May is usually a hard month for me as a teacher.

I'm exhausted. Of the year's mountain-tops and canyon-bottoms, in May it's the low, dark places that seem realest. I've succeeded beyond what I'll ever know with some kids, yet with some I know I've failed. I haven't reached them; I haven't been The One Teacher whose work flips their soul's switch from apathy to ownership. In May my failures loom insurmountable, my successes waft mirage-like. Every lower-cased first person pronoun, every snarky complaint about “having to do work,” every missing assignment — they are rocks tossed into the bucket of felt responsibility tied to my back as a teacher.

May is a month that instigates the internal work that all flourishing teachers must do habitually: separating what is true from what is not, what lies within my power from what doesn't, what I could have improved and what I need to acknowledge as beyond the boundaries of human ability.

And it's also a month to look at what's ahead — that's what I want to write about today.

What big things have you been putting off?

For teachers the best time to reflect on the past year and get ambitious about the year to come is May, not December. This mixture of forward-backward seeing serves a few purposes:

• It helps us to keep from dwelling on the past year's shortcomings;
• It prepares us to use our summer as best we can — for rest, for advancement, for learning, for the things that nourish us;
• It keeps us spunky. Or, at least, spunkier.

The longer I'm a teacher, the more thankful I am for the academic calendar. Don't get me wrong — sometimes I wish I could take my summer vacation and spread it out a bit more through the school year. But I do enjoy the clear beginning, middle, and end we get to experience, year after year.

I also enjoy the power that our extended breaks give us for doing some of the things we need to do but tend to neglect and some of the things we dream to do but tend to put off.

Four Mays ago: the dreaded master's degree decision

I was not excited to get my M.Ed.

Honestly, I begrudged it; I resented the fact that I was being forced to spend hard-earned money (our district, like many across the nation, cannot afford to reimburse M.Ed tuition) that my young family needed. Sure, I'd get a raise — but for local M.Ed options, that raise would take nearly five years to compensate for the cost of tuition. Five years! And in the interim, I'd be driving to the local university a night or two a week, managing my coursework, and, oh yeah, being a husband, a dad, and, for at least nine months out of the year, a teacher.

But four Mays ago — May 2011 — I realized that I couldn't put the decision off any longer. I needed to start on my M.Ed before my certificate expired. It was time to make a decision.

Thankfully, there were more options than the traditional brick-and-mortar master's degree, and I used that month to research them, ultimately deciding on a degree that was both finance- and family-friendly.

If you've been putting off your own M.Ed decision, let me help you out. I created a free, 5-day email course that walks you through indecision. It includes the M.Ed I decided upon and the consequences (all good) of that decision.

Three Mays ago: the “I'm done putting off this dream” decision

I've always wanted to be a writer. I can still picture the conversation I had with my dad. We were sitting in my grandparents' hot tub, and I was sharing with him what I wanted to do with my future. I was a Junior or Senior in high school.

“Dad, I want to be a writer,” I said.

I'm not going to lie — I don't remember exactly how he responded. But I know it was skeptical; I know it was something along the lines of, “How much do writers get paid?”; and I know that I don't blame him a bit. His lack of enthusiasm was hard to take at the time, but let's face it: a lot of people say they want to write a book someday, or that they'd like to be paid to write. Yet how many actually do?

The journey from the hot tub to the teacher-blogger typing these words was a circuitous one. So it goes. I was pre-med for awhile; pre-ed for much longer; a teacher, a busboy, a barista, a teacher again.

But three Mays ago, with five years of teaching under my belt, I decided that it was time. My growing family needed extra income, and summer was coming. I decided, “I'm going to write a book!” So I picked up a used copy of Michael Larsen's How to Write a Book Proposal, and within a few pages, Larsen was telling me that publishers aren't too interested in folks who have a great book idea — even a solid, well-considered proposal — unless they have an established audience to go with it.

Hmm… audience. Yeah. No. I had some friends on Facebook — my mom chief among them — but that probably wasn't what Larsen was talking about. He recommended that aspiring authors develop their audiences and their book ideas simultaneously through blogging.

And here was the critical juncture: I could say,

• “You know, that's cool, Larsen. I agree. It's just that this summer we're having our second child, and we just bought our first fixer-upper. How about some other time?”

Or, I could say,

• “Let's get this goat rodeo started. I'm not sure what I'm doing here, but I'll learn as I go.”

I went with the second one. The blog you're reading is the result of that decision. So is this book and this one. I'm not proud of everything I've written — many of my older posts actually make me shudder. But every single word has been work I needed to do to get here. Want to stop dreaming of being a writer and start being one? I'd love to help:

How will you May forward?

Share in the comments below. Happy almost-done-with-another-year 🙂