What It's Like to Be the Rebel.

What a dickhead tendency

I get a lot of questions. Some of them earnest. Lots of them nosey. Most of them well intentioned. But of all the quizzical conversations that makes the introvert and privacy seeking me want to retreat to the dark corners of the internet - the most common ones all seem to dance around a same theme.


It was accidental, and much later in life, that I figured out my rebel tendency was a tuning fork, an antenna, an internal compass that I couldn’t ignore…no matter how hard I tried. Realizing most people don’t live and die by this can’t-shake-it make-up is something I am still grappling with the jealousy of.

Thanks to Gretchen Rubin’s work I am finally was able to understand it, feel semi-OK with it….and am trying to embrace it and tackle it.

Gretchen’s book and Four Tendencies framework (link to the quiz to find out what you are!) describes how people respond to expectations.

In life we all face two kinds of expectations:

  1. Outer expectations; such as meeting work deadlines or observing traffic regulations

  2. Inner expectations; such as quitting smoking or keeping a New Year’s resolution.

There are 4 different types of people in terms of how they respond to expectations:

UPHOLDER: “I do what others expect of me—and what I expect from myself.”

QUESTIONER: “I do what I think is best, according to my judgment. If it doesn’t make sense, I won’t do it.”

OBLIGER: “I do what I have to do. I don’t want to let others down, but I may let myself down.”

REBEL: “I do what I want, in my own way. If you try to make me do something—even if I try to make myself do something—I’m less likely to do it.” Welp, this person sounds like an utter fucking dick. Oh. Fuck. Wait. Am I the dick?!

Let’s say for example a Rebel wants to be a writer, so she starts writing. No biggie, right? But then all of a sudden people start saying things like “oh my god I love your work” and “I knew this was your path” and they’re sure she’s gonna have a best seller soon. Then let’s say that well-meaning friends ask if she’s got an agent and how often she plans to publish and what content buckets she’s going to focus on and what days and times are best for open rates. Suddenly there are expectations — more than just her wanting to be a writer, people expect her to do certain things or accomplish certain things. UGH.

Best case scenario for this dickhead, she’ll keep writing but resist following the conventional things expected of her like a regular content schedule, a canned approach, a thoughtful strategy. But the important thing is – she keeps writing.

Worst case for the rebel, the external praise and unexpected validations will kill her ability to write, and suddenly she’ll find her dickhead self incapable of doing something she desperately wants to do - simply because other people have expectations, and – now she does too.


Let’s say that this writer, creator, maker, banana phone ringer is also a retired brand, marketing and advertising propagandist and an expert in how to make conversions, create community, build strategies for clicks and eyeballs and all the things she now detests. What if her remorse is so incredibly strong for doing so many of these things for so many years that just knowing that people are loving this new offering makes her feel like a slippery snake oil salesman all over again?

Imagine the mix of what was simply fun and freeing very quickly transformed into something that was viable for success, monetization, a perfected formula, open to industry high praise?

Well. That rebel dickhead might feel cornered….Until she figures out the problem.


I love writing and am loving publishing this newsletter. Your emails and DM’s and voice notes are the high fives and high praise I always hoped to have from my writing. Having even just a few people read my words is an absolute gift. Having thousands, well, it’s terrifying and beyond my wildest dreams. I very quickly wanted to do right by each and every one of you. But the more I try and formulate exactly what you can EXPECT, professionalize this, the less I am able to create.

So, this is me asking you (kinda telling you), that for the greater good… are we all cool with me being all rebellious, experimental-and-shit on here?

Off the bat you know that I will be writing, waxing, and whining about tech, digital and the modern world. Topics like rebellion, curiosity, creativity all will make regular appearances. You’ll definitely hear about parenting my kid without tech and my nostalgic dinosaur fears for the new younger generations. Sprinkle in a little damn the man, down with corporations, capitalism, and attention economy. Some’ll be smart and reported. Some’ll be personal and long. Who knows. I promise I’ll always send you the links, the must reads, watches, and listens. Maybe some philosophical questions with no answers. Maybe some interviews. Maybe a burn book of brands trying to warp your minds and steal your venmo at the same time. (New trend is more stuff to make you simplify your lives….don’t fall for it. It’s still more fucking stuff just wrapped up in “oh my god it’ll make your life so simple and clean and minimal” bullshitty monochrome color products.)

Lots of songs and playlists.

But the more I don’t define it – the more I’ll write.

I know I’m a dick. Can we just accept the Rebel that I am and move onward and upward with this key fact in mind?



P.S - If you take the quiz let me know what you are! I’ll be jealous of most any other tendency. I mean, GOD, who says they’re gonna do something and does it? SO ENVIOUS.