Notes on 'Notes on Roadtrips'

What an outstanding piece of writing. I felt like I was riding alongside @joshm in the back seat of the Chevy Tahoe as I was reading it.

So many of the points and asides resonate with me. It’s as if Josh plucked the thoughts and feelings right out of my head and wrote about them for the world to read. I won’t begin quoting them because I will never be able to stop. The entire thing is wonderful and well worth the time.

Even though we start out trying to avoid “5 top line phrases with bullet points underneath”, we end up with some pretty great top line phrases (and some wonderful bullet points underneath):

1. Show up with heartfelt intensity
2. Start with ‘what could be?’
3. Assume you don’t know
4. You’re on the hook for the team
5. Make them feel something

These values (and the stories behind them) are powerful and inspiring. I hope to embody them in my own work at an early-stage startup and carry them with me into future endeavors throughout my life.

Thank you Josh for writing them down and for taking us along with you on some of your road trips.

Apple Watch Ultra First Impressions

I got the Apple Watch Ultra and if I could sum up my first impressions in one word, it’d be: awesome.

The larger and brighter screen, the titanium case, the nice knobby crown, the new alpine band, the increased battery life, the dual-band GPS… I could go on and on. I was already in love with the potential of the Apple Watch platform as battery tech gets better, and this Watch furthers that love. I am enjoying every day with this iteration, and I’m extremely excited for what future iterations bring!

Is it really about pajamas?

Malcom Gladwell recently slammed advocates of working from home on the Diary of a CEO podcast. Among his quotable lines were this one about pajamas:

“I know it’s a hassle to come into the office, but if you’re just sitting in your pajamas in your bedroom, is that the work life you want to live?”

And this great one about belonging to something:

“If we don’t feel like we’re part of something important, what’s the point? If it’s just a paycheck, then it’s like what have you reduced your life to?”

These questions are not only intellectually dishonest, but intentionally reductive.

Forgive the sarcasm, but I have to ask: did you know that you can get dressed for the day when working from home?

Seriously, it’s true. You not only can shower and get dressed without going into an office, most of us did and still do despite having the option not to. And on the days (or weeks) that we don’t, I’m sure we had a good reason to be working in our pajamas or from the bedroom. You know, like the depression and anxiety that comes from a global pandemic affecting life and loved ones.

And taking this one step further, what if someone decides they do their best work in sweats? Maybe that is the work life they want to live, and there’s nothing wrong with it.

And to the point of “belonging” or “feeling part of something important”: I’ve worked remotely for the last seven plus years for three different companies. I’ve been part of important teams and projects for all three, and have contributed at a high level to the success of the companies.

But aside from the fact you can feel that purpose and belonging while working remotely, is it such a bad thing to want your work life to be a means to earning a paycheck? Is it so terrible to derive your self-worth and your happiness from things outside of work? I haven’t “reduced my life to [a paycheck]”, I’ve chosen to maximize my life by minimizing the sacrifices my paycheck demands of me, namely in limiting my commute and maximizing my productivity by controlling my work environment.

So Mr. Gladwell – is it really about pajamas?

Rating movies on a seven-point scale

Years ago, my friend Dave introduced me to a different way to rate movies: a seven-point scale using whole numbers only (no half stars). He goes into detail breaking down exactly why he advocates for it on his blog.

I recently updated my personal site to use the seven-point scale for my movie ratings, and part of the challenge was mapping Letterboxd ratings to a representative number on the seven point scale. So I briefly wanted to note down how I reasoned about the mapping and what I settled on.

I have found that I’m a little on the generous side when it comes to rating movies on a 5-star scale, so I wanted to lower the curve and have a bit more variation at the top of the scale. While 4/5 doesn’t say the same thing about a movie as 5/7, it feels right.

Airbnb announces their ‘2022 Summer Release’

A couple weeks ago Airbnb announced a new remote work program for their employees, and with that CEO Brian Chesky briefly touched upon their plan to have two major releases each year:

The backbone of how we operate will continue to be our single company calendar with our multi-year roadmap. It’s centered around two major product releases each year—a May release and a November release. Even though not everyone directly works on these product releases, we’re organizing our entire calendar around them to maintain company-wide alignment.

The first of these major product releases is now rolling out, and although many on Twitter are panning it as a letdown after Chesky teased that this announcement would include “the biggest change to Airbnb in a decade”, I think the bigger story is that Airbnb is switching up the typical fortnightly “bug fixes and updates” release notes with a strategy to make a bigger splash twice a year.

I appreciate their different approach.