15 lessons from a year of creating in public

The things that got me past the starting line, through the messy middle, and that keep me going

Your Five-Year Plan is a newsletter about embracing life’s profound uncertainty.

Maybe your own plans went up in flames; maybe you’re considering a big, scary leap. This is your trusty companion while you’re writing the next life chapter.

Welcome to the conversation—and to the adventure that unfolds when your plans go sideways. This is letter #46. ✨

15 lessons from a year of creating in public

The Seattle Public Library, captured on Kodak Portra 400 film

In the first year of writing this newsletter, it seemed that each week arrived with a new epiphany about the creative process. This week, I’d like to share fifteen of these lessons with you.

(Because this project coincided with multiple life transitions—creativity, of course, being one of life’s healthiest coping mechanisms!—these epiphanies were intertwined with the lessons I learned about uncertainty.)

Each realization was closely associated with one of three stages, which is how you’ll find them organized below:

• Some knowledge helped me through the very first weeks of writing in public.

• Others got me through the awkward middle stretch.

• Today, still other lessons are keeping me motivated for the long haul.

Life and creativity aren’t linear, which means that I’ll soon be at the beginning again—of an entirely new creative undertaking, or a new iteration of this one. When I get there, all the lessons about being a beginner and muddling through the messy middle will apply anew. ✨

1) Waiting for perfect circumstances means waiting forever...

Losing my job last year gave me the privilege of boundless writing time—and yet I was beset by the grief of losing my mom, plus the physical effects of chronic stress. Not necessarily a recipe for creative success!

The only reason I started this newsletter? Suddenly, I had a lot to say.

A year later, the evidence is clear: the onslaught of distractions from creative work will never, ever stop. So I give myself grace about my writing deadlines (they’re self-imposed, after all), but just as often, I work through the chaos.

2) …but it’s okay to wait for circumstances that meet a personal definition of “right.”

Before committing to this newsletter, it felt important to pick an organizing topic I could imagine writing about indefinitely (uncertainty, transition, new beginnings), and to create supporting design elements (the tongue-in-cheek logo and cute page dividers!) that made me smile.

This was probably an unreasonably high bar, one that goes against every piece of advice that counsels “Start before you feel ready.” Picking a topic and creating design elements could have become reasons to procrastinate indefinitely.

For whatever reason, they also happened to be the two things I needed to feel secure about this fledgling space. Creating in public offers so many opportunities for self-doubt; I’m glad I did the two confidence-building things first, arbitrary or not.

3) Confidence surrogates are the secret ingredient.

Hitting “publish” on my first newsletter felt wildly vulnerable. Sure, I’d written a blog before, but my mom was its only consistent reader! (Plus, I had comments turned off, and never looked at Google Analytics.) Writing a newsletter, though, meant subscriber notifications and open rate statistics—and, eventually, unsubscribes too.

I didn’t know that I needed confidence surrogates; they just showed up. My dad, my stepmom, and my friends Carolyn and Dan felt like cheerleaders straight out of the gate. I didn’t have confidence in my writing yet—that would come with time and experience—but they did. That carried me.

4) You learn what to write about by actually writing it.

Yes, I’d picked a general topic for my newsletter. But before penning a single word, I yearned for foresight: should I focus on this message? Should I ignore that one? How should I structure the content I’ll be producing?

Some clarity eventually arrived, but that was dozens of essays in. Even now, after forty-six newsletters, my focus is still evolving, and I don’t imagine it’ll ever stop.

5) Writing in public can strengthen loose ties.

After sharing my first essay with friends and former co-workers, I got a LinkedIn message from an acquaintance I’d met years before. His dad’s health was failing, and he thanked me for talking publicly about caregiving.

I’d been terrified to post links to my writing on social media—but his message showed me that for every instance of the private eye-rolling or quiet judgment I feared, there was a genuine connection to be made or strengthened.

6) It’s normal to outgrow almost everything.

Here’s one example: the first few months, I included a chatty little personal section at the beginning of each newsletter. Why? My only readers were my actual, IRL friends, and it felt natural to tell them how my week had gone!

Eventually, the room I was speaking to swelled to include people I’d never met before. It felt natural to change my tone accordingly.

7) Creating in public is an emotional rollercoaster; expect soars and dips.

Between the potential sources of external validation, the weekly spate of unsubscribes (they’re normal), and the stomach-clenching that comes with publishing an intimate essay, creating something for public consumption involves a lot of ups and downs.

Unfortunately, it’s as hard to avoid being swept up in praise as it is to avoid taking a perceived slight personally. Eventually, though, I started expecting the ups and downs, a mindset shift that dampened their impact.

8) It’s hard to avoid stats, but it is possible to adjust their meaning.

Speaking of emotional rollercoasters…

The great thing about writing an email newsletter: it’s easy to understand how many people you’re reaching. The terrible thing about writing an email newsletter: it’s easy to understand how many people you’re reaching.

A newsletter stats dashboard is a neutral tool that can be:

• A) Safely ignored,

• B) Used to make informed decisions, or

• C) To berate yourself for all the ways you’re falling short or underperforming.

It took time, self-reflection, and intentionally defining what constituted “enough” to start picking A and B more often than C.

9) Good writing and thinking doesn’t happen in a vacuum.

I made early friendships with Zac Solomon, Sandra Ann Miller, Chris Anselmo, Aja Frost, and Aliza Sir—friendships that confirmed the importance of stepping out of my office and into community with other readers and writers.

Listing all the other wonderful friendships that followed would cause me to run up against the email-length limit here, so: you know who you are!

10) “What got you here won’t get you there” is evergreen advice.

As in life, what’s appropriate and useful for one stage of a creative project won’t necessarily apply to the next one.

Approaches that felt supportive and calming as a nervous newbie (strict templates and schedules!) felt like constraints once I gained the confidence of experience.

11) Milestones are for celebrating.

Meaningful creative milestones take many shapes, but this applies to everyone: letting a milestone pass sans celebration—preferably with one or more people who’ve supported you along the way—is a missed opportunity.

I passed a subscriber milestone this year that, at the outset of my writing journey, seemed completely impossible. That’s worth toasting to! So I headed out to a new Italian restaurant with my boyfriend, since nothing says “success!” like gorging on handmade tagliatelle.

12) Writing out loud can deliver a more authentic life.

Anyone who knows me offline will tell you that I’m pretty allergic to talking about myself. Writing a newsletter has allowed me to share my inner life, something that directly benefits my existing relationships.

13) Succeeding with one project puts past “failures” into context.

I launched other creative projects that have since folded. Let’s not even talk about the Instagram accounts I launched, only to realize that—yes, in fact, I do still hate Instagram! (Couldn’t have seen that one coming.)

Did that make it cringey for me to try something new…again? Maybe! 🤷‍♀️

Still, after keeping this thing up for a year, I’m quicker to look at past projects as experiments rather than failures, ones that helped me figure out what felt sustainable and what didn’t.

14) Creativity is a teacher.

Personally, it’s taught me about what I want from my career, whether or not writing becomes a central part of the work I do for money.

I’ve loved watching my essays stack up this year, which made me realize: wow, it’s really important that my work keeps me occupied with making tangible things, ones that I can point to with satisfaction: “I created that.” That realization will inform how I lead the rest of my life.

15) It actually does get easier.

I’ve read so much dour writing advice that talks about how it’s always hard for everyone, forever. And in my experience, writing does involve discomfort. Sitting down to a blank page will probably never not suck. Publishing a personal story will probably always give me anxious butterflies.

Still, writing involves skills that improve with practice. (I’d wager this goes for other creative pursuits, too.) Do it enough and you’ll learn what time of day you’re most creative, how many minutes or hours you can reasonably produce words before wilting, and other details that are super-specific to you. Do it enough and you’ll know what to expect when you hit publish. Do it enough and you’ll grow a thicker skin.

And because creativity benefits from practice, do it enough and you might surprise yourself at the ambitious goals you take on next, landing you right back at the starting line of something exciting, uncertain, and new.

💬 What do you think?

I’m curious to hear from you. If you have a creative project of your own, what lessons would you add? If you don’t, which lesson might address any fears holding you back?

Psst: if you’re reading this in April 2024, the book giveaway is still open! Enter here if you haven’t already. 🎉

Had your own plan-in-flames experience? Taking a leap into the unknown? I’d love to hear more. Just hit “reply” to get in touch, or introduce yourself here.

Warmly,
Maddie