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Chris is the founder and race director of the Sheetz to Sheetz trail run, an annual event taking place in Virginia, USA, which sells out in less than 24 hours. Sheetz to Sheetz is a Racecheck Gold Award recipient with a 4.9/5 rating, making it one of the highest-rated events on the platform. As race director, his four-point mission for Sheetz-to-Sheetz includes: (1) bring people of all abilities and backgrounds together; (2) encourage a fun break from competitive races; (3) give back to the community; and (4) promote King George County as a trail running destination. We thoroughly enjoyed this conversation, which I believe contains many gems for first-time organisers and industry veterans alike.

Alexander Tanti: Maybe we can start by telling me a little bit about your background. What did you do before starting to organize races? Are you working on this now full-time? Just some general information would be fantastic.

Chris Chalkley: Sure, I certainly don’t do this full-time. This is a part-time hobby for me. In real life, I work for the US Department of Defense as a project manager, so nothing to do with this at all. My day job is very different, with little room for creativity.

I started running late in life, probably at age 45 or so, and I really enjoyed it. Apart from the physical outlet, it also gives me a social outlet. We do group runs, and when you’re training for marathons, you’re always looking for different sorts of long runs. We have these two stores near us that are convenience stores called Sheetz. And we have two of them in the county. We actually have three, but there are two of them that are separated. They happen to be about 14 miles apart, and a trail goes from one to the other. And so one day, we were looking for what can we do differently for a long run. So I figure that we run from this Sheetz to that Sheetz, and then we’ll figure out how to return.

So we did that, and that was fun. It was a good distance and a secluded trail.

Then when you reach the end, you have a store where you can get refreshments etc..

So that caught on, and we did that a couple of times just in our run group, and then I said, well, why don’t we see if anybody else wants to join us? So that was six years ago, and that was the first year I advertised it on Facebook as a meetup and said, “Hey, anybody wants to come and do this?” and I think the store manager gave us free coffee or something like that. So it’s very low-key, and there were maybe 24–25 people who showed up. But the concept came, and it just looked unique. It looked like something that people would want to do. So I tried it again the next year. And this became a once-a-year sort of thing.

Long story short, it just kind of grew to the point where it’s now 350 people. I’ve got people coming from multiple states. I’m fortunate in that it sells out very quickly, in less than one day last year, and I got all sorts of sponsors and local government participation. So in just six years, it’s gone from an idea, from just something we did for fun into something real.

To me, it’s still very much a part-time job. But more so, it’s a passion and a creative outlet. I get to create all the social media content; I can come up with crazy things along the course signs and, aid stations, and so forth.

Alexander Tanti: I found it really interesting that you said that you found organizing this event as an outlet of creativity, which you don’t necessarily get in your day job. What aspect of organizing races is creative, and how do you know how to use that creativity?

Chris Chalkley: Several things. One is the graphic design elements that go with the race. I’ve always been interested in that. I don’t really have an outlet for that at work. But I do all my own social media and graphics work, and I just released a video highlight of my last race. So that’s all creative. Lets me use Photoshop all day and do that sort of thing. And just the creative energy that goes into defining and coming up with a vision for your race or your event and seeing that through, one thing I’ve tried to do in my race is to make it as unique as possible.

Which is a little risky in the sense that there’s a proven formula that works for races, right? You know, you start, you have a banana and water, and you have aid stations, you get to the end, you get a medal and another banana. That works. And that’s almost every race you ever do. And I’ve done dozens like that, and that’s fine, but I wanted to have something that was different from that. So, first of all, the biggest difference is, it’s non-competitive. It’s not even timed, and I encourage people to go out, take their time, have fun, enjoy the scenery, enjoy each other, and then, I throw things at you along the course to make you slow down, like fun distractions. I have a campsite at the halfway point where there are hammocks where you’re encouraged to take a break and enjoy the campfire. So just coming up with Ideas like that.

Basically, what crazy things can we do that no other race does? That’s another avenue for creativity.

Chris uses race organizing as a creative outlet. Part of the event’s success and longevity is due to incorporating and leveraging his passion for creative work within the race organization. What are your talents and passions? Finding a way to incorporate those into your events will give you a better chance of staying consistent in the long run and finding deep joy in putting up events.

Alexander Tanti: You mentioned having a vision for the race; where did that vision come from? Was it from you participating in races and visualizing the ideal event for you? Somebody might do something for the sake of differentiating, but if they’re not true to that, then it just won’t come out genuine, and people just won’t reciprocate in that sense. What do you think?

Chris Chalkley: I think the first thing that you have to do is just define your mission. What’s going to drive you? What are you gonna stay consistent with as you try all these different things? You know, the fixed denominator regardless of how unique you want the race to be.

So, for example, I said a few things early on. I said I want this to be about community. And that dictates some decisions that you make over the years, such as the size of the race. I keep it small, and the focus is on helping the community. So even things like buying local, instead of buying online. I want to give back, so I set aside a certain portion of the profits to go back to the community, in terms of charity and donations. That is an example of how the fixed denominator for what your mission is, in my case community, drives creativity around everything else.

It’s setting some long-term goals upfront. Being non-competitive, I want it to be more about having fun and community. And then, over the years, you come up with many ideas that may not all work. You know, you try some of them. Some of them never make it. But I’m just adding ideas all day long, all year long.

Then I refer back to the list and say, well could this work, how could it work, and if it’s too much of a distraction or looks too much like I’m doing something just for the sake of being different, then it gets dropped. It has to still fit your race mission and your goals.

Having a core mission defines everything, from how you market the event, your website copy and imagery, all the way to what changes you make every year. Your core mission acts as a compass, helping you avoid distractions and only introducing aspects that align with this mission.

Alexander Tanti: So, you have some basic values that act as your compass. How many years are you running this race now?

Chris Chalkley: This is my sixth year. I just finished the 6th edition in March (‘23)

Alexander Tanti: And am I right to assume that every year, you just introduce a different aspect or you try to improve the event year by year? How do you go about understanding or deciding on what that new feature is? Do you do that via surveys? Do you speak to your customers? At the finish line? How do you decide on, let’s say, these are the ideas of what I’d like to introduce and then all the way to deciding and then implementing that?

Chris Chalkley: It probably starts straight after the race. I send out a survey to all the runners, and the most important part of the survey is the final section. I try to get them to brainstorm and ask what they would like to see the following year. I get a lot of good ideas there.

Then a lot of times I come up with ideas and then run them by my ambassadors and staff. I do just about everything myself, such as the advertising, the graphics, the planning, and even building things for the site and building the race course. But I do have, and I started this, maybe three years ago, a small group of ambassadors. So I’ll put out a call every year and say, “Hey, I’m looking to introduce something different this year, such as this and that.”

And the main thing they do, they’re my listening board, really. I can throw out ideas and say, Hey, what do you think about this? Or I’ll make a graphic, or I’ll make an advertisement or social media campaign. I’ll run it by them first and always get their input. So, that’s been very helpful when it’s a race where you’re the main person doing everything. You need another group to run things by.

Create a small “board of directors” comprised of race ambassadors. Incentivise a few core runners of your events with a free entry to bounce ideas off them. They will help you stay true to your values and allow you to keep a close pulse on your customers.

Alexander Tanti: How do you incentivize those people to join your ambassador groups? Are they just happy to do it for free?

Chris Chalkley: Yeah, they might just be happy to do it for free, but I also offer a free entry and might also give them a little bit of swag, you know, shirts and stickers, that sort of thing.

Alexander Tanti: So you have created this little personal board of directors in a way that helps you with your decision-making process. How often do you meet? Is it like a monthly call?

Chris Chalkley: It’s nothing that formal. In fact I think we only met once online, and that was the kick-off meeting. First, I introduce the Race, its mission and its history. “These are ideals we are going for, and I’m gonna be pitching ideas to you, and I’d really appreciate your feedback”. So there is usually an educational kick-off meeting, and after that, it’s usually through a Facebook group where I’ll just post something and say, “What do you think about this?”. Or, “Here’s the schedule, am I forgetting anything?”

T hey’re my eyes and ears out there. They have their own race groups/clubs across the region, and I ask them to get the word out. But also to be listening. What are people saying? What are people excited about the event? Are they worried about something? So, it’s, it’s very useful to get feedback and also to share information.

Alexander Tanti: You mentioned it’s a 350-person event, right? Do you employ full-time staff? Obviously, you have help on the day, but you said you mostly do everything regarding the website and taking entries and promotions. At which point do you think a one-man operation is no longer feasible and you can no longer handle the workload as one person? Do you think that comes after 500 entries? 600? I’m just interested in understanding to what extent is it possible to run an event by yourself and where is that saturation point.

Chris Chalkley: Well, it is a very small race, and I’m at the limit, actually. And there are reasons for that. First, there’s the physical limitation of how many people we can fit into the narrow trail, and even with waves, I found that 350 is probably about the max number.

We’re also limited by the number of people we can have in the store because we usually gather everyone before and after the race. It’s always cold, and everybody huddles in the store, so you can imagine 300-plus people in a small convenience store. We just completely take over the place. And so, there are only so many people we can do that with. So I’m now at the point where this is the first year I’ve hit that 350 mark. If you’re asking about the saturation point, I think this is probably about it.

You know, if I went beyond that, I would probably need more help. I get by with a lot of volunteers. I do have an assistant. I incentivize that with a small stipend; it’s still very much a part-time thing. The difference between that role and the ambassadors is that this person does administrative work, manages RunSignup (reg platform), and organises the volunteers.

Not a very large job, but it’s just one more thing I can delegate, such as the volunteer emails or something like that.

Alexander Tanti: How do you go about finding volunteers? Because I’m guessing that’s probably a big pain point for many organizers.

Chris Chalkley: It is, in fact, the largest pain point in the last couple of years. I think early on, building out the vision and working out the logistics of race day it’s about finding the right vendors and suppliers. I think I’ve got that worked out now. I’ve got people I know and trust. But volunteers come and go. And you got to find the right ones, you’ve got to train them. And again, if you have this thing where your race is a little bit different from most, even if you have experienced volunteers that have done many other races, I still have to train them on how our aid stations work and how they’re different from your average event.

This year, for instance, we switched to cupless racing, which was a huge transition but also involved a lot of training. I ended up making training videos to say, “All right, this is an important change. And it comes with some risk of bottlenecks. And here’s how we’re going to handle it..”

Training has become an important part of it, but just finding the right volunteers, you know, takes years of building relationships. In this past year, more and more, I’m relying upon my day job coworkers because I know these people already, and I can trust them. My boss helped out this year and had a very prominent role, which was great.

Leverage your own social and professional circle for backup help in case your volunteers don’t show up. Take the time to train your volunteers by creating explanatory videos which you can share.

Alexander Tanti: Awesome.

Chris Chalkley: And then when one of your key volunteers is not available, you have a backup.

Alexander Tanti: So you leverage your entire social and professional social circle for help.

Chris Chalkley: There still is a lot of risk. I’ve got about 50 volunteers, and it’s still going to be people that you’ve never even met before, and they sign up. It’s a little nerve-wracking. But as long as you have people you trust in the key positions, that makes it much easier.

Alexander Tanti: That’s a great segway to discussing a little bit about risk because even though event organisation is not a full-time occupation, it still has to be treated as a business, with all its risks and contingency planning. As you mentioned, many things could go wrong by introducing a new feature, such as the cupless aid stations. You had to explain to people how to deal with these situations. Do you have a list of contingencies of things that may potentially go wrong, and do you educate your volunteers on that, or have it a “manual” to refer to if something goes wrong? I guess in really stressful situations, you have zero time to think. How do you deal with risk when it comes to race day?

Chris Chalkley: It’s difficult to think of everything that can go wrong. As the race has matured, I have taken more action on emergency planning and so forth. The first few years, honestly, I was winging it like most people do for a very small race. But then it gets a little bit larger and, you know, starts attracting people from the region.

And got more engagement and interest from the local government. As I work with several local government departments, I’ve needed to spend more time on risk. The 2022 race brought this home. We had absolutely horrible weather. I mean, the worst weather you can possibly imagine on race day.

And the idea of moving the race at the last minute, I didn’t have that planned out exactly. And I was going by the most accurate weather forecast I could find. All of the forecasts were consistent in saying that you can start the race — it might be rainy and a little windy, but the worst of it will come in the afternoon. So I’m going by that. And then the front came through literally 30 minutes before the race started. The portaloos blew over, and all my race structures were blown away. We had to rip that down as fast as we could. So it was a nightmare, but looking back at it, I was very proud of how my staff and volunteers all came together, and we just knew what to do.

We said, all right, take this down, take that down, we’re not doing this, we’re not doing that, and everybody just came together and made it happen. Now after that, I learned that we really need more of a deliberate weather plan or emergency plan documented.

But like I said, you can’t think of everything. This past year, the traffic control team, a group I hired for the first time, didn’t show up. So it was very stressful. But again, we came together. The guy coordinating the traffic control, who happens to be my boss, just stepped up and said, “All right, here’s what we’re gonna do, we call out for volunteers to help”. Every able-bodied volunteer helped at the start line. We also worked with the local law enforcement, who helped us by blocking traffic as best they could. So, in the end, it all worked out; it was great. I couldn’t have planned for that, but you have to account for risk and take that into your planning.

While it’s impossible to think of everything that could go wrong, it’s important to have contingency plans in place for the usual suspects such as foul weather, marshalls or volunteers not showing up.

Alexander Tanti: Do you have any other war stories to share?

Chris Chalkley: A couple of things. So this year, I ran my own race for the first time in several years. When this started, it was just a fun run, and I said, Hey, who wants to join me on this? So, You know, I actually did the race for the first two or three years, but then it quickly got to the point where there’s no way I could continue doing that. You can imagine on race day; the race director has so much to do. So there were several years when of course, I couldn’t run it. That made me uncomfortable because I couldn’t see what was happening on the course. I couldn’t see how these aid stations were actually operating. And I didn’t always have pictures and photographs to look at later. So I was determined this year to actually run my own race.

I spoke to a friend of mine who’s a race director, and he agreed to fill in for me while I was on the race course. So literally, at the last minute, I made the announcement. “Hey, I’m gonna join you guys today and hand it over to my guest race director”. So I did that, and I jumped right into the start line, and I ran the race myself. The problem was I was not prepared to run my own race. I’ve run that course many times. It’s 14 miles. But you can imagine the stress of race week; I was going on almost zero sleep, and no food because that morning, the wind was howling at about 4 am, and that kept me up. I was panicking about my tents and everything blowing down. So I just ran out the door to the start line to ensure everything was tied down.

And then I just jumped into the start line as if it was no big deal. I was fine until about mile 12, and then it all started to hit me. And I got very, very dizzy. The last two miles were just a blur as I walked and stumbled to the finish line. One of my good friends caught up to me at mile 13 and could tell I was struggling and offered me some food that she gathered along the course. So, lesson learned there, I finished. And after a half hour of coffee and doughnuts at the end, I recovered, but the last mile, I was trying not to pass out.

Don’t participate in your own race unless you’re actually prepared and rested :)

Alexander Tanti: Are you looking to grow the race, or are you just happy as it is? I know you said It’s probably reached maximum capacity, but would you ever consider doing another one somewhere else or the same one, maybe at a different time of the year?

Chris Chalkley: Not for the near term. Maybe when I retire. I’m a few years from retirement, so you know, that might be a possibility to have another event or to help somebody else. Right now, it’s all I can take as a part-time job. My wife would kill me if I made it even larger because even though I say it’s a part-time job, I mean it’s 40 hours a week, for many weeks of the year. Even in the offseason, when I should be doing nothing, I’m still doing 20 hours a week on the race.

So I mean it’s very time intensive. I think it’s misleading to think it’s just a one-time event once a year, but it’s really a year-round occupation. So being part-time, that’s really about the extent that I can take.

Know your limits and how much work you can take on. Don’t compromise the quality of your event if adding more events would mean you get overstretched.

Alexander Tanti: So for people looking to put up a race thinking that even if it’s a small one, they can probably pull it off with just a few hours a week, it’s a bit of an illusion.

Chris Chalkley: Well, It depends. If you’re doing a typical standard race using the proven formula, it’s not as demanding. I’m trying to make it a bit more personal and have been accused of being a perfectionist in the past, so I could see that coming across in my race as well.

Alexander Tanti: Your race has won a Racecheck Gold Award, so this underscores the effort you’re putting in. It’s not easy to get one of those.

Chris Chalkley: I know people who are doing this full-time and people who are doing it part-time. And I think when you’re starting out, you underestimate things like building relationships with and finding sponsors. Coordinating volunteers. So unless you have key people doing those things, it can be overwhelming.

Alexander Tanti: Would you ever consider going full-time? If it’s something you enjoy so much, what’s holding you back from going full-time?

Chris Chalkley: There are several reasons, but the biggest ones are the time commitment and stress. I don’t want to scare anybody off, but it is incredibly stressful to do any event organization. There’s so much at stake on that one day, and everything going well.

So it’s not something I’d ever consider. It’s just more of a hobby for me. I know people that do it for a living, and it just takes everything they have; it consumes their life. I can’t imagine doing multiple events yearly because I put so much into one event. So for me, that’s not really an option. That’s something I considered. As I retire, I do like to give back and mentor other race directors or event directors; that might be something I’d like to do.

Alexander Tanti: And if there’s one thing you could advise somebody looking to start organizing races, what would that be?

Chris Chalkley: The one thing would be to encourage them to set aside enough time to do it properly. Things you think won’t take so much time end up taking ten times as long. When it comes to sponsors, volunteers or anything where you’re coordinating a bunch of people, you’re at the mercy of their schedules, and dependent upon them getting back to you. And it just takes a lot of time, meetings, and running all over the county spending time with people.

Sometimes, you have to coordinate with local governments and organizations. So you think, well I just have to do this and get a few volunteers and some food, but you don’t realize all the other things you must do. Permits, working with local law enforcement and so forth. There’s just a lot to it. So, it’s not something you can’t overcome, but you need somebody to help you. If you find someone or a great resource that can help you to get started and save you all that effort. For example, resources such as this interview series. Or for me, it was the Race Directors HQ which was a great resource for me. I was reading everything I could, trying to absorb everything and save myself some time. When I was ready, I completed a race director certification program through the Road Runners Club of America. That brought it all together. So educate yourself because it will be a lot more than you think.

Alexander Tanti: That suggests that there are certain character traits that a race director should have, like great attention to detail..

Chris Chalkley: Absolutely. Yeah. You have to be a detail-oriented person. And have the self-awareness to realize that if you’re not, perhaps, you can still do this, but you need to surround yourself with people who are that way. So, if that’s not your personality or character trait, then you can still define the vision, and you can still run the whole race. Still, you better hire or find a volunteer that can do the day-to-day planning because there are a million details that have to be tracked and if you’re not good at that, then your race is going to fail.

Be aware of your own strengths and weaknesses. If your attention to detail is poor, find someone on your team to care for the nitty-gritty stuff. Leverage the strengths of your staff to support any of your own weaknesses.

Alexander Tanti: Thanks so much, Chris — this has been incredibly insightful, and really appreciate your time.

Chris Chalkley: Thanks a lot!