You're Never Too Old: To Learn New Tricks

Founders Intro

Starting something new can be daunting, especially when society tells us we’re “too old” for change. But at Hollow Head Threads, we know that adventure and growth have no expiration date. Just look at these legends who defied expectations:

Colonel Harland Sanders (at 65 years old) – Founded KFC in 1955 after years of setbacks.
Barbara Hillary (at 75 years old) – Became the first African-American woman to reach both the North and South Poles.
Fauja Singh (at 89 years old) – Became the world’s oldest marathon runner, completing his last race at 101.

I should probably apologise to Ryan at this point, making him follow this epic list of pioneers... the last thing I want to do is minimise his transformation. It takes balls of steel and a lot of knocks, if nothing else!

So… without further ado… Meet Ryan, a customer of ours who picked up skateboarding in his mid-30s—not just as a hobby, but as a gateway to personal growth, self-discovery, and an entirely new community. I first met Ryan selling him a Trucker Cap at a market in Cambridge, but it wasn’t until he posted about loving our trucker hat (his new favourite!) that I noticed his growing passion for skating.

Getting to know him has been a pleasure, and it’s even inspired my youngest son to take up skating—a hobby that had a huge impact on my own childhood. Thanks mate! My son's brand-new setup is the title image of the Blog!

His Instagram account has tracked his progress from Day 1, and as soon as I saw it I knew we had to sit down and hear his story—how he pushed past doubts, embraced the falls, and proved that it’s never too late to start something new. What is also clear is how starting a new challenge can help your mental health.

Bottom of Form

You can follow Ryan’s journey at:

https://www.instagram.com/cottonbottomskate/

You're Never Too Old For New Tricks; Interview

Inspiration

What first inspired you to pick up skateboarding, and at this stage of life?

I've always had a passion for anything that gets the adrenaline pumping! Growing up, I spent a few awesome years BMXing, but then life as an adult got a bit overwhelming for me. I went through a rough patch and really lost myself. Thankfully, I had some great counselling and met a partner who has been really supportive. With that encouragement, I felt ready to do something for myself again. Skateboarding was something I had always wanted to try, so I decided to grab a second-hand board and give it a shot! That's how my skateboarding journey began!

What were your biggest hesitations about starting something new, especially something as physically demanding as skateboarding?

At first, I felt a lot of hesitation about stepping into public spaces to learn something new, especially as an older person in environments filled with mainly kids and families. It can be intimidating to put yourself out there, and I definitely felt that. However, once I began, my concerns shifted; I became more aware of the risks, like the possibility of getting hurt and being unable to work, and the faces started to fade.

Challenges and Overcoming Them

What were the biggest challenges you faced in learning to skateboard?

I’d say my social anxiety has been quite a challenge for me. It's something I still work on today. In the beginning, my physical fitness and my recklessness slowed me down a bit because I’d jump into things I wasn’t quite ready for. But that same reckless nature also helped me progress quickly in many ways!

Did you experience moments of doubt, and how did you push through them?

Yeah, there has been a few moments were I thought about giving up, I found it really hard were I would learn something and then the next time I skate I couldn’t do it. It’s a massive mental battle and most of the time I think you have to try and relax and trust yourself and the board

How did your body and mind adapt to the demands of skateboarding over time?

I've seen such incredible improvements in my physical fitness, and surprisingly, all those falls I've taken have actually helped strengthen my body, which is a silver lining since I still tend to fall quite a lot! My mind has had to adapt because I tend to hyper focus on tricks and will kill myself trying to achieve something, so I’ve had to adapt and sometimes know when to stop and try another day!

Impact on Life

How has skateboarding changed your perspective on life or other challenges?

I think its brought a brightness back, Its easy to get sucked into all the mundane bill paying and superficial stuff but life isn’t supposed to be that for me and I think skateboarding has made me realign with that outlook.

Has this journey impacted your mental health, or both? If so, how?

Skateboarding has been a game-changer for my battle with depression. For as long as I can remember, I've struggled with it, but when I'm out on my board, everything changes. Each session offers me an escape where my mind is solely focused on the thrill of skating. It's an incredible way to stay present, feel grounded.

Did this new hobby open doors to new friendships or communities?

Yes! Yourself included! I think the skate community is awesome. Everyone is really welcoming and no matter what trick you're trying to get, even if its dropping in for the first time, everyone gets pumped for you! I think the friendships I’ve made along the way is probably the biggest surprise for me, and it’s kinda bought me back out of my shell.

Inspiration and Advice

What advice would you give to someone who feels like they’re “too old” to try something new?

Forget your age! It's merely a number that we can allow to limit us. If you feel inspired to step out of your comfort zone and embrace something new, do it! You may surprise yourself and discover a new way to enjoy life.

If you could go back in time, would you have started skateboarding earlier, or was this the perfect time for you?

I believe the last year was the ideal moment for me to be honest! While I sometimes wish I could bounce back from a fall like I did when I was younger, I think that skateboarding with the wisdom of experience has brought me significant benefits! Though when I see some of the kids absolutely shredding it, maybe I do get jealous haha.

How do you stay motivated to keep improving and enjoying your new passion, whilst losing chunks of shin?

Haha! Yeah my shins and elbows are battered constantly! I think the feeling of getting a new trick trumps any injury though!

Looking Ahead

What are your future goals or ambitions with skateboarding?

I'm not too sure actually, I think just to keep enjoying it and skate as many places as I can! I would like to enter a little competition at some point, and I would really love to get the balls to start skating vert ramps.