4 min read



44 days ago I wrote this:

There's 44 days left in 2021. I'm setting a goal of sending this newsletter everyday through the end of the year. Some days, it might just be a photo, but I'm gonna hit send. I'll take Sundays off.

As my friend Carter pointed out, 44 days excluding Sundays made a target of 38 posts. This post makes 28. I hit 73% of goal.

I feel pretty great about that.

It's worth sharing the backstory of how this came about, and then I'll share a few things I learned during this experiment.

In November, I went part-time at Twilio. I'll write more about going part-time later, but the relevant bit is that I want to make sure I put the extra hours to good use, but I don't have a specific project I'm driving towards right now. Blog posts and photographs work well for me as a creative outlet because they're self-contained projects that can be shipped in an hour or two.

November 18th was a beautiful fall evening in Brooklyn. I smoked a joint with friends on Pier 6 and had this idea on my way home. I got home around 10:30pm, woke up Rachel who had gone to bed early, and said, "Hey, I'm kind of high right now. Can you tell me if this is a bad idea...." She sort of mumbled that it didn't sound terrible, rolled over and went back to sleep. I went downstairs, wrote the post and hit send. When I woke up the next morning, my first thought was, ".... did I actually send that?"

There wasn't much of a plan here. Just an experiment to keep me moving forward that I figured would create value in the absence of a big project. During that experiment, I shipped the most meaningful words I've ever written about my mom. (Dad – yours is coming.) I shared beautiful work being done by friends. I crystalized ideas that have been living vaporously in my head for years.

It's been incredibly valuable for me. Thank you, thank you, thank you for riding along with me.

I'd love to share a few things I unexpectedly learned while working towards this goal:

  1. When I do creative work
  2. What a privilege it is to have friends who care to open this thing.
  3. Which things are more important than consistency


An unexpected benefit of setting this goal has been identifying the spot in my day when I can consistently produce creative work.

You may have noticed a pattern of when these hit your inbox.

Basically – I open up my laptop after Rachel goes to bed. I've found it pointless to try to work on this before we've "closed up shop" for the day – gotten the kids in bed, cleaned the kitchen, walked the dog. Too many interruptions, too many other things that need attention.

That said, at some point in the afternoon the thought enters my mind, "What am I going to write about today?" and that thread runs in the background the rest of the day. But I don't open the laptop until the house goes quiet. Sometimes I know what I'm writing about when I sit down. Sometimes I just pick a couple pictures and try to write long captions for them, and those captions become a couple paragraphs. However the draft gets written, if I don't ship it that night, there's a 50/50 chance I never ship it.

I've always been a night owl. There have been seasons of my life when I've forced myself to become a morning person. It's works for short periods of time. But I just turned 42, and I'm ready to embrace that I do my best creative work after everyone else is in bed.

This wouldn't be feasible if Rachel didn't generously get up with the kids in the morning and let me sleep in. I still am not getting enough sleep, but that extra hour or two has made a huge difference.


The best outcome of this experiment – by far – is a hundred conversations I wouldn't have had otherwise. Every time I hit send, at least of you writes me back. I've connected with more friends in the last six weeks than the last six months. My inbox has been what we wish blog comments were. Lots of encouragement. Life updates. Validation and criticism of my ideas. It's been awesome.

Thank you. Thank you. Thank you.

That also told me y'all were actually reading these things, which made me feel obligated to set some minimum quality bar. In that first post I said, "Some days, it might just be a photo, but I'm gonna hit send." When it came time, I could seldom bring myself to actually hit send on just a photo. If you're giving me a spot in your inbox, you deserve more than that. This isn't your instagram feed.


The first time I broke the streak, my site was down. There was an issue with my registrar that took a ticket to fix, and I had 12+ hours of downtime. I was pretty bummed that night. I wrote a mean draft criticizing my registrar, and almost published it when the site came back up the next morning, but decided to sit on it until the evening.

That day I worked a real-life in-person event for work – with people and everything! – only my second since Covid started. I got back to my room at 1am that night and decided:

1. I don't need to use this space to tear people down. There's enough of that already on the Internet.

2. Tonight, sleeping is more important that shipping.

Those were the first two nights I missed. For most of the other misses, there were similar intentional decisions that, "Tonight, this thing is more important than hitting send." There were also a couple nights where I could have shipped if I had just pushed through. I've got a few posts stuck in the drafts folder.

This has been, by far, the most consistent writing I've done in my life. For context, I've had this blog for ten years and I've shipped a little more than a hundred posts prior to this. I wouldn't have had the motivation to ship 28 more in six weeks unless I knew that people I cared about were reading them.

Thank you. Thank you. Thank you.


It's nearly 2:30 here in New York, on the last night of 2021. The fireworks have quieted down, and I need to sleep. I'll wait until 2022 to figure out what I do here next. For now, I wish you a Happy New Year, and thank you again for going on this journey with me.