The Dangers of Optimism

“I try not to make plans. Because, even the best laid plans etc. etc.” ~Brent Spiner

This isn’t a story of bitterness; and it’s not a story in search of pity. It’s a story about how even when everything is done right, things can still go wrong. As cyclists, we need to understand this. You can do all the hard training and prep for your first century, and then the temperature blazes at 110° all day and you don’t make it. You can plan your race strategy and skip those cupcakes and focus in every right way, but during the race someone makes a mistake, and you end up in something more akin to a rugby scrum instead of on the podium.

It’s also a story to show just how much goes into the events we participate in all the time. A peak behind the scenes, as it were.

This is the story of the Hilton Hill Climb Challenge.

The Concept

Terry, myself, TJ, Danny, and Ronnie, supporting me in my first effort to do 20 laps of Hilton Hill in 2014.

Several years ago, I got it into my head to do hill repeats in a jog-a-thon fashion. An assistant instructor at my kung fu school had made the U.S. National team and would be traveling to China, and I wanted to help. So, I setup a Saturday where I’d ride up and down a hill called Hilton Hill up to 20 times. Four of my cycling buddies joined me. Given that there were only five of us, I just packed a cooler with some drinks, got some cookies and Gatorade and bananas, and threw it in the back of my truck.

The weather turned out beautiful. We rode the hill over and over, for almost 2 hours, cheering each other on as we passed one another. In the end, I did my 20 climbs, and we raised a good sum of money.

Fast-forward three years. I’d now been a member of the greater Tulsa cycling community for seven years. I’d ridden numerous tour rides, volunteered at events, raced dozens of races, and I knew people in almost every casual riding club, bike store, and race team in the region.

This time, instead of just one person making the U.S National team, our school had five people, including myself, and we’d all be traveling to China to compete in the world championships. Given the success of my small fundraiser three years ago, and my much larger network and deeper relationships in the cycling community, I had the idea to revive that hill climbing fundraiser, but this time as a full-on cycling event.

I know what you might be thinking. “Um, isn’t that a little self-serving?” I won’t deny that when I started this, my main goal was to raise funds for my teammates and I. After all, it’s a pretty big deal to be traveling to the equivalent of the Olympics for Kung Fu. But as things progressed, I felt like I was embarking on something even larger. What if this event wasn’t about raising money just for my kung fu team? What if it was about a community of athletes raising money for other local athletes so they can compete at national and world levels?

From that point on, it had little to do with us so much as a first potential test of what this could become, and what it could do to help people achieve their goals.

The Setup

Many cyclists never get into the “setup” side of events. It’s good to know what goes into these kinds of things. I mean, it’s easy to complain that a route had bad roads or high traffic, or that a rest stop ran out of your favorite cookies. But seeing all the pieces that go into setting up a successful event gives you an appreciation for all the things you don’t even consider while actually riding the event.

So, I’ll walk you through what I had to consider:

Hilton Hill: 4% grade, 0.5 miles long.

1. Location: Hilton Hill was ideal for our purposes. It was half a mile long – a good climbable length for beginners, and yet still long enough for experienced riders so they’d have to put in an effort. It averages 4% grade, which again, is shallow enough to make it hard for beginners, but steep enough to add up for the stronger riders. The road is wide, with low traffic, good sight lines, and an East/West direction (which is good, since our wind usually comes out of the South). Apart from the lack of parking and facilities in the area, I couldn’t find another hill that met all the criteria.

With the help of the Creek County Commissioner, we were able to get the road closed and repaired for the event.

2. Safety: There were a few problems with the location. First, though traffic was low it was fast. Cars blaze down that hill – and up. So in order to make it a safe event for cyclists repeating the hill, we’d have to get the hill closed. Closing a road is difficult, especially when you’re in a rural area where it’s hard to determine who even manages a road. Beyond closing it, the hill had some pretty large holes that would pose hazards to descending cyclists. So not only did we have to get the road closed, but we had to get it fixed as well.

I spent months tracking down the right officials, sending e-mails, leaving messages, visiting offices. It wasn’t until I found a cycling friend who happened to know someone who knew the very person that I needed to speak with that I was finally able to get a meeting, and in turn get the road closed and fixed.

3. Parking: Usually, events can find parking in places that aren’t used on weekends, such as schools, or business parking lots. But the hill didn’t have either of those. So the best we could do was to use a school parking lot 2.5 miles away. For non-riders/spectators, we’d have to find a van to shuttle people over, and like a tour ride, we’d have to add signage to get people from the school to the hill.

4. Rest Stop: Rest stops need food, water, Gatorade, ice, tools, tables, tents, chairs, medical supplies, and on and on. I’d setup rest stops before for our club rides, so I had some experience here. However, getting these supplies costs money, so we’d need to find sponsors.

5. Rest Rooms: Rest stops usually need rest rooms. And guess what? A hill on the outskirts of several cities in an unincorporated area has none. That meant finding porta-potties, getting them setup, and getting them paid for. More planning needed, more sponsors needed.

10 climbs would equate to 10 miles (half uphill, half down hill), in 90 min. An achievable – though still challenging – goal even for novice riders.

6. Prizes: Many events are just rides, where the route itself is reward enough. But here, our riders would be repeating the same hill over, and over, and over. We’d obviously need something a little more enticing than the scenery. So we found medals for certain numbers of repeats, and prizes for top climbers. And since this was a fundraiser, we decided to incorporate a raffle as well, which meant finding more prizes, but hopefully in turn raising more money through ticket sales, and giving spectators ways to get involved without riding. This meant talking to dozens of companies, clients, and friends in search of items and support for the event.

7. Scheduling: When would this take place? It’s a new event, so I needed to find a place to fit it in. Too early in the season, and it’d be cold, and people wouldn’t want to challenge themselves to riding hills. Too late and it’d be hot, or interfere with other well-known tour rides and races.

All hands on deck (though slightly bored): all five members of Team USA volunteered, as well as their family members.

8. Volunteers: We’d need a lot of help. Every event needs people to work rest stops, and to watch the course and/or drive SAG. In this case, we needed the same, but we’d also need people to count the climbers (since we couldn’t afford a tracking system). Fortunately, we had my teammates for which the event was raising money for, giving us some volunteers. But we needed to get more.

9. Production: People are visual, especially in today’s social marketing world. They need pictures, and graphics, and videos. That meant I’d need to create graphics and banners, PDFs, take pictures, compile videos, and write lots of content to convey not only the message of the event, but who it’s supporting.

10. Registration: There are hundreds of registration platforms. But this was also a fundraiser. What a lot of people don’t realize is that none of these things is free to use. BikeReg doesn’t list events out of the kinds of their hearts. GoFundMe is really about “GoFundGoFundMe”. That meant I had to go through dozens of systems in order to find the one that was the easiest to use, and would provide the cheapest fees for using them. Would you believe that GoFundMe – despite appearing altruistic – takes 7.5% of all donations? That’s not insignificant. You raise $2,000, they’ve taken $150.

Spreading the Word

This goes back to #9 above. How do you get the word out about a new event? How do you get people excited about it? Many people say they want to ride just to support the fundraiser, but inwardly, they want the challenge, or they want the prizes, or they want to do an event because their friends are doing it. You will get riders who are there to help with the fundraiser, no doubt about it. Cyclists are typically a giving lot. But, there are lots of other motivations you have to take into account.

Though I posted on average 3x per week, the majority of people interested in the event only saw 1 of those 3. Facebook is not very dependable.

I decided Facebook was one of the easiest ways to get the word out. I created an event, and graphics that supported the event. I created an event flyer that described the event. I wrote the stories that described why we were holding the event, and who were were holding it for. But even on Facebook, word doesn’t spread itself. In fact, Facebook doesn’t show everyone every post, even for events people are interested in.

So every week, I had to come up with posts to keep the event top of mind. I wrote biographies for our team members. I created compilation videos for each member. And as we gathered raffle prizes, I wrote posts that featured the sponsors and the prize details. I ultimately wrote 31 posts, averaging 2.5 posts per week. I spent approx. 75 hours writing the posts, producing the videos, writing documents, and compiling images.

Beyond online efforts, I spoke to my cycling friends, describing the event and trying to generate interest among the various clubs and teams. I went to group rides that I usually didn’t do just to make sure I could mention the event a time or two.  I no doubt drove some cyclists insane with mentions of this event, in the way some racers talk up large races they are going to.

Here’s something that should be understood: I grew up being taught not to ask for anything. Literally, nothing. So to this day, it’s difficult for me to ask for assistance. It’s hard to ask people to come to an event, to support me, to donate things. Every company and person I spoke to took a piece out of me.

Living With the Results

After 4 months of planning and work, we had 70+ riders say they were coming. For a first-time event, that would be great! We had almost 150+ interested or indicating they wanted to go. There were no conflicting races or tours that day. We arrived before the sun was up, and starting settings up the course. Weather was absolutely perfect, with a slight breeze to help riders up the hill. Road closure signs, safety cones, tents chairs, tables, volunteers, food enough for 60+ people, on-site registration (including credit cards)… we were set.

28 riders. I’m grateful for every single one.

People started to arrive in ones and twos. I tried to relax and make sure everything was ready for the hand-off so that I too could ride the challenge – I wasn’t going to ask others to ride up a hill 20+ times and not do it myself. But I started noticing something as the start time approached: we didn’t have nearly as many people as I expected. People who had told me personally they’d be there, weren’t there. People who I talked to and sounded excited about the event, well, turns out they just sounded excited.

In the end, we had 28 riders. I literally know hundreds of cyclists across dozens of teams and clubs – from occasional cruisers to hammer heads. From touristas to race junkies. And less than half of the riders who told me they’d come, came. When you have 24 raffle prizes, medals and food and supplies enough for three times as many, and you get 28? Climbing a hill for 90 minutes is somewhat soul-crushing.

[I later found out that shops, clubs, and teams I spoke to about the event failed to promote it, and instead offered their usual Saturday rides and routes. That was definitely a gut-punch.]

So… What Went Wrong?

We even had plans to stagger the start for safety, if a lot of riders showed. That was… unnecessary.

Objectively, not much. One mistake was that – though it was held on a Saturday – it turned out it was Easter weekend (a floating holiday), so some people were out of town. Another mistake was perception of difficulty: people dread hills more than I anticipated. Even with prizes and medals for doing 10 climbs, people heard “hill climb challenge” and viscerally respond with “@#$% THAT!” Parking wasn’t near the event, and the event itself was new, naturally limiting participation.

But the biggest thing that went wrong was my optimism. I had to force optimism upon myself to keep things going. It allowed me to believe that the effort of the last four months would be a big success. That we were starting something new and good, and it would grow and help support other every day athletes trying to compete at otherwise difficult-to-afford levels.

At the same time however, my usually more pragmatic views were pushed aside for the optimism that would allow me to endure the stress of putting on an event, and so though objectively the event was a success, safe and enjoyed by all who attended, and did raise money for the team, in my mind? It was a massive failure.

And this happens a lot in cycling. People train for races, and then the race course is changed, or they’re injured, or some scheduling conflict occurs. Events are held and despite all efforts, the weather turns bad, or people just don’t show. Does that mean that all the effort of that racer in training was wasted? Does it mean the effort put forth by the event promoter wasn’t worth it?

Not at all. The racer is stronger for their training. The promoter has gained valuable experience and is now better prepared should they want to try again.


Optimism is good – it can keep us going even when the odds are against us. And all too often we temper our optimism too much with pragmatism (what’s reasonable) or replace it with pessimism (what may fail).  Yeah, those may reduce the height from which you might fall, but it also prevents you from reaching beyond your limits to succeed.

I hope this gave you insight into what it takes to put on an event. I plan to do this event again, and hopefully – though I’ll remain optimistic towards the outcome – I’ll go in with slightly more reasonable expectations. 😉

Aim high. Don’t be afraid to fall. And most importantly, if you do, stand back up.