Ep. 012: Why The Journey Matters More Than the Destination

Transcript (may be slightly edited for clarity)

Intro

Welcome to the Ashes to Wings podcast where we tell stories of overcomers, and give you tips and tricks to living a fuller more embodied life, here's your host, Jenni O'Connor.

Jenni O’Connor

Hey friends, welcome to Ashes To Wings. Today we'll be talking with Lindsay Oaks. With no money or prior experience, Lindsay Oaks moved 500 miles from her home at the age of 17 to pursue a career as a professional horse trainer. Over the next decade she would learn how to become an entrepreneur, the hard way, while establishing herself as a competitor on the world stage and as a coach to aspiring equestrians. Lindsay now lives in the Chicago suburbs, spending her time teaching horse-crazy kids (and adults) to communicate effectively with 1000-pound animals who don't speak English; and creating strategies for coaches, consultants, and influencers to communicate with the world. Her clients describe her as a coffee-addicted, high-energy smarty pants, who tells stories to teach lessons. Lindsay thank you for joining us today.

Lindsey Oaks

Oh I'm so excited to be here! It sounds so much cooler when you say it like that.

Jenni O’Connor

We all need somebody to write our intros for us.

Lindsey Oaks

Amen. Thank you for having me today. I'm so excited.

Jenni O’Connor

Absolutely. So Lindsay, you were an equestrian competitor and I think most women want to be a horsewoman, on some level. How did you get into competition?

Lindsey Oaks

Awkwardly I would... I would say. I wanted to be with horses from the time I was a little kid, and you know, I just tell people that I was born with it. My best friend growing up also had horses, and I just was convinced that she did not appreciate the fact that she had them. And I just wanted to be just like her. And her parents, her whole family did a lot of riding and they were involved in equestrian sport. And I just dreamed from the time I was a kid, about being involved with horses. So, later on I managed to get my foot in the door. I did own a couple horses as a young person and sort of worked my way through high school and that time of my life by playing with horses. But I never competed or did anything of any merit to make what I did next, make any sense at all, which was that I decided I was going to be a horse professional. And I was going to go to the Olympics.

Jenni O’Connor

With no experience... [both laugh]

Lindsey Oaks

With zero experience or understanding what in the world I actually was signing up for in starting that journey. Not a clue.

Jenni O’Connor

And you were held at that stage?

Lindsey Oaks

I was 17 when I left home, just barely fresh out of high school. I was the youngest in my class so I didn't quit high school to leave but I certainly ran as fast as I could go. Like, a week after graduation I was like "okay well I'm going to Kentucky now and I'm gonna play with horses and I'll see you guys later." And my family bizarrely was like "okay." [both laugh] They were like "if this is what you want to do with your life, go right ahead." and no one ever said, "This is maybe something we should maybe think about a little harder before you go somewhere." They were like, you know, "this is what you want to do with your life, we're fully supportive, go right ahead," and that off I went.

Jenni O’Connor

That's so fantastic that they were that supportive of your dreams, though.

Lindsey Oaks

It's amazing. My parents and I've talked to them about this many times later in life, like, why did you think that that was okay? Why did no one say "Lindsey, this is probably not a great move for you, maybe we should think about it a little more, go to school for a little while and see what's going on." Why would you guys get behind me? And my mom actually gives the coolest answer. She was like look, "when I was a kid my parents told me what I was going to and what I was not going to do, and I felt a little held back in my dreams for a long time. And I didn't really have the guts to sort of just go around them and just do it." Because why would they stop you when you're in your 20s or 30s or whatever, right? But she just said, "Look, I wasn't going to be that person for you and if you wanted to go and do horses and you had no reason to think that you could except that you wanted to, then I wasn't gonna stop you, like, I was gonna push you to wherever it was that you wanted to go." So I suspect that it doesn't really matter what kind of a weird dream I came up with, they would have reacted the same way but it's pretty mind-blowing now in hindsight to think about. They would have been my age now and when I was trying to leave home, and I just can't imagine letting my kid leave and just being like, "yeah, that's what you're gonna do... have fun!"

Jenni O’Connor

It speaks to the trust that they had that you knew what you were doing that you had that level of responsibility as a young adult.

Lindsey Oaks

Completely misplaced. I have no idea why. I still to this day I have no clue why any of us thought that was a good idea. But it did work out in their favor eventually. So I went to Kentucky, if you don't have money or means, which I didn't, then one way that you can learn more about riding or sort of help yourself to the top of this order to reach whatever goal it is that you have, is to become a working student. So in the horse industry, working students make the world go round. They're people who can't afford to pay, and so they work, instead. There's lots of ways to do it, but what I did was I moved into a house with four other girls who were running a farm. A bunch of young girls running a huge, massive farm with like 100 horses. And I worked. I got up in the morning at six in the morning and I started at, maybe 6:30 in the barn, and we worked until seven or eight at night and then we get up and we did it the next day. But it wasn't work for us because we're all horse crazy, and that's all we wanted to do was get our hands dirty and play with horses. And what we got out of that was an education and what it took to have a business in horses. So that's kind of how that works and that's what I did for the first two or three years. I did work, other working student stints that were smaller and were not like 24/7 hour deals, later on in life. But that was my first one for sure.

When I got there, the lady who I was working for had one horse that she had decided was going to be her next big upper level up and coming horse, but this horse had a major flight response so horses, being prey animals, THE prey, right? Tigers and lions eat them? When they're afraid or when they think that a lion is going to eat them, they run. That's their flight response... it's a natural response in them. And this horse had a very very, very strong flight response. And so he got himself into trouble by leaving situations that he didn't need to be leaving. He eventually dumped the rider, the trainer that I was working for, and she got really hurt. Actually she wasn't hospitalized or anything like that but she was down for a few days. And she said, "You know what, this is not the horse for me I'm not young, I don't want to play this game. Let's just get him sold." And I was like, "I need an opportunity. I'm willing to hit the ground!"

Jenni O’Connor

"I can fix him!" [both laughing]

Lindsey Oaks

"I can fix it! It's called horse whispering and all little girls can do it. I saw in the movies."

Jenni O’Connor

"I watched a movie once..."

Lindsey Oaks

"I watched a movie one time and it's possible." So I convinced her, and I convinced my parents, and I convinced a couple of other family friends that I could fix this horse and we were going to go all the way to the Olympics and it was going to be amazing. All we needed to do is buy the horse, and within a couple of years, we would all be successful. And I did manage to convince them and we did manage to buy the horse, which is an amazing success itself. But what I did not understand, is that I wasn't going to horse-whisper this horse into being an Olympic horse. It took a long time to sort of develop something and I got to learn a lot of lessons... life lessons... in failure and hitting the ground and communication. All these fun life lessons that I didn't intend to learn.

Jenni O’Connor

So the horse was a people whisperer.

Lindsey Oaks

The horse was a people whisperer, actually, is how that worked out.

Jenni O’Connor

You know, being able to buy this horse you talked about your tribe often, and how supportive they were. How were they influential in your success?

Lindsey Oaks

They were amazing, somehow, it's just amazing that they would buy into these ideas. Like when I talk about my parents being supportive of me leaving I just think it's crazy when I think about it now. Because I would have been 18 when we bought this horse. If I picture an 18 year old walking up to me and saying, "You need to get $10,000 together, we're gonna buy this horse, and we're gonna go the Olympics." The craziness of it all. If I picture me coming to me for money for that? I would write that kid off immediately. There's no way. So like I don't even know why these people believed me. But it's amazing what happens when you get people together, push towards a common purpose, right? All of a sudden, shared resources can become a huge amount of resources that one person or two people couldn't have come up with. Or when you are problem solving and you have something that needs to be solved... "how do I get from point A to point B?"... six people, seven people can come up with a good idea for you. And between the six of you, they can get you to where you need to go. But you can't do that by yourself. 18 year old Lindsey couldn't have done that without all of these people along the way. But between all of us, we did make a lot of that happen. I never did make it to the Olympics, but the horse didn't make it to a high performance training team and he did make it around the toughest event in North America. He did make it to the top... he made it to the height that the Olympics are run on. So those people helped. Eventually I had a groom, that sort of took over a lot of the day to day care of that horse and some other ones that I had coming up and just part of that business, and she changed my life. Being able to hand off the care of that horse to one person who was going to know him inside and out... we called her his slave, because she was just like his person, you know. If he needed something, she knew it before I did. And that was so much more hopeful than me trying to know everything about him and everything about myself that I would know. Being able to hand that off to someone else allowed me to focus on other parts of the business, to pay for all of this or to focus on other parts of his training and things like that, where just one person just can't do that. And really, it makes the ending so much sweeter. Once you get to that place, why would you want to celebrate alone? It's so much better to do it with a team around you and when a whole bunch of people come together and make something happen. It's just that feeling is something that you can't buy. You can't buy that.

Jenni O’Connor

I love that life lesson of just thinking as a business owner as an entrepreneur, being able to delegate being able to hand things off to people who are more skilled in that area so you can focus on the bigger picture. That creates a much bigger result than anything that you could have ever done on your own. We spoke earlier about the competition that you did make it to, I know, you know, zero about horse scoring, equestrian scoring, but you were mentioning that that's actually stricter standards than the Olympics.

Lindsey Oaks

Yeah, so the Olympics are run just a tiny level under that standard simply because you have a lot of countries being represented by first time horses and riders at that level. And the competition is basically a triathalon for horses, it's called eventing. And one of the phases of eventing, day two, is called Cross Country Day. And you and the horse gallop across several miles of terrain at breakneck speeds over jumps, logs, and into water and out of water, and over ditches and things that don't move. So you can hurt yourself if you're not careful. So the Olympics are run just a little bit lower than that because they want to make sure that people who are getting introduced to that level for the first time, if their first time is at the Olympics, don't hurt themselves. No one wants to get hurt and walk away like that. So yeah, it's a pretty big deal. I will say the first time that we went we were not successful. So, in addition to, like, bringing people along with you, realize that you're not always going to make it the first time. And that's okay. Failure is sort of part of the journey, right? Bringing people along with you on the journey but also realize that nothing ever works out like a fairy tale... like you're not going to horse whisper horses to the Olympics. But if you are willing to learn from your mistakes, you can go and compete at a very, very high level and do really well and be successful.

Jenni O’Connor

Absolutely. I think it's incredible that you were able to take a horse that was basically being written off and get him to a national competition and that's mind blowing. That's amazing. And to do it with the support of a group of people, and I think it's such an amazing underdog story.

Lindsey Oaks

It is. He was such an underdog, he still is. He always was from the beginning because he wasn't like everyone else.

Jenni O’Connor

So, what do you wish you had known, looking back at 17 year old Lindsey, who is ready to take on the world and do all these things... What do you wish you'd known at that age when you first started this?

Lindsey Oaks

The first one is bringing along people for the journey. You can't make it there by yourself, and it took me a long time to intentionally build a tribe. You bring people along by necessity or you bring people along because you need something from them. But at some point you learn that you need to bring people along just for the sake of having camaraderie and having people in your court, and being able to support them in the same way that they're supporting you. That's just maybe a little more mature way to look at that.

And then the second thing is that you're going to fail... when again we just touched on that. Fail intelligently fail in a way that you can learn from. When you make a mistake or something goes wrong, like we did when we went to Rolex for the first time (Rolex is the competition that we were talking about). The first time I went, my horse... I didn't anticipate him being turned on by the crowds, so it was sort of the biggest crowd that we had ever seen on cross country day. There are 30,000 people packed into that stadium, watching you. And so 30,000 People are very loud, and he was very flighty. And so he left, except that the farther we went, the more people there were. And so, about nine minutes into galloping cross country I had to stop him, and retire from the competition because I physically could just not stop him any longer. He was no longer under control. He was not under my control, and then things become dangerous because he doesn't know what to expect next, right? So, when we left, I actually tried to quit riding. It's like "I just don't want to do this anymore." I tried to sell the horse but no one was interested in buying a maniac. [both laugh]

Jenni O’Connor

Oddly enough...

Lindsey Oaks

"You don't see potential on this lunatic?" So I tried to sell the horse. And it sort of took me a good six months to like pout it out, get over myself a little bit, right? And then it just sort of came back to "okay you're still qualified you still have the horse... is the fire still there? Well, yes. Okay, Then let's talk about what happened." And it took a long long time for me to get to that place. So it's okay if it takes you a long time too.

But the first thing that I would say is, ask yourself exactly what went wrong. Like be specific. What went wrong? My horse went a little nuts in the cross country and was running off with me. Identify why that happened: The reason why is because I had no idea that the crowds would affect him, the way that they did. And so, I was totally unprepared in that situation to deal with what happened. And then you've got to decide whether or not you can fix it, you know? Sometimes you can't fix it. Sometimes it's something that happens and you go "you know what, this is out of my control. There's nothing I can do to solve that issue." And then you can walk away, being okay with that right. You don't have to go. "You failed and I've got to beat myself up for the next millennia because I suck at life." It's not what it is. It's something that's out of your control that can't be fixed or something that you didn't foresee that you can't fix, you can't solve. And then you go, "Okay, it's alright for me to walk away here." But if you can identify something that can be fixed... for that horse I could change his equipment, I could put something over his ears like a covering so that he couldn't hear the crowds the same way, and I can improve that situation going forward. And, and so we did, we went back and did that. But what we didn't do was go, "Well is it going to be hard? The unknowns... the what ifs, you know what if this happens, what if that happens?" If you're going to approach it that way, then you're probably setting yourself up to fail again. So, look out a little bit logistically and figure out whether or not that's something that can be done. Sometimes you have to get a little time and step outside of yourself, which is what I had to do. We did go back, and the second time we were, we were very successful, because we had a new plan.

Jenni O’Connor

So it sounds like it's not so much about where you end up is it as about the journey. So what advice would you give for enjoying the journey?

Lindsey Oaks

We spend so much more time on the journey than we do, arriving. And then once we arrive, we set a new goal or we have a new thing, and we go on another journey. And then we have to go and wait until we arrive, again, to celebrate. And I think that that's a little backwards. If we don't find ways to celebrate, or to enjoy the act of getting there we'll never be happy. I know this was a lesson that I learned a little bit late in life, it took me a long time to get to that place because I was a very driven person from early on. It took me failing at a very high level, to realize that I had given myself no grace in a seven year period, to getting to that place. The whole time I could not be happy until I made it to Rolex. And seven years is a long time to be that hard on yourself, and to be unhappy. And had I not failed at a massive level. I don't know that I would have learned that. Had I reached the top and won Rolex and done all the things, maybe I would have believed it was worth it. But then I would have had to go on another journey to realize that that's such a small amount of time to celebrate. That lesson wouldn't have set in, I guess is what I'm trying to say. So, when you're on the journey, set smaller goals within your bigger goals. Set up little places where you can go, "I did this, and I won." Make sure that you acknowledge the times that you're successful. You can acknowledge the times that you're not, too, but it's so much more important to give yourself those little wins, so that you can make this long journey worth it. Because otherwise it won't be worth it to you. To get to the top once you get there, it won't taste nearly so sweet. It's just gonna be one more stepping stone to the next one.

Jenni O’Connor

Isn't it amazing how life teaches us lessons, one way or another? I feel like we almost learn the best lessons through our failures.

Lindsey Oaks

It's almost always best learned the hard way. Anything given to you easily can be taken for granted. Had I won my first time around, and it'd been super easy and all of that paid off, I would not have come away with the same attitude. I never could have learned that. But only through the act of having that really blow up in my face in front of 30,000 people, and then spend six months brooding over it, could I go, "This wasn't it," you know? No one in my tribe was as disappointed as I was. They were just thrilled to be there. They couldn't believe what we had accomplished. And looking back now. It's amazing that we got as far as we did. We took that horse so much further than he ever should have gone and yet for a very long time, I didn't see that. All I could see was how I didn't make it as far as I wanted to go. But when you look at the numbers, I mean, the amount of horses that are meant to be on that stage, that make it are so few. There's something like 100 advanced horses in the nation at any given time. That's the level that he was competing at. And that horse never should have made it to that level in the first place.

Jenni O’Connor

So Lindsay what do you think the biggest lesson is you've learned from working with horses?

Lindsey Oaks

I think the biggest lesson that horses have taught me is how to communicate. How you say it matters. And this is something that my mom taught me actually as a little kid. She said this to me all the time is "you can say whatever you want, just as long as you say it right." And when you talk to a horse, if you walk in with really square shoulders and you look him in the eye, that's aggressive. And even if you say something nice to him in that tone, he's going to assume that you're being aggressive. And people are the same. If your words and your tone don't match, it doesn't work. You have to be a little more consistent and be mindful of the way that you say things. I think that's the most important lesson horses have taught me.

Jenni O’Connor

That's so great. Body language is so powerful. And I've read studies on how, if you say one thing and your body language says the opposite, we just instinctively pick up on the body language and that's the message that we're going to go with. It hits on that primal level.

Lindsey Oaks

It makes us not trust whatever is coming out of the person's mouth. Even if they're not lying to you or being distrustful, it just makes you automatically step back and put up a shield.

Jenni O’Connor

So how did you transition from working with horses to helping people with their personal brand? Because I know you own Lindsay Oaks personal branding?

Lindsey Oaks

I do! It's communication. I'm glad that we touched on this. Communication with horses, has been my life's journey. And a few years ago I started a photography business. I've been... I've played with cameras my whole life. And I really began to help service based entrepreneurs to communicate visually. They needed photos for their website and for their social media and different things like that. And I realized that a lot of those people were not utilizing my photos in a really effective way. They were not communicating well. And so I, just last year, launched a whole new suite of services around branding strategy and helping people to identify their visual identity, their verbal identity, how they talk to people and how they visually talk to people, and the value that they present to them. So that all of those things align and through consistency you build a trustworthy brand. And so people are just automatically attracted to you when you're consistent and you know, you have a very clear vision about what you're offering people.

Jenni O’Connor

If a book was written about your life, what would the title be?

Lindsey Oaks

"Do it now and don't think enough to change your mind." [both laugh] I'm an action taker, and I just had a conversation about this with someone this morning. And she was like, "you just take action, you don't care about the details." I said no I take action, so I can't change my mind. Do it, do it right now.

Jenni O’Connor

Jump in. Love that. Lindsey our podcast is called Ashes to Wings, referring to the story of the Phoenix transforming and rising from the ashes. I like to ask all of our guests this question: "What does rise above mean in your life?"

Lindsey Oaks

To rise above... is to do it anyway. Even when you're scared, even when the timing isn't right, even when you feel unprepared, or when you feel that the world doesn't want you to do whatever that thing is. It's to do it anyway. Don't wait for the timing to be right, don't wait to be less scared... you won't be less scared. Do it still. Do it while you're scared, do it while the timing isn't right, do it while the things aren't going well. If it's worth doing, it's worth doing badly.

Jenni O’Connor

So good. Lindsey I always like to leave our listeners with a bumper sticker statement, so a short summary of what we just talked about that would fit on a bumper sticker. What would your statement be?

Lindsey Oaks

It would say "Invest in the journey, instead of the outcome. It takes years to become an overnight success."

Jenni O’Connor

So good and so true, as all entrepreneurs know.

Lindsey Oaks

Amen.

Jenni O’Connor

I have a few rapid fire fun questions for you here.

Lindsey Oaks

Ooh ok! I'm ready.

Jenni O’Connor

Who would play you in a movie?

Lindsey Oaks

Anne Hathaway.

Jenni O’Connor

Ooh yeah. All right. What technology do you wish existed?

Lindsey Oaks

Ah, the ability to put words back in my mouth. Yeah, to just grab them out of the air and shove them back down my throat.

Jenni O’Connor

You'd be a billionaire. All the awkward people said "yes please!"

Lindsey Oaks

Yeeaaahh! Hands up!

Jenni O’Connor

What are your favorite pizza toppings?

Lindsey Oaks

Hm, sausage, pepperoni, mushrooms, green onions, oh there's something else... pineapples.

Jenni O’Connor

Ooh, in that combination?

Lindsey Oaks

All of them, just put them all together.

Jenni O’Connor

I have not tried that

Lindsey Oaks

Magic. [both laugh]

Jenni O’Connor

What book belongs on everyone's bookshelf?

Lindsey Oaks

"Developing the leader within you." Every person should learn how to lead themselves and others.

Jenni O’Connor

Very nice. And this is my favorite one. What is your guilty pleasure song?

Lindsey Oaks

Guilty pleasure song?

Jenni O’Connor

So like windows down, driving down the expressway, singing at the top of your lungs...

Lindsey Oaks

Definitely something by Taylor Swift, because I will never admit to anyone else that I'm a Swifty.

Jenni O’Connor

So, shhhh, don't tell her secret.

Lindsey Oaks

Don't tell anyone, except everyone listening to this.

Jenni O’Connor

It's too funny because you're my second Swifty fan. That's too funny. She is far reaching. Lindsay I know you have an offer for our Ashes to Wings listeners. Tell us about that.

Lindsey Oaks

I do, it's a tutorial on how to write effective social media posts without pulling your hair out. A lot of the people that I work with, want to be able to show up more effectively online because someone said you should post on Facebook to have a better business but they don't actually know what they're trying to accomplish with that. So this will tell you what you're trying to accomplish with that and how to get the engagement that you're looking for without just losing your mind and spending six hours on every post.

Jenni O’Connor

That's so useful. I know it's a multi business owner, I have to hand off a lot of it because it gets overwhelming. There's so many different channels and so to have somebody like yourself come in and say "okay, here's how to do it" is... what a great offer. Thank you for that.

Lindsey Oaks

Yeah, you're so welcome, it can be a real pain if you have no idea why you're doing it. You're just trying to accomplish something and you don't really know why. That happens all the time so have a strategy.

Jenni O’Connor

And have a purpose behind it. And you can find the link for that offer along with Lindsey social media links on her guest page on our website, that's ashestowings.net/Lindsey-Oaks. Make sure you give her a follow. Lindsey thank you so much for joining us today. This was so much fun.

Lindsey Oaks

Thank you so much for having me and giving me the opportunity to be in front of your audience and tell my story. I so appreciate it. I love it.

Lindsey Oaks

Thank you.

[music bumper]

Jenni O’Connor

It's time for another review shout out. This one's from Christie LR and reads, "Perfect timing. Very excited to have this podcast in my library right now. The inspiration and tools Jenni provides are so helpful. Thanks Jenni." Thank you Christie! Make sure you leave us a rating and review, and you might just hear your review read on the air.

[music bumper]

Jenni O’Connor

So just to recap our episode and talk about a few of our takeaway points that Lindsay covered today there were so many great little nuggets in here. No one makes it to the top alone. Invest in relationships, build your tribe. Fail intelligently. Failure is a part of the journey and oftentimes what teaches us our biggest lessons. We spend so much time on the journey and so little actually arriving at our destination... spend energy celebrating the small wins along the way, enjoy the act of getting there. And then her bumper sticker statement was "invest in the journey instead of the outcome. It takes years to become an overnight success." This was such a powerful episode that fits so nicely with our values at Ashes to Wings. Building your tribe, embracing and learning from failure, and celebrating your wins. I hope this helps you learn how to love your journey a bit more today. Don't forget to check out Lindsay's guest page. Again that's ashestowings.net/Lindsey-Oaks. Friends, thank you for listening. Don't forget to follow the show, rate, and review. See you next time.

Outtro

Thanks for listening. The best way to learn is to teach someone else. So take one thing you learned today and share it with a friend. Find Jenni on Instagram at the_Jenni_O'Connor and online at JenniOConnor.com. Subscribe for new episodes. Until next time, rise above.