On Wonder

[Reader note: This song randomly came on while I was writing, and I think it's a pretty apt tune for this post. So if you'd like the full multimedia readership experience, listen as you read.]

When I first moved to San Francisco, I was literally entranced. I'd be jogging at night, or meandering around neighborhoods on a Saturday afternoon, and I'd say to myself: "I can't believe this place actually exists." It was like some writer had taken all of the ingredients of a perfect town - beauty, friendliness, affluence, an accepting culture - and literally wrote it into reality.

When I would visit Chicago, or Minneapolis, or Ann Arbor, people would ask me what I thought of the west coast, and I'd whip out my shit-eating grin and brag about how I lived in the greatest city on Earth. I knew I was coming off like a smug little prick, but I didn't care. I felt awed, and at home, for the first time in a long while.

Unfortunately, as I've noticed with elevating unease, the feeling didn't last. As with many things that change slowly in our personalities and attitudes, I only discovered this in retrospect. It's getting close to two years since the cross-country move, and a significant portion of my earlier wonder has eroded away.

Granted, I expected this. It's a common pattern that I've witnessed in life (mine, at least). You enter a new environment (a new job, perhaps, or the start of college) with gobs of both excitement and inexperience. As time goes on and experience rises, the sense of wonder begins its inevitable dissipation.

I imagine this is why people tend to bounce around hobbies or vocations, riding an initial wave of excitement just long enough for the sense of newness to run its course. As experience rises, the effort still needs to be spent, but we don't have a reserve supply of wonder & earnestness to propel us through the tough spots. This could apply to living in a major city - we still have to wake up every morning and live our lives, despite greater disenchantment with city life over time - or to mastering a skill like playing the guitar. It sounds sexy and exciting at first, but once we open our eyes to how many hours it takes to become a rock star, vigor evaporates, but the unlearned chords remain.

So how to do fight this pattern? Do we even want to?

Since this is a blog, and I'm basically just talking to myself here, I'll propose a solution to my own question. If everybody who developed a skill or became ingrained in a community faced the kind of perpetual malaise that I described above, then nobody would stick with anything long enough to get good at it. There must be something that replaces the euphoria of inexperienced wonder. That thing is competence, or expertise.

If you stick with something long enough, interesting things start to happen. For one, you actually get good at it. You pick up nuances that are imperceptible to outsiders. You stop making rookie mistakes. You realize that you're part of a community of like-minded people. You gain some confidence that, hey, I know a thing or two about this.

With that comes the satisfaction of someone who's survived apprenticeship. And when that happens, some of the wonder comes back. It's not the same as it was in the beginning, but it's a little more sincere and a little less naive. It's like the entertainer who enters the industry dazzled by the challenge and spectacle of it all, conquers disillusionment, and one day assumes the deep fulfillment of a veteran.

So, yeah: maybe I'm no longer awestruck during my twilight jogs through Pacific Heights. And maybe I've stopped calling my parents every few days to relay some city-life minutia like a freshman who can't believe he's actually going to a real-live frat party. But at least I'm starting to get it. And like anything we want to improve at - playing a sport, building a profession, or becoming a better husband - that comes with its own satisfaction.

The "Stick With What Works" Fallacy

How many times have we heard this before:

If things are going well, just stick with what works. Don't rock the boat.

Probably plenty. But I don't believe in this maxim anymore. Instead, I think: success can lead to complacency. Success hides problems. Just because it seems to be working doesn't mean that you know why it's working, or if it is at all.

At Kace, we had an unbelievable run of success... something like 27 quarters of consecutive revenue growth. And that was great -- everybody is extremely proud of the work we did. But the one big important thing we neglected to do over that timespan was parse out exactly where we were truly being effective, and where we were just riding a current propelled by our partners and the market. When that inevitable missed quarter appeared, we finally got around to the self-examination. And we found that there was a gap between what we thought we were good at, and what we were actually good at.

From Fred (this doesn't apply exactly to the Kace example, but the major point is the same):

One of the things I have observed over the years is that a hard charging sales oriented founder/CEO can often hide the defects in a product. Because the founder is so capable of convincing the market to adopt/purchase the product, the company can get revenue traction with a product that is not really right. And that can hide all sorts of problems.

Be skeptical of your accomplishments. Dissect them. Disprove your company myths. Figure out where you actually performed well, and where you were just lucky (or particularly persuasive). Only then should you begin to feel comfortable sticking with what works.

Key Metrics

Two Cal Newport articles, one from 2009 and one from last month, both tackle the topic of narrowing focus to a pinpoint and only considering feedback specific to those specific goals.

An excerpt from the first post (which I highly recommend reading):

We soon hatched a plan. He would forget the random advice he’d been receiving from various friends and hangers-on — the suggestions to hand out demo CDs in front of radio stations or network to meet the right executives. Instead, he would turn his focus solely onto the Pyramid Club. He would return to the open mike again and again until he was able to win over that crowd. After that, he would progress to the showcase and play to win.

Our logic was simple: if he couldn’t become good enough to win over the Pyramid Club crowd, he couldn’t become good enough to attract industry attention. So why waste energy doing anything else?

And the second, more recent post (also a great read):

My above experiment sweeps these compelling sounding ideas off the proverbial table, and replaces them with an approach backed by data. What matters, it tells me, is something we can call: quality cited papers. In more detail, how many papers per year are you publishing that: (a) are in quality venues; and (b) attracting citations? 

This metric can tell me if I’m improving or not from year to year. Similarly, it provides clear feedback on which of my research directions should be dropped and which emphasized. When deciding whether to join a project, for example, I should start by estimating the expected impact on my quality cited papers value for the year. When deciding whether to apply for a particular grant, the same question should guide the decision.

I take the combined message as follows: be extremely deliberate when it comes to goal-setting, and be just as deliberate about choosing key metrics for tracking progress. We want to have as few key metrics as possible, and we want each one of them to be practically synonymous with goal achievement.

Let's take strength training as an example to illustrate the point. Say I want to become stronger, so I buy a gym membership and starting lifting weights three times a week. Pretty soon I devise a training plan and start tracking my performance on a variety of different exercises: pulldowns, biceps curls, leg extensions, dips, crunches, etc. Each workout I attempt these exercises in whichever order the machines are open, sometimes but not always making it through the entire list. Generally my performance improves, more or less, but the gains are uneven and hard to decipher. Sometimes I do so well on the chin-ups that I can barely perform a curl, and other days I save my favorite exercise for last but find that I've completely run out of energy to do a single rep. It ends up being pretty discouraging because I seem to be moving backwards at something every single workout.

Contrast that with the "key metric" approach: the only metric that I'm going to monitor closely will be the squat. Squatting is the most intense and important full-body strength exercise there is; being able to squat a lot of weight is practically synonymous with strength. You can't squat 400 pounds with a weak core, inflexible legs, or an underdeveloped chest, arms, or posterior. Everything that I consider doing within a strength-training context will be judged against the question of "will this help me increase the amount of weight I can squat, or not?" So, yes, I'll continue to work on increasing my bench press and chin-up numbers, but the squat is the only exercise that 1) I will consistently perform during every single workout, at the very beginning of the lift session, and 2) I will mercilessly demand a personal record from myself each and every time. If the numbers keep going up, then my strength is undeniably improving; all other metrics are just noise.

Attempting to track (and thus allow yourself to potentially panic - or gloat - over) every single quasi-relevant metric is like congratulating yourself for ordering a Diet Coke to go with a 1,200-calorie large buttered popcorn. The key metric is "calories-in-calories-out", not "fructose calories avoided." Remember that in a dynamic system anything that optimizes the sub-parts tends to sub-optimize the whole.

Here's a couple other examples of Key Metrics:

• Cardiovascular fitness: Is my five-mile run time decreasing month over month? NOT: how tired am I after walking up stairs, how fast can I run 100 meters, am I groggy in the morning...
• Work output: Am I increasing the number of high-quality projects I complete each month? NOT: how many hours am I spending in the office, how many random compliments or kudos I receive during the day, how large my most recent raise was...
• Pretending for a second that I have my dream job as an NFL General Manager: Are we increasing the ratio of production to salary expenditure over time? Notice how the very best NFL franchises tend to eschew pricey free agent acquisitions in favor of value and upside. The Baltimore Ravens' GM is clearly not measuring himself against the "how many aging veterans can I re-sign to placate our fanbase?" metric.

Contrast that approach with the Philadelphia Eagles over the past few seasons...

Right Now

Much of our thinking is consumed by the future. Delaying gratification; contriving plans; toiling away in the darkness while eroticizing the image of ourselves as we may one day be.

I've done plenty of this myself: "One day I'll be confident and experienced and rich enough to ask that girl for her number." Or: "Sure, that's a great idea for a company, but I should really gain a few years' more experience before I take the leap." And even: "Even though I was planning on taking that six week work trip to western Europe, I have more pressing work here now, and in any case I can always do it another time."

I'm not ready. I'll be way more equipped to accomplish that later. I don't feel comfortable trying until I know I'll succeed.

What bullshit. It's like a hazing ritual, and you're the pledge.

Not that I begrudge the concept of putting in the reps. Grit and hard work are essential. This isn't about turning down that Saturday night party invitation because you're consumed with finishing the first draft of the next great American novel. This is about turning down that Saturday night party invitation in order to stay in and fantasize about how you're going to totally crush it at the party next week.

We're so wrapped up in who we want to become that we forget to live right now. Think about the very best time you had during your freshman year of college. On the morning of that day, you woke up feeling just like you did this morning. Now it's crystallized past, just like today will be when you're seventy. How many things did you postpone at age 18, telling yourself that you would be ready to do them when you're 25? And now that you're 25, are you still telling yourself that you'll be ready by age 30?

Trust me on this: You are ready right now. If not now, then when?

Some additional thoughts on the subject follow. From Brett & Kate:

Memento mori is Latin for “Remember death.” The phrase is believed to originate from an ancient Roman tradition in which a servant would be tasked with standing behind a victorious general as he paraded though town. As the general basked in the glory of the cheering crowds, the servant would whisper in the general’s ear: “Respice post te! Hominem te esse memento! Memento mori!” = “Look behind you! Remember that you are but a man! Remember that you will die!”

And:

It at once becomes starkly clear the great tragedy in always waiting for your life to begin. If you wait for your life to start, it never will. This is your life, right now. Whether you’re in a college dorm room, or your first apartment, or a brand new house in the burbs. Whether you’re single, dating, or married. This is your life. Whatever it is you want to do, whatever it is you want to change about yourself, whatever it is you want to see and feel and experience in this lifetime, you can’t put it off until your life begins or it will never happen. Get started now.

From Cal:

Am I living well now or preparing to live well later?

If you’re not trying to live well now, what are you waiting for?

And from Seneca (via Tim):

You will hear many men saying: “After my fiftieth year I shall retire into leisure, my sixtieth year shall release me from public duties.” And what guarantee, pray, have you that your life will last longer? Who will suffer your course to be just as you plan it? Are you not ashamed to reserve for yourself only the remnant of life, and to set apart for wisdom only that time which cannot be devoted to any business? How late it is to begin to live just when we must cease to live! 

The fool, with all his other faults, has this also, he is always getting ready to live. 

On Fame

This weekend in Chicago I had an opportunity to eat dinner with some very famous people. It was nothing planned on my end; more of an invitation extended, and accepted, and the next thing you know it's seven hours later and the combined Twitter follower count at the table is well into 8-figures.

Meeting famous people is a funny thing that tends to be both overwhelming and underwhelming at the same time. For one thing, people who look extremely handsome on TV are, in fact, extremely handsome in real life. And they do often possess that swagger, or gravitas, that comes from perpetually inhabiting the center of attention. And despite the aphorism that "famous people are always way shorter than you expect," some, in fact, turn out to be gigantic.

On the other hand, there's the underwhelming/humanizing aspect of the encounter. Even famous female pop stars eventually have to take a crap after a few days. Not to mention a few other funny things I just saw famous people do: hold awkward eye contact, lose their phone in a public bathroom, walk into a chair, trip while getting into a car, tell a lame joke, hold their cigarette like a cornball, and (most intriguingly) eye other famous people with bewilderment.

At the end of the day, the stars really are just like us. The only difference? Risk-taking, luck, and focus.

"Life is a warfare and a stranger's sojourn, and after fame is oblivion." - Marcus Aurelius

Recommended Consumption (March 2013)

• Starting Strength, 3rd Edition by Mark Rippetoe. The Bible of barbell lifting.
• Behind the Book: Lessons Learned and Personal Reflections on Publishing a Bestselling Business Book by Ben Casnocha. Long form article on Ben's experiences writing The Start-up of You, which just arrived in my mail.
• Shut Up and Play the Hits, an awesome documentary film about (and concert footage of) LCD Soundsystem.
• The Fab Five.
• How I Stopped Eating Food. And the follow-up.
• Talent and Production: The Great Emotional Divide, blog post by Matt Waldman. This guy is an unbelievably keen football observer, and writer.

Kevin

Last Thursday I met Kevin, the nicest crackhead in all of the Tender-Nob.

It was 7:45pm and I was just getting back to my apartment at the end of the work day. This was before the Daylight Savings Time switch so it was 100% dark at this point, and both my front and rear bicycle lights were activated. As I decelerated onto the sidewalk in front of my place, my bulbs illuminated a thirty-something man hunched over the stoop at the base of the stairs.

When he first growled something, I didn't totally understand him and figured that he was probably asking for money. Honestly, my first reaction was to tell him to get the hell off of our front porch. I have no problem with beggars but I'd prefer that they don't loiter in front of my place of residence -- we have a hard enough time convincing friends that our neighborhood is non-sketchy.

It turns out that he didn't want money at all: he was asking me to call an ambulance. You see, he explained, he made a very bad decision earlier in the evening. He knew better than to take drugs: they were the reason he was living on the street in the first place. And he had been sober for quite some time, definitely a few months. But that day he decided to smoke some crack cocaine, and now his feet hurt so badly that he couldn't even walk. He asked me, please call him an ambulance so he can detox and receive the treatment & rehab that he really needs.

At first I was a bit apprehensive. My next (completely, entirely non-judgmental) thought was that this would be a pretty clever lead-in to punching me in the face and stealing my cell phone. I went upstairs to fetch Ari to be my second pair of eyes in case this man had nefarious intent. Then we called 911 and arranged for an ambulance to arrive in ten minutes or less.

So we chatted with this guy to kill time until then. It turns out, Kevin (as his name turned out to be) was an extremely nice guy. Or at least as nice as somebody could be while going through a drug relapse. His eyes may have been pointed different directions through the whole conversation, but he wore a fat grin and generously shared the details of his life and how he ended up on the streets of San Francisco.

Eventually the paramedics came, put Kevin in a stretcher, and took him to the hospital. And that was the whole encounter; maybe fifteen minutes at max.

When I started writing this post I wasn't exactly sure how I planned on ending it. Originally I was going to write more extensively about Kevin's past and the tough breaks that led him to the situation he was living through. But even though his story is actually very compelling, it's not my business to spread it. I also thought about comparing the minutia that consumes our days in the San Francisco tech world (viral coefficients and mobile gaming platforms and such) to the suffering of real human beings in the very same city, but that would be patronizing and predictable.

As such, I think I'll just end with this thought: I really, truly, fucking love this city, and I'm trying very hard not to slip into that sort of milquetoast apathy that people get once they're too jaded to remember how fortunate they are to live in a place like this. And that means keeping my eyes open -- not down at my phone, or the sidewalk, or blankly staring off into space pondering god-knows-what.

And that means being grateful. Because we're quite lucky on two levels: one, that we don't often suffer the way Kevin did last week; and secondly, that we're crammed close enough to actually help the Kevins of this world when they need it. If we're paying attention.

A Brief List of Interesting Web Companies

When brainstorming new business ideas, I find it's useful to remind myself that (most of) the best ideas are very narrow in scope. Instead of trying to be all things for all people ("It's a dashboard for managing the intersection of your social, mobile, and real-world lives!"), they just pick one problem or task and find a way to make it 10x easier to solve or accomplish.

To be sure, most companies don't start off this way. It takes a lot of positioning and segmenting work to whittle a company's offering and position down to the ultimate succinctness. But when it actually happens, the effect is like magic.

To that end, I keep a list of inspirational companies that do a great job of this. Here are some recent additions:

• usertesting.com
• DailyLit
• longform.org
• MobileDay
• Yesware
• Voomly
• PivotDesk
• shelby.tv
• InternMatch
• FreedomPop
• Fizzle
• getAbstract
• CoFoundersLab

In addition to the inspirational effect, this list always reminds me that there are a lot of opportunities out there.

Minimum Effective Dose

In part to support my goal of a metrics-driven lifestyle, I've begun rigorously tracking my running performance. One motivating factor is to ensure I'm making progress so I don't waste months spinning my wheels with nothing to show for it. Another is to use evidence of previous improvement to drive myself through tough, demoralizing stretches. And the third reason is to identify my minimum effective dose (MED) for improvement.

Tim Ferriss defines minimum effective dose (MED) as "the minimum dose that will produce a desired outcome." Here's an analogy he uses to describe it:

If you need 15 minutes in the sun to trigger a melanin response, 15 minutes is your MED for tanning. More than 15 minutes is redundant and will just result in burning and a forced break from the beach. During this forced break from the beach, let's assume one week, someone else who heeded his natural 15-minute MED will be able to fit in four more tanning sessions. He is four shades darker, whereas you have returned to your pale pre-beach self. Sad little manatee. In biological systems, exceeding your MED can freeze progress for weeks, even months.

He then uses this in the context of exercise to show how excessive weightlifting does not increase strength over time but rather invites the possibility of fatigue, mental burnout, and injury risk. I've appropriated the same concept to examine my running habits.

Here's the thing: I don't want exercise and fitness to become a primary goal in my life. Since I'm trying to narrow my focus and only focus on a small number of projects at once, treating running like a "big project" will just sap energy from my other intermediate-term goals, like becoming better at my job and learning how to ski. Rather, I'd like it to become a habit that I perform without having to think too hard about it. Therefore, I'm seeking to understand my minimum effective dose for running frequency, which I've defined as "the minimum running frequency that will ensure improvements in proficiency over time." Ignoring for a moment the fact that everybody has good days and bad days, I want to identify the maximum number of days I can allow between runs while still increasing speed and distance each week.

To answer that question, I look carefully at my running logs. Even after only three weeks of tracking this way, I've gained some insight:

• Between my 2/15 and 2/20 runs, my course time (on the same course) dropped from 51:00 to 48:30. This means that five days between runs were sufficient to realize performance gains. My MED is at most a 5-day frequency (meaning that I could probably get away with going 6 or 7 days between runs and still seeing improvement.)
• Due to travel & work conflicts, I went 13 days between my next two runs (2/20 and 3/5). I actually ran a different course these two runs so I can't compare times directly, but I can subjectively state that the run did not go well. My feet felt raw and blistery, I was sluggish, and I felt weak and soft overall. Combining that information with the common-sense notion that "thirteen days is probably too long between runs to see consistent improvement," I can semi-confidently state that my MED is at least a 13-day frequency. So now I know my MED is likely somewhere between six and twelve days, and subsequent runs will be scheduled to measure it more precisely.

It's important to remember that MED will change over time. Incremental improvement eventually takes exponentially more effort (like how I lowered my mile time by 20 seconds last week but elite track & field athletes work for months to shave off fractions of a second.) But the goal is to use MED to schedule runs that ensure improvement without dominating my lifestyle. If, for example, my MED turns out to be 8 days, I'll run once a week until gains start to taper off.

Is this the right approach for marathon training, or to become a world-class sprinter as soon as possible? Definitely not. But I believe it's a reasonable methodology for avoiding effort that does not yield results.

On Focus (and the Law of Complementary Accomplishments)

From one of my favorite posts in Cal's blog:

Once you accomplish something of a non-trivial impressiveness and effort score, you can achieve many complementary accomplishments that have similar impressiveness scores but require very little additional effort.

In sum: success begets success. Once one has achieved something significant and noteworthy, not only will subsequent opportunities appear more frequently, they'll be easier to tackle because momentum & credibility have already been established. In other words, noteworthy accomplishments possess scale advantages.

The trick, then, is to specialize. To maintain a narrow focus in order to burrow deeply into an industry, craft, or field of study. That's the most direct way to get to "significant and noteworthy" territory as quickly as possible.

When I think about particularly successful contemporaries of mine, a few themes emerge:

1. They focused narrowly.
2. They took advantage of complementary accomplishments to catapult themselves into ever-more exclusive opportunities.
3. They migrated to communities dominated by their particular industry.

Here's two examples:

• Andrew is one of my best friends from high school. During the fall of his H.S. freshman year (2002), he volunteered for the political campaign of U.S. Representative Mark Kirk. His responsibilities in that first election were modest: just typical campaign fare like handing out flyers and propping up lawn signs. Kirk won the election, and Andrew participated in roles of ever-increasing responsibility for the 2004, 2006, and 2008 Congressional elections, and then the 2010 U.S. Senate election. By that time, Andrew was one of a small group of full-time paid staff members (he took off a fall semester from Northwestern University to participate in the Senatorial election.) After Kirk won that final election, Andrew moved to Washington to work for the Senator as a legislative aide, where he handled campaign correspondence, met with constituents on the Senator's behalf, and helped craft policy. After gained several years of experience at the Capitol and a letter of recommendation from a U.S. Senator, he left D.C. to attend the University of Chicago Law School.

• Yuriy is a close friend and former roommate from college. He came to the University to study acting after being recruited by many top theater programs around the country. Yuriy spent the first two years of college balancing the life of a frat boy with that of a serious theater student. Unfortunately, after two years of mediocre success at managing these two conflicting lifestyles, he made the difficult but necessary decision to move out of the frat house to a remote corner of campus and dedicate himself to his craft. This single-mindedness paid off with several lead roles in campus productions and eventually a professional role in the Chicago run of The History Boys which necessitated a semester break from college. Yuriy parlayed these experiences into several feature film roles and, currently, a significant recurring role on the NBC TV series Chicago Fire.

It's easy to look at successful peers and say "how on earth did he get a job in the U.S. Senate?", or "I can't believe your old college buddy is on a network television show!" If they eventually become Congressmen or Oscar winners themselves, their accomplishments will seem even more stratospheric and unapproachable. But the truth is that both of these guys -- and most successful people I can think of -- followed a very simple formula to arrive at their present state:

1. Find a unique and challenging role to fill.
2. Remove all distractions.
3. Succeed impressively and unequivocally at that role.
4. Examine the opportunities that now present themselves and pick one.
5. Repeat step 2.

And that's it.

Bottlenecks

About 60% of the way through Startup Lessons Learned, I ran across a particularly interesting quote of Eric's. In the middle of discussing lean deployment methodologies (something that I barely understand but can at least follow loosely), Eric describes the following hypothetical tweak:

Most organizations have their batch size tuned so as to reduce their overhead. For example, if QA takes a week to certify a release, it's likely that the company does releases no more than once every 30 or 60 days. Telling a company like that they should work in a two-week batch size will sounds absurd - they'd spend 50% of their time waiting for QA to certify the release! ...

Imagine moving to a two-week release cycle, with the rule that no additional work can take place on the next iteration until the current iteration is certified.

Okay, I'm with him so far. So the week-long QA cycle is treated like a one week long task in a Gantt chart. That makes the reduction to a two week release cycle seem counter-intuitive. But:

The first time through, this is going to be painful. But very quickly, probably even by the second iteration, the weeklong certification process will be shorter. The development team that is now clearly bottlenecked will have the incentive needed to get involved and help with the certification process. They'll be able to observe, for example, that most of the certification steps are completely automatic (and horribly boring for the QA staff) and start automating them with software. But because they are blocked from being able to get their normal work done, they'll have a strong incentive to invest quickly in the highest ROI tests, rather than overdesigning a massive new testing system which might take ages to make a difference.

Ah-ha. The key bit of insight is: don't assume that task duration is necessarily static. Clever scheduling can apply pressure to drive out waste in a system. When you compress the time allotted to complete a project, your team is probably smart enough to identify and take advantage of opportunities for automation.

(By the way, Eric's original post lives here.)