I was going down.

I landed hard on my hip. For a long moment, I lay motionless on the ground. One second. Two seconds. Three seconds. I’d anticipated a sharp shooting of pain up my leg. Luckily, I was greeted only by a dull ache.

As I picked myself up, I realized my luck was due to the fact that I’d landed in a shallow puddle of thick mud. I’d seriously stained my…


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Back in 2015, I was a landscaper with dreams of traveling the world full-time.

I had recently discovered the wide world of podcasts and was able to listen to them at work. Naturally, I spent nine hours a day binging my way through every online business podcast I could find.

After a month or two of listening, I started experimenting with what I was learning. I built (ugly) websites, and dreamt up (bad) business ideas, all the while feeling (mostly) confident that eventually, I would land on something that would gain traction.

Despite my general optimism, however, there was a…


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To the person seeking to move a boulder to the top of a hill, gravity is an ever-present, malevolent force to be fought with, pushed on, and toiled against.

To the person seeking to move a boulder down the hill, however, gravity is a benevolent ally that takes care of most of the work itself.

We know gravity is a constant.

What’s not a constant is how we choose to view it and how that view informs the ways in which we work with or against it.

Used wisely, simple physics provides many solutions that allow us to leverage gravity…


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The mentality of the underdog is an empowering mindset to own and embody.

The underdog expects that nothing will come easy.

That nothing will be freely given.

That everything they desire must be worked, clawed, and fought for.

The underdog owns her situation.

She doesn’t blame or begrudge, others, fate, or the system she is working to change for her hardships and the inequities forced upon her (even though they may be stacked against her).

She simply recommits to working harder, taking a new tack, approaching the challenge from a different angle. …


Photo by Harlie Raethel on Unsplash

Getting a new idea off the ground is a lot like healing from a broken bone.

New ideas are typically made up of two (or more) disparate ideas that have never been connected and must now be grafted together.

We set them in place, and at first glance, they might look complete. But apply even the smallest amount of pressure and instantly, they splinter back into their component parts.

In order to fuse properly, new ideas must be given support, encased in a protective cast, and given time for the connections to strengthen into something that can support weight.

Over…

Jeremy Enns

Founder of podcast production and content amplification agency Counterweight Creative. Believer in the power of kindness and generosity.

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