Success Along a Nonlinear Path with Dr. Melissa Flagg

Considering switching careers? Dr. Melissa Flagg is familiar with that choice. Beginning her career as a pharmacist, she's also worked in security at the State Dept., in philanthropy at the MacArthur Foundation, as well as many other career fields and places. 

Not only has Dr. Flagg found success on her nonlinear career path, but she has used the diverse skills, life experiences, and lessons learned specifically from the evolving nature of her path to gain the success and fulfillment in her career that she has today. 

Listen to today's episode to hear Dr. Flagg speak about her unique career path, and the guidance she can give from her experiences to others who are seeking to find success along a nonlinear career path of their own. 

Technical Leadership Talks is brought to you by Texas A&M University's Master of Engineering Technical Management, a program that equips working technical professionals for the next step in their careers. 

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SPEAKER_00 0:06

Welcome to Technical Leadership Talks, the podcast that brings you advice, insights, and knowledge from industry leaders and experts on how to navigate managing in a technical field. Technical Leadership Talks is brought to you by Tech Stadium University's Master of Engineering Technical Management, an online graduate program that trains industry professionals for leadership positions. I'm Katie, METM's digital marketer, and your host for this episode. In today's episode, I'm talking to Dr. Melissa Flagg, the founder and president of Flag Consulting. She's also a senior advisor to the Center for Security and Emerging Technology at Georgetown University. Today, we are speaking about finding success along a nonlinear path. So to get started, I wanted to kind of talk about how we met because I feel like it sort of applies to what we're talking about. So I met Melissa at the Master of Engineering Technical Management's Residency Week, where the online students come for the whole week and take classes. But one of the days we have guest speakers who work in industries and organizations who have a experience underneath them that they can give advice, tell their story. And so that's how I met Melissa. And I know you said the reason you chose this topic was because you got a lot of feedback of people saying they liked how you talked about how like non-linear your path was and how you've still been successful. And it really at the moment appealed to me as well because I had just switched careers from teaching high school students to doing this job. So it really, like at the moment, I was going through a lot of life changes. And your uh your speech really appealed to me as well. So when you responded back and said you wanted to talk about this, I was like, oh, perfect. So can you explain a bit about all the careerships you've you've had throughout your life? Absolutely.

SPEAKER_01 1:48

Um, and just I think before I launch in, I will just say I obviously came, I come out of a lot of environments that people dedicate their entire lives to deep expertise, right? Out of academia, out of working for the military, working for the government. And deep expertise is a beautiful thing. And I have a lot of respect for it. And I know many, many people who they've been hugely successful by choosing something that they're passionate about and focusing on that one thing and building their way up through that very specific career chain over their lifetime. And I have nothing but respect for that. But when I was young, I just from like my earliest memories, I've always loved breadth, right? I've always loved the activity of learning something new, but I'm not someone who ever had like one specific deep burning passion that I knew I wanted to be an architect. And I spent my whole life, you know, waiting to become an architect, and then I loved it. That's all I ever did, right? And I had a lot of existential crises throughout my life. People telling me that I had to choose and stick to something or I would fail. So that is kind of why I think this topic is near and dear to my heart, because it took a long time for me to prove to myself that I could be confident in pursuing my passions and that there was some avenue to success by doing that. So, okay, my I started out, I am actually a pharmacist by my undergrad. And that was literally because my dad was a very practical man who said, if you don't know what you want to be when you grow up, you should get a degree that lets you get a job right away, and preferably has a board certification in the state so that it has a very limited applicant pool. He basically told me you can be a pharmacist, a nurse, or an engineer. And I was like, Well, engineering, I don't like math that much. Nursing, I don't like people that much, and pharmacy, that seems like what's left. So I became a pharmacist. I was a board certified pharmacist. I have some hilarious stories from my pharmacy days, um, culminating in one where my uh mentor pharmacist, as I was getting my practical hours, said to me, You're going to graduate school, aren't you? And I said, Yes, sir, I'm gonna get my PhD in chemistry. And he was like, That's good. We both knew probably wasn't meant to do that for the rest of my life. So I went to get my PhD in natural products chemistry. So I was gonna bang around the jungles of the world collecting plants and extracting chemicals from them, and I was gonna cure tuberculosis. So I spent time in northern Brazil in the jungle when I was an undergrad, and then I was in the Atacama Desert in Chile when I was in grad school, and I loved it. And then I realized that for every three months I spent collecting plants in the jungle, I was gonna spend three years pipetting things under a hood. And I was like, I'm too much of an extrovert for this. So, huh, what are we gonna do? Some challenging things happened to me. I was really on the verge of dropping out, and I had an intervention by an undergrad mentor of mine who reached out and said, Come back, do a postdoc with me, give me a year, and we can find some way for you to use your education, but that isn't academic, that isn't in the lab. So I wound up applying for a policy fellowship in Washington, D.C., called the AAAS uh Science and Technology Policy Fellowships. And I was accepted into a fellowship at the State Department. So I thought I was going to be working on sustainable development and uh regions like Africa and South America, and I was so excited. And I arrived in Washington, D.C. Now, my PhD had been funded by the National Institutes of Health. So my entire experience is really around health and uh science. I get there, and the first week that I arrive in Washington, 9-11 happens.

SPEAKER_00 5:44

So I forgot this part of your story.

SPEAKER_01 5:47

Welcome to Washington. No one cares about sustainable development anymore. And I mean, I have lots of thoughts on this. If we we probably should have worried a lot more about sustainable development at the time. Um, but anyway, it was what it was. So I suddenly was thrown into this environment where everything was about security. My boss uh at the time, who I was just uh hands down, probably one of the best bosses I've ever had in my life, he did not want to work with the military and did not want to work on security issues. So I was thrown into dealing with all of these issues around different agencies in Washington fighting with each other, with some agencies wanting to throw all foreign scientists out of the country and other agencies saying that's crazy. So I was this in the middle. So I learned a tremendous amount about research security and I became kind of an expert. It's it was very accidental. So after about two and a half years at the State Department, I was looking around for what I was gonna do next. And I had helped someone who worked for the Navy do some conferences in Estonia. I mean, very random, right? The guy he just called and I helped him. I didn't think anything about it. So he calls me up and offers me a job working for the US Navy in London, uh, doing international science collaboration. So the Office of Naval Research Global has been around actually since just after World War II, uh late 1940s, and it's a really fabulous organization. So I basically just said yes. And then I was like, uh, by the way, is there a job description? He's like, ah, we'll figure it out when you get here. So I pack my stuff up, and a month later I'm moving to London. I don't really know what I'm gonna do. I don't know anything about the military. It was just faith, right? And I was young and it was pre-rent in London. So I get to London, I spend uh two and a half years in London, absolutely love it, traveling the world, and we were really trying to work on some big technical problems of how do you understand the landscape of global science. So an admiral who back in DC for the Office of Naval Research headquarters had asked for us to think of some ways to go about this project that he had in mind. So I really took on this project. He really liked it. He brought me back to DC. I wound up being at the Office of Naval Research for several years. He retires, I go to the Pentagon, I start this office of technical intelligence where I'm doing something very similar. And it feels like this is going to be my whole career. So, fast forward, I've been at the Pentagon for four years. I'm turning 40. I'm having a little midlife crisis probably. And somebody wanders into my office and says, you should apply for this job. And it's a very senior job, and it should be everything I want. It's everything I've worked for. And it happened to be in the intelligence community. And so I'm also leaving on vacation that next morning, and it has to be filled out in the next seven days. So I would have to do it on vacation. So I get on this plane to go to Seattle, and I'm holding this job description and I'm reading it, and I start crying on this airplane because I'm realizing I don't want to be in this super secret room in the basement of the Pentagon for my whole life. And for those of you who've ever been to the Pentagon, you may know that they have these little golf carts with pink blankets that if you have a health crisis at the Pentagon, they put you on this golf cart and they wrap you in this pink blanket and they drive you off to wherever you need to go for medical attention. And I just had this image of myself dying in the Pentagon when I'm old and being carted out under a pink blanket. I was like, I can't apply for this job. But when I decide not to, I sort of roll a grit grenade under my career, right? Yeah. Because everyone's like, but this is what you were working for. So all of my mentors are just losing their minds, you're ruining your life. In the meantime, I start looking for jobs because clearly now I have to get a new job. And I find this job description on the internet, the way that people tell you you will never get a job. I apply cold to this job. It just so happens that they decide to interview me. And after seven interviews, I wind up at the John D. and Catherine T. MacArthur Foundation in Chicago, working on their genius grants program as their science guy. Talk about a 180. Now everything's domestic, everything is super positive. It's all about finding creativity in the world. There's no threat, there's no national security. It's like I've gone to this beautiful little island after this career I've had, right? Of just all the security related stuff. And I say to my boss the first day, I'm never going back to government unless I'm a political appointee and I can actually be in charge of something. And she was like, okay. So fast forward two and a half years, I get a phone call from the White House offering me to come and be interviewed for a political appointee position at the Pentagon. And my boss happens to be in my office when this phone call comes in. And I hang up the phone and she's like, What happened? And I told her, and she's like, one of us is going to be in the Obama administration. So even if I have to put you in the trunk of my car and take you to Washington, you're doing this. So I interview, I get the job, I move to Washington, and I go back to work at the Pentagon. But this time I come back with an incredibly different view of the world, right? I've been away from government. And really, it's what made me actually competitive for this position because I hadn't just worked up the ladder and never known anything but defense. I'd left and I'd looked at science in this country through a different lens. And it really did give me a very powerful new perspective on a job that I knew quite well. So then, fast forward 18 months, and there's an election. And as a political appointee, I am offered the opportunity to find alternative employment. So I pack all my stuff into storage and I go on a road trip for a year. And I literally drive across the country twice, talk to people about the election, and I really start thinking about the things that I've been taught my whole life and that I have been teaching other people at this point. And I realize that I believe the country is changing and that I believe the research and innovation landscape is changing. And I don't actually believe a lot of the things I've been talking about. So one of the things that I think is so important about jobs that take you out of that linear flow is that sometimes it also gives you time to reflect on what you learned while you were there and to really know your own mind because I fundamentally changed what I think I would have done next and for the rest of my career because I took that year off and I really reflected on what I learned. So then I wind up in a series of I work go back to work for the Army Research Lab in Boston. I open up a lab there for them. It turns out that it's not a great cultural fit, but it was a really great 18 months. I think I was very proud of what I did. Wound up then going back to Washington to work for a think tank, the Center for Security and Emerging Technology. And this is the first time I actually wind up in a job where I'm supposed to write. And so again, it's this very different space than what I had been accustomed to, but it's starting to merge a lot of the things that I've learned, which is it want they want me to look at science, they want me to use data, they want me to really understand that landscape. I care about security, but we need both the international and the domestic lens. It really draws on all of these skills I've learned, but now I'm actually creating a public portfolio of what I actually think. So now I have to take a moment to say, I'm no longer in a position where I'm taking what my quote unquote boss is saying and turning it into PowerPoint slides. I'm now the boss. I'm now the one that has to take this career's worth of learning and actually turn it into what I think. And what a powerful two years that was because I created really deep public portfolio of my own work. And that allowed me then, as the pandemic kicked off, to ultimately start my own business and accept some of these positions as visiting fellowships and really begin to take more of a thought leadership role and extremely exciting. And so for me, the biggest challenge of the nonlinearity is that at every step of the way, someone will tell you you're ruining your career. 100%. But the opportunity that that gives you is to own your own narrative and to become really strong in having faith in yourself and not seeking that external validation constantly that someone's telling you you're doing the right thing, just getting confident enough to say, I'm willing to live with the consequences of my action. Trusting yourself, 100%. You cannot do that if you can't learn to trust yourself. There were so many moments where I was like, this could go terribly wrong. Yeah. And trust me, it wasn't all roses, right? I mean, there were quite a few very stressed out nights where I was like, Do I have enough money and savings? But I wouldn't change a day of it.

SPEAKER_00 14:55

Yeah. So when you were going to make a big career shift, what were the conversations you were having with yourself in order to make that big step?

SPEAKER_01 15:03

So I guess there are two things that I really do, and I still do this honestly, even at 51, right? Is that I try to think about two things. One is how do well, maybe three things. What the first thing is how do I feel about it? I think that we have laughed at people for having feelings for the last, I don't know, 400 years, but so many people are highly successful and miserable. And that is simply not a path that I'm willing to walk. And so if my stomach really hurts when I'm trying to make a decision, because I feel every decision in my stomach. I mean, I'm physically nauseous if I'm trying to do something that I know that I do not want to be doing. I think it's really important not to ignore your own feelings. You don't need to tell everybody about your feelings as they'll have opinions and whatever. They get to have an opinion if you give them the right to have an opinion. Uh, I don't give people that opportunity very often anymore. Yeah, um, the second thing is that I don't tend to think about jobs in terms of titles and in terms of rank. I tend to think about jobs through the lens of I have three circles on a Venn diagram. One is intellectually challenging, one is joy-inducing, and one is it earns money, right? It pays the mortgage. Right. And in my money circle, I have both a floor of the amount of money that I have to make each year in order to pay the bills, and I have a ceiling, which is once I get to this amount of money, this should not be the thing that I make decisions based on. I do stupid things when I have a lot of money. I don't want to become a person whose life is so expensive that I have to always make that amount of money at the expense of joy and intellectual stimulation. Those are my circles. Everyone should have their own circles. I don't, I don't know, I don't care, right? I don't uh those are just my circles. So for me, I look at it and I say, how is this rewarding to me? And if I've already hit the floor of my money, is it either intellectually challenging and or joy-inducing as well if it's earning money? Because I'm not going to just make money for the sake of making money if I've if I've already have security sorted out, right? So I'm very clear on what my priorities are. And the third thing is, is it giving me a skill that I don't currently have? Is it growing something in me that um that I want to be better at, right? The CSAT job is a perfect example of this. I am terrible at writing. It's it's hard for me. It is not my natural form of communication. And taking that job and committing to the written word was scary. Yeah. And especially because I had a reputation at this point. So now if I'm bad at it, like it's very publicly bad at it, right? So I talked to the guys that were running CSAT at the time, Jason Matheny and Jude Murdoch, who's now the director, and chatted with them about okay, I really want to do this. I really am going to need some editing support. And I really want to work through learning how to really get my hands around the writing. And I want to teach a class because I had never taught a class. So I taught a class to master's students at Georgetown as well while I was there. And once I had sort of done those things, I was able to move on because I felt like, okay, I got, I contributed really effectively to CSET. I produced products that I was very proud of. And I also gained confidence in these skills that I didn't have when I went in. I don't always tell people, I mean, sometimes I do, and depends on the trust I have with the people I'm working with, like why I'm here. But I always know why I'm in a job, why I'm applying for a job, because that job will be awful at some point. It is work, right? It will always have its bad moments. And unless you know why you're there, it can be very hard to get through those moments. So for me, that's my coping mechanism. And it's very much how I look at decisions on what work, even now, what work I take. I will turn down work if it doesn't align with giving me some skill that I need, using my mind in some way that excites me, gives me pleasure. I'm not, I've I've met met the floor and I'm not just working for any job for money.

SPEAKER_00 19:33

That's a good place to be.

SPEAKER_01 19:33

It is. It's I haven't been here my whole life, so I feel it.

SPEAKER_00 19:36

Yeah. So for those who are listening who are thinking about a career switch, but they're afraid of having to completely start all over. What advice would you give them to where they won't have to basically start from the bottom, lose all their skills?

SPEAKER_01 19:50

I think that for me, anyway, the key has always been that I've built on some aspect of expertise in every job. For me, every job had some aspect of science and technology in it at a very general level, even though there were radically different sectors, right? I mean, defense, philanthropy, uh, think tanks, consulting. So for me, I was able to construct a narrative as to why that wasn't a complete chain, right? I mean, for instance, if you're going from teaching in front of a classroom to doing communications, to me, there that's not a radical shift. Yeah. Everything about teaching is communicating complex ideas to people who have not been introduced to that complex idea before, right? It's almost the exact same skill set that you're using in communications, right? So I think the key is actually that most people spend so much time focusing on the differences in what they're showing out to, and it gives them anxiety, and they're they're focused on the anxiety and the negative aspect of the change, and that it's probably more valuable to spend more time identifying what are the underlying skill sets that are still valuable, and then what's the story over like the arc of my career that I'm building, the narrative I'm building around expertise that's aligned to those skills, not to a sector or not to a linear career path. So when people say, What are you an expert in? I'm like, I'm an expert in actually being a generalist in science and technology and emerging technology. There are lots of people that know more about quantum science than me. There are very few people that know as much about what's going on in the global landscape of science and technology as I do.

SPEAKER_00 21:45

Yeah, that's good. Okay. What about interviews? So, one of my worries when they ask me in an interview, why are you switching careers? Do you have any advice there of how to answer that question?

SPEAKER_01 21:55

For me, again, this goes back to really holding this narrative. We have to follow. Philanthropy people were saying, like, you work for the military. Why are you coming here? And I'm like, well, I work for the military, but what I do is understand the landscape of science and technology. I mean, that's my skill set. And I've been focusing that skill set on the international space. And a lot of it has been focused on threat. And what I really want to do is take all of the skills and expertise that I have and apply it to a space where I can contribute really positively to the world, right? Apply that to my own country. I want to bring all this knowledge and expertise to lift up people for creativity as opposed to identify things that could be a threat. It's the same skill set, but I would like to use my powers for good, right? But that's a narrative that I worked really hard at owning and feeling, and feeling in a way that allows me to communicate it with a great deal of authenticity. So I do think that so much of this is about finding the commonality and then articulating the arc of your career through that in a very positive and powerful way rather than trying to apologize somehow for deciding I'm tired of working in this sector and using the skill in a specific way. I want to, I want to broaden it. I want to apply this expertise differently.

SPEAKER_00 23:22

Okay. My last question is just if you have any last advice or words of encouragement you want to give to anyone who's listening to this and maybe trying to make a decision if they want to do a slight career shift or a big career shift. So any last advice or words you'd like to say?

SPEAKER_01 23:35

Yeah, I guess I would say this based on a lot of the comments I got when after I gave that when I was visiting last year, I think a lot of people, when they are, when they're smart, when they're hardworking, there are a lot of folks around who are sort of mentoring them and they come at it from a place of like really deeply wanting to help. And it's a very positive place, but they sometimes don't realize how hard it can be to take some of that advice if you are a fundamentally different person than the person who's been right. So what I heard was a lot of people coming up to me, especially on the younger end of that cohort, saying, Everyone is telling me I have to stick with this, I have to do this next, or I won't be able to go to the next level. And if I don't, then I'll ruin my career. And I guess my aunt, the comment is kind of for both sides of this equation, right? You're on the mentoring side, all you can do is tell the person what worked for you. And so I want to leave people out of like appreciation for I'm telling giving myself this advice as well. You only take what resonates with you and leave the rest. Yeah. Because I am giving you a very personal experience that worked really well for you, for me, and landed me in a place where I am really happy and I feel like I've been very successful, but it's not for everyone. So you don't need to defend your point of view against my input. Uh, tell me what resonates, leave the rest. And I would give this advice to mentors. Try to be gracious with the people you are advising that they do not need to take all of your advice and you should encourage them to leave whatever doesn't feel good. For the people on the receiving end, you are responsible for your own life. And no job is responsible to change for you. When jobs make you unhappy, you should find a new job. Period, full stop. You shouldn't struggle to try to force a job to be different and for them to want you to do different work, even though they hired someone to do that work, because it is not a good fit for you. And I would say that when you are asking for advice constantly or when you are receiving advice constantly, it can be very hard to hear yourself. And my advice is to spend real time with your own thoughts. I think this is easier advice for your generation than it was perhaps for mine. Uh when a lot of people at my age getting therapy. And I'm a big fan of therapy. I think more people should get therapy. My mom's a therapist, so I'm all for it. I don't think therapy means you're broken. I think therapy means you're trying to know yourself better and to both give yourself a better chance for success and to mitigate the harm that you can cause to other people, right? But I think knowing that you also are going to make decisions that in the moment you think were a huge mistake. And how you look back on that from 50 or from 60 or from 70 years old is going to largely be determined by what you do with that choice. If you decide it's a mistake and you wallow in it and you're miserable, then it will have been a mistake. But if you're like, well, this sucks. But what I've learned is I don't like doing jobs that that make me do X, Y, and Z type of things, but I love this other type of stuff that I'm doing. So I need to start looking for a job that lets me do more of what I love and less of what I hate because I will be happier and they will like me more. I have had at least two jobs where I was like, oh my God, this is the worst fit for me. But I've learned from that and I'm so grateful to those jobs because as soon as I left, I realized like, God, it was such a bad fit. It wasn't malicious, it was just such a bad fit, and it made everyone uncomfortable. And so I guess I would just say the more you can actually analyze what's happening through that lens of what am I gaining? What skills am I gaining? What am I learning about myself? I guess my last piece of advice would be also. I do not understand this obsession with getting better at everything. There are going to be a few things that as you age, you just realize, I hate that. I don't want to be good at that. I don't want to do the work because it's unpleasant. Just stop doing it. Like spend more time being absolutely brilliant at the things you love and less time laboring away at getting 1% better at something you hate.

SPEAKER_00 28:25

Thank you for listening in to today's episode. Tech Leadership Talks is brought to you by Texas AM University's Master of Engineering Technical Management. To learn more, visit metm.tmu.edu.