Lessons Learned Outside of the Classroom - Part I

A few things I learned quickly from my first contract with a client

First of all, this might be the most vulnerable thing I’ve ever written for a wide audience—most of whom I’ve never met. If you judge that, go read Daring Greatly by Brené Brown. Then come back. If you still judge it, you’re pre-Daring Greatly Rhiannon—the one who thought vulnerability looked weak. I read the book and changed my mind. If you think it’s weak, don’t read anything else I write. Go read that instead. 

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I had an almost 20-year career in education

• Started as a counselor-type person for a grant (GEAR UP), working mostly with 7th and 8th graders (and some 12th).

• Spent most of my career teaching English 9 & 10, both remotely and in-person.

• Closed it out as an AP at a pre-K–5 school, then an AP at a middle school—where I resigned mid-year. 

Silver lining? Infinitely bigger than the storm cloud I was fearful of.

I launched a consulting firm and immediately landed a contract with an incredible edtech startup, SyncEd, whose mission is close to my heart (and probably yours, too). Within weeks, I negotiated three more contracts.

We educators? Industrious folk.

For those of you either currently or debating

• Selling on teacher marketplaces.

• Running side hustles.

• Exploring consulting.I want to share what I learned—the wins and the mistakes—so you don’t have to make them. Vulnerability for the sake of making your life easier. And because I said last week that we should share the whole story, not just the Shiny Happy People version.

The first contract — and a hugh a-ha.

I landed my first contract with SyncEd (site linked here), and from the start, I was hooked. An edtech startup, run by smart, kind, innovative people outside education who actually GET IT? No way.

Well—way.

Their app does with data what school and district leaders SHOULD be doing—and I’ll give you a hint:

• It’s NOT making people waste hours on absurd, pointless spreadsheets.

• It’s NOT about fancy color printouts of red ink seas of failure on standardized tests for data meetings that boil down to "Be better." (How? Who knows?)

I joked that I would’ve sold a purse to buy this app myself. I was not joking.

(Spoiler alert: I have discovered a couple of diamond-in-the-rough market that is EdTech, and I will be sharing those folks with you, too.)

Brief synopsis of my lessons learned and a preview of Part II.

I can’t wait to tell you about the other companies I’m working with, but first—let’s talk lessons learned. Some great ones. Some screw-ups. Sharing them not to dwell—but so that if you go this route, you can skip the awkwardness at best, the shame at worst.

Next up, I discuss the four lessons I learned: 

• Reframe Your Role – You’re not just a teacher.

• Ditch the Jargon – Teacher-speak doesn’t always translate.

• Know Your Worth – Don’t sell yourself short.

• Leverage AI – Work smarter, not harder.