I Know Myself Pretty Well, But...

What a bunch of personality tests tried to tell me (and what happened when I saw the writing on the wall)

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.

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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 Seth Werkheiser).

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.

Why I Can't *Just* Be a Product Manager 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.