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Crushing It In Your Own Life While Raising Dauntless Children

Updated: Jan 4, 2021

For many people, having children means putting your personal life and personal goals on pause. How do you maintain your own growth and interest while focusing on being parents? In this episode, Kate Hixson talks with Tommy and Polly Hilleke, an outdoors power couple living in Colorado. They're avid kayakers with numerous awards on their shelf. They've traveled the world jumping from one high achievement to the next. On top of that, they're raising four sons to be absolute savages in a variety of extreme sports - from big mountain skiing to incredible kayaking expeditions. These boys are crushing it at everything that they do. How do you keep crushing it in your own life while raising dauntless children? Find out on this episode where we're exploring life lessons from the world's preeminent overachievers.


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Crushing It In Your Own Life While Raising Dauntless Children?

For many people, once you have children, your personal life and personal goals go on pause. We're suddenly spending our days watching Frozen or Sesame Street and trying to book tickets to Disney on Ice that we forget about who we once were as people. How do you maintain your own growth and interest while focusing on being a mom and a dad? On this episode, I'm talking with Tommy and Polly Hilleke, an outdoors power couple living in Colorado. Tommy and Polly are incredible people. Tommy was once named National Geographic Adventurer of the Year. Polly had a successful sales career.

They're avid kayakers with numerous awards on their shelf. They've traveled the world jumping from one high achievement to the next. On top of that, they're raising four sons and raising them to be absolute savages in a variety of extreme sports from big mountain skiing to incredible kayaking expeditions. These boys are crushing it at everything that they do. They're also good kids, independent, responsible, kind and generous. How do you keep crushing it in your own life while raising dauntless children? Find out on this episode where we're exploring life lessons from the world's preeminent overachievers.

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Welcome, Hillekes, Tommy and Polly. I’m excited to talk with you all. Thank you for taking the time.

Thanks for having us.

You both have four sons. First, I want to hear who is Tommy Hilleke? Who is Polly Hilleke? If you wouldn't mind, give me a little bit of your backstory.

My biggest accomplishment is having the four boys. The backstory is I'm from Alabama originally. I grew up there on a big river, water skiing, swimming, fishing, and southern water sports. After I got out of high school, I got involved with some kayaking. I ended up going to college in Brevard, North Carolina. That was a good spot to be in as kayaking blossomed. The sport of kayaking was starting to blow up and that was in mid-‘90s. I got involved heavily in the sport. I was semi-professional for about 8 or 10 years there. I’m traveling a lot, competing some, doing a lot of exploration of rivers in remote areas. I enjoyed that. Through those travels, I met Polly. We hit it off and then got married in 2004. Polly was from Colorado. We moved out here and started doing this crazy thing raising these children. I worked for the Aspen Skiing Company doing building maintenance. I kayak as much as possible still.

You said you were semi-pro, but I recall you have numerous trophies on your wall for kayaking. Could you give a brief highlight reel of some of your accomplishments within the sport?

I was big into extreme racing like harder whitewater than what you see on the Olympics. Racing like Class 4, 5 sections as fast as you can. I won the Green River Narrows Race six times. The Russell Fork River Rendezvous, 4 or 5 times and a handful of other races around in the west.

You’re casual and humble about it. It's no big deal.

I liked it. It was fun. As far as exploration goes, we got into doing. It’s almost a hybrid between the racing the Class 5 and exploring the rivers. We started with the group of paddlers that I was with got into doing speed descents. We would take sections of river that were difficult, that would maybe take 4 or 5 days to run. We would get all the rapids dialed and the plan for where you had to get out. You had to look and have safety and all that. We would try to do it in one 24-hour push. We did Upper Cherry Creek in California, the Middle Fork of the Kings in California, the Stikine River up in British Columbia and all those one-day descents. I’m trying to think of a few others but those were the big ones.

Polly, you guys were married during this time but tell me a little bit about you. Who is Polly?

I was a working mom. I traveled a lot for my job but an outdoor enthusiast. We spent a lot of time as a family and in my own personal time, whether it was running or paddling or skiing, we love to be outside. Being here in Colorado, we're lucky to have access to the adventures and things that we do. It was a challenging time there when the kids were young. I was working and traveling. Tommy was traveling with his adventures, but it was doable.

Tell us about the boys. You have four sons. What are their names, ages?

The oldest is Kelly. He's 14. Daniel is 13. Dax is 12. Bodie is 10. They're all different but they all share a love for being outside. They're adventurous little guys. Their main interests are kayaking and skiing. Some mountain biking and climbing as well but primarily skiing and kayaking.

Having these four boys, that's a handful. I have a daughter. She's over two years old. She rules the roost around here. I cannot imagine having four and especially all boys. That's cool but what's incredible is that it hasn't stopped you all one bit. You both had strong careers. You were traveling. Polly, weren't you in pharmaceutical sales or something to that effect? You guys were living large and then you have these kids. It hasn't slowed you down. I read about a trip that you did on the Grand Canyon with the boys. Could you tell us a little bit about that?

The Grand Canyon is something that I have been dreaming about for years. Many years since I became a kayaker, I've always wanted to go but I wanted to save it to have that experience with the kids the first time. We had summer paddling. At the beginning of the summer, I would say we were not ready to go, the kids as far as their kayaking skills. By the end of the summer, they were ready. Tommy and I looked at each other and I was like, “We could do the Grand Canyon and we should do the Grand Canyon,” but it's hard to get a permit.

DP 6 | Raising Dauntless Children

The way that permit system works is you put in February for a launch the following year. We got a cancellation permit, which they'll release those random times throughout the year. It's a weighted lottery. I tried in August. I tried in September and we didn't get anything. They had a call-in lottery. They sent out an email on a Thursday and you had to call in Friday morning. We were able to get through. We got the permit. We had two weeks to put this trip together, eighteen days, 280 miles to go down the Grand Canyon. The kids were used to doing multi-day river trips and their kayaking skills were ready. It was a matter of getting people to watch the dog, leave work and all the stuff at home that we had to take care of. The time on the river was spectacular.

Paint a picture for the readers. What is one moment that will be imprinted in your minds forever from that trip?

There are a lot of moments on that trip that blew my mind as far as the progression of the boys, their paddling, being there with my entire family. My parents also went and my sister and her family went. That was a big part of it. The best day was about 80 miles in. You're in the Granite Gorge of the Grand Canyon, which is spectacularly beautiful. It's one of the deepest parts of the Canyon. There's a 30-mile section that has 8 of the 10 biggest rapids in it, plus a whole bunch of rapids that are still big but they're not like the ones that you hear about.

It’s horn, hermit, crystal granite is in there somewhere. That day was incredible because of the scenery. We had a plan like the kayakers would paddle first and set safety for the rafts. I was filming, trying to get as much video of the boys as we could. I put it on them and Polly to be the safety for the raft. Once I was out of the kayak, that takes time to move around. If something had happened to one of the rafts, but seeing the boys react and have that river sense to like, “We're going to go down. We're going to stop in these places.” We’re going to set safety for the rafts. That was cool to see them develop that river sense. Their skills also as paddlers not only to run the rapids successfully but feel comfortable enough to surf waves in the rapids, to drop into holes and do tricks. Throughout the whole day, for me, they had arrived at that point. They were in the element and that was an awesome day. I was proud.

Were they all in their own kayaks?

They're all in their own kayaks.

Bodie, the youngest, I remember reading this is a major accomplishment for him. Could you tell the readers what this trip meant for him?

He's the youngest one to run the whole section. I know there have been a couple of other ten-year-olds that have been down there in kayaks. They have watch rapids or ridden in the raft for sections or days or whatever. Bodie was our goal for a little while. There was an article a few years back about a twelve-year-old girl that ran the whole thing. It was a big deal. I was like, “She's the youngest one at twelve years old. Our kids at that point, they weren't there yet. They were on the trajectory to be able to have the skills to run it at that point. That would be a cool thing that could help inspire.” Giving the kids opportunities to do something great like that helps them inspire other kids. It’s transferring skills from one aspect of your life to another. If I can climb this mountain, then I can take this test or whatever.

I can't imagine the confidence building as well. Many young kids especially in light of this pandemic, there are mental health issues that are being uncovered at an incredible rate. Kids are struggling whether it's anxiety or depression or being out of shape, whatever it is. For your boys to have the opposite experience, to gain all that confidence, to gain the skills, gain the expertise but know that they can do something that's incredible. Ten years old, the youngest person ever to run the Grand Canyon, that is astounding. Polly, what was going through your head in the day that Tommy was describing? What did it mean to you? What were you thinking?

DP 6 | Raising Dauntless Children

I was trying to soak it up the whole time. I was not worried about their safety or their skills. They were ready to do this. It was fun to see them out there with Tommy. Everybody was having a blast. Every day I was trying to be fully present because it was spectacular. They're awesome. They're supportive of each other out there. I'd say, for me, that was one of the highlights. The first big rapid that we got to on the second day was the House Rock Rapid. Tommy was helping the rafts get situated. I went with the boys ahead and they wanted me to film them coming through. I had to run the rapid by myself. All the boys, all four of them, were out on the side of the river scouting the rapid. Hearing them cheer mom on and then watching them come through that first rapid, I was like, “This is no problem. They've got this.”

Do you think that you both are heroes to the boys? Do you think that they're heroes to you?

I'd say they're heroes to me. They blow my mind, the support that they give each other. We learned early on that when we go out and do things, number one, it gives them the confidence. As Tommy said that transfers to other aspects of their life. They've learned that they can do it. How kind they are to each other and the older ones helping the younger ones. It's awesome to see.

It’s not like that every day around the house, to be clear, the chores, day-to-day school, there's arguing and bickering and brotherly love. For whatever reason when they get outside and they're doing something that is challenging, they're at their best with each other, with us. It's cool.

Why do you think that is? I have a two-year-old daughter. I'm trying to raise her to be compassionate, strong, tough and outdoorsy, all these things that are important to me. You have four boys. They're talented. They're skilled. They have teamwork. They have collaboration. They sound like incredible kids. How did you raise them to be like this? What does it look like in the Hilleke household to raise these savages and these warrior kids? What is your secret?

We do push a strong work ethic and hold them accountable for stuff like going out skiing, we put it on them to bring all of their own gear. I might pack some extra gloves, in case, but they know that if they only bring one jacket or wear a sweatshirt that they're going to be cold. We've learned that the hard way a few times. That is letting them be accountable at a young age is key giving them some of that independence, I would say.

The other thing is when they were young, we always call it exploring. We would never call it hiking. We can take the time to check things out, but letting them fall too. They would be jumping up on rocks and in my instinct was to be like, “Don't do that.” They would get bumped up and bruised. That was part of the learning, don't you think?

The curve is a little steep that we've had a few concussions and broken bones.

It comes with the territory.

Tommy calls it free range parenting.

We hear about the idea of the helicopter parents who are right there. They never let their kids fall or falter. They're helping them with everything all the time. While I can see some benefits to that in terms of having that complete and total support. At the same time, it makes much more sense to me, at least to have that free range parenting style, to build their independence, to build their strength, to make them be accountable for themselves and for their own sport, packing their things, getting their gear. I remember hearing about, I forget which son, maybe it was your eldest, Kelly with the Aspen bus ride. Tell us about that. What was that all about?

He started 10 or 11. They love skiing. He wanted to ski with the Aspen Valley Ski Club and be on their development team, the Devo team. He would have to leave school early. Polly and I were both working at this point. For him to get up, to do the afterschool training, he would leave school after lunch on Wednesdays and Fridays. He would have to get ski gear, walk from school to the bus stop, get on the bus, take the bus from Carbondale to Aspen, which is about 30, 35 miles. Get off at the bus and meet up with his group, get his gear on, ski.

A lot of times he'd bus home and have to deal with changing buses. That was a learning curve. We left some phones and gloves and whatever else on the bus a few times. It's stuff. That is an invaluable thing that he has learned. It's coming back to bite us as he's like a teenager and wanting to go with his friends. I'm like, “How are you going to get up there?” He's like, “I'll take the bus. It’s not a big deal.” It's good for him.

Empowering your kids, trusting them. I remember there were some other moms who were like, “Why are you putting your kid on the public bus at ten?” I'm like, “Yeah, he can do it.” The first time he rode the bus, I followed him in the car to make sure he got off at the right spot and all that. Trust in your kids.

It's simple but it's powerful. It's effective. It's a great mindset and a great strategy. Thank you for sharing that. Let me ask you then, because Tommy, you were mentioning there have been some concussions or broken bones. Imagine four boys being raised in the mountains of Colorado, that's going to happen. How do you balance or manage the risk component? For example, are you ever super nervous or scared when you're watching them? Whether it's go through these rapids, you said they're into skiing as well. How do you deal with that?

It's intense. I'm more comfortable in the river setting. I'm a good judge of their river skills and have a good idea of what they're comfortable in and what the risks are on the river. I'm super fortunate to have that. The skiing I get gripped especially Kelly and Daniel, they're doing these big mountain competitions, Daniel and Dax compete in Piping Park. I don't have quite a good understanding like some of the venues that they are on. I can ski it, but I'm not going to be charging down it and jumping off the biggest cliffs. They're going for it. That is their plan of action.

I get gripped with the skiing but I'm trusting them. The Aspen Valley Ski Club does a super good job as far as teaching the kids to ski within their abilities. It's something that I struggle with as well, the risk thing I always have before we even had kids. Finding that balance of what is acceptable risk and it's an ongoing project. I’m getting to where I understand it enough to understand the selfishness of it. That's a big thing. I had to cut that out early on once we had kids. I was still traveling and doing adventures, I had to have a talk with myself about not being all about me anymore and doing the things that I want to do. With the boys, it's the same way. Everybody wants their kid to be the best, be successful, and send it, do that, and be all that. Teaching them to make good judgment calls and only recreate within their ability like paddle within their ability and ski within their ability. Our big rule is don't get hurt. Whatever you're about to do, make sure you're going to stick it and not get hurt. That's a thing that we always say to them.

What about you, Polly?

I worry about them. More so like Tommy, when they're skiing, doing these huge jumps, rails. I do see them checking up every now. Kelly started doing backflips when he was 11 or 12 and was doing them all the time. He over-rotated on one and landed smacked his back. He's like, “I don't know. Maybe that wasn't a good idea.” He learned from that. It's like, “I'm not going to do them unless the conditions are right. He's in the powder.” I do believe in them and I think they have the skills to do the things that they do. I tried not to worry. What I'm worried about is them driving like Kelly's going to get his permit here. I'm like, “That scares me.”

That's hilarious. Something that is like complete rite of passage, it's normal to start driving. That's what scares you. What your boys are doing like these huge competitions, these crazy tricks going down rapids. I'd like to hear a little bit more about their skiing. Same question, can you paint a picture if you guys are sitting at a competition and you're watching them as they're about to go down a course? What does that look like? What are the sights and the sounds when they're competing?

The venues for the big non-competitions are double black diamond runs. Lots of cliff bands, higher consequence to rain. If you fall at the top, there's a good chance you're going to fall the whole way to the bottom. That's the terrain that they're in. They're steep. The way these kids ski them, the things that the judges are looking for. They're not necessarily looking for speed but they're looking for fluidity, which is not stopping. They're looking for a style. They're looking for control, which is a good one, but the object is to ski from top to bottom.

You score points by hitting features. You get a higher score by jumping off a cliff or doing an air into and doing a trick. The kids are wanting to, not only ski the thing without stopping but also throw in some trick or big air or something like that is going to increase the risk. It's fun to watch. It's the energy of the place. You're usually at the bottom of the bunch of the parents and the other kids on the team. They all get super amped before the competitions. It's similar to the paddling competitions that I used to do. There's nervous but excitement. It's a good scene. I like it.

The crowd, people cheering and it's a beautiful scenery. We're lucky out here in Colorado that it's sunny almost all the time. That makes for such a magical day, a magical experience, but going back to what you were saying about the nervousness or the adrenaline. How do you think the boys handle that? For example, they're at the top of the course, maybe they're feeling those butterflies, that nerves. At whatever point in time, they have to get it. It's off to the races and they have to perform and step up. How do you think they do that? How do they turn that switch?

It takes practice. I remember with our oldest, Kelly, his first few competitions, he was nervous and he didn't ski. He usually skis. He held back and was super stiff and that head game takes practice. Our youngest son, Bodie, has got it. He seems to be able to put the nerves aside and ski. He doesn't seem to get too worried about it.

The park skiers are even more amazing to me because they have to perform their tricks. They have it all planned out and all the hits and the rails. I don't like the serene park myself, but those guys being able to, it’s the same thing. The performing under pressure is a skill that it relates good to whitewater. When you're in a rapid, everything is moving. You have to make this move from point A to point B in all this chaos. You have to make that move or else you're going to go into a big hole or crash into some rocks or something like that. The immediacy of what you're doing transfers well from the whitewater to the skiing, that's a good comparison.

Are your boys ever complacent? Meaning, they're doing these incredible competitions. They're going on these big adventures. They're setting world records, in the case of the Grand Canyon trip. Is that it for them? Are they happy? Are they satisfied? Are they looking around the bend at the next race, the next competition?

They always want to progress. Already the kids are doing their ski training and they're trying new tricks. They set goals for themselves. We set family goals too, things that we want to try to accomplish every year. They'll start like Dax, our number three, taught himself how to do a backflip in the backyard all by himself. We have a trampoline. He started doing it off the couch. We have a gymnastics mat. He started doing off the couch and then he started doing it off the picnic table. The next thing you know, he can do it on the ground. They like the progression.

Goals is a good thing. That's a good one. We do a lot of goal setting.

What does that look like, the actual act of goal setting in your household? Is that a particular time of year? Is it a ritual or tradition? Is it all throughout the year conversations?

All of the above. This time of year, we'll look, “We're getting close to the end of the year. Is there anything else that you need to work on?” One of Bodie's goals was to learn to juggle. He's like, “I'm going to try to get ten catches or whatever.” This time of year, for sure, but then we do look at it throughout the year and plan our adventures in our free time around the things that we want to do with the kids. They have financial goals. They have sports goals. They have school goals. Our older two boys wanted to go to this kayak camp in Canada. We paid for it the first year, but we told the boys, “This is expensive. We're not going to be able to do this,” especially if the younger two want to go. They saved up their money to pay for half of the camp. It was a significant amount of money, over $1,000.

It goes back to their work ethic and their sense of independence. I love what you're saying about the constant goal setting and maybe that's part of your secret sauce.

Polly is good about that. We wrote it down, but it's not up on the refrigerator anymore. We usually have it written down on a sheet so that you can look at it every day.

That's what gives you all that constant re-upping or leveling up. It's not enough to have a single goal and crush it, which you both are doing. You're looking at the next goal and the next goal. It's a cycle for you guys. It sounds like. Is that accurate?

I don't know if you've ever reached that point, I guess I haven't reached it yet.

Is there an end goal for you all or as a family? What do you ultimately want for your family?

It’s to be happy. We decided early on where we want to spend our time and our money is sharing these experiences as a family because we love it. They love it. Everybody's happier. You can't put a price tag on the Grand Canyon or all of the river trips that I did this summer. It was amazing. We buy all of our gear at secondhand stores and nobody has anything fancy. That's for sure. Prioritizing those experiences and there are a couple of bigger trips that we'd like to do down the road. Kelly is in high school so we see the next four years like, “What do we want to do as a whole family with him?” We're trying to put a plan together.

Do you think that any of your boys are planning on going pro in either respective sport whether it's paddling or skiing?

They would love to for sure. They'll put in the work for it. I like showing them the other avenues of instruction or guiding because you're still doing it professionally. It goes back to the risk thing. You're not risk-taking at all every day. There's something to be said for professionals that can operate at that elite level. I have a backup plan. You're also giving back more by taking people out, being an influence on your clients or people that you're teaching how to paddle or ski. That's what I would like for them to recognize is that it's not all about them all the time.

Given their wide variety of outdoor pursuits, it stands to reason that they have a significant relationship with Mother Nature. Is that accurate? How do you as a family talk about the outdoors, the environment? What are your thoughts on that?

We're passionate about the outdoors and the environment. Every year, there's a local river cleanup in the valley and we take the kids. They'll spend the day picking up trash. From an early age, I'd say, anytime we'd go exploring or hiking. Before we got in the car, I'm like, “Everybody, pick up a piece of trash, let's do our part.” It's become a habit.

I remember we did a ski mission to this local mountain, Mount Sopris. It's a big day. We break it up into two days and we take the kids. We hike up to this lake. It's about an 8-mile hike. It's the 12,000-foot or almost 13,000, 12,900-peak that we ski. We take one day. We hike into this big basin. The next day we climb the east bowl to the top and then ski back down, back to camp. We'll usually hike out that afternoon. One of the first times we had done it, the boys are carrying their camping gear, their skis, boots, food, and clothes, everything on their backs.

Their packs weigh about half their body weight. We're hiking down the trail and all of a sudden, Daniel, wheels are about to fall off. He sat down a few times and getting crushed. I see him and he's like climbing off the trail down the hill. I'm like, “What are you doing down there?” He's like, “There's a can, somebody left a beer can down here.” He grabs a beer can and comes back up and I'm like, “Good job. We'll take that with us.” In my mind, I remember that day being like, “He's got it.” He's getting it. More so than I had because I would have blown right by.

I love how you both beam when you talk about your kids. For readers, to describe Polly and Tommy, they're glowing. You see the pride in their faces and their smiles. They both have incredible smiles. It almost gives me goosebumps to see this love and pride that you have in them. I go back to a question of, are you their heroes? I would say that you are. You guys are teaching them these lifelong lessons, this way of life, this outlook, this philosophy, and let's face it, you both are cool too.

The reason we both were glowing is we instill these values in them where we try to have these family core values that we all came up with together. To see them, Tommy is telling that story about Daniel, we didn't initiate that or anything. They're taking those values and acting on them on their own. As a parent, that's fantastic.

What are those values if you don't mind sharing?

We call it GREW HIGH. It Grit, Respect, Environment, Wellness, Honesty, Integrity, Gratitude and Respect.

I might steal it and use it with my daughter. It's inspiring to hear from you all, not just your own lives, because you've done incredible things as individuals, as a married couple, your own careers. Now what you're doing with your boys is neat. Let me ask you then if you had to nail down one moment, one day, one trip that you are the proudest of that gives you goosebumps still to this day, that makes your heart want to leave out of your chest, what would it be?

DP 6 | Raising Dauntless Children

It happened summer 2020, it's top of mind. I've had this amazing summer paddling with the boys because I was off. I haven't had the freedom and flexibility to be able to do that. As these cancellation permits came up, I was able to jump on them and go. I wanted to do the Middle Fork of the Salmon River with the kids. I'd been looking for cancellations since the end of May 2020 and nothing was coming up. Those trips get snatched up in seconds. We had gotten back from the Main Salmon. We got back on a Saturday or Sunday. I was on the computer doing stuff for the kids for school.

My homepage was the page, which is where you get the permit. I saw there was a launch date on a Thursday. I called Tommy at work and I say, “Can we go?” He's like, “I got back from the Main Salmon. I can't go.” I was like, “Can I take the boys?” He's like, “Sure.” That night when he got home, it's dark and I'm trying to load up all the gear. There was stuff everywhere. I was driving around in my friend's houses, gathering the stuff that we needed at 9:00 at night. I wasn’t sure. I was like, “I’m going to keep trying until I hit that brick wall, but I'm going to try to make this happen.” Sure enough, everything came together. We made it up there to Idaho and we launched on Thursday. It's 100 miles. We camped out for seven days, me and the boys. We carried all of our gear and our kayaks. It was special. We slept out under the stars every night. The weather was perfect. It was awesome.

That's beautiful in many different ways. The scenery, the adventurous aspects of it is lovely to think about, but what's getting me the most right now is thinking of you, thinking of a mother with four boys camping out under the stars. How many people can say that they've ever done that or that they'll get a chance to do that? For you, that's not an everyday thing by any means. It's special. To be able to do that, you and your boys will never, ever forget that.

I was nervous. I had never paddled a heavy kayak. I'd never done a self-support trip before. I was leaning on Tommy. I'm like, “Can I do this? Are you sure I can do this?” I had some nerves doing it by myself, but the boys, I knew they were solid in the kayaks. I wasn't worried about having to rescue them or anything. There were some unknowns and some risk by taking them out there. You're far into the wilderness. There was nothing. If somebody got hurt, I would have to figure it out. It turned out great.

What about you, Tommy? Have you had a chance to think?

We did a trip. It was crazy. It was right when the lockdown was initially getting started. We had had a hut trip that we had planned all year, which is ski into a hut. From that hut, we build jumps or ski a peak or whatever, tour around and check out the outline. As we were driving there and it was down in the San Juan mountains. They closed the San Juan County as we were driving there. They wouldn't let us park our rig on red non-pass.

We got turned around and we were coming back. It was the boys spring break as well. That's why we'd been planning it for that week. I happened to be talking to my sister on the phone and they have a cabin in Marble Colorado, which has some good skiing around it, but it's not like a hut trip. The renters canceled their trip because of the lockdown. Marble is only 30 miles from our house. She was like, “You guys should go stay up there for the week.” Although it wasn't ideal, our plan was we were like, “We'll go up there and stay a couple of days because it's close if it gets worse or whatever, but we're isolated up there.”

We diverted, went to Marble, went up there and it was a fun week of being outside together. We've done some ski missions where we go and ski peaks, but every day touring. We're like, “We're going to try to go up here and see how far we make it and then ski back to the cabin. The boys were on point with each other. It was not spring conditions, which usually I feel better about taking them out in the spring because the avalanche danger is way less. This was like more winter snowpack. With the boys, we did some quite a bit of beacon, peak in drills and some education, we stop and dig a hole, look at the snow, and being out there with them and having that time.

I don't even know that we accomplished anything except for skiing some pal, we built some jumps and had that time together. That whole week, I don't think there were any arguments. They got along great, helped with the dishes. We stayed in this little cabin that was tight for the six of us. It was an awesome trip. That might've been my favorite one. I had as much fun on that hut trip as I have when I go out with my friends and go on a big hut trip. To get to that point, I’m like, “I'm enjoying this now.”

You are raising the next generation of athletes but also environmentalists and instructors, possibly they could go that route coaching, taking other people out and what an incredible, wonderful responsibility for you to be teaching them those skills. Looking up the snow and talking about it, that is an important aspect of living in Colorado if you're out there in the mountains. Let me ask you, for readers who are interested in you all, where can they find you online? Do you have a YouTube page or social media? Where can they connect with you all?

The kids have their YouTube. It's Outdoor Kids. You can see a video of them skiing. Their Instagram is @Brothers_In_The_Backcountry.

I started following them. I love seeing their photos, little video clips. It's gnarly. They're savages, but they also seem like such good kids. They don't come across as arrogant or anything. They don't take anything for granted, is what I'm saying. They seem like good kids, but they have to be doing amazing things.

If they get anything, they don't have to do the amazing stuff, but they do have to be good kids.

Thank you both for taking the time to talk with me. I loved hearing all about your life and getting to know both of you a little bit more, hearing about your boys. Thank you.

Thank you. We appreciate it. It's been fun.


What an amazing conversation with Tommy and Polly Hilleke, from their beautiful values they share as a family to how they instill a strong work ethic in their boys. There are many takeaways that we all can be inspired by and apply to our own lives. For this session's homework, readers, I want you to focus on how you can make goal setting a habit and constantly be leveling up your life like what we learned from the Hilleke family. We're going to dig in on how you can set small goals, even silly fun goals in order to get that cycle of achievement ingrained in you, head over to and on episode six, download your free worksheet.

This is going to be a fun light-hearted one, but with kick-ass outcomes. Thank you for reading. Many thanks to Tommy and Polly Hilleke for being an amazing guest and sharing their stories with us. Check out their boys on Insta @Brothers_In_The_Backcountry and follow along to see if they do in fact go pro one day. I'm betting they will. For more stories and insights from the world's preeminent overachievers, subscribe to the Dauntless Podcast anywhere you listen. Until next episode, be fearless, everyone.

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About Polly Hilleke

Experienced Account Representative with a demonstrated history of working in the pharmaceuticals industry. Skilled in Negotiation, Pharmaceutics, Microsoft Word, and Biotechnology. Strong sales professional graduated from MontanaState University-Bozeman. Outdoor Adventurer


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