Colleen O’Brien is an accomplished marketing executive with over a decade of experience leading strategic internal and external communications for companies of all sizes—from Fortune 500 corporations to early-stage startups. Currently, she is the chief communications officer for high-end clothing rental startup Armoire.
Previously, Colleen led brand marketing, content creation, and communications strategy for Microsoft’s venture fund M12, which invests globally in early-stage enterprise software companies. Prior to joining M12, Colleen held several marketing and communications roles across Microsoft, and led product marketing initiatives for Windows and Office, driving growth, engagement, and partnerships globally. Colleen produced and hosted Microsoft’s Women in Business and Technology podcast and served as a spokesperson on the weekly YouTube series Microsoft Unboxed.
Colleen has an MBA from the University of Washington Foster School of Business and graduated cum laude from Harvard College with a Bachelor of Arts in film production and a minor in studies of women, gender, and sexuality. Colleen sits on the advisory board of Women in Cloud and is a member of the Forbes Communications Council.
She is also a certified executive coach and a sought-out speaker on the All Raise Visionary Voices speakers bureau, and has appeared at the PRSA Storytellers Series, the Women in Tech Regatta, and Ideagen’s Global Goals 2030 Summit.
In this episode, Colleen and Bryan discuss:
– The connection between mindset and motivation
– Tapping into your network to take projects to the next level
– Building on our skills before learning new ones
The show is shared on the following platforms:
Transcript:
Bryan Wish:
Colleen, welcome to the One Away Show.
Colleen O’Brien:
Thank you so much for having me.
Bryan Wish:
It’s a honor. You’ve been an incredible support in my life and people I know, so glad to do this. Colleen, what is the One Away Moment, that you want to share with us today?
Colleen O’Brien:
The One Away Moment that has been most pivotal in my life was working with an individual named Raphael Aquino Jose, who taught me a really important lesson. That we are responsible for making our jobs fun. And it was this total mindset shift for me. Up until that point, I had sort of thought about jobs as a list of duties that you had to perform, or metrics that you had to hit. And he provided this whole new perspective that sure, maybe those are the to-do list items that you have to check off, but we are in the driver’s seat of making those achievable, in the most fun way possible. We are the creators of the way in which those things get done.
Bryan Wish:
Hmm. Super interesting. So, what led, were you in a state of not happy at work? Or, a different state where you just … Or, is this just kind of naturally, a conversation happened and it just stuck out to you?
Colleen O’Brien:
Honestly, it was working very close to him and having access to the things that he had to achieve, but also witnessing that the way he spent his time every day seemed more exciting and enticing, than the ways that other people were spending their time. And I thought, there has to be some sort of secret sauce there. How do you just find yourself on location, shooting incredible commercials? He was actually one of the creators of the first Microsoft commercials that featured a gay couple on screen. How do you get to work with some of the most exciting food personalities on your campaign? How do you get to work with some of the greatest creative minds in the industry? And, it’s because he was so intentional about how he was getting his work done, and not just what the work was that had to be done.
Bryan Wish:
Interesting. And so when you say, just to clarify, when you say fun, was it, or maybe it’s both. But was it the activities that he was able to cultivate, and be intentional about creating for himself? And you saw that and said, “I want to emulate that.” Or was it the maybe nature in which he showed up, to the work or activities he was doing?
Colleen O’Brien:
Yeah. Well, if you take a step back and think about it, businesses, oftentimes across industries, across sectors, they have shared types of goals, whether it is to drive growth or drive retention. And there are different ways to get those things done. You can sort of go into work with your head down every day and say, “Oh, I have to hit this growth metric. What am I doing? I’m hitting my head against the wall.” Or you can say, “What is the most interesting way to think about this problem today? And how do I make this a goal that helps me achieve other things that I’m interested in? How do I make this pursuit have a little bit more meaning than it would otherwise? How can I shift this list of to do list activities, from things I have to do to things that I want to do?”
Colleen O’Brien:
And it just, for me, it lessened the stress of those metrics. It was an approach to work. It was a philosophy about how things get done, as opposed to a hard commitment to working as hard as possible, or it was taking a step back and breathing some fresh air into the process, instead of just doing what we’d always done before.
Bryan Wish:
Interesting. Okay. So it was, I loved how you said it was a philosophy in which, or how the work got done, because it’s not always just go, put your head down. Come in, do a checklist and say goodbye. It’s you could incorporate fun. You were able to see that, I guess, for yourself, as you kind of bring that around. When you saw him doing that, were you operating in a similar capacity and saying, “Oh, that’s just like me?” Or was the way you were working significantly different and said, “Oh wow. I could do things a bit adjusted?”
Colleen O’Brien:
I was working in a totally different way. I was thinking inside of the box. I was managing social media channels for the product that we were working on at that time. And I was charged with growing our community, with driving more engagement. And every day, I would come sit at my desk, do a little bit of competitive analysis and just hit post on something. And it was a tried and true method. I knew how to do that. I knew how to go through the rhythms of my work.
Colleen O’Brien:
He would instead, take that goal and figure out, what is the most interesting way to get this work done? Who are the collaborators who are going to help unlock that next wave of growth? If I know that this thing isn’t working, how can I consistently be experimenting and collaborating with new people to get the work done, instead of going through the motions? And it really shook me up. It was a good challenge to me. I realized that work and performance was not just getting through a list of tasks. It was really being innovative about problem solving. It was putting myself out of the job, because I had come up with a solution so great that the job didn’t need to be done anymore. And that was fundamentally a shift for me, and has really impacted how I’ve thought about work since.
Bryan Wish:
Well, it’d be fun to, we’ll get to what that looks like today for you, I’m sure. But I maybe want to go a few layers deeper, as if you’re willing to go ride the wave with me. So, you saw this guy, Raphael. He inspired you because you were working in a completely different way or setting. But what I’m curious about is maybe, as you look back at years that preceded that moment in time, and that person who maybe inspired you differently, why do you think, or how do you think maybe you ended up in that moment? Or maybe you were operating inside a box, or you weren’t as innovative, or weren’t as fun with creating the outcome you wanted. Was there anything from college or past experiences, that maybe had you a little more enclosed than you’d like to be?
Colleen O’Brien:
Absolutely. I was a totally by the book individual. I had gone through the process of getting good grades in high school and going to college, and doing what I was supposed to do in college. Picking my major on time, doing all of the activities that I was supposed to do, to make my resume look great for getting that job. I had landed a big job after college. I was very much comfortable with playing by the rules, with getting a list of assignments and knowing how to complete them.
Colleen O’Brien:
It was a comfort zone that I had created for myself. Get this challenge, answer in precisely the way that I know how. The concept of, fundamentally rethink what the challenge is, was totally new to me. Work seemed like a school assignment, or seemed like a task to be performed. I wasn’t infusing the level of creativity that I could, into the process of getting things done. And for good reason. I had been rewarded for doing things by the books for so long. It felt safe. It didn’t waste anyone’s money. We weren’t really taking any big risks. That’s where I was most comfortable playing.
Bryan Wish:
Totally. It makes a lot of sense. I love what you said. I was rewarded for playing it safe in a way. Did something ever inside you, were you consciously aware of the fact that you were playing it safe or by the rules, or was that just all you knew until you did it?
Colleen O’Brien:
So, the first time that I realized I was playing it safe was actually on a college admissions tour. We were talking to one of the students who was leading the tour. And of course, you ask a lot of similar questions on each of your college tours. What are the students like here? What does it take to get admitted? And this tour guide in particular said, “A lot of our students are well-rounded.” Well-rounded is a term that you’ve heard before. They do a little bit of everything well, or lovably lopsided. They have a deep interest and lean into it, and that is what they love. And they don’t sort of feel pressured to do the well-rounded thing.
Colleen O’Brien:
And I remember thinking like, “Oh wait, that’s an option?” It’s just like an option to only do the thing that you love. I thought part of playing this game was doing a little bit of everything, and doing it great. And hearing that for the first time sort of, it was the first time that I felt like there was permission to snub the societal pressure to do everything well. Yeah. So it wasn’t until that college admissions tour that I even thought about the concept of, leaning into only what you love.
Bryan Wish:
Sure. Yeah. That is powerful, to be cognizant of. But what’s so interesting, it sounds like is, you kept maybe again … I don’t want to project, but it sounds like you kept playing it safe to a degree, even after knowing that experience without maybe giving yourself that permission until later on to do it different. Is that fair?
Colleen O’Brien:
It’s fair. But I think I started to dabble. I started to dabble in doing the things that I wanted, versus doing the things that were expected. And, there were these moments where there was societal pressure to stop doing it. So for example, in college, I knew that I was a great writer, and decided that English might be a potential major for me. So I started taking some English classes, but a few were at this intersection of media studies and film production. And that is really where I lit up. Film production and visual media were just, they were life giving for me. I got really excited to go to those classes. I thought about the assignments as incredible creative challenges. And suddenly, I found myself as a film production major, instead of the English major I thought that I was going to be.
Colleen O’Brien:
And I remember standing outside on campus one day, waiting to go into lunch. And a random tourist on campus came over to chat with me and said, “I’m on a tour. Are you a student? What are you studying?” And I said, “Oh, I’m studying film production. I really love it.” And she said to me like, “Oh, what a weird thing to do. In order to get your money’s worth, you really need to be studying philosophy, or history or government here.” And I just thought, what a strange projection, but it was, it felt like a signal from the universe that maybe I had colored too far outside of the lines. Or, if this individual knows better, why don’t I know better? So there were some strange hurdles along the way, where I did feel challenged in straying from the norm, and trying to do things in a more fun, creative, energizing way.
Bryan Wish:
Yeah. It’s so interesting how these signals pop up and it’s, you were diverging from maybe the norm where you went to school. And then, actually someone appears out the blue and tries to push you back in, into the box. I’m sure that shook you a little bit, or just made you question your path?
Colleen O’Brien:
Yeah, absolutely. There are a couple of times in a college, well, in my college career in particular, where I felt like, “Oh, no, did I make a big mistake? Did I take a wrong turn?” The next one sort of showed up during job recruiting season, where I felt like I had totally missed the boat on, what is consulting? How does everyone know what it is and that they want to do it? How did everyone get invited to all of these recruiting events? But yeah, I was sort of going along, really enjoying what I was doing, liking what I was studying, but there were these milestone moments where I felt a little taken aback, and like I had made a wrong turn.
Bryan Wish:
Yeah. So question for you, one more question before we move forward. Yeah. I’ve been thinking a lot about work culture and some shifts that need to happen. And also, how do you … I’m reading a book right now called Unbound about Amazon, and how to, one of the biggest takeaways is about creating a culture of innovation, and making that just a core value of being there, of thinking big. And so being okay to step outside the norm to figure things out. And when you look back sometimes, well, your family or your childhood, this is maybe the first culture that’s extended for 18 years, before you make your own culture. So I would say, what were the dynamics of your childhood culture? And, were there values in that, or things that you saw growing up, where you never saw risk taking, or it was shied away from? I’m just trying to understand.
Colleen O’Brien:
Yeah. So I absolutely think that there is some shared cultural understanding amongst eldest daughters. I think that there’s something to be said about the responsibilities, or the expectation of leadership or initiative amongst eldest daughters. And then, the other thing that is coming in pretty strong for me right now is that, I was an Irish dancer from a very young age, and a competitive Irish dancer. Both my brother and I started, I was four years old when I started dancing. And Irish dancing is not a very … It’s a very rigorous sport, and it’s not a very expressive sport. It is a dance that is, what do I want to say? It is very structured. It’s very strength driven. It is sort of like the opposite of contemporary, modern dance.
Colleen O’Brien:
So that rigor was really driven into me from a mental perspective at school, at my after school job, and my after school activities, but also physically. I was a very rigid person, because from four years old throughout college, I was doing this very structured activity. And I think that the eldest daughter personality also showed up in that space, where there was an expectation of leadership, of contributing positively to the team. Of being a role model for other people around me. So, yeah. I think that there was a bit of a pressure cooker mentality, that started at a pretty young age.
Bryan Wish:
Super interesting. It’s like you had two dynamics or two forces, and then playing in this rigidity of meeting expectations of being the eldest daughter, but also the Irish dancing. I guess I should have picked up on the O’Brien earlier, but now it’s all coming back to me.
Colleen O’Brien:
Yes.
Bryan Wish:
And, you’re also helping me understand why my older sister and I probably don’t get along that well. So, she’s the eldest daughter. So no, I’m kidding. So no, that makes a lot of sense, right. And-
Colleen O’Brien:
Sorry, the lights just went off in here. I’m trying to reactivate them. Give me one second.
Bryan Wish:
Good for the show production.
Colleen O’Brien:
Okay, good. Great. I’m so sorry. There we go. I’m in a photo studio right now. Okay. That’s better. Sorry about that. I’m so sorry.
Bryan Wish:
No worries. I’m only imagining the video. B-roll starting with the lights that go out, and then it’s like, what just happened? So, you had these two forces in your way, kind of led you down this path of rigidity. Yeah, it sounds like when you got to college, you got this inkling of, “Oh, there could be a different way.” And then maybe at Microsoft, Microsoft, right, with Rafael. It was like this inner yearning and inner screaming of, “Oh, my God. There’s so much more for me.” Is that fair?
Colleen O’Brien:
Totally. Yeah. He was this beacon of someone who was wearing colorful clothes and had a very creative network that he could tap into. Who was living very loudly, which was in stark juxtaposition to how I was living.
Bryan Wish:
When you say loudly, was it loudly to you, or was it loudly to others with this blown up ego? I’m just curious, how you would define loudly.
Colleen O’Brien:
I don’t think it is. I only think of it as very beautiful, like a very beautiful living out loud. And I do, I think that in particular, I was living in a very small way at the time. So it seemed so much bigger, but I imagine a lot of people think that he lives his life very loudly and admirably.
Bryan Wish:
Yeah. I guess what I’m trying to say, I think there’s a nuance between living in your fullest expression, which may come and that’s authentic, that may come across to others as loud, versus loudly from, “Look at me. I’m awesome.” And I think, there’s two different ways to straddle the line.
Colleen O’Brien:
Totally. I absolutely hear you. It is a loud that doesn’t get in other people’s way. It’s a loud that invites other people to also live loudly.
Bryan Wish:
Got it. Well, I love the distinction. So, with this loudness that you wanted to maybe step into, or this shell you wanted to break out of, and seeing him with work, maybe do things different, in the way you wanted to embody. What changes did you make in your life from there? What things did you start doing? Whether at work, away from work, on your own creative time? How did you start shaping and recreating the life of Colleen?
Colleen O’Brien:
I think the biggest thing for me, is that I stopped thinking about problem solving as something I needed to do myself, or that I was the only one on the hook for solving a problem. I think, stepping into corporate America, I was sort of, I was scared of taking risks or spending money on something I didn’t know was going to work. And in the marketing function, there’s a really great model, as in several other industries and functions, of partnering with really great agencies, who have best in class knowledge about the thing you’re trying to.
Colleen O’Brien:
So, Rafael showed me that even if I didn’t know the solution to something and I was on the hook for the business problem, there were always experts out there who I could tap. And he did such a phenomenal job of growing his network and figuring out who those experts were. So, he opened my eyes to what strategic partnership looks like, and how to track down best in class professionals who can help you solve those big business problems. Yeah, I think up until that point, I had sort of thought like, “I have to go into a room and figure this out myself. And if I can’t, if I’m not figuring it out, it is because I am doing something wrong.” And he opened my eyes to, inviting other people into the conversation is oftentimes the way to really get things to the next level.
Bryan Wish:
So, well said. And, prior to maybe him showing you how to collaborate and find people to help you through solving problems, or getting to where you wanted to go, or was it asking for help or inviting other people into your life, just something that you didn’t know to do? Or, were scared to do because of judgment? Or, I’m just, yeah, it’s a powerful lesson.
Colleen O’Brien:
I think I’m, after that point, I went to business school at the University of Washington here in Seattle. And what’s coming up for me in answering this question, is that the University of Washington had an incredibly collaborative model for how they taught their students. Everything was conducted in teams. So my team was comprised of a really incredible data scientist from Amazon, a general manager of several grocery stores around Seattle, an individual who is now working at Amazon in human resources, and someone who was at Boeing, thinking about internal tooling.
Colleen O’Brien:
Of course, we didn’t all know the answer to every problem, but we could rely on this collaborative group to answer all of our assignments, to work through all of our challenges. Prior to that experience, my academic journey and even my, a lot of my professional journey, had been very individualistic. Sure, there were some group projects that we worked on every once in a while. Even when I was in my film program, we would do some group filming where we would go on site together. But for the most part, at the end of the day, there was a grade that you as an individual receive. So, I think I had just been really individualistic about, how I thought about performance and achievement, and how things get done.
Bryan Wish:
So, it was being individualistic with this rigidity, which is hyper boxed-in, in a way. Makes total sense. I know-
Colleen O’Brien:
Yeah, I was going into a room and thinking, “I have to solve this problem all by myself. I have the internet that I can consult, but otherwise, it’s up to this brain to solve the problems.”
Bryan Wish:
I think I grew up totally opposite, where it was my mom was like, “Yeah, it’s okay to go get help. You don’t need to do it all yourself,” which is a great lesson as a leader, because you can’t. You can’t do everything, but you can’t become too reliant at times. But I appreciate the perspective in, very formative to you. So it sounds like you have this experience. By the way, beautiful campus at University of Washington. And so you had this experience, you had this incredible team of talent, and you learned how to lean, it sounds like. Lean into them, ask questions, and work in a collaborative way that you had never done before, and never maybe put, threw yourself into the way you did, is my … go ahead.
Colleen O’Brien:
Yeah. So it is, it represented this turning point for me, where up until that moment, or maybe that milestone in my career, I had always thought about like, “Okay, if there are shortcomings that I have, I can take classes, hire instructors, read as much as possible to make that weakness better, and to turn it into a strength.” I was really interested in tracking down, what are all of the things that I am not great at, and how do I get great at them? And it quickly becomes a humbling experience to go through, because there are so many things that you’re worse at than you are things that you’re really good at.
Colleen O’Brien:
What studying at the University of Washington in this MBA program, in such a collaborative setting taught me, was that there is not enough time for me to fix all of my weaknesses. There aren’t enough hours in the day to learn all of the skills that I don’t have right now. It is more strategic to lean on people who know better, who have the experience, who have a strong point of view. So, it was very formative for me. Working in the technology industry, I was convinced that like, “I need to learn how to code.” I went to a coding boot camp over one weekend to try to figure out, how do I get on the right path, now that I’ve started in this industry? And it was so hard for me. I was like, “This is going to take so much time.” And it wasn’t until that experience in business school that I realized like, “Oh, a better use of my time is to lean into my strengths, and sort of hire out for, or find strategic advisors to help me manage those weaknesses.”
Bryan Wish:
Totally. Yeah. That’s pretty exciting. And I, just giving, when you give critical thought to like, “I don’t need to,” it goes back to what you were saying earlier. When you tried to do a little of everything and be good at it, versus really leaning into one thing or something you really loved. And, now that you have this moment or this pivot, I think it was the word you used, and said, “Yeah, I can just lean on people for a turning point. And I can lean on people for what I’m not good at.” But then double down on, “Hey, this is where I can thrive,” and maybe have things that are more life giving.
Colleen O’Brien:
And I’d love to tell you that post-graduation, I was fully convinced that I was on the right path, and that I had made the right decisions, and that I could lean into what I was good at or what I loved. But it’s, I mean, it still rears its head every once in a while. Prior to my current role, I was working in venture capital and I entered into VC as a marketing manager, sort of at the beginning of this wave, where several firms and funds were hiring their first marketing partners.
Colleen O’Brien:
And when I entered into the industry, I thought, my end goal here is to become an investor. As I look out at the landscape, they seem to be some of the most respected individuals right now. It’s a really hot career. They’re helping all of these incredible founders get to the next level. That’s where I need to go next. And it took a solid three years in that industry for me to realize, I don’t always need to be chasing that next thing. I am an incredible marketing and communications professional. And it is okay for me to do that thing that I love. I don’t need to always be stretching outside of this comfort zone, of what I know is energizing and exciting for me.
Bryan Wish:
When you totally, and I think it’s so easy to be tempted to look at other people in the ivory tower, at the pinnacle of and say, “Yeah, that should be my next thing.” And then work towards that. But then inside, is that really it? And it’s like that small voice that’s saying, “Maybe I should be somewhere else.”
Bryan Wish:
What made you realize, you said you were in it for three years. Do you have any distinctive moments on that three year journey, where you realize, “Hey, maybe this isn’t for me. Maybe, and this is an incredible place to be, but maybe this isn’t my true North.” How do you know when to shift?
Colleen O’Brien:
I think I started getting more … This is, it’s a tough question to answer. My immediate response was going to be like, “I started getting positive feedback about my skillset,” but it was much more than external validation that motivated this shift for me. I started feeling more confident about the work that I was doing. I was proud of the projects that I was executing. I had a strong perspective on the work that we were doing, what needed to come next. And I just, I felt more confident in the value of my work. And, it’s another thing worth calling out, because working in the technology industry, I oftentimes found that I felt like a second class citizen as a marketing manager. Because product was king, and our product leaders would sort of decide the direction that we were going to go, and marketing would sort of follow suit.
Colleen O’Brien:
And similarly, in the venture capital industry, the leaders of your firm are the investors. It was difficult to think about having a seat at the table, as a strategic business manager with a marketing background. But I started executing these projects that felt really strategic, and that I was excited to have as part of my portfolio. And that’s when I realized like, “Okay, I can just feel really comfortable and great about the skillset that I do have, about the experience that I have, and the work that I’m doing. I don’t need to be chasing what’s next.”
Bryan Wish:
Yeah, totally. And that’s amazing that you were able to take on those opportunities, and also see the results, and see that, yourself grow through that. Now, feel free to, don’t feel compelled. So my next question is, I guess, one, don’t feel compelled to answer. Don’t feel compelled to say yes. So, it sounds like you were growing, right, and stepping out of the Colleen shell over this period of time. And you saw this bloom, blooming perhaps, at the venture role that you were in. But my question is, do you notice these changes or this sense of coming out of, coming into yourself more and more? Not just at work, but in all facets of your life. Or, is this just primarily at work?
Colleen O’Brien:
It is primarily at work, which is important, because I have wrapped so much of my identity up in my professional experiences. I have a personal role model in this arena. It is my husband who is constantly cultivating incredible hobbies and other interests, outside of his professional experience. But I will say, I am just getting started in this arena, when it comes to life beyond professional Colleen. Yeah, there’s a lot more work to do.
Bryan Wish:
Totally. I think, and thanks for the transparency. We can sure talk more, but I still know what you mean, and I think the last year I spent, to really try and curb that. Anyways, it’s about you. Okay. So take, let’s just, if you want to go down that rabbit hole, let’s. I mean, if not, we can come back to the work. But okay, three years from now, who’s Colleen? I mean, you’re one integrated person, but who’s Colleen beyond work? What are the hopes, desires, aspirations to bloom in all areas of your life?
Colleen O’Brien:
Yeah. So, I’ve recently started chasing this interest in food and food culture. I’ve always loved spending time at restaurants, going on weekend treks to make sure we get the best sandwich in the city, or try the hot new donut in town. But, I’m spending more time cooking, baking, reading about people in the food industry. So, this is where I’m dabbling right now. But, sort of in this ugly narrative that several, maybe several years of hustle culture have created, I sometimes catch myself thinking like, “Oh, should I go into the food industry? Should I make this a professional consideration, and not just something that I’m doing in my spare time?” And when I say, “There is work to do,” that is what I need to work on. Is, there’s so much joy in something just being where you’re spending some beautiful, pleasant, fun time. And my brain is like, “Does not compute.” It doesn’t know how to make sense of those moments that are just fun and pleasurable personally, versus professionally.
Bryan Wish:
Yeah. Yeah. I mean, you could do a food Seattle blog, and for the joy of it without the business side behind it, to share your beauty with the world. I mean, why not?
Colleen O’Brien:
Totally. And, I’m not even interested. I don’t even want to indulge myself in creating too much content around it. I’m really just challenging myself to, how can I experience this and not feel like there’s an assignment attached to it?
Bryan Wish:
Yeah. Yeah. That’s big. That’s really big. Totally, totally resonate. And, that’s beautiful, in the sense where you’re like, “Yeah, how do I, how can I learn to just be or appreciate, without turning into something bigger than it is or should be?” So you can enjoy its natural beauty. But, clearly the brain that you have or the way you live, that’s a gift in a lot of other ways. It’s just the self-awareness of how you harness it, and when you turn it on, because it serves you in a lot of other ways.
Colleen O’Brien:
Totally. And, you’re spot on. Sometimes I will share photos of, here are some fun, foodie things I’m doing around town. And I’ll get messages from my friends about like, “Oh, can you please make a list for me, or document this thing for me?” And it does take a lot. It takes a lot to push back and be like, “No, this isn’t my job. Here are some great recommendations, but I’m not going to formalize this really fun thing that I’m doing.”
Bryan Wish:
Totally. Yeah. You don’t need to engineer functionalized at all. So let’s have a little fun. Let’s say, tell me the name of a best friend that comes up, outside of Seattle.
Colleen O’Brien:
Sure. So my best friend Tracy is visiting in August. She actually works in the food industry in New York and is coming to Seattle next month for a popup. A restaurant popup. And, I’m so excited for it.
Bryan Wish:
Amazing. So, well, I was going to say right, if she wasn’t in the food industry or you had no plans, what would be, if you could design the perfect … A flowing day in Seattle that involved a food tour, what would you do? What would bring you the most joy? You had 12 hours, from 8:00 AM to 8:00 PM and you could eat all day. What would be fun?
Colleen O’Brien:
You got it. So, first of all, I love walking. I love walking around the city. I will go for 10 mile walks around Seattle, clears my head. I love to see the sites. I never feel more connected to the city, than when I’m walking around. So, we’ll start the day off at this spot called Volunteer Park Cafe. They have some of the best breakfast sandwiches in Seattle, and it’s very close to this large park in Seattle, Volunteer Park, which is beautiful and lovely to walk around.
Colleen O’Brien:
We’ll spend a couple of hours there, and then we’re going to head down to another park, the Olympic Sculpture Park, which is right on the edge of Puget Sound in downtown Seattle. There are these massive sculptures down there. The views are beautiful. You can see all these ferries, shuttling out to different islands. And they now have a spot called, Market Fish Monger down there, that makes incredible lobster rolls. I’m originally from the greater Boston area. I love a lobster roll. So, that would be stop number two. And then, maybe we’d finish it up. A little bit north of there, is this great place called Dantini’s. Excellent East Coast style pizza. Very close to a brewery nearby, where we can have some delicious, hoppy Pacific Northwest beers, and their spot opens onto the train tracks. You can sort of watch the trains passing by, too.
Bryan Wish:
Unreal. Anything else?
Colleen O’Brien:
How’d I do?
Bryan Wish:
Okay. I mean, you did great. I mean, I’m headed back to San Francisco in August and I’m thinking, maybe I should come up in the fall to Seattle, and come on this food tour on me, and we can do it. And love to meet your husband, and make it happen.
Colleen O’Brien:
Yeah. Swing on by. Every couple of weeks, there’s a new hotspot in the city with incredible food. And, it’s one of my favorite pastimes.
Bryan Wish:
Awesome. Well, this was wonderful. We touched on work and performance, and fun and play, and childhood and rigidity, and individuals, nature, and food and all the things. I know you in an hour, better than I’ve known you in the last six months. So, Colleen, this was wonderful. How’d I do. Was I okay?
Colleen O’Brien:
Yeah. I mean, that summary was really beautiful and such a testament to all of the different places that you were able to take the conversation. I didn’t quite know where I was going to go when we started. And, it was like a really nice reflection for me. So thanks for guiding us here.
Bryan Wish:
Great. Well, it was easy. You made it very easy. So, Colleen, where, if people want to say, “Hey, how do I meet this awesome person I just listened to?” Or, where do they reach out to you? Share that, and then we’ll close out.
Colleen O’Brien:
Great. I’m really active on LinkedIn. Maybe you could tell from the aggressive professional aspect of my personality, but feel free to add me on LinkedIn. I’m Colleen O’Brien, and my Instagram handle is ColleenO.CO, and that’s where I’m posting all of my food photography from around the city.
Bryan Wish:
Awesome. Well, Colleen, thank you for being here. Thanks for showing up as you did. It was perfect. And, can’t wait to share this with the world.
Colleen O’Brien:
Yeah, thanks, Bryan. It was really fun.
Bryan Wish:
All right.