Biking 2,900 Miles, But in a Chill Way
An interview with Tina O'Brien
Tina O’Brien is 29 and lives in Fort Greene, Brooklyn. We went to college together, but you shouldn’t hold that against her. She recently spent the month of June on an epic bike ride from Florence, Oregon to New York City. We met up in Prospect Park the Friday before she left to talk through how she got into biking, her expectations for the tip, and whether there was anything she was afraid would happen…
Leg Day: When did you learn how to ride a bike?
Tina O’Brien: Very early. I’m from Woburn, about 10 miles north of Boston. Our house was the last house on our street, a really safe place to ride. When I was in elementary school, they extended our street into a double culdesac, two loops on top of another. It was a pretty cool setup. A lot of kids my age moved in, creating a little bike gang. We just zipped around in circles all day. My parents didn’t ride, it was just something for us kids. I didn’t really ride again until after going to college.
When did you get back into it?
It was probably 2017. I started a job in investment banking and just didn’t like it. It wasn’t a good environment. I was in search of a hobby that could fill my free time in a healthy, productive way. I found out my company was hosting a four-day charity ride for the Lymphoma Leukemia Society. They offered coaching for new riders, with scheduled group rides and clinics on how to use clipless pedals. It felt like a really safe and fun way to re-enter the world. And anyway, I had a big girl job and the money for a nice road bike.
The event went from from New York City to Raleigh, North Carolina. We rode an average of 80 miles a day and then hopped on a bus to get us to our hotels. Some people rode for just one day, but it ended up being about 40 of us that rode the whole four-day stretch. It was pretty intense for my first ever multi-day trip, but still fun. And we ended up raising $250,000.
Funny thing, I was by far the youngest one of the group. Other than one 30-year-old, most of the riders were older people from the Wealth Management division. I was only 23.
Did biking come to you easily?
Uh, no. One of my first long rides out of the city ended only five miles up 9W1. I got a flat, and only then learned I had thru-axles on my wheels. That meant my wheels were less likely to be stolen off my bike when it was locked outside, but also that no one could help me fix my flat there. They were like “You have to Uber to a bike shop.” I was so defeated that I just went home.
The next ride was somehow worse. I felt like everyone was paying attention to me as the person who was weighing the group down. But I was able to keep up with the squad that was going at a slower pace. And by the next time I felt like I had the hang of it—though I still didn’t know how to fix a flat.
But you were catching the bike bug.
Yeah, you can just go so far on a bike. I love running, but your body can really only go a certain amount of miles before giving out. Most of the time you’re biking, it shouldn’t feel too strenuous. You can go relatively fast while only expending the energy of a brisk walk or really slow jog.
Probably helps to have as beautiful a bike as you do!
I do get compliments on it. It’s my second big girl real bike. It’s a Liv Langma. Liv is the sister brand of Giant, a pretty well-established bike company. The Liv frames are designed to fit the average female frame a little better. The handlebars are more narrow, the angles are a bit different. It’s definitely more comfortable than my old bike.
It was still … a purchase that made me feel uncomfortable. Like, this is sort of dumb. But I’m pretty confident it’ll last me like 15 years. It’s a carbon frame and has electronic shifting. When I initially shopping around for this bike, I was very much like I’m a mechanical shifting girl. But after trying a couple of bikes with electronic shifting, I had to admit it’s pretty awesome.
It feels different?
It makes shifting literally as easy as pressing a button. It’s just a little click, then you’re in the next gear. There’s no weird in-between awkwardness. With mechanical shifting, you can be on an incline and literally miss the opportunity to shift. You’ll make the switch, but the chain just won’t move. So you just have to suffer in the wrong gear. With electronic shifting, that never happens. You never feel the effort.
How has your riding changed since that point … seven years ago?
I’m so much more comfortable. I don’t get distracted by trying to do things correctly. I can get into a flow state, into a Zen and focused headspace more easily. I’m the type of person that has trouble doing just one thing at once2. I don’t tend to love alone time. I’m pretty social and would almost always rather be around people. But when I’m biking, I find it pretty enjoyable to just be alone with my thoughts.
As I’ve been training to ride across the country, I’ve been doing some eight hour long rides. You have a whole day’s worth of experiences and emotions in eight hours, but all in the context of moment and sightseeing. There’s part of it also where, because it’s movement, I feel like I’m being … productive? I know that’s kind of a psychotic thing to say .. but like, I have a hard time meditating. For me, I feel like this gets me to the same place. Kind of.
I think a lot of people would be surprised to hear a New York City biker saying that it’s a very meditative and zen experience.
Ok, but city riding isn’t what I’m talking about. I don’t particularly love like, the First Ave bike lane3 or going down Second Ave. That’s honestly pretty stressful. That’s not to say you can’t experience a joy biking in Manhattan—after all, people watching is really a top tier activity for me. And I do love that you find yourself in all sorts of unexpected places when you bike. I’ve spent way more time in the Rockaways and Coney Island, really all along the great bike paths of South Brooklyn, than I would have otherwise. You’ll find all these niche, little artistic communities and very diverse neighborhoods. And because it’s on the coast, it always kind of feels like summer down there. Even when it’s November.
When did you get the idea that you wanted to bike across the country?
I started thinking about it when I quit that job in the fall of 2019. I was trying to coordinate a between-jobs trip. But the logistics were just too much to plan for the short two-week break, I ended up not doing anything biking related.
At the job I have now though, you get a month off for sabbatical after you’ve worked four years. About a year ago, as I could see the break ahead, I realized this was probably my best opportunity to actually go for it. I have the physical fitness. I don’t have any children. I don’t have anything that’s tying me in place. So why not actually go for it?
How have you been balancing training for a cross-country ride with planning a cross-country ride?
Nothing about this has been balanced so far. I’ve done the best I can, but I’m not logistically strong. I’ll go on group trips with friends, but I’m rarely the planner. I can be if you need me to be, but I don’t naturally have that skill set. So this has been interesting.
I started planning the route last December. I’m starting in Florence, Oregon, on the coast and ending in New York City. I’ve strung together four really popular trails: the Transamerica Trail, the Parks, Peaks and Prairies Trail, the Northern Tier, and the Empire State Trail. To do them all in a row, you’d have to bike like 4,300 miles. But I only have 36 days. I realized pretty quickly I wouldn’t actually have time to bike every single mile.
So, I’ve arranged to have a minivan with me, driven by rotating groups of friends and family. They’ll do whatever they want during the day unless I have some sort of mechanical emergency or end up being too tired one day. Basically, I don’t want this to be something that isn’t enjoyable at any point.
My goal is to cover between 2,500 and 3,000 miles. We’ll see. My training has been good, though I’ve still never ridden 100 miles more than one day in a row.
What does it feel to ride that long? I’ve never done it.
It’s a big mental hurdle, isn’t it. The century ride is such a badge of honor for bikers. But honestly, it doesn’t feel really that much different past a certain point. What’s the difference between riding for five hours and seven hours? As long as you are eating and drinking enough, avoiding crazy elevation changes and keeping yourself at a comfortable, chill pace, it’s kind of the same.
That said, I’m usually at peak enjoyment levels on rides between 70 and 80 miles. After that, I start to get the sense that I need to wrap things up.
What are you most excited to see on the trip?
Yellowstone will be a highlight. I’m really excited for South Dakota. I think that state will blow my mind. I’m looking forward to riding along Lake Erie. And then, I’m going to do the Empire State Trail from top to bottom, which will be super cool.
But I’m almost more excited to get to have quality time with the people who will be joining me. It’s actually six different groups that are rotating in and out, I’m coordinating with 20 or so different people at all times. My parents are coming for a week, which will be really wholesome. I’m one of five, so I don’t get a lot of alone time with them.
Will anyone be riding with you?
Yeah, I’ll ride with some friends when I’m in Chicago. Then three of my friends will meet me in Syracuse, two of whom will bike with me down the Empire State Trail. Oh, I’ll also have a guest bike with me. I found a $50 bike on Craigslist in Portland that I’ve arranged to pick up when I’m there. If anyone wants, they can hop on that and ride with me for a bit. Otherwise, I’ll meet people along the way I guess, but I mostly plan to ride alone.
What do you listen to when you ride alone?
Oh, I don’t listen to anything when I bike.
Really?
Yeah, no.
That’s crazy.
You’re not the first person to say that. They’ve been like You gotta have a lot of podcasts ready! But I have nothing downloaded. No audiobooks.
WHY?
I just like being fully present. It’s meditative for me! I’m telling you! At the end of a long bike day, I feel at peace. Accomplished. Calm. I guess that’s what being really tired can do for you.
Is there anything you’re stressed about?
Oh, definitely! I think I’m still underprepared in the mechanical department. I know how to change a tire now. But anytime I get a flat on the side of the road, there’s always someone who comes over to help. It’s way easier with help. Even after all this time, I still can’t say I’ve ever 100% solo changed a flat. I’m just hoping the YouTube videos I’ve been watching as research will be sufficient.
Honestly, I don’t think I’ll ever feel fully competent with bike mechanics. Even going to a bike shop can make me feel like I know nothing. In my life, I’m usually comfortable being the person that asks a billion questions. But something about the world of biking is so intimidating.
It’s interesting to hear you say that, you’re clearly an excellent cyclist.
Yeah, I have some hours on the bike.
Is this just a bike culture problem?
Yeah, it’s definitely bike culture. I’m a big runner too. In the beginning of 2023, I started running socially. It was a new discovery for me. And it was such a welcoming environment. No matter your experience, there were always people willing to offer you wisdom, take you on runs. I had no trouble finding people that I could gel with.
Biking is a much harder world to enter. It’s very inaccessible. There’s a lot of obsession with status. People put a lot of value on the physical bike itself—its brand, its style, the gadgets you have on it. There’s also a lot of bikers who give you the “I’m better than you” attitude. Like a very old white European male vibe. I’ve gone on group rides in the city with pretty established clubs and just didn’t find people who were proactively like “"Let me help you learn, let me teach you!” The attitude was more like, “Well, if you can’t keep up, go to a space where you can.”
Why do you think that is?
I think it’s because you can buy speed. You can! You can spend $10,000 on a bike and you will have a huge advantage over someone who has a bike they bought on Craigslist for $100. I also think that because cycling is an endurance sport with a lot of internationally respected accolades, I think it attracts really hyper competitive people.
Have you found spaces in cycling that feel more comfortable?
Oh yeah. You have to work for it, but you can find people. I’ve actually started riding with a group of triathletes. I met one of them through running. As soon as he learned I want to do a triathlon, he invited me to ride with them. They’re all doing half Ironmans this year. They’re more the energy I’m seeking.
Have you wanted to try racing?
I definitely want to do a triathlon. I would enjoy training for multiple things at once. The training for this trip has made me miss other things. I have days where I’m like, I wish I could do a long run, but I literally just have to bike. I still enjoy it, obviously, but sometimes we just need a change.
Do you have any advice for those who aspire to get to your level? Novices like me that have still never crossed the George Washington Bridge on two wheels?
Don’t let the sport intimidate you with all the gear, the lingo. Don’t let that stop you from participating. Carve your own space in the community. Look for the group that suits you best. You’ll have a blast.
9W is the highway that goes up from the Western exit of the George Washington Bridge to Nyack, New York. The route is about 45+ miles and offers 1,500 ft of elevation.
Relatable.
A pretty decent way to get up from the Manhattan bridge into the East Village TBH.
Great article! Amazing woman!
what a great piece!