Welcome to All of the Above, a place where Generalists, folks-of-all-trades, and the wearers of many hats are finally at home. In this column, I explore how those of us who do it all (and love to do it all) can make it work in a world that is obsessed with fitting us into boxes.

I love a personality test. I love the insights they bring and the personal understanding that comes to light. Discernment and decisiveness have historically been difficult for me, and answering a series of questions and seeing an answer spit out has always felt comforting. Here are the answers I couldn’t see myself, the ideas and traits that could only come to light by answering a series of questions (or inputting my birthday, time, and location).

Because, like many others, my interest in personality tests started with Astrology. As a kid (and tween), I’d read my horoscope in Teen Vogue and loved buying shirts, bags, and other merch branded with my sun sign from Claire’s or Wet Seal. Even my first AIM screen name mentioned my zodiac sign (and if you want to know what that screen name actually was, you’ll have to listen to my recent podcast episode with ).

I got more into Astrology, learned what a birth chart was, and dove in. I learned about Human Design, another system that uses your birthdate and time and place.

Throughout college and various jobs, I’ve taken half a dozen personality tests (Myers-Briggs, Enneagram, StrengthsFinder, to name a few). They all tell slightly different stories, as is their point, but I found them comforting all the same.

One throughline across them all is my adaptability and my ability to connect with others (and to connect others). It’s sometimes described in other words — an ability to fit in, to blend, to synthesize and arrange, to manage ambiguity, to finish tasks with little context, etc., but overwhelmingly, these tests (and my Astrology) point to the way in which I can easily fit in and rise to many occasions.

I used to get frustrated by results like these. I wanted to be the achiever, the natural leader, to be seen as organized, to have the elusive Woo pop up on one specific test.

Instead, these tests tell me I am adaptable (also: empathetic, customer-focused, someone who acts without much thought, sensitive, and able to connect people to one another). I found these strengths to be soft and not well-suited for the low-stress, high-earning career I craved.

I also found that where all these tests differed was in the variety of careers they recommended. Many of these tests give you a variety of careers, but I found that if I compared one test to another, my results were really different. A teacher, a social worker, a career in the arts, PR and marketing, HR, law, project management, mediation, “your work should be structured”, “your work should not be structured or traditional”, consulting, finance, operations, leadership, change management, and broadcasting, just to name a few.

None of these felt particularly resonant or interesting, but neither did any of the other jobs.

I kept getting such different results, I ignored them all. I still held on to the results of these tests, but told myself the career advice didn’t fit me and my working style, and for a long time, accepted that as truth. But the writing on the wall for being a generalist was there; I was just too focused on picking the right capital-C Career to see it.

It wasn’t until I stepped back and really looked at the various careers, job titles, industries, and companies (and eventually, my pivot into self-employment), that I started to see this differently.

The Projector in Human Design guides systems and tells me that I work best outside of traditional 9-5 frameworks, but my Taurus Sun/Capricorn Rising craves structure and predictability. The INFP centers values above all else, and my Enneagram 9 speaks to my ability to be easy-going and adaptable. The traits that came out of the other tests I’ve taken speak to my adaptability and humanness, and make it really obvious that I am meant to work in the way I am working right now. It just doesn’t make sense to everyone.

These tests have been trying to tell me something valuable all along: that I can do all of the above, and may even be good at that. There’s a reason why marketing and HR and social work and rigidity and flexibility all came to the surface.

Every test, chart, framework, and set of questions I’ve answered points to different sides of me. I hold complexity, connect systems, and make sense of them for myself and others. I lead with empathy, understanding, and love to manage ambiguity. What I once saw as soft now presents to me as the job itself. A job I don’t have a name for.

Instead of forcing a name, I find comfort in figuring out what the specific actions are. Doing something with my career in startups and tech, honoring each step of the journey, and also acknowledging that I can’t just be one thing anymore.

It’s writing this newsletter and struggling to fully niche down for the last three years. It’s the freelance work I’m paid to do, copywriting, community management, and social media strategy, and I’m having a hard time painting the picture of how that fits into the tech consulting work I know is where the ‘money’ is. I created a discipline, Customer Product Ops, to try to make sense of my decade-plus experience, but it still doesn’t feel like a big enough box to shove my experience into.

It’s hard to articulate all I do (and all I can do that I haven’t had the chance to do yet) to myself, and it’s even more difficult to articulate it to companies and founders. Companies want generalists, but they don’t want to hire them.

What if I stop trying to be hireable and instead focus on all of the things I know I am good at? What if that’s what leads to figuring out how to do All of the Above while highlighting my strengths? Yes, because of tests and charts, but also because I’ve been me for thirty-five years, and while I used to think I wasn’t too good with discernment, it turns out I know myself pretty well.

Welcome to All of the Above, a place where Generalists, folks-of-all-trades, and the wearers of many hats are finally at home. In this column, I explore how those of us who do it all (and love to do it all) can make it work in a world that is obsessed with fitting us into boxes.

After my last layoff1 last summer, I have a distinct memory of looking at the Product jobs on LinkedIn and feeling a pit in my stomach. I don’t want to do that, I thought, or that, or that, or that.

Did I even want to be a Product Manager anymore?

While I was sorting through that very question, I wrote an essay originally titled I don’t want to be a Product Manager anymore, later titled I might not want to be a Product Manager anymore. I never ended up publishing that essay — I probably didn’t want to say those out loud, because there was something I really loved about Product work. Today, I am revisiting that topic with a new perspective.

It’s not that I don’t ever want to be a PM, it’s that at this point in my life, I don’t just want to be a PM. It’s a role that requires you to wear a lot of hats, but it still boxes me in. I’m not only ready to say that, but I’m ready to publish that.

But back then, I wasn’t. I wasn’t ready to close the door, even though I knew in my gut a traditional PM role just wasn’t aligned with what I wanted.

But I felt like I’d worked so hard for that career, and there was still more to do. I wanted the ‘Senior’ tacked on to my title (badly). I had — and still have — this deep desire to solve problems for people, and I became a PM because I think software is a compelling way to do that. I’d placed a target on that title early in my career, told myself, ‘I think I’d like to do that one day,’ and let my career unfold. And eventually, five years after that initial thought, I was stepping into a Product role.

PMs will tell you “Product is different everywhere,” and that’s true, but it’s also an established discipline. There are books written about it, ‘rules’ and best practices to follow, podcasts and newsletters about it, and most importantly, it’s a specific title that, when you see it, you more or less know what to expect.

So when, after five years, I realized there was a chance I wanted to forgo the title and career I worked hard for and that finally helped me fit into a neat box, I’ll admit it — I was scared.

I realized there was a lot about Product work I liked, but also a lot about the work I didn’t like. And there was also a lot of experience I had before becoming a PM, leveraging skills I liked leveraging, that I felt like I wasn’t using anymore (or when I tried to use them, that I faced resistance).

Last summer, while laid off, I joined a Job Search Council after reading the book Never Search Alone. I met weekly with other folks looking for employment, and part of the program is creating a detailed two-pager that takes your strengths, likes, dislikes, and market-fit into account.

While working through this exercise, I started to face the reality that a lot of the things I ‘liked’ and ‘disliked’ didn’t quite match a traditional PM job description. I started to say things like “I want to maybe explore other paths while I also look at Product jobs,” but had never allowed myself to say “I don’t want to be a Product Manager anymore”, even if that is what I had felt.

During a round of revisions, someone on my council noted that everything in my “Strengths” section were very ‘PM-coded’, and pushed me to think of whether I had other strengths (spoiler: I did). Even as I was trying to push myself outside of my box, I found it difficult to actually do so until I was given permission by someone else.

I think I am a decent PM, but is ‘decent’ enough to build my career on? That’s the wrong question, because yes, it is enough. But I, maybe unfortunately, want more than just doing something I’m good at.

When I started actually mapping what I liked and didn’t like, a pattern emerged that had nothing to do with Product, though I think it’s part of what helped me in those roles. I like people, writing, fixing things, and seeing how all the pieces fit together when no one else can. I like the early stages of a problem — whether it’s a user problem, a need for operational improvements, or an issue within a team, working incredibly cross-functionally, and I like making language say exactly what it needs to. What I don’t love is being judged entirely on outcomes I can’t fully control, doing everything right and having it not matter because the numbers didn’t move, and living and breathing data analysis.

None of that is inherent to Product work, but it’s also not not Product work. It doesn’t quite fit in a box, and if it does, I haven’t found the right box yet.

So where does this leave me? On paper, I'm doing this backwards. I quit my job, and now I'm figuring it out. If I were giving responsible advice, it wouldn't be that.

But the first thing I needed to do was to take a step back. Having clarity on what I want and don’t want is a great step, too, but the space between my full-time product role and what I have now is necessary. You might argue that I had this back in June, but I needed to choose this.

What I do know is that being a fixer is at the core of what I want to do. I like seeing what’s a bit messy and helping make sense of it (whether that’s in a product, on a team, or apparently, in my own career).

So far, I haven’t seen any roles on LinkedIn for ‘Fixer,’ and I believe that’s by design. The work I want to do at this time isn’t joining an organization full-time. The problems I want to solve shouldn’t be problems forever, but rather something I can shape and send off to its permanent home when it’s all fixed.

Leveraging the skills in Product, ops, and working with teams in customer-facing roles will lead me down the right path. After all, there’s a lot in those domains I enjoy, and that is where my experience is — the next step is to figure out how to do that on my own terms. That’s the ticket to success.

I know I am not the only one who’s spent far too long chasing titles and a linear career path only to find that it mostly, but not quite, fits. That is, after all, the plight of the generalist.

Next week, I’ll be sharing more about that plight with a wider aperture. If that is you and you have something to share — a feeling, advice for others, a question you’re wrestling with, or advice you need — I’d love to hear it below, and perhaps share it in next week’s issue of All of the Above.

1

I’ve written a lot about my feelings and experiences with layoffs — I’ve been laid off three times, my husband twice, and now we’re both self-employed. If you want more on that, the linked collection is for you.

Welcome to All of the Above, a place where Generalists, Jacks-of-all-trades (not to mention Jills and Jaxes), and the wearers of many hats are finally at home. I’ve found I have a lot to say about career, purpose, and how people like us can fit into a corporate world that so desires to box us in. All of the Above is my attempt at making sense of all of that.

I’ve had this idea for awhile, but haven’t quite known how to start it. Should it be a new newsletter, or just a section? A new newsletter may make sense one day, but for now, I’ve decided to stick with this being a section under my current brand. As this grows, that may change! But for now, this is the way I can give this a go without overthinking it too much (and if you know me, you know I already have the newsletter created…)

Do I need a new logo? I decided I did, and I created this placeholder myself in Canva, which I am stating in case anyone reading this is familiar with my husband’s work and thinks “did he create that monstrosity?”. He didn’t — this is all me, but if this takes off I’ll enlist his help soon enough. Visual arts are not my strength, but I am allowed to do things I am bad at, an idea that I am trying to embrace more and more since it came up in podcast interview with .

I have a lot to say about career, but also don’t want it to take over what I’m doing on This Might Be Cringe. So, I’m carving out a section of that space (for now) called All of the Above. I know there are other Generalists and ‘All of the Above-ers’ out there – so this one is for you.

I originally titled this essay The Plight of the Generalist, but as I wrote this evolved into me reckoning with why I’m even starting a new project now and how it fits into my career history and evolution. Yes, it’s an introduction post. The seemingly throw-away ‘welcome to this new thing!’ essay. But it felt important to write (and don’t worry — The Plight of the Generalist is coming).

Two months ago, I gave two-weeks’ notice at a job I’d only been at for six months. Since I left, I’ve been exploring a self-employed path for myself. I’ve talked about why I quit at length here, but I’ll walk through the situation I found myself in and where I went from there at a high level here.

I’ve been laid off three times since 2022, and since then I feel like I’ve been treading water from one role to the other, trying to grow a career in a niche I put a target on, and then fell into. During my last layoff, I started to explore what being self-employed would look like, and things were unfolding. I snagged a three-month contract in a Product Management role, and really started to see how I could make a career in this space. I found I enjoyed having a set amount of time to go in, figure out a set of problems, and know I’d leave at the end of a set period, having left things better than before.

Six weeks in, my manager asked if I wanted to extend my contract. And instead of just saying yes, I asked about whether or not a full-time role at the company was possible. If I am being honest, that question came from fear I didn’t know I had until I blurted it out. I negotiated a title I’d been working towards, a salary that felt comfortable, and I was converted to full-time. All along, there was a tiny nagging voice telling me to stop this process. To extend my contract, to keep working, to figure it out later.

But my ego kept seeing the LinkedIn layoff posts, the large companies getting rid of employees en masse, and I thought I was doing the right thing for me (and my family).

Unfortunately, that nagging voice wouldn’t shut up. As soon as I converted to full-time, I felt a visceral shift within me. I started to see the work differently. I felt less ownership of my time and my energy — even if the work didn’t change all that much, my psyche knew I was working for someone else now. I tried to push through, but I felt extremely un-aligned from what I knew I wanted and it took a deep toll on me. It’s so hard to articulate what was so difficult now that I am on the other side of it, but ultimately, I think straying so far from my surface made a lot of ‘little’ things difficult for me to manage. Staying in that role accelerated my burnout and zapped my energy in a way that was, frankly, a bit terrifying.

Build your freelance offer on the side, and figure it out while you still have a paycheck, the conventional wisdom reads. And that is wisdom — if I were giving anyone advice, this is what I would say too.

But wisdom is not black and white, and unfortunately often doesn’t understand the nuance and gray areas of our situations. The energy I was giving to my job felt like it was triple the energy I’d given to any other — even though the work wasn’t that different, I got to work from home, and on paper it was a dream! I was in the thick of the worst periods of seasonal depression I’ve experienced (which I can only now see in hindsight) while training for a half marathon, parenting a toddler, and attempting (and honestly, failing) to keep up with all that it takes for adults to keep their homes running smoothly (I’m talking to you, laundry). This created a perfect breeding ground for burnout to infiltrate my life, and made it so that I had no energy at the end of the day to even think about what my next steps could be.

To use the analogy so eloquently shared in our recent podcast interview: I was on a treadmill that was not stopping, and I knew sooner or later I’d have to make the choice whether or not I would fall off or step off gracefully. So, I took some time to get my bare-minimum finances in order, put in my notice, and opened a door without having any clue where it leads.

I am stepping out into a fog, only able to see one step in front of me at a time, but trusting that following the inspiration I feel will open up the world of possibilities.

I’ve been in tech and startups for TEN YEARS (fourteen years if I am allowed to count my experience in Apple Retail), and while I’ve sat on many different teams and have in fact worn those many different hats I’ve spoken about, I find it really hard to articulate that experience. But surely, there’s something there that someone wants, right? I threw together a basic offering on my website that I know needs work. Right now, I’m trying to sell people on the fact that I can do it all, while everyone is begging for me to pick a niche.

I don’t want to pick a niche and I want to do it all, but I also know I need to really spend some time thinking about that and figuring out what that positioning looks like. My hope is that this space can help me (and hopefully you) get closer to what that is.

I am pretty clear on the fact that I do not want to just be a product manager anymore — in my five years in product, I’ve picked up a lot of other skills that are useful, and have found things I enjoy more than some of the more traditional PM work. I’ve been sitting on an essay draft called I Never Want to Be a Product Manager Again since August, that I quickly put on the backburner when I did in fact become a Product Manager again. I’m excited to revisit that here, too.

There’s also an essay I could write where I walk through each step of my career, how it all seemed to unfold without a plan in front of me, and how that led me to where I am today. In fact, this essay started to take that shape, but what I think is important to communicate now is this: in fourteen years, I went from working at Apple Retail to becoming a Senior Product Manager in a very non-linear career path. I refuse to believe that the work I did before stepping into product is irrelevant, and I know there’s a way to leverage it.

In between that time, I slowly figured out what I was good at, what I enjoyed, and the fact that those aren’t always the same. I managed teams, supported users, and implemented new systems. The word ‘operations’ was thrown onto a few titles I had, to capture the fact that I did the things that didn’t fall neatly under other disciplines. I’ve done a lot, worn those hats, and carry that experience with me in everything I do today.

I’ve also learned that employers and companies love having the person who can do it all on their team, but when hiring need to box people in. I became skilled in interviews at connecting the work I did to the slightly different work the next role would require of me, and between doing that well and coming off as ‘likable’ in interviews (their words, not mine, I promise!), I was able to forge a career path in a non-traditional way, that often doesn’t make sense until you look at it in hindsight.

And once I’m hired in my boxed-in role, I become the person who can do all of the above. And because I know that it’s possible, I’m on a mission to figure out how to convince companies they need a fixer, a generalist, an ‘All of the Above-er’ to [insert job here].

Can I do everything? No. I’m not saying I want to do it all, but I want to do more than a box would traditionally allow. And I know there are other people out there who do too. Maybe, even, that’s you.

And if that’s you too, welcome to All of the Above. I’m excited to dig in, to figure out what ‘career’ even means, and to do it alongside all of you.

All of the Above is for you if:

• You’re finding yourself standing in a fog and not sure where everything you’ve done up until this point will lead.

• You’re letting the path unfold as you walk it.

• You’ve answered the questions “what do you do” (or “what do you want to do”) with a series of words and sentences that don’t feel like they make sense together.

• You wish job applications came with an ‘All of the Above (and more)’ checkbox.

• You’ve been laid off or have found yourself in a similar career pause and want to use that as a forcing function to figure out what’s next.

• You know you’re more than a job title, career path, or corporate box but don’t know how to articulate that yet.

• You’d rather pull all your hair out than ‘pick a niche’, and you believe deep down you shouldn’t have to.

• You’re figuring out how to sell ‘I do it all’ without sounding unfocused, unambitious, or confused.

• You feel like you’re alone in a world where everyone around you seems to fit so nicely into their boxes and niches.

Thanks for reading — I am excited to see where this goes, and looking forward to connecting with others who relate to being ‘All of the Above-ers’. Your ‘All of the Above’ might look different than mine. Maybe you’re a designer who’s been looped into research and go-to-market conversations, or a Chief of Staff who somehow started running analytics and product marketing for a company, or the social media manager who also writes internal communications briefs for the company (and holds the keys to all the PR contacts).

If you have a story to share, I’d love to hear it. You found this for a reason, and hopefully made it this far because this resonates.

Welcome to your new community.

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