🖋️ 200 Weeks Later: Reflecting on My Writing Journey
Discover how a weekly newsletter can transform your world like it did mine
I invite you to listen to the audio version of this letter by clicking play above.
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Today, I hit a surreal milestone: 200 weeks of sharing my writing online.
It's astonishing and almost hard to believe—this journey is truly something special.
Devotion to sharing my writing weekly has become the most fulfilling creative endeavor of my life to date.
Growing up, I was afraid of being known. Regrets piled up for being shy. In first-grade gym class playing kickball, I’d make a beeline straight for the back of the line so I wouldn’t have to go up to kick. I’d let the boys who just got home runs go up and kick again before I swung my leg for the first time. Embarrassment terrified me. It’d work great until Sasha, the gym teacher, would catch onto what I was doing. She’d come up and insert me back to the front of the line and have me kick. I’d miss it again and then again. She'd then have the pitcher roll the ball at a turtle speed. My palms would get more clammy, and my cheeks would blush even more because I’d gotten special treatment.
I’ve since learned from that eight-year-old girl that embarrassment is all about how I choose to let others perceive me. Instead of embarrassment, I can grow by showing up even if I strike out. It's about defining the pursuit as fun no matter the outcome and despite any humiliation.
My weekly writing over these 200 weeks is my opportunity to shine. It’s my little sliver of space on the Internet. I dedicate attention each week to sharing what I’ve been learning, experiencing, or surprised by. Ideas itch at my skull, and I feel a dire need to get them expressed.
Among numerous other benefits:
It’s given me structure.
It’s sparked my curiosity.
It’s nurtured my introspection.
It’s created a portfolio showing my work.
It’s gotten me more comfortable with the spotlight.
It’s forced me to distill ideas and curate what’s most important.
Last, and most importantly,
It’s given me the confidence to tell people I am a writer.
Writing has helped me prove that I can show up and kick balls. I can keep chipping away and finish things. There aren’t shortcuts in life. This writing practice has taught me to have patience, keep showing up, and get better at sharing my ideas even though it makes me uncomfortable. The only way to find comfort is to keep showing up in the arena.
On my deathbed, I'll value the words I shared over those unexpressed in the solitude of the night and the day. It feels daring, but it’s what makes me feel alive, and I love feeling ALIVE.
Weekly sharing has been my way of inviting connection into my life. It’s been like my own little act of courage — shouting out to the world through a megaphone that I do have a voice and I am worthy of being heard. Since connection is something I seek daily in my life, this exercise of sharing online has made me more open to sharing in all avenues of my life.
If I were to give twelve tips to my younger self just starting out at newsletter number 1, I would tell her:
It’s YOUR project, so you make the rules. Create constraints as rules and also allow yourself to break them too. Fun and flexibility set you up for success.
Have the writing practice flow into your lifestyle. For a personal project, keep it fun. You don’t want a current working against you. Send it out on the easiest day. Send it out at the most convenient time. Just send it!
It’s *not* lazy to make it easy. You are not a sloth for making it easy. It’s quite brilliant and sets your future self up for success. You’re doing the damn thing, so you might as well make it with ease (and this is why I make a lot of lists because I find them easy to write.)
Have writing serve as a personal reflection process. Reflection is a key part of life that we humans all need for learning and usually forget about. Sometimes, if I go on an epic trip or read a mind-boggling book, I’m speechless because I haven’t allotted myself a container of time to reflect on what I experienced. Make time to reflect.
Only some things you write need to be shared — but write it anyway.
Preserve some of yourself to stay sane. It doesn’t all need to be out there to shine. Vulnerability is courageous. Yes, sure, Brené Brown. Yes, AND having intimacy with yourself is also important. So remember that. The Internet is a magical connection engine, and it is also still the Internet. There are many many people on the globe on it from all different beliefs and backgrounds. The world doesn’t need to know all your secrets. Some things are better left unsaid, and that is up to you to discern. It takes time to find boundaries. I’m still figuring that out, too, so don’t rush it.
Keep showing up to keep the muscles strong. Does it get easier each week? Kind of, but only sometimes. It still feels like day one again every week, but the struggles are slightly more familiar. Writer’s block? Phone a friend. Feeling bored? Write a letter to boredom. Have a headache from staring at a screen too long? Go for a walk.
Make the majority of your life about showing up. If you drop the ball, grant yourself grace. You’re a human, after all. The blemishes and
typestypos are part of the experience. Technically, I’ve missed a few weeks across the four years, but I don’t remember those weeks. What I do remember are the weeks that I showed up — which was most of them.Writing progress isn’t linear, so stop expecting it to be. This pursuit is unlike others in my life, like yards swam. I’ve chosen it not like others. Progress isn’t linear. What gets tracked is subjective. There are numerous ways to measure success, whether by the number of words, hours clocked, books published, or accolades won. For me, it’s meant showing up, doing the thing and finding fun in the learning along the way.
Make it social. Before you write, converse with people about the ideas, and they’ll flow out of you onto the page. I don’t always make the time to do this, but I am always grateful when I do.
Don’t feel like you have to hurry. Wait for the moment — or ahonui in Hawaiian. If an idea doesn’t feel ready to share yet, then know that you can share a different one this week, and the other one will have its time. That is okay to do. Instead write about what gets you skipping down the street or gets you humming Adele in the shower. Not everything in life needs to be coerced. No need to pull teeth if there isn’t a cavity!
Show up, kick the ball, and make it good enough. Perfection is the enemy of forward motion. Progress means moving forward — just keep swimming!
As a writer and fellow human, how blessed are we as mammals to have a written language to use daily? We get the opportunity to communicate with each other and express ourselves. We get to insert curiosity into those words and choose the more precise ones that mirror our thoughts and feelings and ideas.
⏭️ So what’s next?
Writing will continue to be my avenue for exploration, expression, and connection.
I’m giving myself some space to start dreaming. I want this weekly practice to emulate what is alive and stirring in my life. Writing is multifaceted, so I can be patient and explore more of my unique style.
I’ve got a few ideas for tinkering and experimenting more. One is to become more prolific at poetry, like Mary Oliver, who published her first collection at age 28. Another is to get more personal by sharing more letters directly to one person, place, or thing. I’m open to co-creation too.
When I signed on to start this weekly pursuit, I knew I wanted to be one of those writers who consistently showed up rather than some webpage collecting dust with people asking whether I was still alive. I cannot imagine life without this nonlinear pursuit of writing I’ve promised myself to be on.
I have an active mind and life with many ideas and experiences. The end is not in sight—not in the slightest. Every day still feels like day one.
Two hundred weeks in, and I’m still just beginning.
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🙏 Shoutouts
This piece wasn’t created alone. Thank you for the conversations and contributions from Ben Schnieder, Evans McGowan , Matt Yao , Tommy Dixon , Steven Foster , Hannah, and Emily’s car who I recorded this in. And to the Foster writing community led by Dan Hunt and the editors Alice Sholto-Douglas and Felicity Brand. And to my weekly writing group led by Lyle McKeany.
To the Write of Passage online course that pushed me at letter 1 in the way that I needed to begin and to the countless writers I’ve met through it including Michael Dean , James Bailey, Charlie Bleecker , Isabel, Gwyn Wansbrough , Matt Tillotson , Salman Ansari , Michael Ashcroft, Alex Michael , Alice Lemee, Naseem Malik, Nate Kadlac, and countless more alum that (I’m losing track of and) met in the community who continue to inspire my writing journey. 🌟
To a new friend Jeffrey I just met, who has now started writing Letters to Myself inspired by what I’ve created.
To all of you who have been reading this for the past 200 weeks. Thank you for being companions on my journey and love for language and words and writing. The reponses and community has made the ride that much more fun to show up for. It’s been such a joy 🥹 ❤️
And if you’re new and want to sign up, here’s your chance
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Until next week and the next 200 weeks and beyond my fellow learn-it-alls,
Keep on learning,
too da loo
Jen
PS- stay silly and wear sweater sets!
Jen, this is terrific and What A Milestone! So much to be proud of. And I love the picture!
Love this!