Transitioning Careers

About 5 years ago I decided to transition from the nonprofit consulting space into the private sector. I’m now established at Apple, so hey, maybe I have something to say here for people who want to make a similar transition. 

A safety net

First, I want to give a shoutout to my family and the (limited) social safety net this country provides. With both, I was able to make this transition in a safe and dedicated way without much in the way of savings. Savings and unemployment covered 3/4 of my 18-month transition. My family not only covered the other 1/4, but also provided assurance that if it took longer, they would support me. I continue to work towards a future where anyone can have this supported flexibility in their life path.

I also want to shout out my husband, Reed. Reed not only has the audacity to assume such transitions are possible (and was a great cheerleader in the process), but also has management experience, which meant he saw and explained a path forward to me that was achievable. I have never had “ambition” when it comes to my career – I only see things that need to be fixed, and then I try to fix them. If that’s taking notes, great! If that’s coming up with a strategic intervention for communicating about medical questions and needs in the largest refugee camp in East Africa, great! Either is just fine with me. Reed was able to see where I was and where I wanted to be, and draw a line of clear steps between them.

What it takes

How did I know I wanted to do project management, of all things? Well, I have this incessant need to ship things. Unless it’s my career, I have a pretty good eye for assessment of where we’re at, a drive to be visionary about how I’d like the world to be different once we’re done, and an inability to be dishonest about where we’re at in our journey between the two. Other project managers are good at what they do for other reasons, but these are mine. Like, some people are good at politics and understanding people’s motives, and supporting aligning those to ship things in quiet and happy ways. That I am not. But if you just love shipping things, and figuring out how to do that, you’ll be a good project manager.

Other things that help, that I know now: vicious prioritizing, juggling multiple things at a time, clear communication, representing status in multiple ways for multiple levels, consensus building.


So anyway. No shit, there I was, recently told I was being laid off from my nonprofit sector job, and realizing just how tired I was. So I started applying for jobs. I sprayed what was essentially a CV all over job sites, and filed for many jobs every day. I still spent 8 hours of every week day working, whether in applying for jobs, researching “actual” project management, studying for potential data science bootcamp, or working contract gigs that came my way to help make ends meet. It was hard, demoralizing work, and it didn’t actually work.

Reed finally persuaded me to 1/ stop trying to shove everything relevant into a 2 page CV and instead have a clean, easy-to-read resume; 2/ to tell the story of what I had already been doing in the context of what I wanted to be doing; and 3/ to actually work my personal connections. None of these came naturally to me, but I figured what the heck.

Reed talks about “trading up” in positions when moving into a sector. First, get a job at a place few people know about but with a title you’re into. Then, move to a company with more name recognition but for a title that might be a downgrade or slightly off the mark. Then get a job at a slightly better place than the first, again with the sort of title you’re going for. Et cetera.

Being legible

It mattered basically not at all if I knew the language of Agile or the specifics of project planning tools, etc; and instead what mattered was communicating a shared existential angst about what “done” means, anyway, and the ability to get there regardless of what tools were at hand. For this, I communicated the concrete projects I had finished, along with what “finished” meant, who the stakeholders were, the constraints & risks, and what the user impact was.

I radically changed my resume from trying to prove myself to anyone who might listen to instead be clear and concise. Here‘s basically what I used for Truss to take a chance on me, and for Apple to nominally review my resume to be sure I wasn’t a complete rando. Having further developed my knowledge of hiring practices, I’d probably drop the last 2-3 entries on page one and replace them instead with specific projects and details, dropping the rest of things from page 2, giving me a 1-page resume. I’d adapt the few parts of my career and few projects highlighted to be specific to the place I was applying to.

What does that mean for whether or not you should be certified in this or that? Hiring managers and HR are pretty divided on who to let through their processes – if a place is big enough for recruiting/HR to do a first-filtering pass, you probably need certifications because that’s what recruiting/HR knows to look for. All the hiring managers I’ve met couldn’t give a rat’s ass about formal certification. So you either need to decide you’re only going for jobs where you have an in (highly recommended) or are small enough to mean the hiring manager is also the person sorting through resumes; or you might need some formal collections of letters signifying you can sit through a training.

Same thing goes for interviews – use clear, concise language about what you’ve done in the context of user impact and constraints. Talk about how you know how to make hard calls and explain where something is at in the context of where it’s going. Don’t use language specific to your or their field – use language that explains what’s going on to anyone.

My arc

Truss took a chance on me, based primarily on multiple fronts of social overlap and having made myself sufficiently legible that it was worth taking that risk. I worked at there for 2 years, and then it was time to move on. I then absolutely lucked out in that a dear friend was moving positions at Apple and advocated strongly that I be considered for her old position. Nepotism is a hell of a thing, but as a mature queer human, I’m willing to take the nice things that life sends my way. I anticipate being at Apple for a good while longer – there doesn’t really feel like there’s any “trading up,” at least right now. It sure has its problems, but so does everywhere.

This has come at a cost. I would be lying if I made you think it was all sunshine and lollipops. Apple is not exactly known for our ravenous dedication to all things open source, nor for involving stakeholders in our technical and design decisions – two things that have been at the level of identity-defining for me. The people I work with, while lovely, are a mix of people who are dedicated to The Cause because of a deep-seated philosophical commitment to Justice, working hand-in-hand with people who thought infosec was the most interesting part of their CompSci academic path… which makes feeling in solidarity with others difficult. It took me 3 years of soul searching to finally arrive at being ok with having made this transition. It still doesn’t sit right some days. But it was the right choice for me, over all. It might be for you, too.

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