Oof, I am struggling right now. It’s not a new struggle; it’s age-old. See, with the winding down of Optionality, there is an opportunity to decide: What do I most want to do next?

The problem is not lack of ideas or lack of things to pursue. It’s that I have so many ideas. I like so many things. And let me say this with absolutely no humility at all: I’m also good at a lot of things. What I’m not good at is packaging all these multitudes into an understandable “positioning statement.” I know I’m not the only one who stumbles here. We had a whole working group at Optionality that focused on that task.

In the past, I’ve called myself a “generalist,” and I’ve advocated for the value of generalists in a world that seems determined to make you niche-ify. I wrote about this a couple of years ago for Optionality:

Key excerpt:

Lately, I’ve been doing some work that has convinced me that it’s not really that I’m a “generalist.” I am a specialist, but at a cognitive approach to problem-solving, not on a singular topic or at a “particular set of skills.” ;)

My own brain is the oldest asset I own and yet perhaps the least examined. So, I set out to examine it, with the help of my AI tool of choice, Claude. I started out wanting to teach Claude how I wanted it to work with me. I started out giving instructions to the tool, like “Don’t give me answers, ask me questions that help me figure something out for myself.” Like, “I never need you to write for me; I need you to hold me accountable to the qualities I value in my own work.” To do that, though, the work had to get to defining not what do I do, but how do I think; how do I process; how do I create?

And in addition, when do I know I’ve nailed it? What does my own best work not just look like, but feel like? If I believe AI serves me best as a mirror, then I must articulate what I see in that mirror. 

When I pushed myself to answer the questions that arose during this process, I felt myself balk. Partly because I’m not that fond of introspection, so it felt uncomfortable, but also because I’ve been the same way for SO LONG. This is how I operated in school. This is how I operated as I shifted from career to career. It feels inherent and therefore hard to parse.

But I stuck it out in order to find the throughline that connected the dots across my varied career, my writings, and all the times I can confidently say I shone. I came away with what I’m calling a “brainscape.” And now I’m trying to take that brainscape, the unique how, and see if I can figure out the whats I want to apply it to.

One thing I’ve decided for sure out of all this effort is that I’m no longer calling (or thinking of) myself a generalist.

Instead, I am thinking back to a core #BuffyLifeLesson that has been a slide in my talk on this topic for years now, namely that We Contain Multitudes. And that’s a strength.

Buffy contains multitudes, and she is the master of her multitudes. She is committed to building a normal life in abnormal circumstances. This is her throughline, and to achieve it requires triage and ruthless prioritization on her part. It is core not just to successful outcomes for her, but to her internal sense of satisfaction and living according to her values.

From the show’s outset, she advocates to her Watcher (Giles the Librarian who starts out as quite the exasperated taskmaster) that she needs to do teen girl things…date, shop, study school not just slaying. And when her mom and her friends try to protect her, she advocates to them that she must follow her destiny, and that no, she can’t just stay out of the fight, leaving the world to fend for itself against the forces of evil.

Buffy is girly and badass. She struggles in school and is whip smart, especially great at thinking on her feet. She doesn’t make the right choice every time, but she is guided by her own multitudes, and looks to her relationships to provide her strength, not drag her down.

This week in my Buffy re-watch I hit Season 3, and this is where we’re introduced to (spoiler alert!) another Slayer: Faith. Faith comes in looking like Buffy’s shadow self. In the most obvious way possible, being an exotic brunette to Buffy’s blonde cheerleader appearance. But also, in attitude. She’s a spitfire full of bravado and oozing charm. While sometimes Buffy seems burdened by her destiny as Slayer, Faith seems to relish it…it energizes her. We sense she might enjoy it a bit too much…she’s not one for a quick stake in the heart; she likes a good dust-up first.

We learn pretty quickly that Faith too contains multitudes. Underneath her bravado, there is trauma.

Behind the way she extends fights when triumph is imminent, is the fight she lost and doesn’t want to face. As we learn more about Faith and see her in action, we see her charm keeps people at arm’s length because she doesn’t trust people to come through for her if she doesn’t keep them entertained.

Perhaps, as deep down as you can go, Faith doesn’t trust herself. It becomes her greatest weakness. She can’t stick to her story. She switches allegiances to whomever gives her momentary validation. The Buffy Life Lesson to learn from the Buffy-Faith contrast is that suppressing your multitudes gives them control over you, not the other way around.

Even if you’ve built a compartmentalized life that feels cemented at this point, it is always possible to recognize, honor, then even master and make the most of your multitudes. You don’t have to know what you want the destination to be to take the first steps. Maybe it will lead you to new personal pursuits, but it could also widen the aperture as you consider professional ones.

A simple step is to start small and simply think about your adjacencies. There was an exercise we included in the Roadmap to Restoration course we delivered at Optionality earlier this year that included a section to figure out what’s a step or two away from the space you currently find yourself in. If you take your perspective on your skill set up just one level, what is the fundamental mechanism or process that makes you good at the specific box you currently find yourself in? Who or what else would benefit from that same approach? Maybe it applies to a different industry, to a different functional area, to a different target market, or even to a cause you really care about.

If you want to take a look, the adjacencies section is about halfway down on this worksheet:

If the idea of my brainscape work above intrigues you, I’m happy to help anyone go through the same process. I can share the prompts I used, and brainstorm about how you might customize them to be most useful to you.

The question worth asking (as I did, even as it was uncomfortable to do): What are your multitudes? What is the throughline across them? And how can finding that throughline contribute to your sense of satisfaction and living according to your values?

Bonus: Here’s the four playlists, the original Madonna Chill, and the three additional lists Claude made for me. Let me know if you’d like to know how I created them.

Everything about politics feels frustrating right now, I get it. But as easy as it is to invest lots of time in critiquing the side you think may actually care about what you have to say, I’m always here to remind you to invest more time in criticizing the side you want to lose. It’s practically math 🙂 The link above is me sharing a couple of guidelines that help me:

I found an article from a Kentucky newspaper about the whole “Is Mitch McConnell dead, and can/should Governor Beshear do anything about it?” question, and it was really enlightening. I shared it (along with some of my thoughts, because you know I can’t resist) on Threads at the link above.

I watched Season 3, episodes 3 (Faith, Hope & Trick recap) and 4 (Beauty and the Beasts recap)…which aired on October 13 and 30, 1998 respectively.

The core #BuffyLifeLesson in Season 3 Episode 3 is represented by the main essay in this newsletter: The character of Faith recurs throughout this and future seasons, and she represents the internal struggle, overcoming one’s past traumas, and the question about whether it ever becomes just too late for redemption.

The core #BuffyLifeLesson in Season 2 Episode 4 is that women choose the bear over the man for a reason. It explores the range of ways toxic masculinity can affect not just women, but men. But it really does come down on the side that men can take steps to mitigate and manage and heal toxicity. Oz is the poster child for this lesson, and I wonder where on the depicted spectrum Buffy’s creator, Joss Whedon, thought of himself? Or did he see this as him being a good guy and see himself outside the lesson altogether? I’m sure we’ll never know.

I’m here every week, using pop culture (and Buffy the Vampire Slayer right now) as a jumping off point for everything I’m thinking about professional leadership, personal development, political philosophy, and pop culture. I would love you to join me by subscribing. And I would love you to share the link with other nerds like us!