App-etizing

I remember, years ago, reading (possibly in the excellent Design of Everyday Things?) about an architect who designed a college campus without any paved paths between the buildings. Instead, he simply planted grass everywhere, then came back a year later, and paved over the grassless paths worn down where people had actually walked.

I was thinking of that story this morning, as I looked at my phone. As I wrote about recently, I tend to work best when I can sit down and focus. But, sadly, my schedule is too fractured, and (even with my best attempts at streamlining and focusing) my to-do list too long to make everything fit. So, this year, I’ve been trying to do more on my phone, wedging tasks into the interstitial chunks of my day. I journaled on the subway ride to work this morning, for example, and I’m banging out this post on the small screen while on a quick afternoon coffee break.

As a result, I’m suddenly using a bunch of apps that I hadn’t regularly before. Which meant it was probably time to rearrange my home screen.

But rather than my normal approach – trying to plan the theoretically perfect layout – I’m instead taking a page from that college architect: each time I use an app, I drag it to the top left of my home screen. I’m planning to keep it up for the balance of the week. After which, I should have my apps organized by actual priority, sorted into the paths of my real-world daily use.

Photo coming once that’s done. I’m curious to see how it ends up.

Streaking

For years and years, I managed my to-do list in a collection of text files. And, as a dyed-in-the-wool nerd, that worked excellently for me. I leaned on my text editor and a series of scripts to slice and dice with ease.

But as my daily schedule changed, my device usage did, too; I found myself away from my laptop, working solely from my iPad and phone, for even whole days at a time. I auditioned a slew of text editor apps, but could never find a way to make things work even a fraction as well as I had before.

So, about five years back, I switched over to Todoist. Its handling of recurring tasks, and its powerful Boolean filters, got me quickly back to where I’d been in my text-file days.

Still, my to-do list tends to be looooong. So, when I decided to make 2020 a year of focus, I knew I needed to bring in reinforcements. Based on a slew of positive reviews, I downloaded Streaks, and set it up with a handful of my most important habits (including counting Pomodoros spent on my big project for the day).

Obviously, four days into the year, it’s a bit early to tell. But, thus far, it seems like it just might be the boost I need to make my 2020 consistent, and consistently good.

The Small Picture

The last year – the last decade, really – was a whirlwind. Though I’m proud of a lot that I accomplished, all too often, I had more plates spinning than I could keep up with. Work projects, hobbies, time with family and friends; it all piled into a to-do list well beyond what I could reliably complete each day. I made mistakes. Things I cared about, things that I claimed in the abstract were priorities, in practice regularly fell by the wayside. (Cf., my erratic blogging schedule here.)

So, this year, this decade, I’m doing my best to triage. I’m trying to do less, better. I’m paring down my list, focusing in on those things that really matter to me. And, hopefully, I can then do those at least slightly more consistently in the days and weeks and months ahead.

Wish me luck.

Re-Saddling

Well, that went less well than I might have hoped. Precisely eight weeks back, I posted a short entry here, in an attempt to get back to blogging regularly. But, as the ensuing gap makes clear, my intentions didn’t exactly pan out. Still, optimism reigns supreme, and I’m giving it another go.

One persistent issue of late has been the ‘where’ of my work. As I mentioned in the past post, my work schedule has been kind of bananas. On many weekdays, I’m at work by 6am, and don’t depart until 8pm or later. During which, a ton of my hours are taken up training clients one-on-one, or meeting with colleagues about Equinox or Composite stuff. And though that leaves me with pockets of free time throughout any given day, they tend to be relatively short – two hours at most, rather than the long stretches of ‘maker time‘ I find most effective for diving deep into thoughtful work. So, to make the most of those brief gaps, I’ve tried to work wherever I already happen to be at the time – usually either the personal training office or the staff lounge of Equinox’s 53rd St. location.

The problem is, my colleagues are there, too. Most of whom are smart and talented and enthusiastic, but also extremely young. Whereas I’ve been fitness-ing professionally for more than 15 years. So I inevitably get peppered with a ton of questions: what movements should you emphasize or avoid when programming for a pregnant runner? Are there any good exercises or best practices in rehabbing tennis elbow? How do you help someone who repeatedly starts each week with a renewed commitment to eating healthfully, then falls off the wagon completely a few days later? And, actually, I love nerding out on those kind of topics. Plus, I’m naturally chatty, and I genuinely enjoy being helpful. So I get dragged into conversations, eating up one pocket of free time after another.

I came into work this weekend, both for a couple of training sessions, and to try and catch up. On the way in, to avoid the crowds around the nearby Rockefeller Center Christmas tree, I took a slightly different route from the subway than I usually walk. And I discovered along the way that there’s a New York Public Library branch just a block and a half from the gym. Which, in fact, is where I am now. And where I’m hoping to be during at least one or two of those pockets of free time each day for the balance of this week. With luck, hiding out here, where I don’t know anybody, and there’s nothing to distract me (aside from my own brain, and the admittedly alluring shelves of books), will be enough to help me squeeze out a little more real work each day. Hopefully, just enough to make room for daily (or, at least, semi-daily) blogging time, too.

Fingers crossed.

Wave Theory

My father is a lung doctor, but his sub-specialty is diving medicine; if you get the bends while Scuba-diving in much of the Pacific, you’ll get medevaced to Stanford so you can see him.  So, while I was growing up, we spent nearly every summer venturing out to various islands, and I spent a large part of my youth floating and swimming in tropical waters.  (Rough, I know.)  Anyway, one of the main things I learned from that, early on, is that you can’t really fight the surf.  If you want to swim to shore, and there’s a decent swell, it’s nearly pointless to paddle while the water is pulling against you.  Instead, to make it in, you need to calmly tread while a wave draws you towards its face, and then paddle like hell as soon as it reaches you, so you can ride the wave’s momentum toward the shore.

And, in a lot of ways, I’ve found that’s how life works, too.  Sometimes, the waves are pulling against you, and you just need to tread.  But that’s also when you’d best get ready, so you can get as much forward motion as possible out of the paddling once the time is right.  It’s a cycle I’ve lived through countless times.  And yet, even so, each time I’m stuck treading, I feel like maybe I’m stuck for good.

In a lot of ways 2018 has been a treading year.  Or, at least, it has been in terms of external productivity.  From an inside perspective, it’s been perhaps the most meaningful year of my life – a chance to take a hard look at myself, and to really figure out who I am and who I want to be.  But what it hasn’t been is a year of doing, a year of making things, or of making things happen, in the broader world.

In the last few days, however, it feels like all of that self-excavation, and a ton of concurrent plan-laying, is now finally coming to its natural conclusion.  It feels like maybe the wave is just starting to pull me up its face.  It feels like 2019 is going be a big year of forward momentum, a year of happily and productively paddling like hell.

Surf’s up.

25

Since my freshman year in college, I’ve been using more-or-less the same approach to setting goals: I start from 25-year big-picture ones, and then trace backwards from those to 10-year, 5-year, 1-year, 1-quarter, and 1-month goals in turn.  Then, each Friday, I chart out the following week, figuring out what I need to accomplish over the next seven days to stay on track towards the 1-month goals, knowing that in turn keeps me aligned all the way back up.

Through the years since college, I’ve started companies and worked in jobs across three or four different industries, garnered a ton of life experience, and weathered ups and downs of all sorts; that, in turn, has often shifted my shorter-term goals.  But the longer-term ones—the 25-year goals in particular—have stayed remarkably stable.  So much so, in fact, that the last time I really re-thought them from scratch was when I was about 25 years old.

A month back, I turned 39.  In my usual style, I spent a bunch of my birthday thinking about the year behind and the year ahead.  And it suddenly dawned on me that, when my next birthday rolled around, the putative date for those old 25-year goals would then be just 10 years off, becoming my new de facto 10-year goals.  Which meant, in turn, that I needed a new 25-year set.

Starting from 40, those 25-year goals would take me all the way to 65.  And though I suspect I’d likely be one of those guys who never retires, I would hope by then to be at least well on my way towards leaving whatever legacy or positive impact I can on this world.  So, I’ve been spending a little bit of each day thinking through exactly what I hope that legacy or impact might be, what goals I’d like to set that make me push and stretch for the 25 years that (hopefully) lie ahead.  Much like the effective corporate BHAGs – big, hairy, audacious goals – described in the classic study Good to Great, I’ve been looking for goals that both excite me and slightly scare me.  And I have some, by now, just starting to take shape.

Still, I’m giving myself all the way until the end of this birthday year before I call them final.  If I’m hoping this set holds equally steady for the next 25 years, that probably requires at least a full year’s consideration up front.

Taking Stock

My freshman year at college, neck-deep in starting my first company, I got an early taste of worrying about work/life balance.  How much time should I spend on the company, I wondered, versus on classes and homework, or on boozing, socializing, and pulling crazy pranks with friends?

At that point, I had also just re-read Lewis Carroll’s Alice in Wonderland, and I still remember being struck by the exchange between Alice and the Cheshire Cat.  When Alice asks the Cat for directions, he asks her where she’s headed.  “I don’t much care where,” says Alice.  To which the Cat replies, “Then it doesn’t matter which way you go.”

With that in mind, I set out trying to envision an ideal future life, a clear sense of where I wanted to end up, so that I could choose the right roads going forward.  By the time I turned 50, I asked myself, what did I want to be doing?  What did I want to have already accomplished?  Who, really, did I want to be?

To keep things structured, I broke my life down into four broad categories: Work (the things I did for a living, and to make a broad impact on the world), Play (things I did just for my own enjoyment, like writing, playing music, or travel), People (friends, family, and eventually building a family of my own), and Self (mind, body, and spirit).  And, for the better part of a year, I tried to work out a vision for each of those areas that seemed right, that excited and inspired me.

It’s now some 20 years later, and though the age of 50 has inched closer (I’m now just 12 years off), my vision has changed surprisingly little over that time.  Which is excellent, as those long-term goals serve as the basis for my short-term planning, too.  I work backwards from them to 5-year goals (where do I need to be in 5 years on a given goal, to be on track to hit the overall goal by 50?), then to 1-year goals.  And then I translate those, in turn, into either habits for the year (like daily meditation, a monthly museum visit, or a quarterly weekend trip) and projects (big but finite things, like building the Composite client app, which I sort into a long ordered list, then knock off by focusing on one at a time for the first couple of hours of my day).

Most days, I can just get down to work, knowing that, if I stick to those projects and habits, I’m on track to my longer-term goals.  But twice a year – once on my birthday (which happily falls on the middle of the year, in July) and once at year’s end – I stop and take stock.  I look at the big picture.  If I spend the rest of the year climbing the ladder as quickly as I can, those two times, I pause to make sure the ladder is on the right wall.

I start by reviewing my goals – the age 50 ones, as well as the 5 year, 1 year, and project/habits that stem from them.  And then I take a careful look at where I am right now.  During the week between Christmas and New Years, I write in-depth reviews of the four areas of my life – Work, Play, People, Self.  For each, I summarize where I stand, how I fared the past year.  And, for each, I give myself a letter grade, and then see if I need to make any tweaks to my upcoming projects and habits to do better in the year ahead.

Sure, it’s a pretty wonky and time-consuming approach.  But as the world basically shuts down this week anyhow, it’s easy to fit in.  And, for me at least, it pays dividends in purpose, productivity, and sanity for the next twelve months.

DUMB

Over the weekend, I attended a workshop that, at one point, covered the SMART Goals framework: good goals are Specific, Measurable, Achievable, Resourced, and Time-Limited.  I’ve seen the SMART rubric about a thousand times before, and there’s good research that backs it up. But, increasingly, new research – and my own experience, as long-standing readers here are doubtless sick of hearing – indicates that, for many of the things we want in life, habits are actually more powerful and effective than goals.

Goals work best when they’re essentially big projects, with discrete endpoints.  Let’s say you want to rebuild your grandfather’s WWII motorcycle.  Great!  That’s a perfect goal, as it breaks neatly into sub-goals, then into doable tasks in turn.

But imagine, instead, that you want to write a novel, lose 30 pounds, learn Spanish, or run a marathon.  For any of those pursuits, it’s less clear what sub-goals look like, aside from just smaller versions of the same thing (write half a novel, lose ten pounds, etc.).  As a result, those kinds of projects often yield better to just regularly chipping away.  To take the first example, a more effective approach might be to write three pages today, then three pages tomorrow, and then three pages the day after that.  In other words, a novel-writing habit.

So, goals have their place, as do habits.  But while goals have a snappy acronym (SMART!), habits don’t seem to have gotten similar love.  To give them a fighting chance, I took the liberty of coining them a framework of their own: The DUMB Habit.

To illustrate, let’s look at a habit you hopefully already practice – brushing your teeth – as well as a few other examples.  Off we go:

First, a good habit is DURABLE.  In other words, it’s something you could still be doing, productively, six months (or six years) down the line.  That’s the primary factor that differentiates a habit from a goal.  For your grandfather’s motorcycle, you might need to polish the rust off the fender today, but in a few weeks, that task would neither be needed or relevant.  Whereas you can brush your teeth tonight, and you can brush them in ten years; you can do it for however long you have (and want to keep) your teeth.  So, for example, to keep my Italian sharp, for years I used Google news to find and read one or two of the day’s top articles in Italian each morning.  It took just a few minutes, but it forced me to use the Italian part of my brain intensively, in a real-world sort of way, and kept the language fluent.  As long as there was still news in the world, and Italian papers were still publishing, the habit remained DURABLE and evergreen.

Second, a good habit is USEFUL.  Or, put another way, a good habit has a payoff high enough to warrant the time spent on it.  Why do you brush your teeth every morning and night?  Because you’d strongly prefer not to lose those teeth, or have them turn black, riddled with cavities.  To that end, four minutes daily seems a reasonable price.  Weighing the value of habits is important, because while each is often small in isolation, as you take on more of them, they start to pile up.  It’s surprisingly easy to reach the point where you’re spending two hours out of each day on the full stack.  If all of your habits are worth their weight, great.  But it’s also worth occasionally auditing them, just in case some are no longer as relevant. Though I read those Italian articles for years, per the prior example, at some point, without any trips to Italy coming up, without any Italian speakers in my daily orbit, and with a lot other work on my plate, I decided it simply wasn’t worth the time, and I let that habit drop.  But, whether it’s an old habit or a new one, the calculus is the same: a good habit has to have a future payoff big enough to warrant the daily commitment of time; a good habit has to be USEFUL enough to sustain.

Third, a good habit is MEMORABLE, in at least one of two ways.  A lot of habits benefit from having a ‘cue’ – a place, time, or triggering event that reminds you to enact the habit.  Most people brush their teeth as soon as they get up, and right before they go to bed.  Wake up => brush teeth.  An easy, memorable cue.  Other habits, however, are inherently more amorphous.  Let’s say, for example, that you want to cut back on your drinking.  I’ve had a number off friends successfully achieve that by instituting a ‘glass ceiling’: they set a hard rule that they stop after two drinks in a given day.  (Some even count from midnight to midnight, so if they’re out partying into the wee hours on a special occasion, they can hit four drinks – two before midnight, and two after – by ‘using up’ the following day’s drinks.)  Obviously, there’s no specific magic to the ‘glass ceiling’ rule, but the name itself is stupidly catchy and memorable. “Sorry, I can’t have another, I already hit my glass ceiling” is somehow easier for your brain to latch on to – both as an explanation to others, and as an explanation to yourself – than just ‘I should cut back.’   So, whether your habit is tied to a cue, or has a name/catchphrase that lets you rehearse the idea in your mind, a good habit is MEMORABLE enough that you actually remember to do it at the right time.

Finally, a good habit is BEHAVIORAL – it’s a simple, concrete action.  You shouldn’t have to puzzle through what to do when the time comes; instead, you should be able to jump in and get to work.  Tooth brushing?  Put some paste on the brush, add some water, then scrub for two minutes.  Voila.  Whereas something like “eat healthier” isn’t really a clear habit.  Tomorrow, when you sit down for breakfast, you still may not know what to eat.  What is the specific action there?  That’s part of why, in my experience, intermittent fasting (or “IF”) turns out to be an extremely effective and sustainable diet approach for many people.  IF is based around a single, simple behavior: when you would normally sit down for breakfast tomorrow, don’t.  In short, after your last meal of the day, wait a minimum of 14 hours for women or 16 hours for men (I’ll spare you the long, hormone-based rationale behind the different numbers) until you eat again the following day.  Let’s say I finish dinner at 9pm.  Great; then I don’t eat until lunch the next day at 1pm.  That’s the whole thing.  But, miraculously, that has a slew of health and body composition benefits.  In other word, it’s a simple, BEHAVIORAL solution to the thorny problem of a healthy diet.

So, DUMB: Durable, Useful, Memorable, Behavioral.  If you’d like to make a change in your life, see if you can get there with a new habit that fits those four criteria.  Ironically enough, it’s a pretty smart approach.

Single File

In Bird by Bird, Anne Lamott’s wonderful book on writing, she explains the title with a simple anecdote:

Thirty years ago my older brother, who was ten years old at the time, was trying to get a report on birds written that he’d had three months to write, which was due the next day. We were out at our family cabin in Bolinas, and he was at the kitchen table, close to tears, surrounded by binder paper and pencils and unopened books on birds, immobilized by the hugeness of the task ahead. Then my father sat down beside him, put his arm around my brother’s shoulder, and said, ‘Bird by bird, buddy. Just take it bird by bird.’

And, indeed, that works for nearly any kind of project. The whole might be overwhelming, but you can invariably break it down into a series of successive projects (and sub-projects and sub-sub-projects) each small enough that you can confidently take them on.

I’ve long taken that approach to goals, working backwards from five-year (or 25-year) endpoints, to one-year, one-quarter, and one-month waypoints. With that groundwork, I can then focus on just what’s in front of me today, yet know I’m still making progress on the big picture.

Yet I’ve also learned that there’s such a thing as too much sub-division.

Previously, I’d continued all the way back to one-week and one-day breakdowns, starting each day with a list of small tasks across a number of different projects. But because I’d chopped those tasks so fine, I ended up spending my day essentially serially multi-tasking. I never got to spend long Deep Work / Maker Time blocks on a single project.

Now, I stop my breakdown at the month level, then sort the resultant project list by urgency / importance. And each day, I focus only on one single project, the one at the top of the list, for at least the first few hours of the day, before dealing with daily habits (like blogging and emptying my inbox) or small one-off tasks.

Sometimes, it will be the same project for days on end. And though I initially had some anxiety about that – felt like I was leaving the rest of my projects unduly on the back burner – I can now empirically say, having just analyzed a year’s worth of my completion rates with both approaches, that I get waaaaaaaay more done when I take this single-file approach.

In other words, take it bird by bird. But take it by the whole bird, not by the beak and leg.

Zero

I’ll admit to being more than a bit OCD in my desire for a clean and organized workspace. But, from my experience with a slew of coworkers over the years, that’s not an entirely unusual trait. Whether wild creative types or precision-minded engineers, at least 50% seemed to feel and think better when their physical environments were tidy and undistracting, with everything in its right place.

So I’m always shocked by those same people’s email inboxes, which inevitably contain thousands (or even tens of thousands) of read and unread emails. I get agita just from the thought. And, indeed, if you’re a clean-desk type, I’d suspect you, too, would feel similar peace of mind from an equally minimalist inbox.

Try it out yourself, with this simple approach.

First, move all the old stuff into a backlog:

  1. Create a folder (or, in Gmail, label) called “Backlog.”
  2. Select every email in your inbox. (In Gmail, select all using the checkbox icon at the top left, then click the “select all conversations that match this search” link that appears to get select those past the first 50 results.)
  3. Apply the “Backlog” label to all of the messages.
  4. Click the archive icon.
  5. Boom. Inbox zero.

Tomorrow, at some point during the day, your goal is to make sure you empty out every single email that has come in after now. If something doesn’t need action, archive it. If it needs a response, fire one away, then archive it. If it requires a non-email task, a longer response than you want to deal with right now, or is waiting on something, make note of it on your to-do list, then archive it. The important thing is that you get back to zero, daily.

Each day, too, pull up the backlog folder / label, and process part of the way through, starting at the top, the same way you would with the inbox. In my experience, that’s usually faster going, as an increasing percentage of the stuff no longer needs a response as you work backwards. If you have years of stuff in the backlog, once you make it a few weeks (or a month) back, you can probably just archive the balance, as there’s unlikely to be anything active, and if there is – and it’s still important – they’ll email you again.

And that’s it. That’s the recipe for inbox zero. It even works repeatedly if you fall off the wagon, and need to declare a new backlog / need to start again fresh in the future. All you have to do is make your way back to empty again each day, with only a day’s worth of incoming stuff.

People seem to think this requires extra work, but it definitionally doesn’t; if you’re going to respond to an email eventually, it takes the same amount of time regardless of when you do it. So you might as well do it within 24 hours. It’s great to feel on top of your emails. And, as I said, if you’re a neat-freak, the degree to which an empty inbox soothes / allows you to focus on real work is an order of magnitude better than a clean desk.