I used to think I was about as fearless and empowered as any cyclist out there. Then I rode with Cherokee Schill.

When I was in Lexington, Kentucky recently for a Bicycle Friendly Community visit, Bill Cole, founder of Bike Kentucky offered to arrange a meeting with Schill, a woman who’s been ticketed and even jailed for biking to work in the travel lane, rather than the shoulder, of a busy state highway.

Of course, I said ‘yes’ and the three of us met in one of most bike friendly establishments in Lexington, where artistic bike parking awaited us, and the streets getting there were equally inviting.

Earlier that day, when I rode with city staff and advocates like Cole, the focus was on how Lexington could surpass Louisville in the quest to become the first Kentucky community to reach the Silver-level BFC status. We saw a number of promising developments, including a new two-way cycle track on a bridge seamlessly connecting two off-street trails –- truly a perfect place for such a treatment. New bike lanes were being striped and a good amount of bike parking was evident in the downtown area.

So hearing Schill’s story didn’t completely fit with what I had experienced that day. But like most U.S. cities, there’s the good, the bad and the ugly and, if you’re going to bike to work or for other utilitarian purposes, chances are good that much of your ride will be on the bad — or the ugly.

Schill is a single mom with a full-time job, 18 miles from her home. It barely pays the bills, and, when she lost her license for failing to pay a fine at a time when she couldn’t afford car insurance or proper maintenance on her vehicle, she announced one day at work she was going to have to start riding a bike.

Her co-workers thought she was kidding. Having not ridden since she was a child and living and eating like the average American, Schill struggled on her first commutes -- three hours each way. “I’d get to work exhausted,” she told me. “I’d get home late at night even more exhausted.”

Today she can do the commute in little more than an hour and has become one amazing cyclist. But even the most fit would likely think twice about riding with her. Her route? Highway 27, a road with a 50 mile-per-hour speed limit, and a shoulder strewn with debris, gravel and rumble strips that make it very difficult, if not impossible, to ride on safely.

When we teach cyclists how to ride in a safe manner, we tell them to do what Schill has been ticketed for: riding in the traffic lane. In our Safe Cycling curriculum, we tell folks, if a shoulder is unusable because of debris, or because it ends suddenly or turns into a turning lane, it may be safer, more predictable and certainly more efficient to use the right-most travel lane that goes to your destination. And if that travel lane is not wide enough for a motorist to safely pass you without changing lanes, we teach that you, not only have the right to use the full lane, but in fact, in order to protect yourself, and be a good role model for other bicyclists, you have a responsibility to take the lane.

For more than 25 years I’ve been teaching cyclists that you “never compromise your safety for somebody else’s convenience” understanding that being assertive is essential for safe cycling. And that’s what Schill was doing.

When I rode with her it was during the late afternoon rush hour period, in the direction with the most commuting traffic. As I attempted to keep pace with her, a very fast rider, most of the drivers did exactly what the law and good sense say they must do: change lanes to pass. And yes, some of the drivers might have had to take their foot of the accelerator for a few seconds and wait for a break in the traffic to the left of them before resuming their high speeds. But in no way did Schill impede motorists and in no way was her presence causing any inherent harm to anyone else on the road.

Still, a few did seem to get upset (based on the honking we heard) and one motorist made a point of passing Schill on the right by using the same debris-strewn shoulder that she avoids. There was absolutely no one in the left lane at the time, so clearly the motorist’s intent was to intimidate.

Soon, what began as an adventure became stressful. The conditions on Highway 27 are not all that different than many of the highways I’ve ridden on, or even brought groups of League Cycling Instructor (LCI) candidates to ride on as part of their training. We look for situations where shoulders or bike lanes abruptly end or turn into right-turn-only lanes or high speed merging lanes onto freeways because, unfortunately, this is the reality of many cities. The whole point of our training is to empower people to be able to bicycle anywhere. And by being predictable, conspicuous, assertive and alert, experience reveals that it can be done with relative safety.

But for some reason, this felt different. While there are many situations in which you don’t feel quite welcomed by other road users, this truly felt like a hostile environment. I wondered if Schill had become desensitized to the hostilities or if it was just me, projecting onto all of the road users what I had observed from a single motorist.

Or was it because now our actions (in order to be safe) were acts of civil disobedience — as we were driving our bicycles the same way that caused Schill to get the citation in the first place? And now that she had been given the official label of “offender” some motorists felt justified in their display of hostility?

After I said good bye to Schill and turned around to go back to where we had started from, I was faced with a decision: Was I going to continue to ride the way I teach — using the lane the way Schill and I had traveled — or take advantage of the debris-filled shoulder where it existed and not worry about getting a flat?

At first, there was no decision because there was no shoulder to use. But after riding in the travel lane for the first mile or so, taking the lane, by the time the shoulder appeared, I decided enough was enough. And it felt good to be on the shoulder.

But then, suddenly, it disappeared and in its place was a high-speed turning lane. Even though I gave myself plenty of time to look back and merge into the straight-through travel lane, there were just too many cars going way too fast to get into a safe position. So I stopped and waited. And waited. And waited.

After that experience, I fully understood why Schill avoided the shoulder and rode in the travel lane. And that’s what I did the rest of the way.

So what can the League do? It’s a complex issue to think through. Stay tuned this week for more analysis and thoughts on this important topic.