Name: Shequaya Bailey
Age: 38
Hometown: Pittsburgh, Pennsylvania
Occupation: Director of Operations
Time Cycling: 12 years
Reason for Cycling: Initially for commuting—now for health benefits, training, and fun!


I learned how to ride when I was about five years old from my older brother. As I grew up, I continued riding for fun around my neighborhood. Eventually, when I went to Penn State University in 2002, I ended up buying a bike to get around the massive campus.

After college, there was a break in my riding, but when I lived in Atlanta from 2007 through most of 2010, I picked up a used bike to get around and rode that until I moved back home to Pittsburgh, Pennsylvania.

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A year or so after I returned to Pittsburgh, I decided to buy a “nice” bike (back then, this meant a road bike with the curved handlebars) for my commute. Through commuting, I ended up connecting with Bruce Woods, the president of Pittsburgh Major Taylor Cycling Club (PMTCC) during that time. As a result, I connected with and got to know more folks in the cycling community.

I rode my first race in 2013, The McKeesport Grand Prix. Back then, I didn’t really understand where races were or how people found them. I only knew about the few I did because of a friend. It took a few years of fumbling before I started to figure more things out, including how to find coaches and properly train for races.

I eventually started working with coaches and mixing up my training because I wanted to be a better racer, and to be faster. When I did not use a coach, TrainerRoad (a cycling training app) was a phenomenal addition to my workouts—and it still is. The thing I loved most about racing was going fast. I just loved the feeling, and I still love going fast!

Then, in 2019, I learned about The Black Foxes, a group of international individuals reclaiming Black roles and narratives in the outdoors, founded by William Loyd and Ayesha McGowan. I met them on the racing scene many years ago, and we’d always chat whenever we crossed paths. We maintained contact, albeit peripherally, since our first meeting, and in 2019, they reached out to form this collective of folks.

The Black Foxes is now four years old. I love that we are able to celebrate Black voices and share experiences doing activities we love because representation matters.

I enjoy being a cyclist because being on a bicycle is freeing. Riding relaxes my mind and rejuvenates my soul. I also really enjoy giving back to my community with my time by serving as president of Pittsburgh Major Taylor Cycling Club, volunteering on the Bike PGH board, supporting the Major Force Youth Program, and being a mentor for Pittsburgh Youth Leadership, and just trying to be a positive example within my community.

Since September is my birthday month, one of the ways I am celebrating is by doing a short solo bikepacking trip in up-state Pennsylvania, and then I will continue riding for fun until my trip to Spain in October, which will consist of eating, biking, fellowship, and art. After that trip, I will settle into building a base for the 2023 season.

shequaya bailey how cycling changed me
Courtesy Shequaya Bailey

Next year, I plan to focus on more road racing, some gravel races sprinkled in, and of course a little mountain biking to keep things spicy, along with a couple bikepacking trips too.

If it wasn’t for cycling there probably wouldn’t be a Shequaya Bailey here to talk to today! It truly saved my life when I was at my lowest. Cycling continues to lift me up and be a place of joy and meditation. Cycling has taken me to many places, which has given me an even greater appreciation for the earth. Plus, I have met some really awesome people.


These three tips have made my cycling journey a success:

1. Eat and drink well

Your body will only take you to where you want it to go if it is properly fueled. So eat foods that make you feel good and drink water (and electrolytes!)

2. Stay on top of maintenance

Giving your bike a once-over is good practice because it will help you identify any issues before your ride, like problems with air, brakes, chain, or tires. Having a professional tune-up at least once a year will make sure your bike and parts are in tiptop shape. The mechanic should identify and rectify any issues.

3. Find the saddle for you

Being that cyclists spend a good portion of their riding in the saddle, having one that fits your sit bones properly is key for comfort. Sometimes this search can take a while, but it’s worth it. Some shops can measure your sit bones and will allow you to use test saddles until you find the correct fit.


Shequaya’s Must-Have Gear

Apple iPhone 13: I love to take pictures and videos while I’m on my rides, and the iPhone comes in handy for that.

Velocio Women’s Bibs: I love the fit, chamois padding, and the colors.

Hammerhead Karoo 2 Cycling Computer: I love the mapping features, that it helps me figure out where I am going, and it keeps track of all my data so nicely.


We want to hear how cycling changed you! Send your story and submit your photos to us via this web form. We’ll pick one each week to highlight on the site.

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Emily Shiffer

Emily Shiffer is a freelance health and wellness writer living in Pennsylvania.