from the ’16 archives.

This is the Week Ahead (WA) format email I’ve been sending out on Sunday nights.

The goal is simple: we all have close friends that we want to stay in sync with and friendly acquaintances we want to bring more into the fold. We all want to hear each other’s thinking.

At first this was driven by the thought that offline 1v1s should really be accelerants to discuss something deeper and wider….with the appropriate context. We waste so much coffee time catching up and asking questions any twitter follower could. And I can barely piece together someone’s mental and emotional state via check-ins, professional tweets, 20 secs of snapchat, etc.

Why couldn’t I just stay in sync with the 5, 10 or 20 parallel lives that I care about most?

We’re all waking up to go to the gym, headed to work, back for event, hanging around at home…but most importantly — what’s in each of our minds and hearts.What are they thinking and scheming, what are they going through, how can I be of help, how can I be excited for them…and vice versa.

So a few months ago, a small cohort just started sending these regular updates (mostly forward looking, lot more candid and genuine that any social media post, life+work) and the result has been pretty incredible.

Here’s a quick note I sent a friend asking why I did this as he didn’t quite get it at first…especially as he saw me in various social feeds.

It’s simple. with no formal rules, just some inspired structure.
— A few personal notes, few professional notes.
— Be candid and real.
— Mix of recap and future looking.
— Not an email newsletter.
— Candid enough to warrant folks not feeling comfortable forwarding.
— Sunday night sends.


A few notes from 12 months of writing.
— It’s an awesome mental exercise to pull up last week’s WA as you construct your current one…simple but refreshing and helpful way remind yourself of what you just were up to and if there are any ongoing trends that need to continue or stop.
— The first WA is always the toughest. It’s a fun question to ask yourself, what 3–5–10 friends are really my true friends…individuals that I don’t have to ask permission to email and who would appreciate this insight into my life.
— Add as many people as you like. Most friends have started with 3–5 bcc’d recipients. Keep adding friends, family members and trusted acquaintances up until the point where by adding someone, you know that you would start editing your writing…mistakes, aspirations, observations and thoughts should be fair game for this inner circle.
— It definitely takes 2–3 WA sessions to have it click in single player mode…the reflection, taking stock of your life and hearing yourself think will become addictive (in a good way).
— Find your cadence. every week → popular, every other week is good too. 1x a month can turn into a chore or too curated of a recap.
— Sometimes there are people who have similar DNA and interests as you….who you become digitally friendly (calls, emails, tweets) with….but you haven’t met yet because you happen to live in two different cities…sometimes the WA is the best way to level up that relationship.
— Ever feel compelled to grab drinks and catch up with a friend when you’re visiting in their city? Natural and good feeling. But why do we need to “catch up” when each of us is on our phone or computer 12hrs a day? Just send 10 sentences each week and you’ll feel like connected best buds year around. That rare coffee, beer or dinner should go in deep, funny, creative, vulnerable, random directions…not “how’s life”, “how’s everything?”, “you like your job?” and “seeing anyone?”
— Once you start receiving WAs from close friends, you’ll start to realize seeing their snaps, reading their tweets and liking their FB photos almost becomes icing on the cake…maybe even optional. Their curated and select social media is really rooted in the 5–10 bullet points they share you with on Sunday nights.
— No one is too close to not receive a WA from. You will be completely surprised by just how much more there is to learn about and listen to from your roommate, best friend, and significant other.
— Some people like to start counting weeks at the bottom of their note. #Week1..#Week2..etc helps slow down life a bit.
— Similar format to the WA to explore. The Elephants. Five Things I’ve Learned Since Becoming an Elephant.
— If you want a social out and simple description, the bit below has worked well.

Description to potentially include:

What is this email?

A Week Ahead email is something a few close friends and I have been experimenting with the past few weeks. Great way to stay connected, potentially be helpful and just have a nice awareness of what one is doing or thinking about if you didn’t grab coffee or read a few tweets.

Think of it as a quick, intimate and fun stand up amongst your inner circle.

It’s kinda like seltzer…you gotta try it twice before you realize it’s awesome.

That’s it.

building NYC products and teams. // 🗣 w/ modern friends. big heuristic guy.