The Overlap is sunsetting 🌅

I'll no longer publish this newsletter

Black Mountain, Idyllwild, CA | September 2022

I’ve decided to sunset The Overlap. Sudden decision, I know.

I no longer have the stoke and passion to write this newsletter that I used to have.

I used to be really into org design in 2016-2019. And then product management in 2019-2020. I started this newsletter to examine the similarities between both.

I wanted to look at the entirety of what it takes for teams to do their best work. A product team’s product is only as good as how they organize, strategize, communicate, decide, and act. How organizations work determines whether they achieve the outcomes they want. But organizations rarely practice reflecting on their how. We move on to the next project, we don’t address deeper issues, and we turn a blind eye from addressing dysfunction when everyone literally feels it. And, it’s a shitty experience for everyone. Who wouldn’t want to feel effective, engaged, and fulfilled at work?

Improving the way product organizations work is still meaningful work to me. But lately, I struggle feeling excited to write about it every week.

Product and org design feel like remnants of an old me. An old me who lived in New York City and was excited to integrate what I was reading and learning into my work. I feel like it’s hard for me to unsee possibilities for how organizations can work better — my brain is literally wired this way because it was my first job out of college. But I don’t think about the way we work as much as I used to. Post-pandemic, I’ve started to value things outside of work.

I’ve been struggling to accept that I’m not as passionate about product and org design. This has been strange to come to terms with. I’ve always seen myself as the org design guy at work. And a product and org design writer. It’s a part of myself that’s shedded — I’m slowly accepting this.

I do enjoy writing. (Perhaps more specifically, I enjoy having written more than I do writing.) Writing is my way of making sense of reality, messiness, life. Writing reminds me of what’s most important to me. Writing helps me help others see things in a different light. I just don’t want writing to feel like work. I want to write only what I’m excited by.

I don’t want The Overlap to become dull and dreary

From visakan veerasamy’s I Don’t Wanna:

I don’t want to repeat myself in a dull, dreary way.

[…]

There’s repetition that’s interesting — coming from a new angle that feels fresh, significant, meaningful — and there’s repetition that’s dull and dreary, recycled pablum.

I worry that The Overlap will become recycled pablum. I want to create what I want to create. And always bring something fresh to the table.

Now, I force myself to write it every week. That’s not a great sign.

I wrote Define your leading and lagging indicators because I knew it wouldn’t take me long. It took me 1 hour to write and edit. But I don’t ever want to think, “What’s a topic I can quickly publish?” I want to think, “What’s a topic that I’m genuinely stoked to write about?”

More from visakan veerasamy’s I Don’t Wanna:

I don’t want to… do homework. And that’s what a lot of my essay plans feel like right now. Homework. My last day of school was in 2009, and it’s been 13 years since and here I am sitting around feeling frustrated with a bunch of homework that I’ve assigned myself. Gosh.

Wait, didn’t you just start a paid newsletter?

Yep! I did.

And a few of you have graciously paid the annual subscription. If that’s you, I’m going to email you directly and ask if you’d like a prorated refund for the newsletters you haven’t paid for. (I’ll refund $70 minus $7/month for the amount of months you’ve subscribed.) It’s up to you if you want that prorated refund. You can choose to support me by keeping the $70 payment. Or you can choose to receive the refund. Completely up to you.

I’m afraid I’ve disappointed many of you by quitting this newsletter. But I only want to give The Overlap readers writing that I’m genuinely stoked about.

So, what do you want to write about now?

I’m not sure. I reckon I’ll be able to answer this question by living it out (rather than theorizing).

Some questions I’ve thought about:

• What have I learned about love thus far?

• Why do I love climbing outside so much?

• Why should climbers choose just to boulder or just to sport climb? Why not excel in both?

• How do I foster community while always being on the road?

• Why does seemingly every solution to interpersonal conflict always point back to self-awareness and communication?

• How can different generations in the Filipino community better understand each other? And how might this improve our collective mental health?

I’m proud of these three essays I wrote last year:

• I live with my parents and I’m okay with that

• on practice

• My 2022 year in review

I don’t read as much about business and organizations these days. The only business-y thing I read is John’s The Beautiful Mess. No surprise to you as a reader of this newsletter. His newsletter inspired me to write mine.

If what I’m reading is any indication for what I’ll eventually write about, I’ve been enjoying:

• bookbear express

• visa’s voltaic verses

• The Pathless Path

• Michelle Varghoose’s Newsletter

• The Paradox of Goals

• Over-indexing on freedom

Thank you! It’s been a good run.

You are the reason this newsletter is successful. Thank you. For reading and giving these words an audience.

1221 subscribers. 14 paid subscribers after five paid editions. 61 editions. Many great comments. I’m happy with how The Overlap ended up.

Who knows, maybe I’ll be writing about this stuff again.

For now, The Overlap will sunset. And my interests will continue to wander.

–tim