Navigating Career Pivots (Kyle Hagge, Chief of Staff to the COO at Morning Brew & Co-Host of Per My Last Email)

What's up, everyone? Welcome to Founders Journal. And you might be noticing that I am not Alex Lieberman. I'm not the executive chairman and co-founder of Morning Brew. So unfortunately, you're stuck with me, Kyle Hagge. But I do at least work at Morning Brew, where I'm chief of staff to our COO, and I'm the co-host of the podcast Per My Last Email, which gives you the hot takes and tactics to navigate work life. But today, I am filling in for Alex on Founders Journal, and we're gonna talk all about career pivots. This is a topic that I am super interested in. I've seen a ton of pivots in my own career, and often when I'm talking to other people, they're really curious about how they might be able to pivot their career into a new role, into a new industry. And so I hope by going through my career journey and then giving you some tactics, you'll be better able to think about career pivots and then hopefully act on a pivot if that's something you are interested in. So let's bust right into it. Who am I and what's my background and career that will help illuminate my career pivot point? So I graduated from the University of Minnesota. It's similar to the University of Michigan where Alex went, but a lot better. And I graduated with a philosophy and political science degree. So 2 degrees that don't really set you up for a job right out of college. And so I actually did AmeriCorps for 2 years. AmeriCorps, I was working with a nonprofit called College Possible, and essentially I was a high school teacher for 40 juniors and then 40 senior students in Milwaukee. I then pivoted and I went and got my master's degree in political science, kind of doubled down on this degree I wasn't already using. And while I was getting my master's degree, I was working for the housing authority for the city of Milwaukee. So I was getting exposure to government, I was getting exposure to public housing, I was getting exposure to business development and working with a ton of partners in the community. And I was also freelancing for a civic tech company called BallotReady, where essentially I was going into small counties across the US, figuring out when their elections were held, and then taking that data, which is actually really hard to find in smaller counties, putting it online for it to be easily accessible. And it was when I was in grad school that I actually loved doing podcasts. So it's kind of a full circle moment that I've been doing some of the podcasts at Morning Brew. And so I started my own podcast, and this podcast was called Bridge the City. It was all about helping people in the local Milwaukee community figure out how to make a difference. We had this idea that people really did want to see change in their community, their neighborhood. Oftentimes they look for national politics, but there's a ton of low-hanging fruit in their backyard that they could get involved with. So that really helped me grow my interviewing skills. We interviewed everyone from community activists up to the governor of Wisconsin and everyone in between. Once I graduated from, uh, my master's program, I got probably the most fruitful cold email of my life. And we'll, we'll talk a little bit about the power of weak ties and the power of growing your network. But I actually got an email from the former CEO of a Fortune 500 company. Uh, the company was called Cree and his name was Chuck. And this email basically said, hey, I know you're doing this podcast on the side and I know you are at, uh, Marquette University. I'm an alum of Marquette. I'm retiring as CEO after 16 years of this publicly traded company. I took the company from $50 million to $1.6 billion in revenue. And would you want to chat? And I was like, Chuck, I just saw $1.6 billion. I'm totally there. So I went and got coffee with Chuck and he talked to me about what he wanted to do in his, you know, quote unquote retirement. He wanted to run a podcast all about innovation. He was writing a book. He wanted to do a ton of speaking engagement. He wanted To create a ton of content that benefited students and the broader ecosystem of entrepreneurs and innovators around all the lessons he had learned growing his career, growing the company Cree again from $50 million to $1.6 billion. And so that's how I got my first job out of grad school was actually I had started doing a podcast myself just out of the love of the game. Someone recognized that I had the skills and then they reached out to me. And so I got really lucky. And from there I worked with Chuck for about 2 years. Again, we did a ton of podcasting. I helped him finish his book. We did a ton of great content and curriculum for students at Marquette, and I felt like I got almost a mini MBA just from working with everyday Chuck, someone who had executed at a super high level, uh, for a Fortune 500 company. Then I also kind of took this Bridge the City model where I just started doing things that I was really interested in, and I started this very small startup called JoyBoost where it essentially was a wireless charger no cords, no outlets required that you would stick on the back of your phone and it could charge your phone. So if it's a late night, you're at the bar, you're at 3%, you need to get home, you could purchase one of these products and make sure that you have enough charge to, to safely get home. And I went through a very small startup accelerator with that. I was talking to some VCs about raising capital, and that's when I actually also was applying for Morning Brew. And I got the job offer at Morning Brew to be community manager. And I actually, like, did not want to be the CEO of a wireless charging startup company. It kind of was this idea that got more legs than I thought it would. And so I actually stopped doing that and I went and took the job at Morning Brew. And I started at Morning Brew February 2021, and I've grown in my career here as well. I was community manager. I worked my way up to director of community. And now, as I mentioned at the top of the show, I'm chief of staff to our COO. So hopefully that wasn't super, super boring. But I wanted to bring all of those experiences up to illuminate the context that I want to talk about career pivots now. And so this is for someone who's maybe stuck in— they feel stuck in their role and they really want to move roles. This is for someone who's maybe found themselves working in one industry a ton and they feel like, damn, I've built a great reputation in this industry, but I don't want to work in this industry anymore. How do I get to a different industry? Or just in general, anyone thinking about making a transition in their career. So I have some tactics for you all that are going to help you think through and hopefully achieve any sort of pivot you're looking for. So my first tactic is to use side projects to create credibility. I think it's easier now more than ever to just start building. And so the number of people I've seen that have turned small passion projects into credibility to land full-time gigs or parlay them into better job offerings is so high. And so my one piece of advice is if you're looking to make a career pivot, say you want to work in podcasting, but you've been a financial analyst your whole life, no one's going to trust you that you can do that. They're not going to give you the benefit of the doubt. Fortunately, making a podcast basically costs nothing. You need like $8 for Riverside. And so you can just start doing podcasting and there's going to have 2 benefits. The first is you're going to figure out if you actually like doing it. It's one of those things that once you get into the details, maybe you don't enjoy it. If you do, that's great. The second thing it's gonna unlock is that credibility factor. So when someone says, hey Kyle, you're a financial analyst, why do you think you can run a podcast? You can say, hey, I've actually been doing this podcast on the side. I've done everything from scripting to production to audio engineering to hosting. So I know the full lifecycle of a podcast. And so the proof is in the pudding. I can do it. Using these side projects to create credibility in a role or in an industry you wouldn't otherwise have is a really, really good tactic. It's what allowed me to turn this kind of fun podcast I was doing on the side into a full-time podcasting role at Marquette University. My second bit of advice for career pivots is to have more experiences outside of your comfort zone. I know this is a big cliché, but sometimes clichés are accurate for a reason, and this one is definitely that, uh, Herminia Ibarra, she's a researcher, uh, at the London School of Economics. She has this great quote I love. It's, it says, you don't learn who you are through theory. You learn who you are through practice. And so one issue I see with a ton of people that wanna make career pivots is actually sit back and they just think about what they like. They do a lot of self-reflection. They do a lot of kind of looking at their intuition. I'm not anti-self-reflection. You should still be doing that. But sometimes you just don't know if you're gonna like something until you do it. And so the worst thing you could do if you're trying to make a career pivot is to think you like something, make a successful pivot into that role, and then you're like, shit, I actually don't like this. I wish I would've practiced a little bit more. So having more experiences outside of your comfort zone, going and dabbling in whatever it is you might want to try, meeting new people that work in that industry and figuring out what it's actually like. Getting a little uncomfortable is so important to actually understanding what you like, what gives you energy, and what you don't like. An example of this in my own life, maybe a sillier example that was really fun, is I moved to New York and I really was kind of had my first community role. That was my first role at Morning Brew, and I didn't know a lot about it, to be honest. I had like some experience in community, and I think I was able to draw on a ton of my past jobs to make me great at that job. But I really wanted to learn about how to build, particularly in real life communities in New York. And so I got with a friend and we launched this thing called Stoop and Sip, where essentially we found 13 stoops across New York. We invited pretty much any weak tie we had to a specific stoop, and then there would be 6 strangers that would come to their stoop. We had drinks, we had snacks, and they would just talk on the stoop. And then eventually stoops combined into stoop super stoops. Patent pending on that language, and it was really, really fun. And again, it just taught me wow, I got out of my comfort zone and I really like this. And two, the barrier to entry to doing some of these things is really, really low. All it does take is a concerted effort. So my advice number two is to have more experiences outside of your comfort zone. Third tactic, and this one is so important, is do not forget your weak ties. This is actually where all of your opportunity. lies in pivoting your career. A weak tie is essentially a second-degree connection, a connection. It's your cousin's friend that works at Goldman that you don't really talk to, but your cousin can make an intro. It's that friend you met once in high school that now they're in your city, but you haven't talked to them in about 5 years. If you go on LinkedIn, it's all your like second-degree connections. Why these are so important, and Dr. Meg Jay, she wrote the book Defining Decade, talks a ton about weak ties. That book was highly impactful in my own life. This is where your opportunity lies, because basically all of your first-degree connections, all the people you're really close with, those opportunities are already baked in. You're already aware of them. Your weak ties are these people that you have some sort of connection to, but you don't really understand what's in their network. And so if you want to grow in your career, you want to make a pivot, you want to meet a bunch of people you wouldn't normally meet on a day-to-day basis, it's going to be through those weak ties. And so leaning into reaching out to people maybe you haven't reached out to before, having a coffee chat with someone that's really close to you and saying, hey, who else in your network would it be good for me to talk to? You can build a really, really great portfolio of other people that are interested in you, interested in your career, can give you advice as you're thinking about making one of these career pivots. An example from my own life, I moved to New York. I knew about one person, probably the first. 100 days in New York, I got 50 coffees with anyone on Twitter that A, said they lived in New York, and 2, would respond to a DM of me saying, hey, can we grab coffee? I was able to build a really great network of weak ties, and I've had so many opportunities come from just sitting down with a quasi-stranger for 30 minutes, learning more about them, telling them about what I want to achieve. Sometimes that turns into something beautiful. So focus on those weak ties or building more weak ties. into your life. It's gonna increase the surface area of luck. It's gonna make a career pivot a lot easier. All right. My 4th piece of advice is writing, AKA turn what you know into what you can show. I think that there's an issue with a lot of people that have worked across a variety of different roles in their career. They have a ton of knowledge, but they don't really put that knowledge out there the same way I was making a podcast and that got some attention and got me to a next role. I've seen the same done with blogging or writing or publishing your thoughts online. This can be really scary for people, but again, it also builds this almost magnet that's going to attract opportunities to you the same way that Chuck had reached out to me because he knew of my podcast. My advice for you is if you're like, Kyle, yeah, I can write, I know the English language, I can type on a keyboard, but like, what should I write about? Is to think about going into an interview. You probably have done this many times. You're prepping for interviews, uh, when you're going through that process and you have an expectation of what the questions are going to be. And then you think about an answer. Do that with writing. Think about what questions, if I was trying to make a career pivot, would people ask me to ascertain if I'm right for this role, if it's the right fit for me? And then take those interview questions, put them in a blog post and write down what your answers would be. Again, this is going to give you more credibility of like, hey, I've actually been really thoughtful about pivoting into this space. I know these are the questions I'm gonna be asked. Here's my thoughtful replies to them. Here's how I'd think about that. It's increasing your credibility, but also if you do it in public, you're gonna be a magnet for more opportunities coming to you and you might just stumble into exactly what you wanted. All right. The 5th piece of advice is to embrace your beginner's mindset. Steve Jobs, not to be the quintessential guy referencing a Steve Jobs quote on a podcast, but he He had this great quote about, uh, getting fired from Apple was the best thing that ever happened to him when he got fired the first time, because he said, I felt the lightness of being a beginner again. And a lot of people, when they go to make a career pivot and maybe they achieve that career pivot, in comes the imposter syndrome. Like, damn, I, I kind of made this pivot by doing a side project and I don't have any formal training in it. And, and I'm really worried about this next step. And I think that quote speaks to how you can flip that kind of naivete, that imposter syndrome into an advantage. And that's all about embracing the beginner's mindset. Chuck, who I've mentioned now probably 7 times in this podcast, he had a great quote that said, the problem with experts is they know what's not possible. And so when you come into a new industry and you don't have a ton of formal training, you actually have a ton of fresh perspectives. You almost haven't been beaten down by the best practices of that particular role. You haven't been put in the box of what people have said is possible or impossible, and you have this great opportunity to come in and actually do things differently, be more innovative, come up with new ideas that people that have worked in the industry have just discounted or said, oh no, we could never do that. And so leaning into your naivete, not away from it, but embrace that, the fact that you're a beginner, embrace the fact that you're probably gonna be able to take your dots from your previous role into your new, uh, job as whatever you've made a successful pivot in, that's actually gonna be an advantage and lean into that. Okay? My final piece of advice, this is good advice for anyone in their career, particularly if you're trying to make a career pivot, is to get great at storytelling. No one is going to connect the dots in your career except you. And if you're counting on someone when you're sitting across, uh, them to have an interview to try to make a career pivot, to understand your career journey, because if you are trying to make a pivot, it has probably been a windy path. You probably are a bit of a generalist. They're not going to do that for you. So you have to be really effective at telling a compelling career narrative. And that narrative is going to change based on the role you're trying to get. So when I was trying to get a community role at Morning Brew, I was taking the community experiences I had with the podcast I had started. I was taking the community building experiences I had with 40 high school students building a cohort, getting them to show up 2 hours after school. I was like, if you can do that, you can do anything. And so figuring out how, like the, the through line of your ex— your current career, how that connects to the role you want, what are those dots? How do you connect them in a really compelling way? And then how do you get great at telling that story to the person you're, you know, interviewing, uh, or being the interview of to get this new role? That's gonna be super critical. That's also a skill that's going to help once you have the role. Anyone that can be an effective storyteller that can, you know, take a random set of dots and create a compelling narrative is going to be a great leader. They're going to be a great employee. And I think people are really drawn to people that can tell effective stories. Okay. So these are a quick rehash of all the tactics. Use side projects to create credibility. Have more experiences outside your comfort zone. Don't forget your weak ties. This is actually where all the opportunity lives. Write, a.k.a. turn what you know into what you can show. Embrace your beginner's mindset and get great at storytelling. I hope that's effective in helping you think about your career, and in particular, if you're looking to make a career pivot, I highly recommend running through all these tactics and seeing where they get you. All right. Thanks for listening. I hope you found that advice helpful. My name is Kyle Hagge. I'm the chief of staff to our COO here at Morning Brew and the co-host of the podcast per my last email, a show that gives you the hot takes and tactics to navigate career life. Thanks for tuning in to Founders Journal. I'll see you around.