The Power of - and Path to - Becoming a GeneralistFeatured

About a decade ago, I started thinking about how I wanted the rest of my career to look. I wasn’t so driven that I thought I should have everything mapped out, but there was a tendency for companies to ask current and prospective employees, “Where do you see yourself in five years?” I never had an answer for that question!For a long time, I thought there was something wrong with me because I couldn’t envision myself five years in the future - that I wasn’t ambitious enough, not forward-looking enough, or even that I was too lazy to strategically plan out my future. I thought I was content to let things happen to me, instead of making them happen for me.I was surrounded by people with big plans who spent their free time enrolled in courses, networking, blogging, and otherwise owning their careers in a way I somehow didn’t feel inclined toward.On top of this, there was a real sense that to be successful, you had to “specialize.” If you were in marketing, your career path would be easier if you settled on demand gen, or PR, or social, or content. But I wanted to do it all!Doing a little bit of everything is my specialty - and over the last five years, I’ve come to realize that’s okay. I’ve tended to take on communication-centric roles because that’s where my skills and interests naturally lie, but being versatile has served me well.At first, I thought doing a variety of tasks would point me in the direction of what I liked and was good at, would give me an idea of where I should “niche down.” What I came to realize was wearing many hats was exactly what made me happy, productive, and fulfilled.That’s why Chief of Staff is such a great role if, like me, you’re more inclined to be a generalist than a specialist. I work cross-functionally to support my executive team peers in strategy, goal-setting, and high-priority initiatives. I also take on “special projects” - the things that need to get done, but aren’t anybody’s job, per se.When I look back, I think I was unknowingly directing myself along this career path. It didn’t feel intentional at the time, but I think that’s because it’s hard to articulate a role that’s naturally broad. I hadn’t heard of the Chief of Staff role in a non-political or military sense until eight or nine years ago. Even so, it’s a role that’s so customized to the company, it’s impossible to give it a single standard definition.If you’re a Jill-of-all-Trades, like I am, here’s some guidance that I hope will help if you’re feeling stuck or unsure what kind of role to look for:Internship ProgramsIf you’re planning where to go for post-secondary, consider somewhere with an internship program. The opportunity to do (hopefully paid) work will put you at a tremendous advantage when you graduate: you’ll have “real” experience and hopefully some idea of what you do and don’t like doing.Think Small, Medium, LargeIf you’re looking for a job, consider small companies: you can make a bigger impact, you’re less likely to be pigeonholed into a set role, and you’ll have more frequent, direct contact with the leadership team than at a large company.If you’re at a medium company, that’s a great opportunity to become a people manager. Nothing says you have to have direct reports to progress in your career, but it’s worth trying so you can figure out whether or not you enjoy it. If budget is tight, see if you can make the case for hiring a post-secondary student intern for a semester. Government subsidies are often available to cover their salaries. Plus, it’s an opportunity for you to help someone who’s at the beginning of their career as you once were.If you’re at a large company, make it known that you’re interested in learning about different areas of the business. Volunteer to take on “side of desk” tasks - the things that need to get done but aren’t high priority. You can dip your toe in this way across various functions to see if any of them appeal to you. If one does, see if a secondment - a short-term stint - is possible in that different role or department.Ask if you can job-shadow a colleague, ensuring you don’t distract them from their core job. Clarify one or two specific outcomes you want to achieve to ensure you stay on track - these should benefit the business and the other person, not just you. Sit in on meetings and take notes. Figure out which reading/videos you can consume to figure out the basics, and prepare concise questions you can ask them at regular check-ins. CoachingIf your company doesn’t have a coaching program, ask if you can start one. Pair “junior” and “senior” colleagues in similar roles together. Optimize for learning on specific areas of growth over a defined time period, rather than continuous, open-ended relationships. Again, it’s a chance for trying something to see if it’s suitable for both parties, and an end date makes for an easy out.MentorshipThis is different from coaching because it’s an external relationship with no end date and has open-ended objectives. A mentor acts in your best interest, not that of your employer; for example, they may advise you to look for job opportunities elsewhere if they think that’s what’s best for you, which a colleague is unlikely to do.A mentor should be someone significantly senior in their career to you, so that it can be a long-term relationship as you progress in your career and take on the roles your mentor may have already had.I found a mentor through the local chapter of the American Marketing Association, which I’m a member of. That was over two years ago, but to this day, I can contact my mentor any time to ask her advice.Look for associations, groups and communities (like Elpha!) that have mentorship opportunities. They don’t have to be formal programs, but should have a large network you can tap into.Use these forums to put the word out that you’re looking to connect with people who’ve had the kind of career path you’re interested in - you’d be surprised how much strangers are willing to help others.Personality TypeSome people roll their eyes at Myers-Briggs and its ilk, but I find them useful for articulating the things you already know about yourself, but may not be able to put into words. Something like the Clifton Strengths Assessment is also good because it lists the roles suited to your personality - good guidance for you to go on LinkedIn and find people in those roles that you can connect with.NetworkingWhen you invite people to connect on LinkedIn, always include a brief note about why you want to talk to them - they’re more likely to accept a request from a stranger if they know why you're asking. When you’ve connected, ask for a 15-minute phone call, and send your questions ahead of time. Make it as easy as possible on them, since they’re doing you a favor.Getting UnstuckFiguring out your interests and strengths is hard - it requires self-introspection, and it’s a lot harder to judge yourself honestly than others. A few years ago, I sought mentorship because I was feeling stuck - like I’d been in the same field too long, but I didn’t know how to make a switch or to what. My mentor gave me this exercise:Identify Your 4 Non-NegotiablesIdentify the 4 non-negotiables that give you a sense of professional purpose. These shouldn’t be table stakes (eg, good culture), but are more things like “having a say in company decision-making,” or “being able to work on increasingly important projects.”Here’s how:Write a list of all the crappy things you’ve hated about jobs/workplaces Write a list of all the things you’ve liked about jobs/workplaces/coworkers you’ve had, including volunteering or other activitiesWhat I found was that for all the things I hated, usually the opposite was something I likedTimebox these two activities, say 15-20 minutes eachPut the lists away for a couple days, then come back and circle your 4 must-havesIdentify Your SuperpowerYour superpower is something you do really well. This one is often tough to figure out because it could be a skill that you do so well and so naturally that you take it for granted. Ask around and think about feedback you’ve been given in the past. You could also do something like above, where you list the things you’re good at, then take a couple days to figure out what commonality enables you to be good at those things.Putting Them TogetherWhen you think about the kind of job and workplace you want, you have your non-negotiables and superpower to guide you as to what you should be looking for, where you'll do well, or how to create a role for yourself.As you’ve probably guessed, all of the above are things that have happened over the course of my career to lead me to where I am today. Some required deliberate effort and thought, while some occurred by lucky happenstance. Try not to get too discouraged if you’re struggling - none of this is easy, and it all takes time.I’m more comfortable than ever with being a generalist. I just had to have faith that I’d get there in the end. You will too.
Thanks for this!
So nice to read this, thank you Megan. I feel like a lot of the advice out there is about specialising, and I like the idea here that you can specialise around super strength without having to pigeon hole yourself into a role.
Yes! I just applied to a job that was looking for "a generalist in the best way". My heart was so happy to read that companies know we exist! But also, that "in the best way" says we have a long ways to go in deconstructing skillset hierarchies imposed on us. What you're nudging up against is the power of skirting the narrow confines of a traditional/masculine/one earner household linear track.That's no small thing. I don't believe we will ever fully escape it under late-stage capitalism, where employers benefit from imposing career constraints as they isolate us from each other into specialist channels and rank us in financially valuable categories that prevent us from, say, building collective worker power and unionizing...but the peek of light between the clouds for us generalists is really encouraging.
Thanks for sharing this. I am absolutely a “Jill-of-all-trades.” About every 2-3yrs, I always pause and think about whether or not I want/need to specialize and I always end up deciding not to. Haha. Last year, I was looking for a chief of staff role in the USK12 education world. Unf the timing didn’t work out for any of those opportunities. So instead, I decided to pursue the ultimate “Jill-of-all-trades” job and took the plunge to launch my own edtech startup and am now the Founder and CEO of my company.
Love this; very strongly echos how I view what I want from my career. I've always struggled with that "where do you want to be in..." question -- because I like to let opportunity play an influencing role.
This is amazing, thank yoU!
Thank you so much for sharing this @MeganWheeler!! I relate so much to everything you shared. The "where do you see yourself in five years" question? The absolute worst. Even ONE year ago, I couldn't have predicted I'd move to Costa Rica and start a new job in the middle of a pandemic. I love personality tests but usually score almost dead in the middle of all traits... which probably shows how adaptable and fit for a generalist I am? 😂The first 5 years of my career were spent in a very large company where being a generalist was actually discouraged. Even though I still did well, it led to very difficult career conversations and was just overall not a great fit. However, I recently started a new job with a company of ~20 and AM SO MUCH HAPPIER. A generalist was exactly what they needed. I don't even care that I'm somewhat drowning in opportunities and things to do haha because it's so fun to continuously learn and apply new skills.I hadn't considered a Chief of Staff position before. I know definitions vary, but is it somewhat similar to a COO role?
Wow, Mollie, what a big step to move to Costa Rica for a new job! What is the job? My sister has always wanted to move to Costa Rica.And yes, I score in the middle for all the personality tests too!
Hi Jess! I actually moved to Costa Rica for my husband's job - he's an R&D engineer at Boston Scientific and accepted a 3 year assignment at their manufacturing facility down here. Didn't expect to be quarantined for much of it, but we're enjoying it so far!
Hi Mollie, sounds like you found the right path for yourself, even if there were struggles along the way. CoS can be like COO - it really depends on the how the company structures the role to fit their needs. Would be happy to chat 1:1 if you want to DM me!
This post made my day! I have always said I'm interested in too many things--college was filled with internships in different areas and a major that was the broadest engineering major possible. Honestly I've always been a little concerned about being a generalist, so I'm very happy to see your post! I finally began to thrive in my previous position, when I was given the freedom to take on tasks that I wanted from different areas (I ended up wanting all of them haha). My current position is another small company where I'm a little more specialized, but super high-touch with decision-makers and able to take on different tasks within my role. Excited to see where I'll go from here!
YESSSSS!!! All of this! 🙌🙌🙌The other thing I would add that’s valuable when you’re a generalist is being okay with taking a role that you’re excited about and can make an impact at even if it is in a different or new industry.I went from an agency to an A/V company and after a few years I felt like maybe I messed up. Maybe I left the agency/design world and won’t be wanted by other design companies. But then I found my current job (honestly a dream), and my mix of design background, project management and technology experience and opportunities that I got from the A/V company made me not only a candidate but I got hired. I like doing so many different things that didn’t necessarily seem to go together, but it’s all valuable experience. And recognizing that was one of the hardest parts about being ok with being a generalist.
Thank you so much for this article! It came to me in a moment that I was reviewing my choices here in Canada. But you are right, I love being a generalist and there is nothing wrong with that! The job market needs to understand that transferable skills are valuable and a person with a different background or from a different industry can add a lot of perspective to any business.
This is awesome, I'll share it with the community :)