How I think about retrospectives

I believe in self-improving systems, and retrospectives are a core way of reflecting and then changing behavior accordingly. There’s a lot out there on what a retrospective is, formats to use, and other techniques, so I’ll just highlight my facilitation thoughts on them here. This is influenced by the CAST handbook and my own facilitation background.

Must be blame-free / a psychologically safe space

People will not open up and be actually present and interrogative if they don’t feel safe. It is your responsibility when setting up, facilitating, and debriefing to make sure the system is what is being critiqued, not the humans within it. The humans made the best possible choice they could given the circumstances they were in, so let’s change the circumstances in the future. Make this explicit early and often. As Charity says on the sticker on my megaphone, “communicate positive intent.”

A picture of a megaphone focused on a sticker in Lisa Frank obnoxiously bright styling, "communicate positive intent." Additional stickers that are visible are the Priceless Baroot, the edge of a pleading taco emoji, and one that seems to ready "...necessarily a crime."

Must be scoped well

If people don’t know what they’re talking about, they won’t talk about the same thing, and getting to concrete outcomes will become nearly impossible. Focus on a specific project, timeline, or outcome. Communicate this early and often.

Should encourage creative thinking

Whatever format you pick should be mildly novel (not so novel that it disrupts how people approach things, but novel enough to edge them out of their comfort zone). Use a different prompt set or a different tool, but rarely both at the same time. Ask more of people to engage and challenge them into someplace new.

Needs to lead to concrete, actionable tweaks

If you don’t arrive at experiments that will change how you’re behaving, you have wasted everyone’s time. I like to set aside about 1/4 of the time of the retro to listing, refining, and then selecting one or two these experiments. I ask the following questions:

  • What will change if we take this action?
  • What would prevent us from making the change?
  • How will we know if we’re successful or not?
  • When should we check back?
  • What is our next step, and who is responsible for it?

I only pick up 1-3 concrete steps to take after each retro. I track them just like any project, and I report back on them before the next retro to show that the time and vulnerability is worth it.

One goal should be building trust with the team

A core part of the system is team trust, and in improving the system, we should be focused on building that part of it. By being blame free, enacting suggestions, and pushing people to engage more, we build that trust. If something about the retro process is eroding trust, pause and reassess your approach.

Historical income

So I found some of my old tax documents and figured I’d map what the income trajectory has been like for me since I started working at 16. I often held 2-3 jobs at a time before moving into a nonprofit career, before deciding I was tired of the constant stress of paying rent and moved to the private sector.

Chart of income over time, boxed out for what was going on in life at certain points. Boiled-down summary follows in blog post.


Moving to full time work with an undergrad degree 3-4x’d my income.
Moving from jobs to a career tripled it.
Moving to the private sector doubled that again.
Leveling up to senior increased by about 50%.

November Joy : a very funny ring

When Reed and I were talking about combining our lives, he made it clear that if we were going to have a kid, he wanted to get married. I wanted to have some complex legal arrangement we could welcome more people into over time as equals if it made sense, but he said that was Too Much and could we please just do this one thing normally. Fine.

We got married back in 2019, and I started off with a family heirloom ring his grandfather had. Which I lost about 4 months later because I was climbing all the time and taking rings on and off (mostly off). Whoops and yikes. Reed bought me a simple gold band from Costco and told me I could lose as many of those as I wanted, within reason.

It’s been about 6 years since then, and I’ve kept track of the same ring the whole time. I think I’m ready for a Big Boy ring again! But this time, I want it to fit my aesthetic more closely. I also wanted to celebrate getting a new job, and this seemed like a nice way to do that.

So Reed starts Doing His Research Thing, and finds that there is indeed an entire market dedicated to simple black or grey rings with blue highlights. Do you want to guess where these bad boys come from?

A dark grey ring with a cobalt blue inside that very slightly shows around the edge.
Not the ring I ended up with, but similar

They’re masculine rings for cop spouses. They’re thin blue line rings. So now I’m very joyfully wearing this thing that is blatantly flagging for absolutely the wrong thing, and I am delighted that if I ever get booked for my activism I might cause a lot of extra confusion. And, it’s spot on for my style!

But then, I didn’t want to give a cop ring website money, so Reed kept doing research and found enough water marks on enough photos like the one above to figure out all of these come from one manufacturer in China. So it also only cost like $40! So now I get to have backups, too.

Token Aikido

A couple weeks ago, a neighbor reached out to me to ask me if I’d like to be visible for the city. Our little suburban home resides in a sanctuary city, for which I am endlessly grateful and also wish had significantly more teeth. For Trans Day of Remembrance, the mayor wanted to recognize a local trans person. I’m from the midwest, and have often been seen as the only trans person in a social group, on a team, and sometimes even at a whole organization (until, of course, people see me and start feeling confident enough to come out themselves). So sure, if you are willing to give me the mic for 2 minutes, I’m happy to do The Thing.

Willow speaks about trans visibility to their city’s City Council. Transcript follows in blog post.

Here’s roughly what I said:

Hello, and thank you so much for this step in standing with trans people. I’m honored to have become a San Leandran 5 years ago, to raise my 4 year old here with my spouse, and I look forward to (hopefully) spending the rest of our years here. I am agender and queer, and use they/them pronouns.

The few trans friends I have made in San Leandro are moving away, because standing with us in a safe room is not the same as standing with us in the streets. Standing with us in the streets also means standing with the other scapegoats of this authoritarian regime, our immigrant neighbors. Some immigrants are trans folks who escaped countries unsafe for them only to find this country becoming the same. We believe this unaccountable ICE presence rounding up our immigrant neighbors could come for others next. 

When the country doesn’t have our backs, our state must. Disappointingly, Gavin Newsom is throwing us under the bus. When our state doesn’t have our backs, our city must. I’m must report that our city refuses to stand against ICE when they actually show up, leaving our militarized police force only militarized against its own citizens and not against a reckless federal takeover in our neighborhoods. 

So what can you do? Look at ways to demilitarize our police force— especially if they are not willing to stand with us to protect our neighbors. Stop storing sensitive data about us via things like Flock cameras that can be hacked or forced to be shared with a reckless federal force rounding up long-term residents, regardless of if they have us citizenship, kids, or are strengthening our community. Consider hiring a sanctuary consultant to figure out how to live up to our sanctuary policy with real action, not just this talk – although the talk does mean something. 

I know these are medium-term actions, so here is something you can do tonight, when you get home, to promote solidarity with your trans neighbors: start using your pronouns consistently in public emails and writing. Add them to your email signature lines. Tomorrow, add them to the city website. 

A reckless force has come to our city. Soon, they could be knocking on my own family’s door. With this limited official support, I continue to build solidarity with my neighbors. My neighbors have my back as I have theirs. Neighbors, please check on each other. I believe we will get through this and build something more beautiful together. United we will. Thank you.

The back of my vest reads "Less Gender. More Throttle." And "Queers Never Die" around a skull. My button reads "fix shit up." The suit pants, vest, and shirt are bespoke from Crown Tailor, the shoes custom from Al's Attire, the tie I forget. I am also wearing secret purple suspenders from Dashing Tweeds. The fade is from a local barber shop, the dye I did myself.

I worked on this for nearly a week and a half, getting feedback from neighbors who know more about our local politics, about local concerns, and about speech writing. I am forever grateful to them for helping shape this into something that calls for responsibility without setting everything on fire (like the first draft). Thank you also to my sweetie Mark for capturing the photos and neighbor Whitney for capturing the video. The official video, including comments I made later in the session, will soon be available on Video Central.

Empathy without Responsibility

At the end of each year, I pick a word or phrase to guide the following year. Sometimes it’s really impactful, and other times I barely remember it, and sometimes I even miss the mark. Last year’s was one I was particularly nervous about.

My phrase for 2025 will be something I’ve already begun working on – empathy without responsibility. I was exhausting myself by always wondering if I was focused on the right thing, always doing triage on what might be a better use of my time. Instead, I’m going to focus on what is in front of me and what I have some influence over. I can send money to Translifeline and if a trans kid from Florida shows up on my porch I can house them. But I cannot drop everything in my life to move to Florida to fight the good fight. What I am already doing matters, and I should focus on it.

This is something I had even begun thinking about months before the end of 2024, and realized I needed to pin my year to it. One of the conversations I have had with Reed is about how having a drink helps me give myself permission to disengage from the world. “I am now off duty” I am broadcasting by imbibing. And as someone who is nearly always “on,” that is a useful tool. However, learning to turn down if not off is a skill worth acquiring, and so I set out for the year.

I’m working two approaches: classifying and trusting.

For classifying, I’m determining if something is actually classed into a category that I do have responsibility for. Ends up this is a much smaller set than I initially felt it was. I’m still responsible for a lot — my role in the household, being a parent to my child, an organizer for my neighborhood, the steward of some extra cash to give to others, etc. I am NOT the responsible party for getting an unhoused neighbor on their feet, but I AM responsible for being kind to them and being sure they know about nearby resources and maybe helping them get to those resources. I can also be responsible for making sure that nearby resource knows I have their back, volunteering occasionally, and donating when I have extra. I am not responsible for how Locke does in the classroom, but I am responsible for guiding his behavior when he is at home, and making it clear to the school that I have their back while also having his. Etc.

The smallest circle is the lightest in color, and reads "circle of control" with a pointer that continues "what we can directly control or impact through our thoughts, words, and actions."
The next circle, which encompasses the smallest circle entirely, is slightly darker and reads "circle of influence" with a pointer that continues "The concerns we can do something about. We do not have control over the outcome, but can influence it with what we are able to control."
The final, darkest circle encompasses the other circles and reads "Circle of concern." with a pointer that continues "Wide range of concerns of which we have no control over the outcome."
Screenshot

For trusting, that means I am also trusting the other people in my network and neighborhood to do what they are responsible for. I stay out of their way except for when I have something to offer that might help. I build unlikely friendships with people who have very little practical overlap with me but with whom I am ideologically aligned. I deepen friendships with people similar to me but doing their things further afield so we can align with and learn from each other.

But! I am still looking for tools to deepen this practice. A very dear, very long-time friend of mine is also an exceptional facilitator and is doing a free session on just this thing on Tuesday, November 25th from 9:30a-12 PT. You could come learn with me if you struggle with similar things. It would be great to see your faces there.

They didn’t know we were seeds

Nearly everything I do is for the Collective. I am pre-disposed to it. I was raised to it. And after a lifetime of reflection, I remain committed to it. “They tried to bury us. They didn’t know we were seeds.”

This is part of a series on my Santa Perpetua tattoos. You can read the rest in the tattoo category on this blog.

Willow lays on their side on some blue carpet. Their right forearm has tattoos made of black ink spatter with blue seedlings sprouting and interconnected people.

This one I simply feel in my bones. It’s on my right forearm because I am right handed, and this sentiment fuels my interactions with the world. No further pontification.

I’m so grateful to Santa for making it beautiful. She melted some transfer paper in water, splattered me with the water, and then meticulously tattooed each spatter mark.

Ok so maybe I do have ADHD

When I had some cognitive space back in 2022, I ran through some diagnoses intakes with my psychiatrist. We decided not to review for autism because the test is time consuming and there isn’t really anything you can do with the results. For the OCD intake I was like “of course I do these things, any rational person behaves this way,” (no, they do not). For the ADHD intake I was like “I do not have trouble activating to do things or focusing on them once I’m doing them, so this isn’t me; EXCEPT for when I’m on my period, in which case absolutely yes.”

Then I went on testosterone and things got a little more gnarly. If you do a search for this, you’ll see that hormones (estrogen in particular) and ADHD have some interesting correlations that may in fact be causation. Some tendencies I’d always had got more extreme.

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The job hunt

So I’ve just signed to start in mid-December as the manager of the AppSec team at a well-known platform. I’m REALLY excited for this for many reasons I’ll get into after I’ve actually started and it feels real. I’m really excited to be able to talk about this part of my life again.

I’ll do a separate post about how I structured my consulting because that’s it own fun setup, but I wanted to take a moment here to talk about how grueling the job hunt is right now and to offer some scaffolding, because being intentional about things is how I stay sane when in a chaotic situation.

This is long because I have a lot to say on keeping track, experiments in approach, and what actually worked this time.

Resources mentioned in here:

  1. Job hunt tracking spreadsheet
  2. Sankey HTML file and associated page/image
  3. Financial burn-down spreadsheet
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October Joy : Forecasting

I’m going to do something incredibly indulgent for this blog post and tell you about something nerdy that has been bringing me a lot of joy.

As y’all know, I’ve been looking for work. In the meantime, I’ve been contracting on three main fronts:

  1. Security hardening, including implementation work (know what needs doing but don’t have capacity to get it done? I will get it over the finish line)
  2. Tool implementation and training (think a tool would help your business but not sure how to set it up? I will get it set up based on your specifications and then train you)
  3. Organizational theory and scaling guidance (nerd out about which practices make sense, when)

So far, I’ve helped a network org transfer fully out of the Google ecosystem to Proton, Tresorit, and AirTable. I’ve gotten a technophobic ED of a different org onto a password manager, ending an existential threat to the funding organization. I’ve helped a lawyer automate a lot of her data entry with Clio so she can focus on clients. I’ve nerded out with the ED of another nonprofit about how to scale his organization as he moves from his most recent successful phase into 10x growth of participation. Next up I’m helping implement a retention & deletion policy for two different orgs. Plus a bunch of other stuff! Fun!

But how am I doing, financially, with all these moving pieces? I created two pieces to help me track things: a projection of contracting load, and a projection of overall expenses and financial sources.

  • For the contracting load, I used AirTable because of how much cross referencing and automation it allowed me to do. This is where I keep track of clients, contracts, expenses, and income. It even has how I’m doing against goals, and has projections for income out into the future. It’s fabulous and I’ll show a templatized version to you if you ask.
  • for the overall financial health, I used Google Sheets because I want to use formulas in some cells until I adjust them for actuals. I estimated monthly spend based on known shared account contributions and historical numbers for each month based on how I tend to live life. I then listed out sources of money — unemployment when I don’t have contract work, contract work, savings of various sorts. I then anticipate burndown rate on each source of money based on projected expenses, and when I’ll start pulling from a different source as needed.

These were SO MUCH FUN to build, AND it gives me a sense of predictability and stability in uncertain times. I now have more confidence that I can keep myself and my family afloat, and have more ease in having a good time on occasion because I know where I’m at with the numbers.

Experiments in being anticapitalist

Priceless was founded as an anticapitalist event. I’m not sure how it worked for the original False Profit crew, but for our Priceless Planners crew, and ongoing discussion has been about wealth disparity within the Planner community. The vibe has been that while we question capitalism, many of us are also doing well enough under capitalism that it’s primarily a theoretical discussion with well thought out experiments in how to HOST an event for others that’s anticapitalist. We set out to change that last year by taking on a radical experiment of moving from volunteer-only organizing (we do pay our food vendor, medical staff, and security staff; along with paying artists and musicians to help us host our event) to paying a couple roles. This is how that went, and what comes next.

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