Figuring it out as we go along

Believe it or not, everyone else is doing that, too.

“I’m sorry, can you explain what that means?”

While I don’t remember exactly what my question was about, I clearly recall the moment.

I was 26 years old, and had recently been promoted from producer to managing editor of iReport, CNN’s participatory journalism initiative. It was a big jump. Suddenly, I was responsible for overseeing a seven-person team; establishing legal and ethical standards for verifying user-generated content; collaborating with a variety of departments; setting goals and tracking metrics; determining yearly strategies; and doing many more things I wasn’t entirely sure how to do.

In my new role, I was invited to bigger, higher-level meetings, where I felt completely out of place. I’d nod cooly as people threw around various terms I was unfamiliar with, all the while furiously scribbling notes to myself, such as, “look up what KPIs means!!!” (It’s classic corporate speak: Key Performance Indicators.)

My situation wasn’t that rare. Plenty of people get promoted to management positions with little to no training, left to figure the job out on their own. The way I approached my newfound position wasn’t that unusual, either. I kept my head down, worked as hard as possible, and tried everything I could to cover up the fact that I didn’t know what was going on. 

But no matter how hard I tried, it was never enough. There was always some new phrase, workflow, or system that I didn’t yet understand, which left me feeling increasingly frustrated and overwhelmed. Then, one day, in that over-my-head meeting, I broke. 

I interrupted the rapid-fire conversation to ask what was going on. My question was followed by a beat of deafening silence, during which I wanted to crawl under the conference table in embarrassment. Finally, a colleague chimed in with a very gracious offer.

“Sure, I can walk you through it after the meeting!”

My admission, as vulnerable and awkward as it was, felt a bit like magic. My coworker gave me the background I needed, and even went as far as to share some related articles to get me up to speed. The most helpful byproduct of his guidance, though, came from his own admission: He told me that he’d been in my shoes, too, and wished that more people would be willing to speak up when they needed help. 

That moment — actually admitting that I didn’t know what I was doing, and receiving reassurance in response  — led to an invaluable life lesson. 

None of us know what we’re doing all the time. Sometimes that can be a disappointing thing to discover, like when you realize that your parents make mistakes, or that your boss also doesn't know how to handle a certain situation. It can be a liberating realization, too: No one has all the answers, which means you don’t need to have all the answers either!

There are a lot of things I’m figuring out in life right now. I’m learning how to freelance, and how to wean myself off of those job promotions and Big Important Meetings. I’m learning how to be in a new partnership, and how to not let my own grief and comparisons cloud everything. I’m learning certain things over and over again, with fresh insights each time — like how to be a good friend, give compassion to myself, care less about what others think, and relax more often.

I’m also learning how to manage and write this newsletter. Just like during those CNN iReport days, I’m figuring out My Sweet Dumb Brain as I go along.

It’s been two months since we introduced paid subscriptions to My Sweet Dumb Brain. Overall, things are going well. I’m proud of recent essays I’ve written, and have plenty of ideas for future issues. My editor Becca and I are getting better and better at working together as time goes on, and we’re seriously over-the-moon appreciative of those of you who are paying to subscribe (thank you!). 

Still, there are things I’d like to improve. Behind the scenes, I’d like to settle into a better writing routine, and continue to hone my instincts for which topics will resonate most. Publicly, I’m planning to tweak some of the subscriber-based approaches I announced in August that don’t make as much sense in practice.

Instead of limiting one newsletter a month to non-subscribers, I’ll be making most of my essays available for anyone to read. Lots of readers expressed they enjoyed one of the first subscriber-only essays I published, but frustratingly couldn’t share it publicly within their circles. That will happen less often! (That post, by the way, is now available to everyone.) 

I’m also planning to send out additional mini-posts to subscribers. Quick thoughts about something happening in the world! A behind-the-scenes look at a story I’ve written that’s published elsewhere! Fun pep talks ... just because! In addition to Wednesday newsletters, paying subscribers will get short emails like these. I won’t clog your inbox — promise! — but will drop by with little unexpected surprises from time to time.

One of my favorite things about working on the iReport team was how often we’d say, “We’re figuring it out as we go along!” There was no precedent for participatory journalism, which meant we were literally writing the rules and identifying best practices in real time. It was a sometimes scary, but mostly liberating environment — one that allowed creativity and innovation to flourish.

Newsletters have been around for a while now, but newsletters with paid subscriptions are a relatively new phenomenon. The best path to grow and improve My Sweet Dumb Brain is uncharted, putting me once again in a challenging and exciting position. I don’t have bosses calling the shots for me like I would in the corporate world. I do, however, have a trusted editor and whip-smart readers to lean on.

It’s helpful to remember that I’m not doing this alone. And if I get stuck? I’ll do what I did in that meeting. I’ll raise my hand and ask for help.



Good job, brain

I'm reading:Maybe You Should Talk to Someone” by Lori Gottlieb. This memoir, about a therapist’s own experience going to therapy, is immensely enjoyable. There are so many good and relatable insights! For me, this is one of those just-one-more-chapter books, which is awesome, except when it comes to my sleep schedule.

I’m inspired by: Fall’s arrival, and the season’s permission to let go of things.

I'm aiming to: Get my inbox under control. Now that I’m no longer traveling so much, I’m trying to make time for decluttering — at home and online.

Additional resources

  • Here’s a compelling case for opening up and being vulnerable.

  • From 99U: “The real trick to producing great work isn’t to find ways to eliminate the edgy, nervous feeling that you might be swimming out of your depth. Instead, it’s to remember that everyone else is feeling it, too.”

  • If you’re interested in creating a paid newsletter, Substack has some great advice on how to succeed.

Let’s hear from your sweet dumb brain!

This week’s exercise is more of a request: I’d love to hear more from you. What topics would you like me to explore in future issues of My Sweet Dumb Brain? What has especially resonated with you in the past? What’s bothering your sweet dumb brain lately? Just-because nice comments are really lovely, too.

Your feedback is invaluable — it keeps me motivated, helps me correct course, and gives me fresh ideas. You can reply directly to this email to share whatever you’d like. I’m listening!

This newsletter is written by Katie Hawkins-Gaar. It’s edited by Rebecca Coates, who, like any other parent on planet Earth, is still figuring out this parenthood thing as she goes along.