Chris Donohoe on Quitting The Corporate World & Founding His Own Firm

[01:00] Paul: Welcome to The Boundless Podcast. I'm Paul Millerd, and I created this podcast because I'm passionate about making sense of the future of work and having conversations with the innovators, creators, and thought leaders who are carving their path in today's fast-changing world. You can check out the podcast and more on boundlesspod.com. Chris, welcome to the podcast today. I'm looking forward to talking to you. I think people are really going to enjoy your energy and passion.

Now, you recently took the leap to working on your own and setting up a consulting brand called Uncommonly. I love how you positioned it as a message for what you want to cause in the world while still being authentic to who you are. Now you sent me a bio and the first line is you introduce yourself as the founder of Uncommonly and also an avid fan of Survivor. Question for you, what does Survivor have to do with consulting?

[02:10] Chris Donohoe: Oh, Survivor has to do with everything in life. And thank you for having me, by the way. Survivor is a really good microcosm of how the real world works, because the idea is that you have these people on teams competing against one another, forming alliances, building coalitions that may or may not hold together for more than just one vote, one voting block. And that's how life is. And I think consulting is just a reflection of life. I mean, you're constantly navigating all these relationships and trying to get stuff done and hopefully make things land in your favor.

[02:49] Paul: So the consultant is like the, uh, the Jeff Probst position of trying to figure out what's going on though, right?

[02:57] Chris Donohoe: No, no. The consultant is the player. I mean, you're in the weeds and you're in these complex organizations where things are rapidly changing and there's all these personalities and dynamics at play. And as a consultant, you're trying to rally people and make your outcome be the outcome that sticks. Awesome.

[03:17] Paul: So I'd love to step back and hear more about your career journey. I think you have a pretty interesting path. Uh, so you were most recently a consultant and pursuing that path as a freelancer, but you started as a teacher. Um, how did, how did that shape, uh, where you are today and, um, how you've thought about your career?

[03:38] Chris Donohoe: Yeah, I think that teaching is the foundation for everything I do now. It's. The hardest job I had. It's also the most rewarding job that I've had. And I say this all the time to people who are looking to make a career switch, or people who have been especially teachers, that the skills you learn there are super transferable. So what I mean by that is you learn as a teacher how to set a big goal for your kids, then how to create the, the assessment that you're gonna use to measure them against that big goal.

Then you create all of the content to actually deliver to them. Then you see where they're at against the content, and then you measure your progress. You're living through this instructional life cycle, and I think it's one of the most transferable skills in, certainly in corporate America that you can have.

[04:31] Paul: I like it. So yeah, let's, let's talk about acting. You posted a video of you launching your brand Uncommonly, and it also links to some videos. You've been vlogging for a while. Would love to hear how that started for you, and also might want to just tell people what vlogging is.

[04:51] Chris Donohoe: Yeah, I don't really know what vlogging is. That's a good question. I create all these videos. I don't, I never consider myself really a vlogger, but I guess that is what it is. I would define vlogging first and foremost as just putting video content into the world, but with a— you're the center of it and it's just your ideas. It's kind of like a spoken blog.

That's how I think about my content. And mine came about because I started working with a life coach in March of 2017, and she was constantly asking me, what do you want to do? What do you want to create? What do you want? What do you want? What do you want?

And she would ask that question over and over again. Literally, you're sitting in a room and you'll do an exercise with her where she says, "What do you want?" And then you say it. Then she'll ask you again, "What do you want?" And you just keep doing it for 6 minutes. And one of the first things that I started realizing I wanted was to be an influencer, to be able to put compelling ideas out there, to be able to have a voice. And I thought, well, what's a really good way to do that? I like video and I like talking and I think I'm a interesting talker.

So I started filming myself walking down the street selfie style in New York City, and I just committed to posting twice a week for 4 or 5 months. And now I have this whole little database of me walking down the street talking.

[06:20] Paul: Any unexpected lessons from doing that?

[06:24] Chris Donohoe: Very, very practically speaking, I realized that the level of energy you need to have when you're talking into the camera is dialed up like 20 times higher than what you think it needs to be. Because if you just talk normally, it comes off super flat. So I found myself screaming into the camera and I didn't anticipate that I would have to dial up my already very zany personality for it to really shine on screen.

[06:50] Paul: Somebody gave me the advice before you're giving a presentation, look, do it in a mirror, but do it screaming. That way when you're presenting to an audience, you still have that energy, but you're not as a madman because you'll naturally kind of slow down when you're in front of people. Yeah, I think, I think the energy definitely comes through. I think of one of your, so in one of your original videos, you were talking about careers and you weren't at the point where you had chosen to kind of take your own path as a freelancer and you described yourself as a 2-year career hopper. I love that. I love that term.

I think that's what a lot of work is going to become. So how did you get from 2-year career hopper to pursuing the freelance path?

[07:32] Chris Donohoe: No, I'm not. And that video that you referenced, I think it's called— it's something about why you should quit your job right now or how to quit your job. And in it, I kind of tell a fib because I say, I'm not looking to quit my job, but I know a lot of you guys are and you should. And the truth was when I posted that, I was very much already starting my own company on the side. And I just didn't want my previous employer to get super suspicious if I stretched the truth. And, but no, now that I'm on my own, I'm not thinking of it in 2-year segments because I feel like I finally have the freedom to build something.

I've never felt empowered in any of the jobs that I've had up until now being on my own to really build whatever I want or create whatever I want. So at the 2-year mark, unless there's an opportunity for you to really have a stake or have some skin in the game, then it just becomes boring. It's Groundhog's Day. And unless there's really a clear career trajectory, then I just, I felt always trapped, like I needed to get out of there. And now that I'm on my own, I don't anticipate that that will be the case, mainly because I think there's an opportunity for limitless creation for me to just keep building and creating whatever I want on my own timeline.

[08:57] Paul: Right. Yeah. And where's the focus now? Are you— I know you put a lot of work into kind of launching your brand and thinking about the principles behind that. What's keeping you energized right now?

[09:10] Chris Donohoe: I'm really excited about the inclusion and diversity space right now. I think that this is not only is it societally a really important thing to be thinking through, building organizations that are actually reflective of the communities in which we live and work. And I mean diversity in the broadest sense. So any of your protected class statuses, of course, and then even things that aren't protected class status, ideas, background, beliefs, Those, that type of diversity also matters a lot. And not only is it important in society, but I think right now it's having a, a moment in the business world. I think business leaders are thinking and talking about this topic more seriously than they have previously, and there's a real appetite to get it right.

And I see this most prominently playing out on, in kind of the recruiting and talent management space. So it's how do we recruit How do we attract top talent that is diverse? And once that talent is in the organization, how do we actually support them and give them meaningful career pathways and meaningful channels to pursue? And that's, that's straight up talent management and building organizations that support people from many different backgrounds and achieving the goals that they have for themselves.

[10:31] Paul: Yeah, I love that. I, I mean, you probably have a similar experience as me in consulting. You've probably worked with very diverse teams, but I think you hit on a really key point. Which is that in a lot of these companies, there really isn't diversity of ideas. There isn't diversity of levels of people. There isn't diversity of age.

And we still default to who's the, who's the highest-ranking person in the room, who's the highest-paid person in the room. And I mean, there's so much opportunity there.

[11:03] Chris Donohoe: That's right. I was working with a data security software company on my most recent project as a freelancer. And They were launching a new go-to-market strategy for all of their sales force for 2018. And it was, it was very much a large shift within their organization in terms of how they were going to sell, how they were going to go to market, how they were going to interact with customers. So my job was to kind of come in and get everyone pumped up and roll out this new, this new strategy and align people so that they're bought into it. And this organization, I just, I haven't worked in a in an organization that's so homogenous in quite some time.

Really interesting people, very cool people, but I was shocked when I walked in the door for the final day of workshops and it was just bro city. It was a good old boys club through and through. Pretty much a very white male, 45 years old, sales guy. That was the demographic. And I just, you know, working in New York City, that's not what my day-to-day usually looks like. But those pockets, I think that picture that I just painted of that organization is, I think, very representative of what a lot of our companies look like.

And it's certainly what a lot of our leadership teams look like. And that's an even bigger issue.

[12:34] Paul: Yeah, I think one of the— so one of the challenges I've noticed from this is that, I mean, even for me personally, I didn't have a— there wasn't a big diversity of male role models. So how did you experience this? It's— there's kind of that one archetype of the male role models. I actually ended up having a lot of women who I really looked up to and inspired me. But what are you seeing in terms of this?

[13:02] Chris Donohoe: My entire life has been, I think, from, from a mentorship perspective, dominated by, by women. And the people that I've looked up to, not only professionally but personally, have always been women. So I think that it's, it's definitely been a challenge for me to, to find male role models that I look up to at work. I did work with one excellent— it's hard to find role models in general at work, I think. It's really hard to find mentorship.

[13:30] Paul: Is that a corporate world thing, or do you think it's just people aren't wired to kind of think about mentorship and those things?

[13:39] Chris Donohoe: I don't know, because I think of all the different spheres or domains that I've operated in over the course of my life. I was an athlete. I was always on an athletic team or part of athletic programs. I did chorus in high school and I was religious for a season of my life. And so when I look at the religious community, when I look at the athletics community, when I look at the arts community, I do see mentorship. I do see people stepping up as leaders and forging the way.

And I don't see that same thing in corporate America. And I think it's been really hard for me to find people who actually want to take the time to invest and cultivate me as a person and to invest in my development. So I do kind of think it's a corporate thing.

[14:33] Paul: We have some work to do, but hopefully we can make a dent. Yeah, I think in one of your other videos you talk about the line, bad leadership, failed leadership, lack of decision-making, toxic work environments. Now, I've also seen a lot— I do have some hope. I think I've seen a lot of organizations really thinking about how do I build high-performing organizations, but so many organizations are stuck in this trap. Like, what do you think are some of the drivers for that?

[15:05] Chris Donohoe: Yeah, I should say that I have also seen things done the right way. So I'll answer your question, but before I do, I just was recently working with an agency. They're a technology and design ideas agency that is now looking to move into the business transformation space, which is really where I play most often. And I've been working with them in partnership, and I've been so impressed with the way that they collaborate, share information transparently, and work together on a day-to-day basis. Again, I'm not, I'm not baked fully into their culture. So I'm sure there's issues there.

Anytime you have more than one person in a room, there's going to be tension or issues.

[15:48] Paul: Right.

[15:49] Chris Donohoe: So, but they're doing it right. And I think that when I think, when I think about the difference between how they're operating and how they work versus some of these other organizations, it's, they, there is a clear commitment to collaboration and to ideas. So many organizations are not really thinking about ideas and why ideas matter, or if they are thinking about it, it's one or two people, but there's not really the political will to make it a place where people really will share information and will really, you know, generate awesome stuff together. Most organizations just don't, don't prioritize that because they're so in the weeds with getting the day-to-day done. So, you know, I don't know exactly what the drivers are, but I do think that when you prioritize ideas, you get better outcomes from your people.

[16:47] Paul: Yeah, I love that. I think that's the second time we brought up ideas, but I think this is emerging as so important because more work is becoming complex. You need creativity to kind of figure out, carve new paths, create new content. And the power is shifting to the frontline people creating. And if we don't have the idea meritocracy, to borrow a phrase from Ray Dalio, it's really hard for those companies to kind of shift and serve clients as, as they want to be served.

[17:23] Chris Donohoe: That's exactly right. Meritocracy is a really good word for it too, because most companies are not actual meritocracies. They are, uh, I think of companies more as like little feudal manors where there's a very limited supply of power and influence and also money to go around. And the people at the top are hoarding it for themselves. And I think the lower down the ladder you get, just the less opportunity there is to really prove yourself or get a piece of the pie for yourself.

[17:55] Paul: Yeah. I think, That's also something that kind of drove me to pursue the freelance path. I think I was scared of becoming that person, um, because I think on the, on the margin, it's very easy to kind of fall in the trap and say, well, I deserve this, or, um, I've worked hard and people have, like people at the top, they've put in their time, they've put in hard work, they've maybe dealt with even more toxic work environments. So it's a, it's a hard challenge, but I think like looking in the long term and stepping back has really helped me. Kind of make sense of things. Is— does that resonate with you?

[18:28] Chris Donohoe: Yeah, that's a great point. A lot of these people who are now in positions of, uh, power have endured a career that was probably riddled with so much drama and trauma that I just don't have any interest in living through that cycle, uh, myself. Also, as a freelancer and now as a business owner myself, every single time that I put effort towards something, I can expect to get a return. So I know as a freelancer that when I put in an extra day's work, I'm gonna get paid for that extra day's work. And that if we, if it, if more work needs to get done, I'm gonna get paid on top of that. So even financially being incentivized to go above and beyond is so much more, it's so much more of a reality in the freelance world.

Compared to working as a full-time salaried employee where you can go above and beyond, and unless the right person will acknowledge and then also reward you for it, then your effort is really going to go unrecognized.

[19:30] Paul: Yeah. So, so when did you first know you weren't cut out for the default path?

[19:37] Chris Donohoe: I think that I've always kind of understood this about myself. I just didn't know that it would lead to me starting my own company by the time I was 30. So my family overall is just unconventional in the sense that everyone— there's a very— there's an entrepreneurial thread that runs through my family. Now I'm not saying they've been successful entrepreneurs, I mean, I— but I think of my grandma, for example, we call her Mima, and she—

[20:05] Paul: her—

[20:05] Chris Donohoe: most of her adult life she spent on weekdays driving around town going through people's garbage and finding clothing and home items and decorative items that she could then take to the flea market on Saturdays and Sundays and sell at a marked-up price. And sometimes she would spend the week kind of sprucing it up. She was very creative. She would rearrange things, paint them, whatever it was, and then go sell it at the flea market. And I watched her professionally, that's what she did for a living, my entire adolescence. Childhood and adolescence.

And similarly, you know, my, my, my uncle started a business, not wildly successful, but he worked for himself. My brother is an entrepreneur and works for himself. I think we just have that work for yourself mentality, and I've always had that as part of who I am. I just didn't know how it would manifest in my specific context.

[21:02] Paul: Yeah, when So I've been talking to people who take this freelance leap and what you often find is that you're like the initial experiments or side hustles or activities on the side. I think for you, vlogging was probably one of those things, but they start building your confidence and you start slowly building piece on piece before you take the actual leap. I think a lot of people think you just kind of jump out there and start on your own, but what were some of those building blocks for you that helped you build the confidence to, uh, take that leap?

[21:35] Chris Donohoe: You're— that's a great point. I think for sure starting my vlog and going out there and building a YouTube channel was a confidence boost. And additionally, all of the career experiences that I've had leading up to this point were equipping me to do this. I just didn't realize it. So specifically consulting, for example, I was at a point in my consulting career where I was already selling work I was managing client relationships. I was also delivering the client work.

I was project managing my own initiatives. I was bringing in new logos to my company. So I was able to get a master services agreement in place with a large insurance company. So I had all of the skills that I was building to then be able to do this on my own. And it got to a point where I said to myself, if I literally just keep doing what I'm doing, I stop doing it for you guys and I start doing it for myself, I'm going to be wildly successful. So there was really not a huge leap like you're saying, because I just kept doing what I was already doing.

[22:40] Paul: Yeah, I think, I mean, I'm like you, I'm a 2-year career hopper, maybe even less than 2 years, but I think you, you realize looking back that doing random things that might not seem connected give you all this combination of skills that give you a lot of confidence to kind of move in a lot of different directions.

[22:59] Chris Donohoe: Yeah, and the best thing about consulting is you get really good at change and adaptation. And I think about, you know, I'm 30 and I've worked at over a dozen Fortune 500 companies, not including the firms that employed me. I've worked at two different consulting firms, and I've had clients at over a dozen Fortune 500 companies across the insurance industry, the pharmaceutical industry, across publishing, media, and entertainment. I've worked in corporate philanthropy. So that set of experiences, just getting the opportunity to get bounced around and thrown into lots of different situations and then having high expectations to perform in those situations, I think has equipped me with, I call it change resilience. I think I'm just very resilient and able to just get thrown into things and figure it out.

And I'm really comfortable doing that in ways that I think a lot of people who have more traditional career paths or who have stayed longer at one company, they just don't have that same experience of having to be resilient and getting really good at change and uncertainty.

[24:04] Paul: Yeah. So if you're giving advice to somebody earlier in their career, how would you advise them to build that resilience? Just leave, leave your job like your video was getting people to do.

[24:18] Chris Donohoe: I think as soon as someone has an idea that they want to try something else, they should go. They should leave. I think if you wake up and you say, this is not my future. If you can say definitively, this is not my future, then you need to get out of there. And that doesn't mean leave immediately, but start laying the foundation to move. And I also would not fear the idea that if I jump every year or if I jump every 2 years, then my resume is going to be called into question.

I think that anyone who calls into question your resume because you jumped every 2 years does not understand the direction that the workforce is going and doesn't understand what the future of work looks like. And I wouldn't take that person's opinion very seriously.

[25:00] Paul: Right. Yeah. You don't want to work for those people.

[25:03] Chris Donohoe: Yeah. And you don't want to work for that person. If someone's idea of work is that you need to suffer through something for whatever, whatever number of years they think is an appropriate amount of time, then that's just not the person I even want to be working with to begin with.

[25:17] Paul: Yeah, agreed. I've, uh, I've had people say when they're interviewing me, well, you are a job hopper, but, uh, we do need your skills. Yeah. And we can't find someone with your skills. So it's like, okay, perfect. So I had to, uh, do the job hopping to end up here.

[25:35] Chris Donohoe: That's it. That's such a good point. I've never had someone, you know, people pretend they have a problem at first. Like they love to pretend that they're like, well, it looks like you've jumped around a lot. But at the end of the day, when you're delivering a grand slam interview and you're clearly wildly capable of doing the job, they're going to want you. Because this is also the truth of corporate America.

It's a revolving door. People are moving in and out of companies nonstop. So, and everyone believes that the silver bullet is outside their organization right now. If we just had this next person come in, they could really own, they'll own this initiative and they'll really see it through. And as long as that remains the trend, I mean, I think there will always be demand for for new people and organizations. And just consulting itself is built that way.

As a consultant, you're constantly changing, going on to new projects. I personally love to see when people have bounced around and have lots of different experiences.

[26:36] Paul: I asked people what to not ask you, and you said, "Are you scared or nervous?" It's funny, I've gotten this question a lot, and I think it probably says more about the people asking the question. Uh, but people still have so much fear in the workplace. I think, uh, maybe you have those family influences that give you more confidence. Um, maybe it's just the things you've, you've gone through. But, uh, how do we fix that? Like, how do we get people to realize that they have so much capability and opportunity out there?

[27:13] Chris Donohoe: You know, That's a really good question. People have to generate it on their own. I think— I don't know if you've read these articles out there. There's a bunch of them on Medium. People write about this idea that most people are inclined to kind of settle for average or even above average, but maybe not for greatness, like their true most powerful version of themselves. Most people will settle for a lesser version.

But what's interesting about that is that means that there's more people competing within that mediocre space than there is at the top. And I think that then you have all these people competing for kind of just average jobs, average salary increases, average work in terms of how meaningful it is, when really they could probably, if they would take a leap, generate something on their own that is far greater than this mediocre world that they're being kind of— that they're being sold. It's being sold to them and they buy into it. So the answer for me is about asking people, what do you really want? If you could create anything, what would you create? Having them generate those answers.

And then if that answer doesn't match their current situation, supporting them and coaching them to the outcome and to change their behavior to get the thing they said they just wanted. But there's no way unless someone generates the idea for themselves or generates the vision for themselves, there's no way to convince them that they should make a move or that they're capable of it. They have to first want the thing. They have to want it.

[28:56] Paul: Yeah, I love it. It's about setting those bigger aspirations. I never made that connection before, but it It makes so much sense, right? If you're competing for the middle, everyone's in the middle. So setting those higher aspirations, it's really the Elon Musk playbook, but you don't need to go that crazy, but kind of the same thinking.

[29:18] Chris Donohoe: Yeah, I think, think of it this way, competing for the middle, you said it so succinctly, that's what I was trying to say. When I was at my last company, there was a team, I was on a team of 22 people, probably one person is going to get promoted. We're all ready for it. We're all seasoned. We're all veteran, awesome, all-star people. So you've got 20 people competing for one promotion in a year and it's not even a great promotion.

It's like this tiny little incremental— it's like your job's not really going to change, you know, just a tiny little incremental move up the ladder. But on the outside of that, it's like, now I've started my own company and I'm looking to generate $1 million in revenue this year. And build a team of 5 people. That's a way bigger goal, but it's actually easier for me to build my own company and be successful than it would have been for me to get that promotional spot because there's— I'm doing it. I can literally go out and create this thing on my own. I don't have to compete with 20 other people for this measly little middle ground thing that is actually not even what I really want.

But I have to say that that's not what I want. I have to be willing to say, "I don't actually want this promotion. I want to build a business," or, "I don't want this promotion. I want the job of my boss's boss, and I want it tomorrow, and I'm ready for it." So once you start to set the big goal, then you can break out of that whole cycle and you can start to see what you're really capable of.

[30:44] Paul: I like it. I love the passion there. I like the big goal. Hopefully people listening can help you achieve that. Yeah. So what does the leader of the future look like?

[31:00] Chris Donohoe: The leader of the future is aware of who they show up as. So, and the leader of the future is obsessed with who they are being. They're not obsessed with the revenue. They're not obsessed with the, the business model or expansion or growth. They're obsessed with who they show up as. And as people, we don't ask that question enough.

Who am I showing up as today? Am I showing up as love and joy and kindness and passion and energy? Or am I showing up as fear and doubt and loneliness or any of these other things that we show up as. Once you're aware of who you're showing up as, the beauty of it is you get to choose. You get to choose who you want to show up as. And if you show up as love, you're going to make decisions from that place.

And if you show up as compassion, you're going to make decisions from that place. And if you show up as power, you'll make decisions from that place. And that is what the future leader will do. And that's what we need. It's not just what they will do. We need them to do that because otherwise people are on autopilot and they're operating from their automatic responses and their survival mechanisms.

And that's just no good for anybody.

[32:29] Paul: I love it. I smell another video or at least an article around that topic.

[32:34] Chris Donohoe: Yeah, it's probably a video. Awesome.

[32:38] Paul: What— so are there any influences you've had? It can either be a book or a person or, uh, something you've seen that has really inspired you to get where you are today?

[32:51] Chris Donohoe: I— this is gonna sound silly— I love Tyra Banks. I think Tyra Banks is like just the be-all end-all in terms of being resilient and scrappy. When you think of her, how she did what she did, she started off as a model when she was like 15. By the time she's 19, I don't even, I don't know, I don't think she went to college actually, if I'm correct. Like Tyra Banks, I don't think went to college. She just converted a modeling career into a business empire.

She's had television programs, she's had cosmetic lines, she's made a whole business out of modeling. And she's pivoted. She's the type of person who when, oh, I'm not 22 anymore, I need to figure out like where I can, how I can change to keep myself in this game. She does it. She does it over and over again. She's reinvented herself so many times.

And that's so inspiring to me. I think, and not to mention, you know, she's a woman of color and she is just, I think she really does show up authentically and I appreciate that about her. In terms of like closer to home, like people that I really respect and look up to, you know, it's just, I'm thinking specifically in my career, but it's so sad to me. Honestly, I haven't had many people that I look up to say, "Yeah, I'm gonna do it like this person did it." I think that's why I've had to do it on my own because I'm like, every time I look up to somebody, I'm like, "No, I'm not gonna be you." I think that so much, so frequently where I look at someone and say, "I will not be you when I'm at that age." I look back at some of the people who managed me when they were 30, and now that I'm 30, and I'm like, "Are you kidding me? Like that's how you chose to do this?

Like you were so terrible as a manager." And I just don't want to be that person. So sadly, I think day to day in the business world, no, there are not a lot of influences. I mean, personally, yes, I have many wonderful friends and, you know, and family who inspire me, but not in the business world.