
“Jill, you’re up first.”
The second I hear the words, my stomach flops. My hands quiver as I pull my rope from the saddle and fumble through the coils, trying desperately to look competent while feeling the exact opposite.
You see, the movies have it all wrong.
They make you think when you finally do the thing you’ve wanted your whole life, it will feel heroic. Cue the epic soundtrack. Slow-motion victories. The triumphant moment where everything clicks into place.
But in real life, it feels more like a red face, pounding heart, and waves of nausea.
Sometimes the victory is hidden right in the middle of the most cringey, exposed, embarrassing moments your brain can conjure up.
Honestly, I think we need to talk about that more.
Learning to rope at age 40 has been humbling in every possible way. And not just privately humbling. Publicly humbling. The kind where you think, I cannot believe I just did that in front of actual people.
Missed shots. Dropped ropes. Bad swings. Lost dallies. Hitting my horse in the head with the rope. Hitting myself in the head with the rope. I’ve done it all, and then some.
And it does NOT feel good. It’s mortifying and horrifying and yet… I keep going back for more.
Now more than ever, I understand why it’s so hard for adults to learn new skills later in life.
It’s acceptable for a child to be a beginner. We expect it. We even cheer it on.
Adulthood is different. By the time you’ve built an identity and gathered some life experience, you’re used to moving through the world feeling somewhat capable. You know your lanes. You know how to protect your image and avoid looking like an idiot.
But when something new calls to you—or life demands a new stage of growth— just like that, you’re a beginner again.
And let me tell you: awkwardness hits a lot harder when you’re 40 than when you’re 14.
The humiliation is thick, man.
So lately, I’ve been repeating one phrase to myself over and over:
Embarrassment is the cost of entry.

I think one of the biggest reasons people stay stuck is not because they lack discipline, talent, or information. I think it’s because they cannot tolerate the feeling of looking foolish.
Because embarrassment rarely feels like a simple, harmless, Oh well, I messed up.
It feels more like: Oh no. I didn’t just mess up— I got exposed!!
And it burns. It burns right through the polish and performance and exposes the part of us that says we like growth—but only if said growth happens in a dignified, aesthetically pleasing way.
But my darling, that’s rarely how growth works.
Growth is awkward. Clumsy. Stretching. It kicks your ego square in the teeth.
But that is the cost of becoming. And it is worth every penny.
Because what is the alternative?
Whenever I feel scared of being seen in my fumbling beginner hood, I weigh the options. My conversations with myself go something like this:
Option A: Protect your ego. Stay in your lane. Keep up the appearance of competence. Avoid embarrassment. Avoid gossip. Avoid looking silly. But go to your grave never exploring the thing that tugged on your soul.
Option B: Go all in. Chase the dream. Ignore the peanut gallery. Let yourself be seen trying. Maybe look foolish. But actually live my one wild and precious life (thank you Mary Oliver.)
When I frame it that way, things get clear, fast. So I lean in.
Even when my face is red. Even when I feel like I’m drowning in self-consciousness. Even when I miss yet another calf with six cowboys watching.
Being a beginner has a way of stripping you down to the truth. It forces you to face yourself. It shows you how attached you were to that shiny image you’ve so carefully curated.
But if you can stay in that discomfort long enough, you eventually earn the greatest reward of all:
Real confidence.
Not the curated, surface kind. I mean the battle-tested kind. The kind that comes from walking straight through the fire, sticking with the thing, and coming out the other side with a few scars and a head held high.
That kind of confidence is life-changing.
And that’s why I keep putting myself in these wildly awkward situations.
Not just because they might eventually make me better, but because they’ve taught me I can trust myself.
And once you realize you can survive embarrassment, it loses some of its power.
That’s a superpower you’ll use for the rest of your life.

In starting a business.
In shifting your worldview.
In learning to cook, to ride, to lift, to lead, to make art, to build a life that actually fits you.
Even in leaving behind an old identity and fumbling your way toward a truer one.
So many people aren’t stuck because they’re incapable. They’re stuck because they are unwilling to be seen starting at ground zero.
So these days, when I feel the familiar flush of self-consciousness rise up… when I miss yet another calf… when I feel the weight of not being good yet… I try to remember:
This is not proof I’m failing.
This is proof I was brave enough to enter the arena. This is proof I have not arranged my whole life around protecting the illusion of competence.
And that feels like a worthwhile trade.
I doubt I’ll ever be a great roper, though I hope I get better eventually.
But I do know this:
Every time I pick up my rope and try again, I become someone I respect a little more.
And that is reason enough to keep going.
-Jill
P.S. My embarrassment mantra comes from this quote by Ed Latimore: “Embarrassment is the cost of entry. If you aren’t willing to look like a foolish beginner, you’ll never become a graceful master.”
P.S.S. These photos make me look way cooler than I am. Kudos to our amazing photographer, Kelly from Rugged Grace Photography.




This reminds me of a quote by GK Chesterton, “If a thing’s worth doing, it’s worth doing badly.” The value is in the attempt, the willingness to try. Good for you in getting out there!
That’s such a great quote, too! Great advice. 🙂
Ah! Jill! It’s awesome that you are learning a new skill at 40! I had just been able to take horse riding lessons at 40… then medical issues kept me from it for years. I am hoping to get back to it at 55! Next time I go to Minnesota I hope I can get by your restaurant to meet ya! You are an inspiration to many! Thank you for sharing.
Thanks for commenting. Please know that I’m rooting for you -both in health and to learn new skills no matter your age!
As we get older, we have to keep trying new things or we limit ourselves to “staying in our lane” and not growing. Trying new things is hard and also invigorating. Stay young-feeling and try new things or get old, stay in the recliner, and talk about “the good old days”.
Yes! It’s hard AND invigorating! Thanks for sharing that line with me. 🙂
Didn’t Huxley say “egolessness is divine?” Indeed to be free of the fear to disappoint. I love to sing and sing in a band. Band practice is so fun but I don’t like gigging. The fear of a mistake, disappointing, etc. Yet time after time people and friends try to assure me that they are grateful for our music! Sure we are a geezer band doing our best to entertain…why isn’t it enough? It is! We must all stop being so critical and hard on ourselves. Play the game con Brio! It’s one life and we better live it and pack it full.
Indeed, we are our own greatest critic. I hope you push yourself and keep experiencing your favorite things – even if it’s a bit challenging. I’m rooting for you!
Well said. I appreciate your vulnerability and keep at it! I know nothing about horses and or roping but it does remind me of a quote the great philosopher, Wayne Gretzky and somewhat well known hockey player famously said: “You miss 100% of the shots you don’t take…”
That is another great quote about this type of thing. Thank you for sharing!
Excellent, beautiful and BRAVA! 🙂
Jill well written thanks for sharing your journey. I was thinking our nation for the most part has become too comfortable. If folks would leave that condition and be willing to take on challenges personally and collectively they would be changed as well as those around them.
Thanks for writing. I think you’re right about our nation becoming too comfortable. Maybe if folks like you and I keep pushing into some discomfort (no matter our age!) we can inspire a new generation. 🙂
Good for you Jill, I’m so proud of you for starting that early! And not being afraid to talk about your failures. I started at 65. I bought an old house and renovated it with my 64 year old brother, then planted 40 fruit trees. People thought I was crazy, and sometimes I thought so too :o). I’ll be 73 this year and still working at it. BTW I’m a woman and by myself, my brother passed away in 2020. I so wished I had started when i was younger! Keep it up girl! ?
I’m so proud of you for all that you have accomplished! Thank you for sharing with me. 🙂 Please know that I’m rooting for you in your wonderful life adventures!
Even though it’s acceptable for children to be beginners, soon enough they will likely be afraid to try something they long to do for fear of being judged. You are setting an amazing and authentic example for your children as they witness you living your dream anyway. Also, thanks for the Mary Oliver reference.
Jill, I’ve been a fan since your first book and have followed the podcast and blog ever since — but somehow never left a comment until this piece pulled me in.
Your framing resonates, though I’d put a slightly different label on it — at least at age 74. For me it’s less embarrassment than feeling incompetent which is a different animal.
Two of my sons-in-law play basketball, and so does my ten-year-old grandson. Acquiring sons-in-law after raising daughters requires a different mode of bonding than I was used to, and the mode that presented itself was shooting hoops at the local gym or park. I was reliably last picked in elementary school. My only experience with basketball was 5th grade where the kid at whose house we played delighted not just in blocking every shot I attempted but jamming the ball back into my face then laughing hysterically and pointing at me. Basketball and I parted ways.
But recently — basketball again.So here I am, the one being taught now instead of teaching. In most rooms I’m the more experienced person. With a basketball in my hands, that completely reverses — and staying open to that reversal, letting them lead, is the actual cost of entry for me.
Thanks for writing a comment and sharing your ideas on incompetent vs. embarrassment. I see your point! And I’m proud of you for playing basketball with your family – that is something that I’m sure they either appreciate already or will in the future. Please know that I’m wishing you the BEST in your life adventures. Keep pushing yourself to experience new things!