Horsing Around: My Unique Side Hustle

Hey all, Tawnya here.

It’s no secret that those in the personal finance community are the kings and queens of the side hustle.

Of course, blogging in and of itself is a side hustle for a lot of us, but beyond what little money we may make from our sites you’ll often also find a plethora of unique money-making schemes that help us supplement our income.

These side hustles range from the common, to the exceptional, to the downright bizarre.

But, in all the articles I’ve read I’ve never seen anything quite like my unique side hustle, and I’d bet almost none of you even knew this was something one could actually get paid to do. You get the best of both worlds when your side hustle is also your hobby.

While certainly not the most bizarre of side hustles, I can certainly claim it to be one of the most unique.

I work at dressage shows.


At this point you’re probably wondering what the heck a dressage show is, although if you’re astute you’ve probably gathered from the title that it has something to do with horses.

Not to worry, all will be revealed!

First, let me explain what dressage is, then I’ll take you on the journey to how I began getting paid to horse around at dressage shows.

This is my unique side hustle.

What Is Dressage?

The Basics

Dressage is a French word meaning “training,” and is one of the most challenging of the equestrian sports.

Before we go any further, you need to know that dressage is pronounced “dress-aahj.” Remember, it’s French.

If you haven’t previously had some exposure to dressage, the best way to describe it is the type of riding where the horse appears to be dancing.

Ah, now you know what I’m talking about!

Classical dressage can be traced back to the work of Xenophon (born in 430 BC), and developed from cavalry movements and training for battle. It is riding in harmony with the horse, and the aids given to the horse by the rider should not be apparent to an observer. Emphasis is placed on the seat and leg of the rider, which allows the rider to collect the horse.

When collected, the horse shortens its frame and stride, resulting in elevation and increased suspension in its steps. Collection allows the horse to be light and balanced on its feet, and to perform the rigorous movements required in dressage.

The Moves

While classical dressage included the airs above the ground (moves that involved controlled rearing and jumping), modern competitive dressage focuses on a different, but still challenging, set of movements.

These movements include:

  • The extended gaits – the horse stretching its legs and body to lengthen the stride
  • Flying changes – switching canter lead so that one front leg or the other lands last
  • Pirouette – a small circle equal to the length of the horse
  • Passage – an elevated trot in which the horse appears to float
  • Piaffe – trotting in place with the legs lifting as high as possible
  • Tempi changes – flying changes where the horse switches canter leads every 2, 3, 4 strides, or every stride (skipping)

These movements require a certain level of natural athleticism and ability from the horse, and take years to train and perfect. Because of the high level of athleticism needed, dressage horses tend to be various types of horses known as warmbloods, and high-level dressage horses can cost upwards of $100,000 or more.

The Levels

Dressage training involves moving up through a series of levels, ultimately building toward the highest level of Grand Prix.

The levels are as follows:

  • Training Level
  • First Level
  • Second Level
  • Third Level
  • Fourth Level
  • Prix St. Georges
  • Intermediaire I
  • Intermediaire II
  • Grand Prix
  • Grand Prix Special

The lowest level is the Training Level, which only requires the use of the basic gaits of walk, trot, and canter. As the horse and rider pair moves up the levels, new and increasingly difficult movements are added.

The Tests

So, how is dressage evaluated?

Each level (Training through Fourth) is broken up into four “tests,” while the more advanced levels (Prix St. Georges up) are comprised of one test for each. For each test, the horse and rider must perform certain movements at various spots in the dressage arena.

A dressage arena is 22×66 yards and is marked by 12 letters around the perimeter as well as five imaginary letters within the arena.

Movements are expected to be performed exactly where specified by each test, and each movement is given a score from 0 to 10.

At the end of the test, the scores are added up and converted to a percentage. The horse and rider pair with the highest percentage score wins the class.

In addition to the tests described above, Freestyle tests can also be performed in which the rider and horse perform a certain set of required movements to their own choreography. These Freestyle tests can be performed at any level and are set to music, making them particularly enjoyable to watch. In addition to the movements, Freestyle tests are also judged based on choreography and music selection.

The Judge

Dressage tests are evaluated by a judge, and for the higher-level tests, several judges. The judges are placed in “boxes” around the arena, and there will always be a judge at letter C (opposite from where the horse and rider enter the arena).

Seated with the judge is a scribe, who records the scores for each movement and writes comments made by the judge during the test.

It takes many years and much training to judge at the highest levels. Judges are sought from all over the country and the world to judge high-level shows.

In fact, the highest-level shows (Nationals, World Equestrian Games, the Olympics, etc.), as well as the shows riders use to qualify for them, require judges from multiple countries to be present. Especially at international competitions, the diverse judges panel helps to ensure that horse and rider pairs from certain countries are not favored over others.

How I Began Working Dressage Shows

So, how did I get into this side hustle?

Let me assure you, it was quite by accident and coincidence.

I’ll start by saying that I did used to ride horses when I was younger and have ridden low level dressage. Because of my past experience, I knew what dressage was and had a good understanding of how things worked before I got into working shows.

My foray into dressage shows as a unique side hustle actually began as volunteer work back in college.

I met who is now a very good friend of mine my freshman year of college. Part of the reason we bonded so quickly was because I actually knew what he was talking about when he mentioned his family business of dressage.

In fact, my friend’s family owns the largest and most well-known dressage barn in Oregon. Aside from being a well-known boarding and training facility, they annually host one of the largest dressage shows around the Northwest.

Thus, I began volunteering at Dressage at DevonWood over 10 years ago, and I began to learn the ins and outs of large dressage shows.

During this time, my friend was also doing contract work for other large dressage shows in California. These shows featured Olympic level riders, a panel of international judges, and needed A LOT of volunteers to run properly.

The combined need for reliable volunteers and my friend’s involvement resulted in me being flown down to Del Mar, California to volunteer as an e-scribe (inputting scores on a computer during the test) twice while in college, and once more after I graduated.

Even after that opportunity ended, I continued to volunteer as an e-scribe at Dressage at DevonWood every year, until 3 years ago when things changed.

My friend had transitioned into running the events at DevonWood and asked me if I would like to work part-time at some of the shows in addition to the big show in the summer. He needed a reliable crew to come in as needed, and for all hands to be on deck for the main show.

Of course, I jumped at the chance to get paid for something I was doing anyway.

As a result, 3 years ago I began working at DevonWood events part-time, with the main gig being Dressage at DevonWood in July.

My duties vary depending on what show I’m working, and I may only work one other event besides the main show a year.

As such, I’ll focus on my job for the main show.

I just wrapped up my third paid Dressage at DevonWood show, where I’m responsible for hospitality. This duty includes chauffeuring judges from the airport to the hotel, from the hotel to the property, and from the property to dinners, the hotel, and the airport. I also ensure that the judges have everything they need while judging, and that lunch orders are gathered and delivered to staff and judges. In addition, I manage issues as they arise and fill-in wherever necessary to make sure the show runs smoothly.

And what do I make from this side hustle?

The days and hours I work depends on my availability each year, but I will make around $500 for the 3 days of the show (Friday – Sunday). These are full days, beginning with judge pick-up at 7:15am and ending with judge drop-off at 9pm or later.

Despite the long hours, there are many perks besides money. All meals are included for show staff, and my job in hospitality includes nice dinners out with the judges. My close proximity to the judges also affords me the opportunity to have many conversations with them, and to learn and improve my knowledge of dressage. I also get to hang out with a great show crew, many of whom are my friends outside of the shows.

After 3 years, I finally feel like I know my role inside and out and look forward to potentially expanding this side hustle. In fact, there were multiple times this year where our show staff was encouraged to contract out for other shows.

Whether my friends and I can eventually turn this into more than a very part-time gig or not, I wouldn’t trade the fun I have those 3 days of the show for any other side hustle.

Moral of the Story

Side hustles come in all shapes and sizes, but I’d bet my unique side hustle is rarely done.

As a result of experience and coincidence, I have worked my way into working at dressage shows for a modest supplementary income that may eventually become something more.

But the best part about this unique side hustle is you really don’t need any experience at all to participate. Anyone can become involved with dressage shows by volunteering, gaining experience, and eventually, maybe you too could find yourself making a side-living horsing around at dressage shows.

All you need is the willingness to learn and the opportunity.

Are you interested in side hustling at dressage shows? If so, check into local shows in your area to get started volunteering and see where dressage takes you.

Talk about Money Earned!

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