Saul Bellow on the news

Saul Bellow - It All Adds Up

I can’t remember exactly why I bought this book but several years ago I picked up a collection of Saul Bellow’s essays, It All Adds Up: From the Dim Past to the Uncertain Future. The title of an essay caught my eye — “The Distracted Public” — so I read it last night. Bellow’s comment on the news could have been written yesterday:

I confess that like millions of others, I still need my news fix daily. Civilized people evidently find it necessary to maintain, inwardly, a high level of excitement and are apt to feel that their vital forces must be replenished by headlines.

So it’s politics and murder, famine, planes exploding in flight, drug wars, hostage taking, the latest developments in the superpower drama. The average duration of a scandal or a disaster is not long, and since terrible events are presented by networks whose main focus is diversion, entertainment, quick change, we are always en route to the next shock. It is the agitation level that matters, not this or that enormity. And because we can’t beat distraction, we are inclined to join it. A state of dispersed attention seems to offer certain advantages. It may be compared to a sport like hand gliding. In distraction we are suspended, we hover, we reserve our options.

It’s a good essay largely about the role of the writer in lifting the rest of us above the “moronic inferno” (what an evocative phrase!) of modern life. Notably, this essay was written as a speech that was delivered in 1990, long before Twitter, long before Fox News, and long before the commercial Internet we know today. A lot has changed since then but maybe not as much has changed as we thought.

Six months with the Apple Watch

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Six months ago, I bought an Apple Watch. I had been doing some research for a talk I gave to a local economic development group in my hometown (“Technology, Craft, and Local Economies“) and had somewhat of a throwaway line about how we’ve gone from supercomputers that send people to the moon to computers that we wear. I did some Googling and came upon stories about Apple Watches saving lives. This expensive watch suddenly seemed a lot less inexpensive so I took the plunge somewhat half-heartedly since I’ve never been a watch person. The specific model I bought was the Apple Watch Edition GPS + Cellular, 42mm with Gray Ceramic Case (Series 3).

You can find deep reviews of the Apple Watch with a simple Google search so I’m just going to list some of the things I like most:

  • The watch. This is really mundane but a watch is really useful for my coaching work. I go to the client wherever they are. Some rooms have a clock and some don’t. As I started coaching, it seemed awkward to check the time on my phone. I didn’t want to be the guy digging in my pocket to check the time while a CEO was in the middle of explaining a difficult issue. At the same time, I have to keep myself and the client on schedule, so a watch is unusually helpful for the work I’m doing. The alarm on the Apple Watch is unobtrusive and I can use it to buzz when we have 5-10 minutes left in our session to make sure I focus on wrapping up and closing any remaining loops without interrupting the flow.
  • Heart monitoring. I mentioned the “Apple Watches saves lives” stories above that first caught my attention. A friend recently had a surprise diagnosis of Atrial Fibrillation (AFib or AF) after a trip to the emergency room with some unusual symptoms. He told me about the Apple Heart Study at Stanford. You install an app on your watch that looks for irregular heart rhythms and if you have one, the app will connect you to a doctor for further monitoring. I ran the app for weeks before getting an “all clear” from it. The Apple Watch can detect hypertension and sleep apnea. On a more mundane level, because your heart rate is being monitored whenever you wear the watch, you learn a lot about what makes your heart beat faster or slower. Jack Dorsey found, for example, that testifying in Congress raises one’s heart rate. In the initial period, I started to understand how mundane activities (taking stairs, running for the open subway door) affected my heart rate and how much cardiovascular exercise I was getting when I wasn’t officially “working out.”
  • Activity mindset. The “close your rings” mentality baked into the watch is incredibly motivating. If your rings aren’t closed for the day, you get a friendly alert (example: “A 5-minute brisk walk will close your Move ring.”) Quite often, I’ll jump up and walk around the living room or maybe around the block. On days when you close the rings early, it feels great. Some mornings I close all but my “stand” ring by 9am and I feel like I am truly winning at life.
  • Sleep tracking. Sleep tracking is an inexact science and there are lots of articles out there about why wearables aren’t completely accurate but in my experience they seem at least directionally accurate so you can see improvements even if the baseline isn’t exactly right. I’ve been using the Apple Watch to track sleep using AutoSleep. I wear the watch when I’m sleeping and it has helped me understand my sleep patterns better than I ever have. For a while, I would note anything unusual I did before going to bed and wake up to see how I had slept. For example, just one or two drinks in the hours before bed killed my deep sleep completely. Late dinners did the same thing. On the nights with no alcohol and a relatively early dinner, I got high quality sleep. I figured this out after a couple of months and I have never been more rested and aware of how specific behaviors affect sleep. I had always heard this but seeing it reflected in data from your own body is much stronger evidence.
  • Consistent workout monitoring. I try to go to the gym regularly and tend to use the elliptical machine and stationary bike. As anyone who does this knows, the calorie and heart rate readings you get on these machines can vary widely. With the watch, I just go to the Workout app on the watch and choose the activity and the watch takes care of the rest (and with WatchOS 5, automatic workout detection kicks in and the watch just “knows” what you’re doing). I used to take a photo of the screen on the workout machine when I was done and enter the numbers into a spreadsheet for tracking but now I just let the Health app keep track of it for the most part (though I still regularly dump the data from the Health app into a comma-delimited file using the QS Access app)
  • The ability to leave your phone at home. I have the version with cellular service built in so I can put my AirPods in my pocket, leave my phone at home, and run an errand without worrying about missing a call or a text.
  • Waterproof. You can wear it when swimming (I wore it in the ocean this summer) and in the shower.
  • Control volume on a Sonos from the shower. This seems almost silly but I LOVE this feature. I have a Sonos in the bathroom and I listen to music in the shower. Sometimes you just want to turn a song up and if your watch and the Sonos are on the same wifi network, you can do that by turning the knob (aka the “Digital Crown”) on the side of the watch.

When I bought the Apple Watch, I wasn’t sure I would like it. Six months later, I love it. I feel more informed about my day-to-day health and that has unquestionably made me healthier. I’m not sure how I lived without it.

A book that changed me: A People’s History of the United States

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Today is Columbus Day, a holiday that makes me think of one of the books that changed the way I view the world in a truly fundamental way (and a book not without its problems, which I note below). I first read this book when I was 19. The first pages were startling in their framing of Columbus’ “discovery” of the “New” World. From the outset, Columbus’ arrival is told from the natives’ point-of-view — something I had never considered up to that point:

Arawak men and women, naked, tawny, and full of wonder, emerged from their villages onto the island’s beaches and swam out to get a closer look at the strange big boat. When Columbus and his sailors came ashore, carrying swords, speaking oddly, the Arawaks ran to greet them, brought them food, water, gifts. He later wrote of this in his log:

They . . . brought us parrots and balls of cotton and spears and many other things, which they exchanged for the glass beads and hawks’ bells. They willingly traded everything they owned. . . . They were well-built, with good bodies and handsome features. . . . They do not bear arms, and do not know them, for I showed them a sword, they took it by the edge and cut themselves out of ignorance. They have no iron. Their spears are made of cane. . . . They would make fine servants. . . . With fifty men we could subjugate them all and make them do whatever we want.

These Arawaks of the Bahama Islands were much like Indians on the mainland, who were remarkable (European observers were to say again and again) for their hospitality, their belief in sharing. These traits did not stand out in the Europe of the Renaissance, dominated as it was by the religion of popes, the government of kings, the frenzy for money that marked Western civilization and its first messenger to the Americas, Christopher Columbus.

Columbus wrote:

As soon as I arrived in the Indies, on the first Island which I found, I took some of the natives by force in order that they might learn and might give me information of whatever there is in these parts.

The information that Columbus wanted most was: Where is the gold?. . . .

. . . Columbus’s report to the Court in Madrid was extravagant. He insisted he had reached Asia (it was Cuba) and an island off the coast of China (Hispaniola). His descriptions were part fact, part fiction:

Hispaniola is a miracle. Mountains and hills, plains and pastures, are both fertile and beautiful . . . the harbors are unbelievably good and there are many wide rivers of which the majority contain gold. . . . There are many spices, and great mines of gold and other metals. . . .

The Indians, Columbus reported, “are so naïve and so free with their possessions that no one who has not witnessed them would believe it. When you ask for something they have, they never say no. To the contrary, they offer to share with anyone. . . .” He concluded his report by asking for a little help from their Majesties, and in return he would bring them from his next voyage “as much gold as they need . . . and as many slaves as they ask.” He was full of religious talk: “Thus the eternal God, our Lord, gives victory to those who follow His way over apparent impossibilities.”

From here, the book’s nearly 700 pages cover American history all the way through the Clinton presidency. The book has its critics, like Stanford University School of Education Professor Sam Wineburg:

He says that Zinn’s desire to cast a light on what he saw as historic injustice was a crusade built on secondary sources of questionable provenance, omission of exculpatory evidence, leading questions and shaky connections between evidence and conclusions.

I’m not a historian so I can’t comment on the accuracy or inaccuracy of specific parts of Zinn’s book. From a layman’s perspective, though, the opening of the book appears to quote primary sources (Columbus’ logs) so I feel comfortable setting aside the core critique at least for this section. Zinn’s work has been so politicized that I looked for other sources to corroborate his point-of-view on Columbus’ arrival and found this story from the Smithsonian which also includes quotes from Columbus’ logs:

Columbus had no doubts about how to proceed, either with the lovable but lazy Arawaks or with the hateful but industrious Caribs [the Arawaks’ enemies]. He had come to take possession and to establish dominion. In almost the same breath, he described the Arawaks’ gentleness and innocence and then went on to assure the king and queen of Spain, “They have no arms and are all naked and without any knowledge of war, and very cowardly, so that a thousand of them would not face three. And they are also fitted to be ruled and to be set to work, to cultivate the land and to do all else that may be necessary, and you may build towns and teach them to go clothed and adopt our customs.”

It’s so easy to get into political/cultural wars when discussing these subjects but I think going in that direction can obscure an important lesson that should be universal. My takeaway from reading Zinn is that we can’t recognize Columbus without also telling the story of the Arawaks, even though it makes us uncomfortable. History provides no blank slates. In modern times, when we talk about the hot “new” neighborhood in town, we must also recognize and honor the people who have been displaced. When we lionize CEOs in the business press, we have to also recognize the stories of the workers in their companies and in the supply chains that enable their businesses.  It’s not always comfortable but any honest history should tell the whole story, and I’m grateful to Howard Zinn — even with his flaws — for opening my eyes to that perspective.

Blogging vs. Twitter

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Chris Shiflett and I were talking recently about blogging and how Twitter had sucked some of the life force of it out for both of us. Ideas that might have become blog posts were getting distilled down into 140 (and then 280) character tweets and something was lost in the process. Chris came up with a “tweet only links” philosophy (with some important exceptions) and I signed on. This is the essence of why in Chris’ words:

I’ve been blogging for more than 15 years, but I blogged far more in the first 5 years than in the 10 years since. While there are many factors, I think joining Twitter drove the decline of my blogging habit more than anything else. Now, if I have something to share, I’ll write a sentence or two on Twitter and be done. Twitter lets me scratch the itch.

If I have something to share going forward, my hope is that this commitment will compel me to blog about it. If I can’t take the time to explore a thought by blogging, I should link to someone else who has. Twitter can still be great for spreading ideas, but it’s not a particularly good home for them.

I love Twitter and have been using it since January 2007. It’s good for banter and (as Chris notes) spreading ideas but the core ideas have to live somewhere. As well-crafted as some tweet storms are, they essentially disappear into the ether after the signal-boosting stops. In June, I wrote a 14-part tweet storm about how to become a foster parent:

 

Unless you were watching me tweet on that day and were interested in becoming a foster parent at that moment, this tweet storm faded into the ether. It felt good to write and perhaps it inspired a person or two to take action, but it’s not a way really get the word out in a durable way. If I had blogged about it (and maybe I should), there’s a pretty good chance my post would show up in a Google search. I know this because after blogging for fifteen years, I still get emails about years-old blog posts but almost never get engagement on tweets that are more than a few days old. On Twitter, twelve hours ago is deep in the past and yesterday is ancient history.

I’m going to try to be more mindful about how I use Twitter vs. when I write things down in a blog post. There’s part of me that thinks we would all be better citizens of the web (and the world) if we adopted the philosophy that Chris laid out. We would have to think more about what we’re saying, string thoughts together more coherently, write them as if they will live on forever, and really commit. We would waste less time writing important but transient content that gets shoved aside in a matter of hours. We could write without worrying about Twitter’s policies or changes in the algorithm or the inability to change our minds by editing our original thoughts. We could fully own what we say in every sense of the word (this, of course, assumes blogging at a domain you own and Fred does a good job of explaining why that’s important).

It’s a totally selfish wish, but I also would love to see some of the dynamic new voices I see pouring their hearts and minds into Twitter write more long-form content in blogs. We need those voices and I worry that their considerable talents are muffled by putting so much work into content that is designed to be transient on top of all the work of defending yourself on Twitter. Twitter is a great complementary tool to writing and online engagement but it’s not the end unto itself if you want to create long-lasting, durable content on the web. I’m going to try to remember that going forward.

Comments are disabled. Feel free to respond my tweet about this post on Twitter.

Image credit: Todoran Bogdan

 

Oklahoma! at St. Ann’s

Oklahoma! cast

I serve on the board of St. Ann’s Warehouse in Brooklyn and it’s one of the most gratifying things I do. I’ve been involved since 2014 but have gotten much more deeply involved over the past 18 months. Live theater can be an antidote to so much of what ails society right now — one of the few remaining shared experiences in an on-demand world. Studies have shown that the shared experience of live theater is so powerful that it can synchronize strangers’ heartbeats. I have such respect and admiration for Susan Feldman, who as the artistic director for St. Ann’s has been bringing amazing theater to NYC for almost 40 years now (here’s a nice profile of Susan in the NY Times in 2015). Seeing each season develop from “we’re thinking about bringing this to Brooklyn” to the actors on the stage on opening night of a show is an incredible experience. Every production starts with major risks and obstacles that must be overcome and there’s a real “show must go on” mentality to the work.

This season kicks off this year with Oklahoma! (tickets) which the NY Times listed as one of five shows to see in NYC this October:

From the story:

The version that St. Ann’s Warehouse is presenting at its Brooklyn home (through Nov. 11) was first seen in 2015 as part of the Bard SummerScape series north of the city. Directed by Daniel Fish, it is not only inclusive but also communitarian, featuring a dark interpretation, a diverse cast, an immersive staging — and a chili dinner during intermission.

I saw early sketches of the staging at a board meeting several months ago and “immersive” is right. I won’t spoil it with more details but check out the huge photo in the NY story mentioned above. And, yes, there is the chili dinner at intermission.

The show features Rebecca Naomi Jones, who plays Laurey and was profiled in the Times yesterday:

Whether you love live theater or just want to try something new, go check out Oklahoma! Tickets are on sale now. See you at the show.

 

The role of blogging in my life

I recently read Fred’s post about his fifteen years of blogging and tweeted about why I admire Fred’s blog:

I think of Fred as an “old school” blogger, and that’s a compliment. He prioritizes writing regularly over polish. His writing is idiosyncratic. Some posts encapsulate decades of hard business lessons, some posts are about deeply personal milestones, and some posts are about last night’s Mets game. Occasionally, Fred just posts a video. Some posts are mundane and some are revelatory. I like this style of blogging because it gives you a broad sense of the actual person behind the blog, not a lopsided view based on a specific professional agenda or personal interest. I wish more people blogged this way.

I realized after reading Fred’s post that I, too, had been blogging for 15 years in one place or another and writing publicly for 17 years, and that got me thinking about the critical role of writing generally and blogging specifically in my professional career and personal life. (This is a long post because I had never really thought about it in totality!)

2003-2005: My InfoWorld column and the dawn of blogging (for me)

Most people know me through my work at Etsy (and maybe even Yahoo!) but before all that, I  had a “real” writing gig. I joined InfoWorld in April 2001 as CTO doing actual CTO work but when they noticed I had an English degree and decent writing skills, they asked me if I would write a column for CTOs. At the time, the CTO was their prime target audience. I signed up to write a weekly column at InfoWorld called “CTO Connection” (somewhat still findable via Google) that ran from June 2001 to August 2005.

I had never done anything like it before. For 4+ years and 200+ columns, I had a strict weekly deadline to deliver 580 words to the copy desk — strict word count and deadline because the column was published in print (it had to fit on the printed page) and the presses rolled at a certain time whether you were ready or not. (I never missed press time because you simply did not miss press time!) I came up with the topic every week based on what was going on around me and never really lacked for topics to write about. The words came easy some weeks and some weeks were excruciating. I built a passionate reader base at the time and regularly got fan mail and a good dose of hate mail (one known trick for creating a fury was to criticize Apple). My boss was occasionally cc’ed on the emails, particularly the ones where a reader said my column was so off-the-mark that I should be immediately fired both from my writing gig and my operational CTO gig. The feedback was constant and I learned a lot from it, not the least of which was how to handle constant, sometimes aggressive critique from the outside world while staying focused and keeping my head on straight. This came in really handy later in my career.

My real blogging career began in January 2003 when I launched a blog at InfoWorld (part of IDG) as a way to break out of my word count restriction, respond to points raised in reader mail, talk about random things of interest that popped up, and connect to the CTOs who were reading my weekly column.  Remnants of it are available at the Wayback Machine. I jumped right into blogging with no fanfare or even recognition that I was blogging. My first post was about benchmarking Apache. My second post was about a redesign we did and how InfoWorld was now running on Linux on cheap Compaq DL360s (and I mean really cheap — we bought them for pennies on the dollar from the partly-IDG-funded Industry Standard when it imploded not long before. I personally unloaded them for our sysadmin’s van.) Notably, those first two posts were on a Saturday and Sunday, which was truly radical for what had been a weekly print publication: no gatekeepers, no copy editors. The words went straight from my head to the blog. (Incidentally, Blogger was acquired by Google just a few weeks later, so it was a heady time for blogging.)

I continued blogging and even started a podcast at the very end of my time at InfoWorld (around spring 2005) though it only ran two episodes before I left for Yahoo. In the two episodes I produced (I did all the recording, production, and editorial), I would talk to a working CTO about their work and then some unique interest, often shared. With my friend Jon Williams (then CTO at Kaplan Test Prep), we talked tech and a little about playing guitar (here’s the mp3). And in the second episode with Mike Dunn (then CTO of Hearst Interactive), we talked about surfing (though this episode is sadly lost to history). I developed a lot of productive and fun personal relationships with CTOs in every industry during that time, from startup CTOs to Fortune 50 CTOs, and I still keep in touch with many of them. None of that would have happened without the writing gig. I learned that writing publicly can help build long-term relationships.

2005-2008: A special time at Yahoo! and finding the love of my life

When I joined Yahoo in summer 2005, I announced it on my new blog on my personal domain. One of the things I learned from my time at InfoWorld is that owning your own domain was the only way to truly own your voice forever and my new personal blog was the recognition of that. Yahoo! also had an astoundingly liberal personal blog policy (PDF) that was more or less “anything goes” at a time when a big media storyline was “Person gets fired from company for blogging,” like this one. While I was at Yahoo, I ran the Yahoo! Developer Network and posted on that blog, too. Even in my corporate blogging, I tended to obsess over both the content and the headlines (like this one: “Smells Like Dunkirk Spirit” about the travails of a Yahoo Hack Day in London that was weirdly interrupted by storms that caused it to actually rain indoors). Still, my personal blog output dwarfed what I put into the corporate blog. My fairly regular personal blogging from that period turned out to be a nice historical archive of some really interesting times at Yahoo. What seemed like mostly a side hobby then has become a treasured record of a special time for me, professionally and personally. I’m grateful that I took the time to do that, and on my own domain. When a book came out several years back that featured a detailed chapter about that time at Yahoo! and my and others’ roles in it, those posts also came in handy to help me recall some of the best stories and anecdotes from that period. And during that period I captured the two best stories of all: getting engaged and ultimately married to the then and still love of my life.

2008-2011: Moving to NYC and being CTO at Etsy

In 2008, my friend Caterina Fake (herself and “old school” blogger) introduced me to the Etsy team and, long story short, I announced I was leaving Yahoo! and going to Etsy to be their CTO in July 2008. You can see my excitement at moving to NYC, an excitement that has not waned even a little in the decade of being here (as I quoted John Lennon in that post: “what a bad-ass city!”) There was a companion post on the Etsy blog (then known as the Storque!) and a couple of weeks after I started in September 2008, my first communication with the Etsy community as CTO was also on the blog (executive summary: things were in bad shape and we had a lot of work to do). It’s easy to look back at Etsy today and see its success as obvious and pre-ordained but it certainly didn’t feel that way when I wrote that post. The site was crashing more or less daily at the time. In the macro world, Lehman Brothers infamously collapsed into bankruptcy just the day before that blog post. I had been in NYC for two weeks and had just stopped sleeping on an air mattress when my boxes arrived from California. There was a part of me that thought I had truly terrible timing — why did I move to the center of the collapse of the financial system for this? My memories of that time were less of the “I’m so excited about this challenge!” variety and more “what have I gotten myself into?” Reading that first post today, I can feel the underlying anxiety of the time — how many incoming execs use a “ticking time bomb” metaphor in their inaugural posts to their customers? But I was glad to have a blog where I could tell the truth and start to get to know the community. The blog was a great vehicle for that kind of writing and blogging was a really natural form of direct communication to me at that point.

We had a big rebuilding job to do at Etsy and blogs came to the rescue in another way. We used a blog called fix.etsy.com to communicate during outages, which were very frequent when I first arrived. Ironically, the first major outage happened the day after my “ticking time bomb post” and fix.etsy.com itself was down so we had to bring that back up quickly to even be able to give updates on the main site outage (this moment is preserved in the Wayback Machine). Thank goodness that one of the beautiful things about a blog is you can get it up and running and start publishing almost immediately. I was at a bar with an important recruit during that first outage and was excusing myself regularly to manage the situation from the bathroom. (The recruit must have thought I had a medical problem giving how much I was going to the bathroom.)

In my first year or so, we had to take the site completely down for 4-6 hours per week almost every week to fix some core issues (as mentioned here), and fix.etsy.com was the critical line of communication. The tone of fix.etsy.com was very much “just the facts” (“8:00am: Etsy is currently unavailable and we’re working on it”) but I felt genuinely bad about what the community had to endure during that period so we tried to make the pain at least a little more entertaining. Back then, Hulu had a bunch of free movies you could embed on web pages and I noticed The Godfather trilogy was available, so I once raised the idea of offering parts 1 and 2 on the “we’re down for maintenance” page for the simple reason that they had an almost even six hours run time. We had a lot of time to fill while we did the work and people get bored waiting. We smartly decided that Etsy seller videos on a loop made more sense. Even this simple status blog had a community feel. When one of our key ops engineer’s wife went into labor, we had to cancel scheduled downtime and posted the news and a baby photo on the blog. The Etsy community of sellers could be tough but always with an underlying sweetness and I remember this moment being celebrated. (Celebrating the birth of a baby on an announcement about site outages somehow so perfectly captures the Etsy ethos of the time).

As engineering started to gain momentum, the constant firefighting started to recede into history and we had more interesting things to talk about than just keeping the site up. In February 2010, we conceived of and launched the Code as Craft blog (still running strong) when I published the first and second posts along with the About page. In the early days, I acted as kind of an editor-in-chief and encouraged engineers to write the kinds of posts they wanted to read and I promised we wouldn’t put it through a PR filter. Every engineer had a distinct voice and I wanted to bring it out. I was also being very pragmatic. I knew the blog could be a great recruiting tool and that engineers can smell bullshit 1,000 miles away. We kicked off the Code as Craft speaker series later that year with Fred Brooks, one of the legends of computer science. The work we were doing, the blog posts with the voices of real engineers, the amazing speakers, and the work itself was a key driver of the recruiting flywheel we built at the time. The Code as Craft talks sold out in minutes, people had fun and learned a lot when they visited the office, and everyone we interviewed seemed to come in knowing what we were all about just by reading the blog. Code as Craft turned into a very strategic recruiting tool for the company. It was also really fun and a badge of honor and rallying cry for engineers on the team. When I left my CTO role to take on the CEO job at Etsy, I passed the engineering torch to Kellan and John on the Code as Craft blog and entered the next chapter.

2011-2017: Being CEO at Etsy during a time of massive growth

Enter blogs again. When I made the transition to CEO, I announced my new role on the Etsy company blog with a story about Mary Haggerty, an Etsy seller I met in an unlikely place. Then I continued to post various updates throughout the years that mark key moments of my six years as CEO — a period where Etsy grew immensely by every qualitative and qualitative measure you can think of. Etsy used to publish a “weather report” with key company data so I’m able to see in the archives that in my first month as CTO at Etsy (September 2008), everyone was excited about breaking the $300,000 sales mark in a single day and $7.93 million in goods were sold that month. By the time I left in 2017, our run rate was ~35x that. During that period, I wrote a guest post about recruiting and culture for Fred’s “MBA Mondays” series on his blog. Generally, though, I found it harder to write as regularly as a CEO, but I did find a little time to write, like this post where I had a key insight about Peter Drucker and culture change that was just dying to get out. And once you’re leading a public company, your communications as a CEO and duty to a variety of stakeholders make any communication from you potentially fraught (just ask Elon). That made the off-the-cuff, no-gatekeeper style of blogging that I enjoyed much more difficult so my personal blog went largely dormant at the time.

When my time was up at Etsy, I wasn’t able to say any final words via Etsy channels but the archive remains and I’m grateful to be able to look back and remember how the company developed and grew in the nine years I was there, from my “what have I gotten myself into” early days of intense tech pain to leading a publicly-traded company (its own kind of pain but I think of it as perhaps more noble “pain at scale.” Ha. Sort of.) It was an extraordinary time in my life and every day I think of some new reason to appreciate my time at Etsy.

2017-present: Going solo. . but not really

Post-Etsy, I was professionally unaffiliated for the first time in my working life. The most common question I got was “what are you going to do next?” My blog had been largely dormant but I had still been maintaining the domain. I realized that the blog gave me a means to (in more traditional PR terms) “put out a statement” to answer the “what’s next?” question once rather than answer it a bunch of times in email. So I wrote a blog post and tweeted it out. It felt good to have no gatekeepers again. Then I updated the post in September as my sense of what the next stage of my life was going to look like came into focus. I haven’t really been “solo” during this period as much as I’ve been working differently, i.e. not just for one organization but for many. Since my “what’s next” post I have developed a nice coaching practice working with Reboot and have been enjoying being closely involved at Cornell Tech (got some interesting stuff brewing there – stay tuned). I’m more active in my non-profit board roles at St. Ann’s Warehouse and The Jalopy Theater and School of Music. I have been able to spend time doing the deepest thinking and reflecting of my life and have a backlog of things to write about. I started a newsletter last year that went dormant when the coaching business suddenly took off so I might get that going again. We’ll see.

So much of online writing today is about short-term “hot takes” and pursuing claps and virality but I’ve learned over seventeen years of writing publicly that one of the key benefits of writing online is that it supports your own memory.  A blog post provides a contemporary voice — yours — from a specific moment that doesn’t generally allow you to either glorify or denigrate lived history any more than it deserved at the time. It’s life as it happens. Blogging is also a way of laying the groundwork for the path ahead and creating virtual checkpoints to later reflect upon to get a sense of the progress you’ve made. That’s a long way of saying that I think I’ll be doing this for a while longer.

Writing this post made me realize again how valuable archive.org is to the Internet, so I made a donation. If you feel the same way, here’s how to donate.

 

Advice to CEOs: digging out from a jammed calendar

My friend Lara Hogan published an email I had sent to her way back (“Advice for a new executive“) and it turned out to be super-helpful to a lot of people based on the engagement with her tweet about it. In a similar spirit, I’m publishing a previously-private email I sent to a startup CEO who was asking me for tactical guidance on how to dig out from a jammed calendar that he felt was preventing him from thinking strategically and focusing on bigger things. I was asked for similar advice multiple times since then so time to publish. I think this advice is generally useful to managers at all levels. Below is what I wrote, with only minor edits.


First, make sure you are prioritizing your core CEO duties first. I think Fred does a good job of articulating what those are in this post. In short, 1) keeping everyone on the same page with vision and strategy, 2) recruiting, and 3) making sure you have enough money in the bank (fundraising and revenue activities).

Some questions to ask:

  1. Are there meetings where you feel like you’re doing someone else’s job that isn’t filled? (example: you’re doing the work of VP of Engineering in addition to your CEO duties) If that’s the case, focus on filling that role. Start with the one that will give you the most leverage and save you the most time. The difficult part is that it is MORE work to fill a role than to “just do it” sometimes but waiting only means your life will suck longer.
  2. Are you holding meetings to compensate for the weakness of someone on your team? (example: you attend sales-related meetings that really should be run by VP of Sales but you don’t trust that person to do the meeting the way you want, so you attend).  Apply appropriate pressure on your VP of Sales to do the job (and I’m specifically referring to the “feel pressure / apply pressure” concept that Ben Horowitz has written about). If you don’t feel confident in that approach, it’s probably time to put a plan together to replace that person ASAP.
  3. Are there meetings you attend that you can delegate fully to someone else? Are there any high-performance people on your team who could take on more responsibility? Make that happen.
  4. Are you having any 1-on-1’s that aren’t essential? Everyone will want to spend time with you but make sure any 1-on-1’s are a good use of time for YOU. Kill the ones that aren’t a good use of your time.
  5. Are the meetings you have useful with clear agendas and followup items? (Nothing wastes time like useless meetings) This HBR article (“How to Design an Agenda for an Effective Meeting“) is a useful framework to evaluate whatever you are doing now. It outlines an overall approach and includes a sample agenda. Also see Ken Norton’s post “Meetings that don’t suck.”
  6. Do you have any recurring meetings that have outlived their usefulness? Kill them.
  7. Are there projects/initiatives that are low-value but take up a lot of your time? Consider killing them.
  8. Are you leveraging your executive assistant to the fullest? Do you have the right EA? It’s a bit of work but I suggest the “quarterly time analysis” that Matt Blumberg talks about in this post about how he works with his EA. The post overall is useful. Over time, you can teach your EA a rule set to enforce the way you want to spend your time.

Sometimes you’re just in a period where things are going to suck and you’ll be working a lot of hours for some period. You want to minimize the length of those periods but sometimes it’s unavoidable to have a packed schedule. In those cases, the best you can do is try to get a good night’s sleep every night, eat well, and exercise. Good luck!