My First Paddleboarding Experience, The Messy Win I’ll Never Forget

I’m writing this so much later than planned, but trust me, I had a whole movie happening in the background.

I literally lost the bag that had my diaries in it.

I visited Playa del Carmen in November, had this beautiful paddleboarding morning, and the second I got back, I wrote the whole thing down. I was so sure I’d edit it and post it as soon as I landed in India. Then came the delayed flights, the long waits, the tired brain, the whole airport mess, and one bag just… vanished. My diary was inside.

And I’m not even exaggerating, I was praying like, please God, please Universe, bring it back. Those pages hold my notes, my moments, my little insights, everything I build from.

I was also talking to the Universe like, okay if you want me to take this as a sign that these diaries are actually needed for the goals I’m chasing, then please return them to me!!!

Yes, I emotionally blackmailed the Universe. A little.

Anyway, I got my bag back. After so long. After thinking I might never see it again. Super Grateful!!!🥹

I opened it, caught up on everything, and I felt ready.

So here it is. One of the most unforgettable mornings I’ve had in a long time.

This Was More Than a Getaway

I had been planning this Playa del Carmen trip for a couple of months.

I was eyeing it for a while because I genuinely needed it. A complete break from my non stop work mode. I wanted space. Sun. Slow mornings. A reset.

One of the things I’d been excited about on this trip was visiting my mentor Jaymi. I also joined her VIP coaching experience while I was there, and it ended up adding so much more depth to the whole experience. It became one of the most meaningful parts of my time in Playa. It felt less like sessions and more like being guided through life, while actually living it.

We did a lot together as part of her VIP coaching experience, salsa dancing, taco night, beach coaching, an amazing photoshoot and other little things that made the whole trip feel alive, including sunrise paddleboarding too. And honestly, this trip brought me closer to myself. I saw what was holding me back, and I also saw myself handle it, in real time.

Grateful for her guidance, always.💜

And Jaymi, she’s been such a wonderful mentor. The calm, the clarity, the support, the way she holds space while also keeping it real. I feel really grateful to have her by my side in this journey.

And among all the eye opening experiences, sunrise paddleboarding hit the deepest. Because it wasn’t only fun. It was personal.

Also, 2025 has been full of my “firsts”, planned ones, unplanned ones, the ones that scared me, and the ones that made me feel alive. And my Playa del Carmen trip added a couple more to the list, my first paddleboarding experience, and yes, salsa dancing too.💜

A Very Personal Yes

When Jaymi told me sunrise paddle boarding was included, I said yes instantly.

And then my brain was like, excuse me… do we remember we don’t swim?

I’m not scared of water exactly. I’m scared of what water has meant for me.

Boats are fine. Kayaking is… complicated. I tried it years ago with my ex and it ended in a fight, so water never became this cute “healing hobby” for me.

And then there’s the deeper layer, childhood. I had a moment in the ocean where I almost sank. Maybe it wouldn’t sound like a big deal to someone else, but my brain filed it under danger. And once your body learns fear, it doesn’t care how grown you are now.

Also yes, I still don’t know how to swim.

But something in me was tired of living around this fear. I didn’t want it deciding what I get to experience.

So I signed up.

The plan was sunrise paddle boarding, and then a life coaching session in the middle of the ocean.

I honestly saw it as a chance to loosen a fear I picked up as a kid. That fear had been quietly blocking me from experiencing the vastness of this whole element. So I decided, we’re doing this. No backing out. Discomfort is basically the entry fee for growth anyway.

And I felt safe enough to try because Jaymi was there, and we had an instructor.

And I’m genuinely glad I did. It felt liberating.

After this, I’m learning swimming. Consider it my next little rebellion against old fear.

Sunrise did half the therapy before I even stepped in

The craziest part is we planned it on the same day I was flying back to Montreal.

So I woke up early, had my chai, Jaymi picked me up, and we headed to the beach. It's called Mamita's, if you are taking notes and want to try the paddle boarding!

https://video.wixstatic.com/video/8e0208_edddb36afdb04dd1abc452b248150552/1080p/mp4/file.mp4

Proof I say yes first, then process later. One hour before Sunrise paddleboarding. 😂

When we reached, I remember the vibe so clearly.

It was calm. Peaceful. Almost unreal.

People were meditating. Some were just sitting there quietly. Some were running along the shore. And it hit me because I hadn’t seen mornings like that in so long, where the world isn’t rushing you and you’re not rushing yourself.

And then add the ocean waves, that soothing sound, the sky slowly turning lighter, and the sun sitting on the horizon about to rise. I felt grateful. And a bit emotional.

Because I genuinely never thought I’d get to experience this. And in that moment, I forgot the fear I was carrying.

I was fully in the present moment. For a minute, I forgot I even came for paddleboarding.

And then… I didn’t panic??

It started fast, and I fully expected panic, but I didn’t get it.

It turned out to be a group activity, so Jaymi and I joined in. They handed me a life jacket. The instructor walked us through a warm up and explained most of it in Spanish, then switched to English for us. He knew I was new, so he set me up with the board, had me walk beside him into the water with the board.

Here’s the funny part.

Before this, I had already lived the moment in my head a thousand times. I kept imagining how terrified I’d feel when I stepped onto the board and the water was right there, with nothing holding me except balance and courage. I kept telling myself, yes, it’ll be scary, but we’ll get through it.

And then the moment arrived.

And it was completely different.

Our instructor told me to lie upside down first, then sit up slowly once I settle later, then come onto my knees and as I hopped on it, pushed the board a bit. The board moved with the water, just enough to remind me that this isn’t solid ground.

I tightened my core because you can fall straight in, no corners, no walls, no “safety rail,” just you and the ocean.

And I didn’t feel fear.

Weirdly, I felt… peace.

It felt like I was flowing without fighting it, like I could let nature lead for a second.

And it reminded me of life in the simplest way, we suffer so much in advance.

We rehearse fear, we run worst case scenarios, we brace for impact.

Then the moment arrives and we realize we were capable all along.

Anyway, I drifted again, just like my board. Back to the story. 😃

Why Was I Always Drifting

I started pedaling the way the instructor taught us and moved toward deeper water.

I was the slowest one, obviously. I was trying to figure out the pedal rhythm while also trying to stay balanced. Jaymi and the instructor stayed close and kept correcting me, grip it like this, hold it like that.

Certified first timer moment. ✅

Also, can we talk about how this is a workout. A real one. My arms were working, my core was working, my pride was working. I was so focused on learning that I didn’t even realize I had been scared earlier.

The water felt refreshing, the wind was cool, and the sun was slowly rising like it was taking its time. Ocean, sunrise, paddleboarding. Such a gorgeous combo. And then the tricky part started.

That morning the current was pulling away from the shore, so we had to keep pedaling back toward the shore every now and then so we don’t drift too far out. They’d set up this floating boundary line too, weighted markers showing how far we were allowed to go.

And that boundary was actually there to protect us, but for me it turned into a magnet. No matter how hard I pedaled, my board kept drifting toward it. No matter how hard I pedaled, the current kept pushing my board toward it. And yes, maybe some of it was my beginner skills too, because I kept bumping into it again and again while everyone else looked like they were nailing this.

Most people in our group were standing on their boards like pros. A couple of them even fell straight into the water, but they were totally fine, because of course they knew how to swim. From the looks of it, this was just… normal for them.

The boundary kept saving me..and roasting me. 😅

I kept shifting around to stay steady. But standing, nope. I had no interest in becoming a headline.

I kept thinking about the balance of trying new scary things, instinct and logic together. Instinct says try it, challenge yourself, face the fear. Logic says don’t push so hard that you turn a good memory into a trauma story.

Also, if you’ve been reading Life With Ridi for a while, you know this wasn’t my first “say yes while shaking” moment this year. I’ve been collecting these little proof points, the ones where I do something unfamiliar, survive the awkward part, and come out feeling more like myself.

If you want more of these stories, here are a few blog posts you’ll probably enjoy too:

• [Stepping Out of My Comfort Zone, Part 1]

• [Stepping Out of My Comfort Zone, Part 2]

• [Stepping Out of My Comfort Zone, Part 3]

Anyway, I drifted again.

So Jaymi was watching from a bit far as I kept running into that boundary and kept asking, “Did you mean to go there?” 🤣

My Brain Picked FRIENDS at the Worst Time

While I was pedaling on my knees, trying to stay stable, I felt this intense sharp pain near my right thigh.

Out of nowhere.

And immediately my brain went to the TV show, FRIENDS. Jellyfish. Monica screaming. Joey and Chandler trying to “save” her. 🤣

If you’ve watched FRIENDS, you know exactly what scene I’m talking about.

I looked down and saw a big weird insect on my leg. I pushed it off instantly and it fell into the water, but the pain was still there, proper sharp. And my brain went right back to Monica again.

And I started laughing in my head because if anyone ever tried that “pee to fix the sting” situation on me, I could actually do it easily because of where I got bitten. I know. I know. My brain is slightly unhinged.

But honestly, I admire my talent for creating comedy in my head while I’m literally in the middle of chaos.

Anyway, I kept pedaling.

And of course… that wasn’t the last twist.

Okay This Is Where It Got Real

Only later did I realize how much my nervous system was taking in.

Everything was new, the water, the current, the effort, the fear underneath, the adrenaline, and I didn’t notice the anxiety building in real time.

But it was there.

Quietly stacking up under “I’m fine, I’m fine.”

Jaymi was closer and I told her I was feeling nauseous. Motion sickness from the waves, anxiety, maybe both. She told me to take deep breaths and remind myself I’m safe, I’m doing great.

I did. I felt better for a bit.

And then I threw up.

Into the ocean.

Yes. The chai I drank early morning came right back out, and I rinsed my mouth with salt water🥲

I felt embarrassed, and it was also funny, and also anxiety inducing, all at once.

I was so glad paddleboarding came with drone shots in the package too. And I was even more glad it didn’t catch that exact moment. Imagine.😆

Me vs. The Waves, Round 2

Since I was still nauseous, I decided to go back to shore early.

Everyone else was still enjoying the experience, and I didn’t want to throw up again and start hating something I was actually enjoying.

I let Jaymi know, and started pedaling toward the shore. Meanwhile Jaymi was just taking it all in, the sky, the waves, the whole beautiful scene around her. She’s an ocean baby for sure.❤️

Now here’s what I didn’t know, I didn’t know how to land properly. We were supposed to come back together so the instructor could guide me.

The board was strapped to my ankle. The waves near the shore were intense.

And I started doing calculations like, if I hop off and the wave pulls the board back, my ankle is coming with it, and this board is heavy, and I will become entertainment.

So I decided to make my own way.

I hopped off as fast as I could, detached the strap before the next wave came in, and tried to lift the board.

There is a certain way to lift it.

I was not doing it.

The way I tried to lift it while also trying to stop it from drifting again with waves was hilarious. I looked like a clown. I was wobbling, struggling for balance, dragging it like it was a stubborn suitcase.

I asked myself a thousand times, what the hell am I doing?

I was also looking around to check if I even landed at the right part of the shore.

Anyway, I finally managed to drag it onto the sand.

I was squatting and pulling it.

If anyone on the beach saw me, I hope I gave them a good laugh 😂

Then Jaymi reached and landed smoothly and lifted her board properly, and I was like, okay… so that’s the technique.

We took pictures after, me holding the paddle like I conquered a battle.

Because I did.

Sting, nausea, throwing up, current, boundary bumps, shore chaos.

And yes, I might have missed a few moments of the sunrise while dealing with all this, but honestly, that day, the sun saw me rise too.

Earned this picture, no discussion.

Coaching, but Make It Beachside

We were supposed to do a live coaching session in the middle of the ocean, but after everything, we switched plans and did it at this brunch spot called Lido.

Coaching, carbs, and waves!!!

Jaymi took me there, and we talked through what happened. She also asked me a few questions that were left as part of the life coaching, and then we did future visualization too. It was expansive!!!

Also, I tried to speak Spanish while ordering, and the only thing that came out was “para mi,” and then I immediately returned to English!

I had red velvet pancakes, and Jaymi had a delicious bagel. So good.

And the spot was right by the beach. We were sitting on chairs placed on the sand, and the waves were almost touching our feet.

So… What’s Your Scary Yes

This whole experience is unforgettable for me. It wasn’t just a “fun activity.”

It was me taking a fear that’s been living in my body for years and showing it who’s in charge now.

I’m glad I did it. I’m glad I said yes even though my brain had a full fear playlist ready.

And I’m writing it here because I know I’m not the only one who has something they’ve been postponing because it feels scary, or unfamiliar, or “not for me.”

So here’s your gentle push from me, pick one thing.

One small step. Do it safely. Do it with support. Do it even if your hands are shaking a little. You don’t need to feel fearless first, you just need to be willing enough to begin.

And then… I flew back to Montreal.

I’m proud. ✅

My flight was in a few hours, which means I went from sunrise paddleboarding chaos to airport mode in the same day, very on brand for me.😜

But I carried this memory with me, proof that I can do hard things and still laugh in the middle of it.

And while I’m editing this, I’m smiling because I ended up enduring another round of airport chaos after that too, and somehow still laughed and enjoyed parts of it even in the middle of the mess.

Now tell me, what’s one thing you’ve been wanting to do but you keep hesitating?

Reply, DM me, comment, whatever feels easy. I want to cheer for you.💜