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331. Why You Should Suck at Something New Every Year (Guest Post)

Posted on April 30, 2025April 29, 2025 by caritagardiner

[The essay below is a guest post, with permission from author Guy Kawasaki. I recommend you check out/follow his Substack and podcast.]

The beginner’s mindset: your secret weapon for staying sharp.

Guy Kawasaki's avatar
Guy Kawasaki
Apr 23, 2025

In a world that’s constantly changing, the ability to learn and adapt is your greatest asset. Trying something new every year keeps you flexible, creative, and ready to tackle whatever life throws your way. Plus, it’s a hell of a lot of fun.

Try Something New

When was the last time you tried something new? I mean really new—something that made you feel like a total amateur? For me, it was surfing. Picture this: a sixty-year old guy flailing on a foam board, getting pummeled by waves, and swallowing enough salt water to season a year’s worth of meals. It wasn’t pretty, but it was transformative.

Learning to surf taught me more than just how to catch a wave. It reminded me how to embrace failure, stay curious, and push through discomfort. That’s the magic of the beginner’s mindset—it keeps you sharp, adaptable, and open to growth.

Challenge Yourself Annually

Here’s my challenge to you: every year, pick one new skill, hobby, or activity to tackle. It doesn’t have to be monumental. It could be learning to play the ukulele, taking up salsa dancing, or finally figuring out how to bake sourdough bread without creating a hockey puck.

The point isn’t to become an expert—it’s to reignite your curiosity and remind yourself what it feels like to learn. Trust me, there’s nothing like being a beginner to keep your brain firing on all cylinders.

Learn from Failure

When I took up hockey in my 40s, I was terrible. I could barely skate, let alone handle a puck. But every time I fell (and I fell a lot), I got back up. Over time, I improved—not because I was naturally gifted, but because I embraced the process.

These experiences taught me resilience, patience, and the value of a growth mindset. They also made me more empathetic. When you struggle to learn something new, you gain a deeper appreciation for the effort others put into their own growth.

Embrace Vulnerability

Trying something new requires embracing vulnerability. And vulnerability, appropriately, comes from the Latin word vulnerabilis, meaning “able to be wounded.” In my case, the wounds were physical: torn meniscus from hockey and cracks to the head from surfing.

Wounds, however, can also be psychological because of the challenging effects of failure and of embarrassment. Hawaiians have a great pidgin term for embarrassment: “make ass” as in “making an ass of yourself”…but I digress. So embrace making ass—nobody cares and hardly anyone will even notice.

Take the Leap

So, what’s your “surfing” this year? What’s the one thing you’ve always wanted to try but never dared to? Go for it. Embrace the awkwardness, the failures, and the small victories.

CTA: Reply and share what new skill or hobby you’re tackling this year—I’d love to hear your story!

Mahalo!

Guy

Thanks for reading Remarkable People! This post is public so feel free to share it.

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[Carita here: I totally agree with everything Guy says and wonder, what will you make ass doing this week/month/year? I'm open to suggestions for what I can fail at soon. Please share ideas in the comments.]

4 thoughts on “331. Why You Should Suck at Something New Every Year (Guest Post)”

  1. Brenda Cudney says:
    April 30, 2025 at 3:55 pm

    I love this essay! I try to learn something new each year, as a type of birthday gift to myself.
    Thank you for encouraging others to try new things. I have found this is also a great way to make new friends, as well as the other benefits.

    Reply
    1. caritagardiner says:
      May 1, 2025 at 11:30 am

      I’d love to hear about some of the birthday things you’ve tried. Maybe during next diving season, we can come up with a fun new thing to learn together — just not diving, okay?

      Reply
  2. TvS says:
    June 12, 2025 at 1:20 am

    Parenting pretty much satisfies this for me.

    Reply
    1. caritagardiner says:
      June 12, 2025 at 10:18 am

      I hear you. Kids make it tricky because as soon as you figure things out about them, they change!

      Reply

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WHAT I DO

I serve as a class dean and teach English to high schoolers at a boarding school in Connecticut. I’ve earned a Bachelor of Arts (Amherst College), an Education Master in Learning and Teaching (Harvard University Graduate School of Education), a Master of Arts in English (Bread Loaf School of English), and most recently a Master of Fine Arts in Creative Writing with a certificate in the online teaching of writing (Southern New Hampshire University).

As a writer, I hope to capture the complexity and joy of life in the New England boarding school world. On this site, I share what I know about trying to write fiction while deaning, teaching English, coaching, and doing the other tasks associated with helping to raise over six hundred other people’s children.

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