A book by its cover
Charity's philosophy on coaching should not be judged by its appearance
“As long as there aren’t any action items for me” she giggled, was the condition she agreed to, and later I found out that meant a lot more than just for this interview. She said she was tired due to work, but was willing to spend an hour with me, and it turns out she had a lot to say. Charity’s opinions are strong, even with depleted energy.
While she might be controversial to the industry, she is certainly not conflicted in her view. Lots of things Charity brings to the tech twitter-sphere would appear to be contradictions to long understood norms. But when you really listen, and take in the underlying intention, you learn there is a deep empathy that her positions come from. A place of equity, inclusion, and kindness. And if those are contrarian positions, that should be fixed. She’s a rebel for good, and a clear thinker on many topics that are usually very complex.
Books and music
The room she was in looked really interesting. The kind of room that would draw you immediately to the bookshelves to gaze at what must be hundreds of books. Floor to ceiling. Mostly non-fiction, because as she later tells me fiction isn’t for her. She looked just as she does in almost all the conference videos I’ve seen of her and it’s very apparent that her appearance reflects her personality. The hair color and tattoos, just like her blog https://charity.wtf are bright, joyful, and direct.
Charity lives in San Fransisco but would love to live in New York City for a few years. She also says “I’m not a New Yorker though”. There is a certain set of attitudes or mentality that she doesn’t feel she has, but she wants to be there for some time. And someday Switzerland or the Netherlands.
Raised on a rural farm, the oldest of six, she went to college at an early age for piano. Her path to the software industry wasn’t planned. In fact as she puts it “I saw there were no women in the college computer lab, so I went in”. It’s not clear that even then, she knew most of her life in software would follow a similar line of thinking.
Growing up she had just books and music. A complete loner is how she describes herself. The loner aspect came up again later on, but for different reasons. What stands out is she is unique, and doesn’t understand the idea of patterning yourself after others.
I asked if she still plays piano and she said “not really, it’s mostly utilitarian.” But she also said she had recently bought a keyboard as she gestured to the room behind her. It seemed to me there was more, so I asked if she used music to inspire her. As I would come to expect her response was unexpected. Music is a tool now.
“Pet Shop Boys and New Order means it’s time to sit down to pay the bills”.
There is a way she describes music as sort of a mechanism to do something else, and I wondered if going to college to play piano, only to end up a leader in the software industry was any early indication of this.
The books in the back of the room continued to get my attention so I asked if she used books to guide her work or if her work drew her to books. “There’s too much emotion in fiction, and managing and working with people makes that a lot” she said, as she described the books as mostly non-fiction.
She doesn’t believe in inspiration. It was a refrain for the hour that we spent together. I found it really interesting and tried a few times to poke at the idea, but every time she met me with pure and clean self-determinism. It’s unsurprising I guess, and the more we talked the easier it was for me to understand. It’s something I think many people might say about Charity: she has a way about her responses that are quick, pointed, extremely logical, and yet are just surprising enough that it takes some time to really digest.
“I’m cynical in the most cheerful way”, she says for example. It sounded like a way to self-deprecate but it also was very clear that most of her motivation comes from cynicism and the problems at hand. She was very clear that she is spite driven. But not bitter spite, as she puts it, rather the kind that is fuel for the work. She used the word spite, and in the moment I understood her. But on reflection I wondered if that word isn’t what she means. She isn’t interested in hurting or annoying people. Instead she’s interested in being driven by things of her choosing, and that are important to her. The word that came out was “spite”, but I now hear the word empowered. I’m not correcting the word she used, I’m saying she taught me that motivation can come in many shapes for each of us. One way is not superior to another.
It became increasingly more clear that Charity wants to have hard conversations. Not in order to be contrarian or confrontational. Rather it’s because she feels they’re necessary. She said she wasn’t raised in a family that had them, and that seemed to motivate what she was saying. Be direct. But also be fair and kind. Kindness comes up quite a bit when talking to her.
At the end of the conversation I asked if she was a pen or pencil person. She’s a pen person and doesn’t believe in erasing. Just use a different color and scribble over it. Lots of markers everywhere. She said she liked Japanese gel pens. It was a quick response and it was my impression that matches with how she operates in her day-to-day. I don’t take her as someone who’s precious about work. There’s things to do, let’s do them. Keep moving. Erasing just takes away time.
Growing up in a pretty conservative background, she enjoyed being the “token Republican in the Bay Area for a while” as she put it, and again this sounded like the loner description. But now she finds herself to be leftist. Don’t be fooled however. She’s not a joiner, but does respect institutions. It’s just that there are complexities that she understands about them, and coupled with her loner tendency, she appreciates them as much as she believes they should be challenged. “I’m a member of the resistance”, she added. The topic of power came up and she doesn’t want to debate power’s history of successes or abuses, instead she believes the right question is “what should you do with power?” There is a deep pragmatism about this question, and it seems to reflect her bias for action.
Another interesting description of power came up when I asked near the end of the interview: “if you could call someone right now from any time in the past, who would you call and what would you say?”. She was clear that the phone call would be a significant opportunity. She would want to give information to change history. To pick a pivotal point in time and give someone the information they would need to directly impact history. Do it for good, and to correct the bad history. Very utilitarian.
I asked about social media in a fumbling indirect way, hoping to hear her opinion on how it has changed power and societal norms today. She said she’s happy that it has propelled social justice, but also asked “Where do we go?” That question was more important to her. She is fiercely private and admitted that she didn’t always do social media well. Even at Linden Lab and Facebook, she only created her accounts at the last moment, and due to necessity.
“I always knew I didn’t want to be poor.”
She says “I always knew I didn’t want to be poor.” This seemed like a typical mentality to have for someone in tech, but I sensed this had more to do with power than money. She has a complicated position on power and it comes out when talking about capitalism. Her description of the tech industry was balanced between “we have a lot of privilege and money so we should do something positive with that”, and not every one gets the same benefits and that should be addressed too. As capitalism came up, she repeated the sentiment about wanting to make money. But she was pretty clear: “I want enough”.
Expectations will turn her off
This was an interesting note I made about our conversation. She explained to me that she appreciates the book “The Four Tendencies” by Gretchen Rubin and that she was a Rebel tendency. I hadn’t heard of the book, but as she described it, and herself, I started to become intrigued. Charity described herself by saying “If you tell me I have to do it, I won’t. If you tell me I can’t do it, I will”. On the face of it, those are complicated positions to hold, but perfectly match her rebellious spirit.
This was unsurprising given all of the punk description she had given herself earlier. And as I’ve come to learn from the book, the Rebel tendency isn’t pejorative. In fact it’s quite a strong position, that supports self-preservation with self-driven bias for action. I could sense in the moment that Charity was expressing her innate authenticity and that the Rebel tendency gave justification for that. I took the online quiz, and it turns out I too am Rebel tendency.
Coaching is not for Charity
Charity would never take coaching and doesn’t seem to think she’s good at giving it. Uh oh. This was clearly an example of having a hard conversation given that my biggest goal for this interview was to discuss coaching! Instead of coaching, she’s “spite driven” she said. Not bitterly, but rather “fresh and clean” spite has fueled her in her career. As she described her journey in tech, she was adamant that each step was either in the direction of rebellion or in the direction of proving to others that in fact it was possible.
She has what she called a “coach”, but she described this relationship as a way to not put that burden on her co-workers. I considered this to be very thoughtful and responsible. It was the kind of thing someone might say to respect the idea that we all need help, and that it is our responsibility and not others’.
It’s not a faux strength she puts on about not needing coaching. You realize quickly you’re talking to someone who has opinions and is honest about them, and has very little concern for your perceptions of her. Sorta. She cares. But it’s not what drives her, rather it’s her rebel tendency. It’s her internal fortitude that moves her and as she says “I’m motivated by what needs to be done”.
You shouldn’t necessarily pattern yourself after others, because it’s critical to maintain your authenticity was the point she made. So while she said “those who can do and those who can’t teach” as a demeaning way to describe coaching, the way I interpret that from her is that it’s important to heed advice, and it’s critical to learn, but it does not mean that you have to be a supplicant, a word she used to describe how she felt about being a mentee. And in a very terse way to remove any confusion, she said “I’m not a supplicant”.
Some of the best advice I’ve heard
The thing that I couldn’t get over in the time we spoke, is how Charity says she doesn’t believe in coaching, but if you were to read her blog you would be confused to read all the coaching she does. In nearly every post she has written I read a coaching narrative. And I guess it’s all semantics because if you just scan for the word “advice” in her posts - you’ll find it everywhere. And I would advise you to pay good attention. It’s high-quality and very pragmatic, while being just surprising enough to keep you on your toes.
My favorite topic that Charity covers is the idea that there is a bi-directional path for people to take regarding their careers. You can go from management back to individual contributor as an example, and for some of us we should. Her own experience with this is a powerful demonstration, and her thoughts on the topic are extremely useful.
This kind of thinking is pretty unique. The word rebel comes to mind again. How liberating it is to recognize that you can and should give management a try, but don’t lock yourself into the false idea that in doing so you close the door to going back. And be damned sure you feel no shame or regret for having given it a try. There are no rules.
The main takeaway you should have from Charity is that authenticity is more important than finding a model or a pattern to follow. Be rebellious in your journey to find yourself. But along the way it is important to listen to others who have been there. One person’s coaching, is another person’s advice and you are unique in the world so take what you need.
Near the end of our time together, Charity said there is a “hunger and need for apprenticeship” in software. She hates the superiority of coaching but totally believes something like it needs to happen. And she emphasized “with kindness.”
I shared with her my thoughts about the need for unique and individualized coaching, and she responded “context is everything”. She added that coaching implies an authority position and sometimes that appears to have an inappropriate reward system for the coach. Mentorship creates an inferiority relationship that she doesn’t like. Her point is authority should not be a reward. But it’s perceived that way in many areas of tech. “How do we defang this?” she asked. The context in which coaching is given is really important.
She’s not interested in the answers to old questions. Charity would rather look at the context that we have now and ask better, more informed questions, about how we can improve the developer experience with coaching (or whatever word you like).
Let’s not use the old dashboards of “employee satisfaction” that give us the answers to questions we’ve already asked. We are each unique in our needs, so let’s be able to ask new questions. Let’s trace the experience of each developer uniquely through this software industry and get the best insight on how to improve their world. Thank you Charity!
This is the first in a series of profiles in software. If you enjoyed this subscribe to continue getting the series. I’ll be writing profiles of industry leaders and interesting people from all areas of tech every month.