One evening in May 2020, my buddy Dave and I drank a bottle of wine and watched “The Palio” documentary. At this point in the pandemic, I had essentially been locked in my apartment alone for two months, so I borrowed the neighbor’s dog to take him for a walk. We walked to Dave’s.

For those of you who don’t know (which is probably most of you, because why would you?), the Palio is one of the oldest and most dangerous horse races in the world. It was first held in 1482 and has been held semiannually on July 2nd and August 16th since 1701.

During the race, the jockeys ride bareback three times around the Piazza del Campo in Siena, Italy, whipping each other and flying off their horses to a screaming (and sometimes sobbing) crowd of 40,000. The race typically lasts 1 ½ minutes or less.

Each “district” has their own team – also known as a contrada. The jockeys and horses are selected at random for each race.

Bribery is at the forefront of the Palio. Each contrada gives their jockey money to bribe and make deals with other jockeys. Historically, jockeys that are suspected of throwing the race suffer beatings at the hands of their contrada.

In Siena, your contrada is part of your identity.

It’s intense.

Ever since that fateful (and illegal) night at Dave’s, we’ve been determined to go to this horse race. We forced my partner Marty to watch the documentary, and he, too, developed a yearning for the hoofbeats of Tuscany. Never mind that tickets are expensive and hard to come by; we were going to experience the passion of the Palio.

And that’s just what we did.

The Contrada Dinner

There’s a contrada dinner the evening before the Palio. At this dinner, the districts allow tourists to dine with the contrada in the streets of Siena to raise money for their bribes and pay their jockey. We were assigned the “Leocorno” contrada (or “Unicorn” for those of you who aren’t yet fluent in Italian).

I read online that it’s polite to buy and wear a fazzoletto – a scarf that matches your contrada – so we popped into a shop before heading to dinner. Although we knew virtually nothing about the politics between the contrada, we wanted to show our support.

We strolled back onto the street sporting our new duds and walked for less than two minutes before being stopped by a thin older woman. She looked at me, pointed at my scarf, and rattled off something in rapid Italian. Her face looked very serious.

Having absolutely no clue what the woman said, I looked at her with wide eyes and responded: “I’m so sorry, my Italian is terrible. English or Spanish?”

Her expression softened slightly. “Your scarf – you are in the enemy territory of your contrada. Do you see the flags? This is Little Owl. This is not where you should be. Go up that street.”

I thanked her, repeatedly, and we shuffled off in the suggested direction. Mildly horrified, I promptly removed my scarf and Dave, Marty and I made our way to dinner.

Let’s Feast

When we arrived at dinner, we were greeted by hundreds of contrada flags, trumpets, and long, picnic-style tables set for at least 400 diners. Our scarves were back in fashion.

People milled about excitedly in front of a large, elevated table where the jockey, contrada captain, and other people of importance would eat and give speeches. Two TVs were set at either end of the dinner so people would have a good view of the head table.

We were served a remarkably delicious 4-course meal, bottled water, and an endless stream of Chianti for 70 euro. Although I typically don’t eat meat, I respectfully wolfed down heaps of prosciutto and steaming wild boar. There are no accommodations made for vegans or vegetarians at the Palio, and I can’t imagine the reaction you’d receive were you thick enough to turn your nose up at their food.

The dinner began to wind down around midnight; not due to lack of entertainment, but because of a rapidly approaching thunderstorm. The sky flickered and people fled, buzz achieved and bottles in hand.

The Lead Up

There are countless complicated traditions leading up to the Palio. Parades through the streets, additional contrada dinners, four practice races (which you can watch for free in the center of the piazza), the blessing of the horses in their respective cathedrals… the list goes on and on.

Palio Race Day

The city brings truckloads of sand into the piazza for the Palio, which they pack down until it forms a thick, hard layer over the cobblestones. If it rains, the sand turns into a slick, soggy clay that’s impossible walk on, let alone run a horse across.

Although it had rained the night before, the scorching Tuscan sun had sufficiently dried the sand by the time of the Palio. We took our seats at 4:30pm in the front row of the bleachers at the San Martino bend – i.e. the corner where jockeys are notorious for taking flight – and waited expectantly for the festivities to begin. The race wasn’t scheduled to start until 7:00pm, but we were told that there would be plenty of fanfare in advance.

I was snacking on a caprese sandwich when the decorated calvary emerged from one of the entrance points and started galloping around the track, brandishing silvery swords. Lead by an intimidating woman with a perfectly tight bun, they pointed their swords at an invisible enemy and attacked. As the calvary rounded the bend towards the exit and their show came to a close, rain started to freckle the ground.

Seconds later, the cloud yawning above us let loose. 

The Race, Round Two

I was admittedly a little happy that the race had been rained out. It extended my adventure in Siena. We were staying in a beautiful, old-fashioned apartment at the edge of the city that was quiet, comforting, and reminded me of my grandparent’s house. The next morning, I took a bubble bath and enjoyed my high-voltage coffee in the tub.

Knights in full suits of armor marched dutifully forward, not giving any indication that they were nearing heat stroke. Every few minutes, a jockey would ride past wearing traditional high-fashion robes from the 1700s. A duo of flag twirlers from each contrada competed for the honor of winning best performance by executing synchronous moves, including one-legged twirls and half-splits.

This remarkable processional continued for two hours, until I was hiding in Marty’s shadow and cursing my fragile skin.

Despite the caricature that was being created, this was not a joke or a lighthearted performance. There was no smiling. The Sienese approached their Palio duties with a prideful seriousness. This was tradition, in its purest, finest form; there was to be no deviation from the plan.

When the track was finally cleared, the piazza began to quiet and the jockeys made their way to the start line. People began to “Shhh!” one another until the anxious crowd was blanketed by a heavy silence. The starting order was to be determined, at random, and announced over a loudspeaker.

“Leocorno, uno!”

Tittia, the best jockey, riding arguably the best horse, had just been given the best spot in the lineup. Our contrada was positioned to win.  

A growling murmur spread across the piazza, laced with feverish energy. My hair stood on end.

The rest of the jockeys were announced, in order, until the lineup was completed. Each announcement was echoed by the same uncomfortable rumble.

Unlike most horse races, the Palio is started by a “run-in” jockey, rather than the pop of a gun. The run-in jockey stands behind the line of riders and, as the name would indicate, starts the race when he chooses to run. The run-in jockey rarely wins, but he is in prime position to help or hurt the likelihood of the other jockeys winning. His start is strategic, and the starting line process can take upwards of 30 minutes.

The horses spun around anxiously while the jockeys whispered and bartered with one another. Although we couldn’t hear it, hundreds of thousands of dollars were being verbally exchanged as jockeys attempted to gain leverage or plot against enemy contradas.

All eyes were on the run-in jockey. He sat back, feigning relaxation and looking over the lineup watchfully.  

The tension made my teeth ache.  

I suddenly realized that I wasn’t just excited – I was scared. For the jockeys, the horses, the emergency responders lining the sidelines. For the unpredictability of the course and the chaos that would inevitably ensue.

The starting line dissolved into disorder and the jockeys were forced to exit and reenter, effectively resetting the start line. The horses stomped, kicked, and tossed their heads in irritable anticipation. Minutes passed as my heartbeat thudded in my ears.

And then, seeing the perfect opening, the run-in jockey pounced.

The piazza erupted in a thundering scream.

Leocorno immediately took the lead, holding tight to the inside of the track. The other jockeys followed, mere hoofbeats behind. As they rounded our corner, the horses desperately surged forward and mud rained into my hair. 

Pushed to breakneck speeds, two of the horses collided on a narrow turn and three jockeys flew off their horses and onto the track. One of the jockeys covered his head as hooves pummeled him.

I watched with awe and horror as the emergency responders swept in and pulled the jockeys from the piazza. Unharmed, their horses continued the sprint for the finish line. (Strangely enough, riderless horses can win the Palio.)

Tittia created a sizeable gap between himself and the other jockeys at the beginning of the second lap. The crowd at the center of the piazza seemed to pulse with urgency.

Riderless horses whipped by, wreaking havoc in their wake. Without the guidance of a jockey, their movements were dangerous and erratic.

On the final turn, Tittia raised his hand in the air and yelled, knowing he was victorious. Spectators jumped the barriers and poured onto the track, horses still galloping wildly towards the finish.

The closing cannon erupted and people screamed. Screams of victory, of agony, of relief. Leocorno flags paraded into the piazza while supporters of Little Owl (the enemy contrada) ran towards the exit, howling. A girl on the track let loose a guttural, animal scream that was unlike anything I’d ever heard.

The emotion was so incredible, raw, and real. It was a little unnerving.

A couple seated next to us decided to join the celebration on the track and were immediately confronted by a wild horse. They jumped back into the bleachers sheepishly.

I stood there, watching the Sienese tears flow, wondering if I’d ever cared about anything with such intensity. I shared but a fraction of their passion, and still felt the inexorable power of the Palio.

The jockeys were released from the hospital the next day.

The Palio is a snapshot of history. It reminds us of the birth of competition – of tradition, and of sacrifice. Not so long ago, entertainment relied upon the collective experience of risk and danger. That memory lives on in the Palio.

Want to watch the whole race? You can see it here.

Got the travel bug? Send me a message to learn more about the Palio or join me at my yoga retreat in Costa Rica in March, 2023.

My first job out of college, my boss asked me to create a “vision board” to hang next to my desk. When I asked him what I should put on it, he said, “Anything you want to buy with the money you earn! Maybe a car, or a purse, or a house – dream big! Something you really want to work for to remind you, every single day, why you come into the office.”

I remember looking at a blank sheet of paper, wracking my brain. Over and over, I asked myself: “What the hell do I want to buy?” Crickets.

Eventually, I told him I didn’t really want to buy anything; I wanted to travel and see the world. He suggested that I choose a car instead. So, I printed out a picture of a jeep and hung up my vision board. Traveling wasn’t a very realistic goal, anyway, given that I only got 10 days of vacation per year.

(If we’re being honest, buying a jeep wasn’t a very realistic goal either. I was making under 20k at the time on a “trial period” – barely enough to pay rent.)

Every day, I would come into the office at 8am, grab a cup of coffee, and glare at the jeep.

Then, I would sit at my desk until 5pm, stealing longing glances out the window and feeling like I was wasting my life.  

This lasted for about a year until I quit. Three months later I became a freelance marketer and yoga instructor, booked a one-way ticket to Spain, and left to indefinitely travel the world.

Rise & Not Grind

I’ve said it once and I’ll say it again: fuck rise and grind culture.

Working yourself to death is passé. (Say it again louder, for the employers in the U.S.)

A fulfilling career and happy life should not require that you work 50+ hours a week and juggle multiple jobs.

We should not normalize being overworked and underpaid.

Make It Count

If my boss had asked the right questions, he might have been able to keep me around a bit longer. The most important one being, “What motivates you?”

Yes, in my land, flexibility reigns supreme.

But more importantly, I need to feel like my work is making the world a better place. I want to contribute to something bigger and more important than myself.

Now, when I look at the marketing consultancy I’ve built, I am surrounded by clients who treat their employees with kindness and respect. They care for others, give back to the environment, fight for human rights and are wildly passionate about what they do.

I work with incredible people who are changing the world. That, in my mind, is far more important than a flexible work schedule.

Et tu, Brute?

On that note, take pause and think for a moment. What drives you?

As my ex-boss learned, we aren’t all motivated by the same thing. My unpredictable lifestyle (and paycheck) would drive plenty of people nuts.

Do you want job security? An environment where you can continuously learn? Maybe you want to make your own schedule?

These are the questions that employers should be asking during your interview. These are the things you should be fighting for.

And remember, if you can find your “why,” chase it, and make money with it… well, then you’re one of the lucky ones. Not everyone has the privilege to build a career that aligns with their dreams.

Want more Madison? Send her a message to talk shop about marketing, mobility, or join her at a yoga retreat!

First off, I’d like to make a sweeping declaration: women are incredible. They are resourceful, inspiring, bewitching – and if you’re a woman, then you’re probably already aware of how awesome we are. In the past few years I’ve fallen madly in love with women, and it has unequivocally changed my life. I want you to fall in love with women, too.

Now, before we get started, I need to make a few clarifying statements. I am not romantically in love with women (although I’m sure if the right woman came along I could be) – I am in love with their deep, lasting friendship. I truly believe that female camaraderie is an essential part of daily life.

This post is not about male friendships (which I have many of), so don’t hit me with that “BUT WHAT ABOUT MEN? MEN CAN BE GREAT FRIENDS TOO!” diatribe. Yes, of course male friendships are awesome. But that’s not what this is about.

I’m not someone who is particularly… social. I love doing things alone (and often prefer it), but that doesn’t mean that I can’t recognize the role that female friendship plays in my life. When your heart is shattered because the bottom dropped out of your relationship or you have yet another hysterical pregnancy scare, sisterhood is everything.

Step 1: Admit You Have a Problem

When I was growing up, I wasn’t the biggest fan of women. Sure, I had female friends, but there was always this strange, underlying hyper-competitive edge. I judged what other women wore and how they looked. Believe it or not, I even made the painfully embarrassing claim that I “just get along better with men.” All in all, it’s likely that my inability let women into my heart revolved around my own insecurities and the fear that I would never be “good enough.”

In short: it had nothing to do with women, and everything to do with me.

I would, however, like to argue that my aversion to female attachment wasn’t entirely my fault. Film, television, magazines and even novels have normalized this idea that women can’t be friends – or at least they can’t be friends with someone outside of their “clique.” Women are portrayed as catty, cruel and sometimes just plain MEAN. These mediums, just like adolescent me, have it wrong. So what’s the point of this rambling essay? The point, my friends, is that if you don’t embrace, foster and nurture your female friendships, you’re missing out on one of the most beautiful parts of life. In a time when it is increasingly important that people of all gender identities unify and support one another, there is no excuse to be trashing other women or – at best – keeping them at an arm’s length.

Step 2: Make a Change

If this concept is new to you, NO SHAME. Again, we’ve been given a skewed template of female friendship. For the sake of your future happiness (and the happiness of everyone on the planet) I’ve compiled a list of easy instructions that will help you build lasting, meaningful female relationships.

If you want to fall in love with women, please don’t:

• Hate on another woman’s outfit. This wasn’t excusable in high school, and it definitely isn’t now. If you have a problem with what another woman is wearing, I suggest you take a very long, hard look at what that says about you.
• Sleep with another woman’s partner. I’ve done this. I was young, dumb and woefully insecure. I will also never do this again – and here’s why: I would be absolutely crushed if another woman did this to me. Remember that she isn’t faceless or nameless. She is just like you.
• Tell another woman that she “can’t.” Maybe she wants to open her own business. Maybe she wants to get her master’s degree. Maybe she wants to build a greenhouse and learn hydroponics. Cool! Whatever it is, tell her she’s unstoppable – not that she should stop.
• Gossip. You’re better than this.
• Call another woman slutty. As the great Christina Aguilera once said: “The guy gets all the glory, the more he can score, while the girl can do the same and yet you call her a whore.” It’s NONE OF YA DAMN BUSINESS.
• Be afraid. Women are warm, beautiful, open-hearted creatures. Approach them with kindness and watch your world transform.

Now go make it happen. Fall in love with women.

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Want more Madison? Send her a message to talk shop about marketing, mobility, and – duh – to be her friend! 

P.s. This one is dedicated to all of the incredible women in my life. You inspire me daily and I love you endlessly. Send me your favorite photos and I’ll add them to this super girly slide. 

It’s 2020. You’ve decided that you’re sick of feeling like shit and you want to start exercising. That’s amazing! Whether you’ve decided to lose weight, build muscle or simply live a healthier lifestyle, it can be difficult to navigate the fitness world if you’ve been embracing your inner couch potato for a little too long. Are you scared? That’s fine. Starting a fitness routine can be incredibly intimidating. Not sure where to start? That’s fine too.

In a world filled with useless fitness information, I am here to provide you with the truth about getting fit in the New Year. No bullshit. Real tools that you can actually use to achieve your goals. Am I a fitness guru? No. Nutritionist? Absolutely not. Am I selling you something? Nope. But I can tell you one thing: I’ve spent years using exercise as a tool to make me happy – and I want you to be able to do that too.

I just want everyone to be happy.

Truth #1: There Is No Magic Pill

You’ve heard it before and I’ll say it again: here is no magic pill. There is no “secret” to getting fit in the New Year and losing weight. These are the rules of the game:

1. Exercise Regularly
2. Eat Healthy

That’s it. Easier said than done, right? If anything looks, tastes or smells like MLM, then it is – and it’s designed to rip you off without providing you with any results. Tiny tea (laxatives), belly wraps (water weight) or diet pills (probably arsenic) do not work – so don’t waste your money looking for the easy way out. There isn’t one.

Truth #2: “Fitness” Can Be Different for Everyone

I’ve tried at least 50 different fitness routines. Yoga, pilates, kayaking, hiking, crossfit, cycling, rock climbing, swimming, dancing, lifting weights, running, snowboarding, kickball, chopping wood… do you catch my drift? Fitness doesn’t mean that you have spend two hours on the elliptical. You can – and will – find a form (or forms) of exercise that you actually enjoy. You just have to keep searching until you do.

Truth #3: You Don’t Get to Stop Working Out

It always blows my mind when people reach their fitness goals and then they just… stop. It’s lunacy. If you want to be healthy and live to watch your great grandchildren have children, then you don’t get to stop working out. Ever. Now hold up – I’m not saying that you have to be a fitness freak for the rest of your life, but you do need to prioritize moving your body a few times a week. You can take a break for injury, for self-care, for… whatever you feel like, but you should always return to some sort of a fitness routine.

Imagine this: you’ve spent the last two years learning how to speak Spanish. You’ve worked so, so hard figuring out how to conjugate verbs, ask where the bathroom is, and order a beer. At last, the day that you’ve been waiting for arrives: you’re fluent in Spanish! All your hard work has FINALLY paid off!

And then you never speak Spanish. Ever again.

That’s what it’s like when you bail on your fitness routine.

Truth #4: Nobody Is Judging You

You know those super fit people that look like they fell out of the womb doing crunches? They were beginners once, too. Everyone knows what it feels like to walk into your first class, get your first membership or try your first (horrific) round of burpees. We have all been where you are and we’re cheering you on. Laugh at your mistakes and remember that fitness should be fun – sometimes even silly – so don’t take it so damn seriously.

Truth #5: You Deserve to Be Happy

When I was 22, I had a therapist give me a prescription for exercise. She said, “Madison, I want you to exercise for 45 minutes, 3 days a week. I don’t care what you do.” At the time I was incredibly annoyed – “So, you’re not going to refill my Xanax?” – but after a month… I felt better. Healthier. Happier. Stronger. It was like someone made winter a little less wintery. I was eating my vegetables and drinking less booze. I didn’t understand it at the time, but the best side effect of a regular workout routine isn’t an improved appearance – it’s an improved state of mind.

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Want more Madison? Send her a message to talk shop about marketing, mobility, getting fit in the New Year and beyond.