The secret life of a Generalist: from square peg to happy camper
We dive into: The 4 Archetypes of a Generalist, a framework for squiggly career progression, I'll then spin these into real-world examples of what a *delightful* generalist career flow could look like
And then... a pinch of spice 🌶️ I'll be busting the myth that generalists can't reach mastery
Confession: when someone asked me “so what did you do?” I’d cringe. Worse still, I’d often get actually anxious at the thought of having to stumble my way through “well, ya know, lots of things…” or “I’m an all-rounder” or “you know that saying jack of all trades? Well that’s kind of me but in modern-day form”.
I’d be met with a raised eyebrow. Blank stare. An unsure nod and awkward smile.
But why? Because we generalists don’t fit into neat, tidy boxes that society prefers. It’s not until you realize that your generalist nature is a feature — not a bug, that you can really fly 🦋
I remember so clearly wishing I could have a one-word answer. What do I do? Easy! I’m a marketer. I’m a developer. I’m a writer. The dream! 😻
But that’s because I didn’t know anyone else like me. At the time, my contracted title was the Director of Misc (true story!) and I felt like a big, ol’, lonely square peg in a round hole.
I wish I’d come across this article back then. Maybe it’s the sign and validation you’ve been looking for. If it is — please do let us know by sharing your 2c on your social media platform of choice (tag: @millytamati).
Without further ado, Katie is back with an epic dive into:
🏕️ 🤫 The secret life of a Generalist: from square peg to happy camper
When I ask Generalists how they knew they were a Generalist, I often hear a version of the same story.
Because there is no test in school that sorts people into Generalists and Specialists, this realization typically happens mid-career.
People go through their work journey without the language to describe their experiences.
Instead, they have a tug-of-war between feeling and acting differently, and also trying to be the same as the people around them so they can ‘succeed’.
Eventually, they have a lightbulb moment and realize there is a whole group of people that are different in the same way they are: The Generalists.
We’ll follow Jane Generalist through the typical stages of uncovering her true identity.
Stage: I noticed I was different.
We start here.
Jane Generalist goes about her schooling and career. She follows standard practices. Along the way, she notices that some things about her are different.
She changes jobs more frequently than her peers. Her career is taking jumps instead of heading up a ladder. She doesn’t feel compelled to develop deep expertise in a single area.
At first, she thinks this is just her (especially if she doesn’t have mentors or advisors who understand what is going on). She assumes everyone else is wired a certain way and she is the odd person out.
When Jane tries to raise her concerns or describe her experience, it falls on deaf ears or she gets a blank stare back from her manager.
From there, she makes a logical leap to ‘there must be something wrong’. So she keeps quiet and internalizes this as a ‘Jane problem’.
Stage: I tried to follow the standard path
Because Jane thinks there is something wrong with her way of thinking and working, she tries to assimilate.
She asks her mentors and managers for advice and adheres to the best practices for establishing her career and earning promotions.
She takes the recommended courses, gets certifications, and jumps at stretch opportunities.
Jane takes steps to make sure her work looks and feels like the company’s standard. She doesn’t want to come across as a square peg in a round hole.
Stage: The tendencies keep coming back
This approach works for a while.
But when it comes time for evaluations, Jane keeps hearing the message that her unique talents aren’t valued, and there are gaps between her and her peers in their specialized skillsets.
The feedback is hard to reconcile against her own learning goals and development objectives.
At the same time, Jane gets bored and wants to expand her skills in ways that don’t align with her current role.
She decides to do things her way - promotion be damned - and deviates from the standard path. She takes unrelated roles. She jumps industries. She tackles problems outside her usual scope. She builds her breadth of experience.
Stage: I accepted I was unique and figured out what that meant
Once she stops trying to work like everyone else, Jane’s ability to creatively solve seemingly impossible problems flourishes.
Jane recognizes something critical.
She sees that she can jump into any role and do a pretty good job. She can learn quickly and establish relationships that help her find answers (even if she isn’t the expert). Her track record of successful projects offers proof that maybe her way isn’t so wrong after all.
She still struggles with how to describe this ‘secret sauce’, especially in job interviews or when someone wants a 90-second summary of her career, but she knows that she has a special skillset.
Jane feels increasingly comfortable in the patterns that work for her: moving into new domains, solving problems by seeing connections that others don’t, and investing in relationships.
Certain roles become more attractive - product manager, operations manager, Chief of Staff. She seeks out opportunities where she can make a big impact AND keep learning.
Stage: I first saw the definition of Generalist
Then, Jane hears the definition of Generalist and a lightbulb goes off.
“Generalists are expert learners, versatile problem solvers, and big-picture thinkers who can effectively apply these strengths across varied fields and roles. They are skilled at spotting relevant patterns in complexity and are often empathetic and future-focused.” (From Erica Warp)
She sees that it isn’t just her. And realizes that what happened early in her career wasn’t a ‘Jane problem’. It was actually her Generalist mindset shining through!
Jane finally has the words to describe what makes her such an effective operator.
Stage: I found my community and learned how to leverage my skillset
Finding the language is the first step in discovering the community. Jane soon stumbles on the whole group of Generalists hiding in plain sight!
As she gets to know them, she is struck by how they are so different thanks to their broad interests, yet so similar in other ways.
She feels seen and understood by her peers for the first time.
She sees how her Generalist skillset is a massive strength, not a weakness.
She meets other people facing similar challenges and has a safe place to ask for support.
She is a happy (Generalist) camper 👏 💃
👋 If this saga sounds familiar, you just might be a Generalist! Welcome :)