I’ve put this off for a while.
Sharing the career stories of others is exciting.
Sharing your own story, in your own words, is scary.
It feels good to lift others up. It can feel icky to do the same for yourself.
But in the name of transparency (and having been challenged by my incredible support system to do so), I’m sharing my own career story in the most authentic way I know how.
My story follows one of the primary themes we’ve seen across all the other generalist stories I’ve shared thus far: There’s no roadmap for how we navigate our careers.
Interests change. Priorities evolve. Opportunities emerge. And we’re never done learning, exploring, and finding our way.
We can’t judge our past selves for decisions they made with our past-self insights. All we can really do is learn from our experiences and apply those learnings as we continue to move throughout our careers and lives.
If this theme or my story resonates - please reach out. I’ve love to hear from you.
Here goes….
I sometimes wonder if I self-identify as a generalist because I’m extremely indecisive.
After all, how can you choose one thing until you’ve tried everything?
While it was possible (although annoying) to try lots of flavors at the ice cream shop before choosing one, it’s been a bit more challenging to do the same thing with my career.
It always felt like there were so many limitations that prevented the kind of experimentation that might have been truly helpful for career navigation:
Having to choose a major right off the bat in college at age 18
Wanting to have a “real job” and trying to fit into a box to make that happen
Adhering to limiting job descriptions that ask for years of experience in a given function
Feeling like it’s too late to try anything new or having to start from 0 to do so
Part of me has always wished that I could have taken part in a career circus. A way to try a variety of things and see what I like. Maybe something like Beaufuscorps in Germany. How cool would it be to do something like that every few years?
Honestly, I think I came to be a generalist because I’ve let my career be guided by areas of interest and problems I was looking to solve for myself instead of by specific functions or roles.
I was a language major (first Italian, then Spanish) because it was my dream to one day become bilingual.
I studied abroad because I knew classroom learning wouldn’t be enough to achieve fluency; I needed full immersion.
I became a Study Abroad Advisor because I didn’t leverage any of the resources offered by my university to help me figure out how to study abroad and ended up muddling through the process myself, choosing an independent program, and struggling for years to get my credits transferred. I wanted to make sure other students took advantage of university resources to not have to go through the challenges I faced so that they too could have a transformative educational experience abroad.
I taught English overseas because I wanted to live overseas and remote work wasn’t really a thing quite yet. It was the only avenue I saw to be able to live in another country. (I also thought picking up Brazilian Portuguese could be cool.)
I worked on Semester at Sea because it was essentially a free trip around the world and I was able to leverage my study abroad experience to get in.
(Mini-retirement #1): I went to grad school because I didn’t know what I wanted to do next and my GRE was about to expire. I chose an open ended program to continue exploring what I wanted to be when I grew up. By the end of the program I still had no idea, but I did start to get curious about the startup world.
I got a sales job at a digital nomad travel startup because it was basically Semester at Sea for adults and it enabled me to be remote and travel the world. Working to help people of all ages get to have transformational experiences overseas resonated with me. I got exposed to all different types of careers - especially non-traditional and non-linear ones.
So many people were seeking out this experience because they weren’t sure what was next in their lives or careers, which really drove home the point that there’s no roadmap for navigating our careers. Walking them through the possibilities and digging into these deeper questions was exciting. Even though I was helping others, I was really using it as an opportunity to answer those questions for myself.
Ultimately, the high pressure and trying to meet overly aggressive sales quotas was not for me. While working in sales was most aligned with my past as an advisor - it was really just to get my foot in the door. Ultimately, my goal was to transition out of sales within the company, but that opportunity never presented itself. When the company downsized, it was back to square one on what on earth I wanted to do next (as long as it wasn’t sales).
(Caveat: I enjoyed understanding people’s problems and guiding them to join our program if and when it was a fit. I didn’t enjoy quotas or feeling pressure to push the program on people that weren’t ready for it / couldn’t actually afford it).
(Mini-retirement #2): I was really lost. I knew what I didn’t want to do (higher ed, sales), but it was all I felt qualified to do. I took on projects (the original Unstuck Project!). I took courses (altMBA). I tried to start a podcast. I experimented and explored. I questioned what I actually cared about and what I actually enjoyed doing. I had no real guidance here; I was just practicing following my curiosity, sharing my story with my network, and stumbling my way to the next thing.
I fell back into sales because that’s what my resume said I could do. Fortunately, this time was with a micro-internship gig platform that at least felt aligned with what I care about because it focused on project-based learning and portfolio building as a means of career discovery and navigation. It felt good to promote an org whose mission resonated with me and kept social good in mind.
The fact that it was such an early stage startup enabled me to expand beyond sales - establishing processes, writing playbooks, experimenting with copywriting, marketing, design, and strategy. I didn’t feel like I became an expert in any of these things, but at least I was in an environment where I could try them out and see what happened.
(Mini-retirement #3): Parting from this job coincided with covid lockdowns, so this mini-retirement involved lots of time alone, reflection, music, and becoming a cat mom.
My work with Unstuck Project helped me land a part-time gig with a program that supports people transitioning careers. It felt so aligned with so much of what I had lived. Unstuck Project had given me a level of credibility that surprised me, but I ran with with it.
A few months later I got connected with a founder through a niche Slack community that was looking for a true generalist that cared about education. And again, a feeling of extreme alignment. I got to do and try just about everything - sales, customer success, onboarding, tech support, customer education, product marketing, user research, advising on product, testing, bug bashing, community management, event management. I got to have a real impact on a product I was truly excited about that was helping an audience that resonated with me - educators.
At this point, my career started to make sense to me. I could see my throughline. I was supporting live online learning programs. Learning programs that embraced the non-traditional learning styles I had seen had the biggest impact over the course of my career - project-based, cohort-based, career-oriented, etc. I was on a team building the tech to help them bring their courses to life. I got backstage access to how these courses were developed and executed and it became my responsibility to empathize and understand the associated pain points involved.
And then, as can happen with startups, our runway dwindled, belts tightened, and drastic decisions had to be made.
While there I remember having that sinking feeling of - what happens when this (inevitably) ends? This role has been carved out for me. My boss has given me free range to explore, but had also encouraged me to double down on work that I truly enjoyed and where I could bring value.
How could I ever communicate that to another employer in the future? What other employer will ever be looking to fill this kind of role?
It was like I had become a unique puzzle piece that I didn’t know where or how could fit anywhere else. The extreme privilege of crafting a role that fit me turned into a major conundrum of fitting in anywhere else.
Looking back on my career trajectory, what are the themes I see?
Following my interest and what makes sense for my life at the moment. I’ve consistently used professional experiences to accomplish non-work-related goals (becoming bilingual, living overseas) or to solve problems I’ve faced in the past or was facing at the time (not leveraging study abroad resources, wishing I had tangible work experience and career exploration opportunities in undergrad, providing cohort-based/community-oriented learning opportunities because those were what had been most impactful in my professional development journey).
Cold job applications never got me anywhere. I got the study abroad job by offering to work as an intern first while still in school. I got the gig-platform job by applying for an actual gig (even though they were for college students and I was 10 years out of college by that point) and getting a call from the founder for an actual role. For every other role I had a referral or some sort of connection, mostly through professional communities I had joined and engaged with or from events where I had requested coffee chats with the speakers to connect.
I’ve never gone super deep into any one function. I’m happiest when I’m wearing multiple hats (although this has led to some serious generalist imposter syndrome when it comes to finding the next thing).
At my core what do I enjoy most? Hearing and sharing people’s stories, then using them to help others and solve problems. I love brainstorming, providing resources, broadening horizons, and exploring possibilities.
Where can I find that in a job description?
For now, I’m not sure. I’m still in exploration mode.
But I do know one thing for sure: Focusing on things that excite us propels us forward.
I’ve put Unstuck Project on the backburner to focus on my own job search. But in doing so, I’ve lost my fire. I’ve lost the feeling of impact, growth, appreciation. Maybe it won’t be weekly, but I’m committing to returning to sharing these stories. Turns out my own story was the scariest to share. The rest will be labors of love and pure joy. Bear with me and stay tuned. :)
Your writing is such a pleasure. Looking forward to continuing to enjoy these stories.