The Leap: How Kristen Reynolds Went from “Not Qualified” to Leading Chicago

What does it take to make career moves that everyone else thinks are impossible?

In this episode of Learn Tourism's Business Class podcast, Stephen Ekstrom sits down with Kristen Reynolds, President & CEO of Choose Chicago, to explore the mindset behind one of the tourism industry's most remarkable leadership journeys. From public relations and lobbying to leading destination organizations in New York and now one of the world's premier visitor destinations, Kristen shares how curiosity, confidence, and a willingness to take risks helped her overcome every "you can't do that" moment along the way.

They discuss career growth, imposter syndrome, leadership, lifelong learning, family sacrifices, and why the future belongs to leaders who are willing to bet on themselves. Along the way, Kristen reveals the four principles that have guided her success: passion, purpose, performance, and positivity.

Whether you're a student, emerging professional, or seasoned destination leader, this conversation is a masterclass in turning ambition into action.

Business Class is brought to you by Learn Tourism, the nonprofit academy - harnessing the power of science, business psychology and adult education to advance the tourism industry and build sustainable economies. Learn how to engage your community, win over stakeholders and get more visitors at learntourism.org. 

Transcript

SPEAKER_00 0:00

We talked a little bit before about your leadership style, how you ended up working in destinations. I think what we might want to talk about is how you can grow from destination to destination and what you're most proud of now in Chicago.

SPEAKER_01 0:14

What I talk about most to other people. So I just feel like that's usually the question I get asked from people privately that they kind of want to know how I did it and how they can continue to grow in their careers. I'm Kristen Reynolds, president and CEO of Choose Chicago.

SPEAKER_00 0:48

There is a huge smile on your face when you say that. What do you love most about being in Chicago?

SPEAKER_01 0:54

I'm just living out my dream right now. I'm living out my professional dreams, my personal dreams, living in a major city, living downtown, being in Chicago day in, day out. And it's just now embarking on summertime shy, which is the best time of year to be here. And so there's a lot to smile about.

SPEAKER_00 1:14

You know, you went from one coast to another, sort of, you know, with a view of the water.

SPEAKER_01 1:19

I went from Arizona to New York first. So that was really coast to coast. And then I came kind of the center of the country. And I think Chicago's a great amalgamation of both of those kinds of destinations that I came from. And it's the perfect next step in my career. But it's really an incredible, vibrant city. There's something to do 24 hours a day in this city, but it still feels comfortable and suburban. So that's what I really love about it the most.

SPEAKER_00 1:49

So your career journey has had a few major leaps. A lot of folks are hesitant to take, you know, from a meeting standpoint, leisure, and then hopping into the tier one seat. How have you managed to make that happen? And what advice would you have for somebody else who's looking to do the same?

SPEAKER_01 2:09

You know, it's interesting. I just had something on my Instagram. I just posted a story like a me over the weekend, and so many people were like, yes, yes, yes, yes. Because it said, you know, sometimes the the choices that you make and the leaps that you decide to make, especially if they're high risk, can seem completely unfathomable or and sometimes unstable or insane to other people. And honestly, that's how my career has always been. I feel like I've always taken those risks. I've always followed my heart and my passion and really believed that I could step into whatever role it was and rise to the occasion. Always believed in myself sometimes, and most oftentimes more than a lot of other people believed in me. And that's okay. I think another piece of advice I saw in one of the CEO masterclasses was you have to believe in yourself almost to the point of delusion. Because every job I've done was something that I had never done before. I'd never worked at a resort and I went to be the head of PR. I'd never worked at an association and I jumped in. I'd never been a lobbyist and I became the lobbyist. I'd never even worked at a DMO and I became the CEO of Long Island, New York. And I had no convention experience other than working to get one built on Long Island. And everybody said you could never step into a tier one destination without convention experience. And yet here I am a year later. I think you just have to believe in yourself and make sure you are willing to do the hard work. A lot of people ask me, like, do you sleep? I see your Instagram and you're everywhere all the time. And you know what? I do work really hard. And that's what I told the search committee up to Chicago. I said, if I'm given this opportunity, I will not be outworked. And I love what I do every day. So to me, I wake up with a smile.

SPEAKER_00 3:55

What has been something that surprised you about Chicago?

SPEAKER_01 4:00

Well, I think when I first came to Chicago, even when I was getting introduced, it felt to me so overwhelming, like such a major city. How could one person ever be responsible for representing and promoting this entire city with so much depth and breadth and 77 neighborhoods and so many cultures? I wasn't sure how I was going to be able to do it. But I think once I'm here and immersed in it and a Chicagoan, it really is one city, one destination, and it's a community. Just like any other destination and community, the size and scope is certainly bigger and the pace is faster. But it feels like a big, small town. Everywhere I go, I run into people that I know, and people have really embraced me here. So I'm very grateful.

SPEAKER_00 4:43

When you talk about stepping into leadership, you mention having self-confidence. I talk to people and I say, that's having some faith that you're not going to let yourself down. And that you're you're going to work hard to make yourself proud and to live up to the expectations you set for other people. And the other part of it is a commitment to learning.

SPEAKER_01 5:04

My husband says that about me. He always says, like, I think the thing he says he loves the most is that I'm curious all the time. I don't think I know everything, first of all, but I want to learn. Um, and so that curiosity, I think, is really what brings that what people call energy because I want to be there. I want to be at the table, I want to be always learning, always seeking, always striving. But yeah, it is a daily struggle. I think the confidence, it's definitely one of those things that when people ask, like, how did you get the confidence to apply for this job or that job? And I'm like, well, I just looked at the people that were there before and I'm kind of like, if they can do it, I can do it. And it doesn't seem like, you know, I mean, we're all just humans and we all bring our own set of skills to the table. So I kind of just approach things. Sometimes I say, like, Elle Woods, you know, like what, like it's hard. Like sometimes you don't know what you're not capable of doing. You just go for it. And I do approach things in that manner. But the other thing, I remember when I became a lobbyist in Arizona and I was the lobbyist for the state tourism industry, and I'd never been a lobbyist before, but I knew deeply about that industry and the ROI that it brings and the value that it brings. And I lived and breeds it for decades. So I remember telling at the time the director of Arizona Office of Tourism, Sherry Henry, who was a great mentor of mine, I said to her, scare. It's I'm scared because I just I don't want to let people down that have given me this opportunity. And she said, good that you're scared and you should stay scared because when you get comfortable is when you trip, is when you make mistakes. If you stay scared, you stay on your toes, top of your game, you wake up every day, and I don't take anything for granted. And I remember her advice, and I've carried that with me.

SPEAKER_00 6:52

What's something you would like to learn this year that may not be expected of you?

SPEAKER_01 6:59

Oh gosh. I don't know if it's not expected of me. I think there is so much to learn when you go to another destination and you've never lived there before. And I've done this multiple times now. I remember when I went from Arizona to Long Island, everyone kind of thought I was having a nervous breakdown or like, she's crazy. Why would she do that? And by the way, I did that as a single mom with two young daughters by myself, and that was a huge leap. And kind of doing it again, people are like, how to upend your life is a big deal. So I don't know that it's unexpected of me, but I do have so much to learn about this city, about all the different neighborhoods, still, that so many I have yet to visit, and there's just not enough hours in a day. There's still a lot that I'm really excited to learn because I, as you can probably tell, I'm a very competitive person. I like to challenge myself. So the convention side of the business, which was always a stickler for me, by the way, I got turned down many times. People wouldn't even interview me for jobs because I didn't have convention experience. And now I represent the largest convention center in North America. And so my big goal is to be the leading expert on conventions and group business in our industry. I don't think people expect that of me, maybe, but it is kind of part of the job description.

SPEAKER_00 8:19

In what ways will you measure your own success?

SPEAKER_01 8:26

Oh gosh. Do we ever really feel like we've achieved that goal when we're in it? I saw this TikTok and I love this lady. Her name is TikTok Mima. And she's kind of nuts. She drinks a lot of coffee and taps her coffee mugs, and she's this inspirational speaker. And she spoke to me in a moment when I really needed that kind of boost. And she was saying on her presentation that look back at your former self and think about what your former self would have said about what you've achieved today. And take a minute to just relish in that and enjoy it. Because you heard me saying a minute ago, it's not good enough that I'm here. I want to be the leading expert and I want to move on to the next thing. And it's always achieving, achieving, achieving. But I do think that it's important to take those pauses and to stop in our moments when we have achieved our lifelong dreams and ambitions. For me, I just wanted to be the CEO of a DMO and I had achieved that. And now to be the CEO of Chicago, which is arguably the greatest city, not only in the country, but in the world, it's infathomable to me. I can't even believe that I'm here day in and day out. But it's important to take a breath and just live in that stand in that gratitude and say, I've done it. I have achieved success beyond my wildest dreams. And I should be thankful and applaud myself for that a little bit, and then always be striving to move forward. So really, I've achieved success more than I ever thought in my life. And I never really want to stop that growth.

SPEAKER_00 10:03

So a two-part question. Number one, when you're shopping for your next opportunity, or when you were shopping for this opportunity, your last opportunity, what was something you looked for in each of those communities that may not have been part of the job description, but you thought was important? And then the second part, how did you know that this was home? When did you feel like this new destination was whole?

SPEAKER_01 10:26

It was different for me at different stages of your life, I think. The first, when I moved from Arizona to Long Island, really what I was looking for is something big enough to make me sell my house and moon. There were other jobs that were CEO positions that I had been offered. But for me to sell my house in Scottsdale and upend my life, it needed to be really quote unquote worth it. Until I found New York, when I got the offer from New York, I was like, this is worth it for my next step in my career and what I want to do. And it was a, and I didn't know anything about it. I didn't know about Long Island. I didn't know at the time that it had the best education in the country and it was an incredible place to raise my daughters. And it was really like a Norman Rockwell painting come to life that you get to live. And the proximity of New York City was gonna just it changed their lives. So for that decision, it was, is it worth it? And is it enough for me to go through all of this? And then when it came to Chicago, and my next opportunity that I was looking for when Chicago came up, I had really established such a great quality of life where I was living on Long Island and I loved my life so much that it was less about the destination I want to represent. And it was about where do I want to live? Where, what is gonna make me happy? Because I realized at that point, again, I'd kind of already fulfilled my dream of being a DMO CEO. And for me to move again, it needed to be someplace that I really felt like I wanted to be all the time. I was able to be a little bit choosy in Chicago. My husband's from the suburbs of Chicago, and we would come here all the time to visit his family. So I knew I knew this city and I knew this is where I wanted to be. So it depends. It depends on what you're looking for. You know, each person is in maybe different times in their lives. And I knew Chicago was home actually just recently when my daughter came back for the summer. Because, you know, we left our big our house on Long Island in the suburbs and we became empty nesters and all of our kids went to college. But when my kids want to quote unquote come home for the summer, that's home is where my kids want to come home to.

SPEAKER_00 12:40

That makes a big difference. What did your kids say about you getting this opportunity when you announced it to them?

SPEAKER_01 12:45

Yeah, I think my kids, you know, they had I don't want to flip how difficult that transition was in our lives when we left everyone we know and loved behind and started over just the three of us, and then ended up meeting my husband on Long Island, and then we blended our families and became kind of like the Brady bunch. But we were settled, and so they were kind of like, Are you sure you want to do this again? And we get Chicago's amazing, and they've always supported my career aspirations, but I think they were hesitant to leave behind the life that we created, but then they were going to college, and then when I got it and moved here, they came with me to IPW when we were hosting. And to watch, to be with me when I got to speak on stage in front of 6,000 people and to walk through the field museum at the opening party and have people from all over the world want to talk to me and meet me and congratulate me. I think they I think they really realized, like, wow, that's our mom, you know, and they're very proud of me and supportive of me. And I'm incredibly grateful.

SPEAKER_00 13:52

What has been the most interesting question you've been asked on a podcast or interview recently?

SPEAKER_01 13:58

Well, I haven't done as many. I've been asking more of the questions because we launched our podcast all for the love of Chicago recently, and that's been fun because I'm as a podcast host, you get to ask the questions you get to learn so much from other people. Somebody asked me just the other day what my unusual hobby was. Like, what's an unusual hobby? Something that people don't necessarily see on the internet. And so I just, as I mentioned, a very competitive person and I'm a very driven person. So I just finished my 1500th pure bar class. I go to Pure Bar, which is like a workout Pilates kind of thing. And I've been doing it for 10 years. And I just did my 1500th class and it was a big deal. I got to sign the 1500th bar, and I'm the only person that signed it thus far in my whole studio.

SPEAKER_00 14:51

Wow, good for you.

SPEAKER_01 14:52

It's a big deal, yeah.

SPEAKER_00 14:53

Well, what do you like to ask people when you're hosting?

SPEAKER_01 14:56

I like to hear about people's hearts. We start every with every question with what do you love about Chicago? And it's fun because you get to hear things. And I always say you can't say the people because everybody says the people. Yep. And so it's fun to hear people's answers, especially when you challenge them. But I always like to find out the why. Because at the end of the day, again, somebody told me this early in my career when I was just starting my family and I was like workaholic, and they said, you know, five years after you're gone from your job, doesn't matter what title or position you held, people in your company won't remember who you are. But your family will always remember who you are. And so it's really important that in this hustle-bustle world that we live in and these career-driven opportunities that we're that we're able to pursue, that we remember to prioritize the things and the people that really matter. And so I really like hearing about the why when I talk to people and what drives our decisions and what really is important to them in their lives. I think that's what really ultimately connects all of us together, are those emotional reasons.

SPEAKER_00 16:09

When you think about that contribution you hope to make to Chicago, how would you define that?

SPEAKER_01 16:18

So when I left Long Island, if you looked at my LinkedIn when I announced that I was leaving, and when people came by, not just like hoteliers, but people that from the chamber and from commercial real estate places that in the community, they came by to hug me and to give me little bracelets and little plaques and picture frames. And they said the number one thing people said is, thank you for what you did for Long Island. Thank you for what you did for our community. And I feel like if you listen to the podcast, All for the Love of Chicago, because we just launched that this past year under my leadership. And I think that is again to get people talking and to build that community pride and to make sure that I feel like what I do as a DMO leader is I like to connect the community together first and then share that with the world, as opposed to doing it the other way around. And I think that's the difference in my strategy and approach, and it's felt on the local level. So I think hopefully what people will see that I'm bringing to Chicago is that love and passion for the city and for the residents of this city and for the businesses to be successful here. That's the priority, and then that will resonate into success when we drive visitors because everyone will want to be someplace or people want to live. Hopefully, when I leave Chicago or retire or whatever it is, they'll say thank you for what you did for Chicago and for uplifting our city.

SPEAKER_00 17:47

Well, did I not ask that you wish I did?

SPEAKER_01 17:55

I think what kind of legacy do you want to leave for future tourism industry or DMO leaders? Because I really do think that our industry and our world is changing so so rapidly right now that it's a crazy time to be in this industry and in this economy. So I just really hope that our future leaders never give up on themselves and on their dreams and make sure that I call it my four Ps. And it's passion, purpose, performance, and positivity. And those are the four things that really I think keep you going day in, day out, year after year, if you have those four things. And if you don't have those four components in your life and in your career, you should find a place where you do because I think they exist.

SPEAKER_00 18:51

Yeah. Anything you'd like to ask me?

SPEAKER_01 18:54

Oh my gosh. So you are kind of also that person that upended your life, right? And you kind of prioritized. Yeah. So what is your next chapter? How are you settling in and kind of coming off of that wild ride?

SPEAKER_00 19:15

Well, it's funny, I'm still on the wild ride and still a nomad. I'm still traveling all over North America. I moved from a van into a bus that has a dishwasher. Wow. So I'm I'm traveling fancy these days. But what I tell people is I have my aha moment was about 11 years ago. And that was when I realized as much as I love to travel and I love to try new food and visit new places and meet people and all of these things and art and nature and science, what they all had in common was that I love to learn. And I have landed in a space where when one teaches to learn, and I get to share with others while also learning from them. And I think in the destination space, we learn as much from our visitors about who we are as we hope to share with them, if not more. So that has been really, really exciting for me. You know, since we first talked, learn tourism has grown to over 75,000 students and learners. We've got 65, 70 different destinations that are running the training and education programs through us all over the world. We had 100% retention year over year, but to keep that retention rate to continue learning. We had our staff meeting today, and one of the things that somebody said was that I like how whenever we have a moment of where we might feel not aligned with our partners, we approach it from what can we learn? How can we be better? And to be better today than I was yesterday, and better tomorrow still, that's the goal. I apply that to my work, I apply that to helping raise my niece, to travel, to meeting new people, and all of that. You know, to be better today than I was yesterday.

SPEAKER_01 21:09

What do you see in the future for our industry or just in general?

SPEAKER_00 21:18

The most successful destinations are gonna be those that lead with the values visitor. And I say values, not value. It's one thing to get somebody who's gonna buy the least expensive trip to wherever because they can. That's great for spring break, but for the long term success of a destination, it's defining who you are, why you do what you do, and finding visitors who are aligned with that. And then teaching the visitors who are in the destination and teaching your frontline workers how to engage those visitors so that they are better visitors while they're there. And I think individually, destinations are doing a great job at expressing who they are and what's important to them and what their community values are, whether that's stewardship, preservation, culture, vibrancy, you know, all of these things impact. I hope in the next 18 months, and this is a hope, that destinations on a much larger scale, whether that's regionally, nationally, internationally, can elevate those values that bring us together.

SPEAKER_01 22:38

Our jobs are big. I'll tell you that. It's not just about selling hotel rooms and selling convention exhibits. It's a big role that we play, I think, in the community, in the economy, and across the globe. So it's not to be taken lightly. And I think to your point, those of us who do it uh with the right goals and mindset can really make a difference.

SPEAKER_00 23:05

Yeah. And to do so in such a way that matters for the individual down the street, for the person who's working outside of the tourist district, for the person that just came to visit on a whim. It makes a big difference for people in a lot of ways. Thank you. Thank you for what you did.

SPEAKER_01 23:24

Thank you. I love our industry and I feel very, I've said it million times, but I feel very lucky. It's a lot of work. In fact, I was just reading again one more I wanted to show you. It said, uh, I came across it and it said, what a privilege to be tired from work you once bent the universe for. What a privilege to feel overwhelmed by the growth you used to dream about. What a privilege to be challenged by a life you created on purpose. What a privilege to outgrow things you used to settle for. I just love that. And that is that is what growth and achievement is all about. So great to talk to you again.

SPEAKER_00 24:00

And chatting with you is always a pleasure. I can't wait to see you in Portland in a couple months.

SPEAKER_01 24:05

Yes, I will be there.

SPEAKER_00 24:06

Fantastic. You might see the bus rolling around town.

SPEAKER_01 24:09

One more question. How do you decide where you're gonna go next?

SPEAKER_00 24:13

So every year there are a couple of events on my calendar, and it's a big game of connect the dots between them. I'll be in Portland for DI. Well, I haven't explored Oregon and Washington, so I figured I'll make my way up there and spend some time. Today I'm in Montana. So yeah, it's gorgeous. And every time I talk to someone or meet someone that's someplace interesting, or I see something online or in my social feed that looks kind of cool, I add a pin to the map. And I just play a big game at connect the knots.

SPEAKER_01 24:44

Okay, that's great. It's better than throwing a guard.

SPEAKER_00 24:48

It is a lot better than throwing a dart, but I will tell you, when I first started this, I would plan three months in advance. I don't do that anymore. I don't do that anymore, with the exception of having to plan for my niece. We picked out where she's gonna go to summer camp. It's gonna be outside of Portland. But to have the freedom to spend as much time as I want in a cool place, if I find a cool place, yeah, to immerse myself in exploring the experience that is today, that has become more and more important.

SPEAKER_01 25:19

Yeah, you never know what tomorrow holds, right?

SPEAKER_00 25:22

No, tomorrow is a great unknown, but I've got a beautiful view outside my window today, and I'm grateful for it. Okay, good.

SPEAKER_01 25:28

Well, thank you for answering all my questions too. And I will see you soon in Portland.

SPEAKER_00 25:32

Thank you. Have a wonderful afternoon. I appreciate you.

SPEAKER_01 25:35

Bye.

SPEAKER_00 25:35

Bye bye.