Hey there, fellow accidental techie! 👋

Reader, let me ask you something.

When did you last stop and actually take stock of how much you know?

Not in a "humble brag on LinkedIn" way. I mean genuinely sitting down and acknowledging that you have built real, hard-won technical knowledge — not because someone trained you, but because you figured it out under pressure, often alone, usually while something was on fire.

If you're like most accidental techies, the honest answer is probably: not recently. Maybe never.

We're good at cataloging our gaps. The stuff we don't know, the questions we deflect, the moments we quietly Google something before a meeting so we can sound like we knew it all along. What we're not so good at is recognizing what we've actually built.

Each one explores a different dimension of what it actually takes to move from reacting to leading. Not in theory. In the context of your actual nonprofit, your actual constraints, and your actual career.

We're starting with Skills because it's where most accidental techies sell themselves short the most.

What's in this issue:

✅ The certification trap — why chasing credentials before taking stock of what you already know keeps you stuck

✅ Your Zone of Genius — how to figure out where you're genuinely strong vs. where you're just surviving

✅ The three-column audit — a 15-minute exercise to get honest about your skills without spiraling

✅ Stop underclaiming — the one habit shift that changes how leadership sees your technical expertise

✅ The Accidental Techie Course— the waitlist is now live for a 6-week course to go from reactive to intentional tech leadership.

✅ Jobs in nonprofit tech — this week's roundup of roles worth a look

✅ What I'm reading — articles and resources across the sector worth your time

QUESTION

In March 2020, I was two weeks into an office move and had just hired my first operations associate.

We had brand new office space. New furniture. A whole onboarding process built around being in person together. And then, in the span of about 72 hours, none of it mattered.

I had to get our entire organization onto Zoom — fast. Rewrite onboarding from scratch so my new hire wouldn't feel like he'd joined a ghost town. Redesign meeting cadences. Work with senior leadership to figure out what "inclusive remote workplace" even meant when nobody had done it before. Build new systems to track progress toward goals when we couldn't see each other. And try to help hold the culture together during a global pandemic.

No playbook. No IT department. No time.

What I remember most isn't the chaos of that first week. It's the moment I realized I'd actually done it. Not perfectly. But the org was running. People were logging in. My new hire wasn't drowning. We were figuring it out.

EXPLORE

The first instinct most accidental techies have is to go find a certification. Makes sense. It's structured, it has a clear endpoint, and it looks credible on a resume. I did this too. I pursued my Salesforce Administrator certification after years of working in the platform, partly because I wanted something official that said I knew what I was doing.

The cert was useful. But here's what I didn't expect: I already knew most of it. I'd learned it the hard way, under pressure, when things broke and I had to fix them. The certification formalized something I'd already built. It didn't create it.

That's worth sitting with.

The certification trap isn't that certifications are bad. It's that accidental techies often treat them as a starting point when they're actually closer to a finishing move. You go looking for a course to feel legitimate before you've taken stock of what you already know.

Gay Hendricks, in his book The Big Leap, describes four zones we operate in: Incompetence, Competence, Excellence, and Genius. Most of us spend a lot of time in Competence. Things we can do fine, but that don't energize us. Excellence is where we're genuinely strong. Genius is the narrow zone where what you do well also aligns with how you're wired.

That distinction matters because they require completely different responses.

If you're strong at systems thinking — seeing how tools connect, where data flows, why a process keeps breaking — that's a skill worth building on deliberately. It's also probably something you're underselling right now. You're calling it "IT stuff" when it's actually operational strategy.

If you're in Competence with something like network security — you can talk about it, you haven't broken anything, but it doesn't come naturally and you'd rather not own it — that's worth being honest about too. Not every gap needs to become a specialty.

Treating every skill gap the same way is exhausting. When you're stretched thin and wearing five hats, trying to become excellent at everything is a fast path to burning out while staying mediocre everywhere.

There's something harder to say here too. A lot of accidental techies carry real imposter syndrome about their technical skills. Not because they're incompetent. Often they're the most capable person in the room on this stuff. But because they learned in the field instead of in a classroom, and somewhere along the way they decided that made their knowledge less real.

It doesn't. Practical knowledge built under constraints is harder to develop than textbook knowledge in ideal conditions. You learned how to migrate a database while staff were waiting on you and leadership was asking for updates every two hours. That's not a gap. That's a credential.

APPLY

Start with an honest audit, not a wish list.

Take 15 minutes and write three columns. Column one: tech skills you feel genuinely confident about. Column two: skills you've been faking your way through. Column three: skills you actively avoid or quietly defer to someone else.

Don't judge any of it. Just get it on paper. The goal isn't to feel bad about columns two and three. It's to see clearly what's actually going on. Most accidental techies are surprised to find column one is longer than they expected.

Pick one thing in column two and get honest about it.

Not column three yet. Column two is where the real leverage is. These are skills you're already using, just without full confidence. Pick one. What would it look like to actually get solid on it in the next 30 days? Not expert-level. Solid. "I understand this well enough that I don't have to bluff" is a completely reasonable goal.

Maybe it's finally reading the actual documentation for a tool you've been clicking around in for two years. Maybe it's watching a few hours of tutorials on a platform you inherited from someone who left. One thing. Thirty days.

Stop underclaiming what you already know.

This one sounds soft. It isn't. If you don't own your expertise, nobody else will. Leadership takes its cues from you. If you talk about your technical knowledge with constant hedges ("I'm not really an IT person, but...") they hear that. It shapes what they ask you to weigh in on, and what they don't.

You don't have to overclaim. Just stop underclaiming. Find one area from column one where you've been downplaying what you know. Practice describing it without the qualifier. Not arrogance. Accuracy.

I'm building a 6-week cohort course so you can go from Accidental Techie to Intentional Tech Leader. Sign up below to learn more