Tag Archives: work

The job hunt

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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

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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.

The secrets we keep

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I now know that saying you work at Apple is like saying you work at the government. Which part matters a lot.

I worked in Security, Engineering, and ARchitecture (SEAR) for the last 5 years as an Engineering Project Manager (EPM). I had a key role in helping Contact Key Verification, Blastdoor, Advanced Data Protection, Forgotten Passcode, Legacy Contact, Child Safety, and some hardware improvements ship. I was doing infrastructural work to continually improve security across the keychain, certificates, cryptography, authentication, insight and detection, endpoint security, and sandboxing. I made sure we got our certifications. I helped Red Teams and fuzzing to be effective. Not all at the same time. But 2-4 releases in flight at a time, and 3-6 teams on board at a time.

A lot of what I worked on I can’t talk about. And I will continue to not talk about until they ship. That was the problem.

I thrive on talking to a wide variety of people about whatever they’re passionate about. I invest in my network, and my network loves me back. It is deep and powerful. I love getting groups of folks to discover something collectively that is new to each of them. I love making weird connections between groups to help them be better. Apple works on the pushing-a-pimple-out-of-a-circle innovation route, a choose-the-best-from-set-options route, and I work the novel-graph-connection-to-make-something-new route. And it was slowly crushing my spirit.

At first, the company was big enough that I was still able to make graph connections. But that wore out quickly as we ran into disclosures and folks not being able to talk about what they actually knew and were passionate about. I still did senior-level technical project manager work while not in my lane. I tracked projects, I mentored folks. Things shipped. But I struggled. I wasn’t happy. I didn’t have anything to talk about with my husband or son when I got home from work. Reed, at one point, pretended that I worked a miniature golf course experience production company. When I vented about a coworker (the only part of work I felt comfortable talking about with non-disclosed folks), he’d sagely nod while thinking “ah, hole 3 is really coming together.”

I tried this experiment for 3 years of trying to have non-productive hobbies. You know, cross stitch and stuff. And it just didn’t work for me. I applaud the folks who can turn off, I will fight for our rights to have time to do things that are not governed by capitalism. I read sci-fi in bed for sure, but I didn’t like trying to take up spare hours on weekends not organizing people. I’m like a Border Collie or something. And I want to talk to people about it. I want to be able to make sense of the world by connecting what I know to what other people know. It’s hilarious to me that Apple TV is what Severance is on. I get the “surprise and delight” thing, but ends up I do not like surprises or getting them.

Securing a billion people without them having to care or notice is a pretty compelling argument, so I stuck with it for 5 years. I worked with many incredible, driven people. But for me, the same reason I struggle with role playing tabletop games is the same reason I struggled at Apple — I am my whole self, with all of its facets, all of the time. I can keep a secret (snitches get stitches!), but I can’t keep a whole part of my life secret.

So, I’m looking for work. Here’s my portfolio of things I’ve done. Here’s my resume. And I’m dipping my toe back in with the disaster zine, digital estate planning, security consulting implementation with Myeong at Tiny Gigantic, and facilitation gigs in the meantime. Let me know if you have a me-shaped hole, because trying to do not-me-shaped things sure didn’t work. I’m a work horse, and I’m good, and I also really like sharing.

Identity Work

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As anyone who has ever spent more than 5 seconds with me probably could have predicted, I hang a lot of my sense of self-worth on my work. And while I don’t always mean what I get paid to do, I certainly do mean that as well. As I once said at a hacker conference panel on taking money from tainted places: “no one could ever pay me enough to not do what needs doing.” As in, while other folk can be happy doing net-neutral (or even net-negative) work as their day jobs, I cannot. I have a complete mental block on it and cannot do it, regardless of how I spend my non-work hours. To each their own – others are able to balance the impact they have in the world in various ways, and I’m honestly a bit envious of them.

That means the jobs I have, I believe in. Whether it was Jigsaw or Geeks Without Bounds or Aspiration or now Truss, I see my “job” as being part of a collective effort to change the world for the better. I don’t leave my work at work, and I don’t like taking vacations. The world is a mess and the only way it changes is through our active effort. No, I will not put my laptop down. (I am actually working on this, to my benefit.)

This also means I can be a mess sometimes, because of work. Because of financial needs, and political systems, and growing pains, my ability to act within or through an organization can be disrupted. Which would be fine, except I have rough time with it. It is, as I like to joke, a direct reflection on my moral character.

So I brought this challenge to my amazing therapist. They asked me great questions about how I interact and perceive needs, and my identity in regards to (and beyond) work. But it still didn’t land.

In thinking about who I would be without connection to others or beyond the actions I take, I realized how much I ascribe to the Buddhist idea of just being a collection of molecules brought together in this moment. That life is meaningless but that we give it meaning. And that meaning is created through action and connections. So to try to describe an identity outside of connection and action is impossible for me to do.

What does this mean about my relationship to work?

A great conversation came up in the #kids channel at Truss a bit ago, about how people explain to their kids why they go away all day. And folk fell pretty squarely into two camps: “everyone has a job (including you),” and “capitalism is a system we exist in.” And I realized in this conversation about managing 4 year olds that I have grown up in an environment which says “everyone has a job,” but that the “we have to survive in capitalism” narrative far better aligns with how I actually view the world. There is a difference between responsibility to a system (the former), and responsibility to the people within that system (the latter).

How do y’all think about responsibility and creating meaning, and how it does or doesn’t overlap with your work?

PS, aside on how the American Dream / Work Ethic is actually protestantism and a plug for this great piece from back in the day from Quinn.

more adventures of Willow

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So this job I’m taking over involves being the keeper of the Special Pens. Pens which are only given out one or two at a time to people who are deserving (ie, those who make money for the firm instead of those who just support them). It’s a tough job, I know, but somebody’s got to do it. After taking careful inventory, I had to have a way to protect these pens. Because I am not allowed a locked drawer, like an angsty teenager and their own room, I had to come up with another way.

Now, if this were the serving industry, I would simply leave a note that said something to the effect of, “if you take pens, I will stab your eye out with one.” (similarly, on scissors, one might write “if you take these, I will cut you”). But this is not the serving industry. Something I’ve come to know as “tact” is required. But I can’t just say “PLEASE DON’T TAKE PENS” because that’s too… dull. And I can’t say anything passive aggressive because it makes a small part of me die.

So this is my approach. Let me know what you think.

I would also like to point out that our OS is so old that I have to screen-print into PAINT for God’s Sake, which charmingly also captures old-school Word’s attempts at fixing my syntax. Love it.