How should I create annual writing goals?

Hint: That’s the wrong place to start

“Clarity of mission is a powerful cornerstone of success. Knowing what you want gives direction to your life — every word, every action, every association, can be accurately chosen and harnessed to precipitate your desired outcome. What you eat, when you sleep, where you go, who you talk to, what you allow them to say to you, who your friends are, can all be corralled and launched toward your wildest dreams.” — Will Smith, Will (p. 214)

There are pithy, universal essays about the writing process. This is not one of them.

This is a personal exploration I’m writing as an act of discovery and accountability. I don’t guarantee it will make any sense to you at all. You don’t have to read it. So why am I writing it? Well, writing is one of those anomalies, an unparalleled perfection of balance of thought and action, so by writing this in public (hitting “publish”), I’m striving to write my way towards my writing goals. Like laying down the track as you go. Like I said, not pithy. Let’s get into it.

Without vomiting up the entire backstory of my life and writing dreams, suffice to say I’ve been on a journey as a writer. We can skip the overstuffed act one-two-three structure and just start the tape at the dawn of the pandemic, when burnout as an entrepreneur led (read: forced) me into a sabbatical from my decade-plus career as a journeyman healthcare analyst and blogger.

I focused my entire being into therapy, creative writing, and physical rehabilitation for a bum achilles. It turns out intention and hard work pay off: 20+ months later I’ve transformed my sense of self as a creative writer, and rebooted* my body, mind, finances, career, and relationships around that new identity.

*Apparently, this “reboot” is one of those painful kinds that requires multiple restarts and loading screens, because perhaps I’m actually in the process of installing a new OS upstairs. My psyche and sense of identity still feels like a bag of parts, or an island of misfit toys at the time of this writing, rather than some unified and cohesive sense of self-as-writer or writer-as-self.

If you’re totally lost by now, like I said, you really don’t need to be reading this. There’s more stimulating content pretty much anywhere on the interwebs. It’s just that — I need to write it, and know why I’m writing it. Which brings us back to those goals.

As Tony Robbins has shouted into my memory, FINDING YOUR WHY is the most important part of motivation-building and goal-setting. So before exploring how to set my goals, or what goals I should set, I’ll deliberate here on WHY am I writing about my writing goals. Why do I want to set goals? Isn’t the joy of writing enough?

• To gain clarity on my ambitions and dreams beyond just “I want to be a writer.”
• To expand my sense of self-as-writer beyond just creative writing, or business writing about business and healthcare. To connect those two things to a bunch of other things.
• To span genres, explore new styles, push the boundaries of my craft and trade so that when I say I’m a writer, I really believe it. So that it’s not a question of day job versus hobby, but a conviction. Ikigai fits the bill:

• To boost my confidence in writing about my writing, which I’ve learned will help me dramatically as I try to “make it” as a published writer, apply to conferences, workshops, residencies, mentorships, fellowships, and publishers. But I’m interested in more than just playing the game with agents and publishers and editors; my real “why” is to go deeper and challenge my own understanding of craft, my creative process, and my own “theory of fiction.” To understand what I’m writing, where it’s coming from and why, and where that rabbit hole goes to…or comes from…
• To create a learning framework that sets me onto a career-and-life-altering trajectory, i.e. getting better at getting better. Using writing as the magic process for myself to explore and expand my subject matter, style, and purpose, intentionally and discretely. Hippie-dippie “The Secret” stuff? You betcha.
• To learn more about screenwriting and film adaptations of prose so I can position myself to break into those kinds of project opportunities by studying them with intention and learning my way into the game.
• To organize my historically messy/sprawling/poorly defined goals around both reading and writing into a project framework that I can assemble, brick by brick, into something that provides me structure, protection, a platform, or other stuff.
• To expand my sense of purpose in writing, to better understand how I feel I can and should show up in the world as a person, as a man, as a creative, as a dare-I-say, artist.
• To reinforce and affirm that what I am doing is important to me, and reinforce and affirm that what I am doing is an important thing to be doing at all, or even more important than doing other things (like making money).
• To know what I am writing for, and who I am writing for, and learn how to develop a fluid outlook on those things, based on ongoing dialogue with an evolving kaleidoscope of people, ideas, topics, media, rather than as a fixed and rigid sense of self, position, perspective.
• To practice writing and develop my voice.
• To really stop giving a shit about what other people will think. To grow comfortable dancing with my words like nobody’s watching.

So — Now that I have my murky sense of purpose in the above list, how do I set up specific goals in a way that sets me up in turn to accomplish them over the course of a calendar year? Here are a few thoughts based on what I’ve learned as a fail-forward, real-world-MBA/MFA-sort-of writer over the last decade-plus.

First: Review what “data” you have

It’s useful as heck to review past writing goals. None of the stuff on that list happens overnight. In fact, this whole exercise itself is the result (too early to call it a culmination) of years of frenzied self-improvement strategery. So, I used the last 20 months as a dataset of goals versus results, intention & achievements, as well as a bit of 80/20 analysis (what 20 percent of the efforts generated 80 percent of the “results” I feel good about?).

There’s no wrong way to do this, except of course not to do it at all. My meta-level takeaway: The more organized I become with my goals, the fuller a picture of the results I’ll be able to see. Measure → manage, etc.

Second: Imagine tangible results

With goopy existential self-improvement stuff like this, it’s useful as heck to refine these impulses into the most concrete, tangible results you can imagine. For this too I’ve relied on Tony Robbins’ RPM method as a pinhole exercise that forces me to weave my loose threads together into a singularly focused purpose.

Mine this year will be to create a single project that serves as a “container” for numerous, and hitherto disparate and disorganized goals. Spoiler alert: you’re looking at part of it right now. If I focus on executing on this one project for the whole year, I’ll be damn-near guaranteed to end the year off closer to the above objectives.

Third: Set up accountability

Ensure there’s an accountability mechanism, because otherwise it’s not going to get consistently done. This one’s super important because it balances out my fire-in-belly ambition with the tempering disappointment of innumerable failed goals, rejections, and disappointments from years past.

The fact of the matter is that writing is intrinsically solitudinal. I just made that word up! But it’s true. If achieving your goals comes down to reliance on willpower or discipline or intensity of desire alone, there will be some lapses. Maybe not for you, but sure as heck for me. If it’s just me “pushing” — it’s a matter of time before I get lazy, I get demotivated, I get despondent, or I justify other priorities, and my progress lapses.

Which is also, by the way, part of the process.

2021 was the closest I’ve ever come to consistent month over month diligence. Honestly, I did pretty great, going from zero to five published short stories in a single year. But in ’22 I’m changing the game up: My accountability will be to my writing community of a handful of specific people with whom I’ve been sharing my work in an ad-hoc way for months. The aforementioned “single project” will be targeted at these individuals, which introduces a component of social accountability (the “pull” to complement my “push”) that I will be enhancing with some financial accountability as well.

Fourth: Don’t overthink it…

…and don’t be afraid to break your own rules. This whole article is an example of me overthinking it, and thus breaking this very rule about overthinking it. Don’t overedit. Don’t overanalyze. Don’t be like past (and let’s be honest, present) me. Just freaking write. I’m not trying to be clever here — it’s important to relinquish a degree of control. This is art, not science. At least it is for me. It’s gonna get messy, and it’s gonna get weird. At least it will for me.

That’s all I got for now. If you’re a random stranger on the interwebs who’s read this despite my disclaimers and protestations, and you want to stay looped in, feel free to follow this pub for more random writerly writings. Or don’t. I’m not doing this for you. ❤