Learning How To Give and Receive Love

When I announced recently that I was leaving a group I belonged to, there was a huge outpouring of love. People came out from the woodwork to tell me that they loved me and would miss me. A bunch of people even told me something along the lines of, “I feel like I took you for granted because I thought that you would always be around.” It was interesting - if all of that love had always been there, then why couldn’t I feel it, and why hadn’t it been expressed before? I talked to a friend about this, and she noticed something similar when she moved from New York to San Francisco. All of a sudden, there was love coming at her from places she never expected. People were going to miss her, but prior to that moment, they never seemed to care.

So, why is this? I think it’s hard for people to tell other people about their true feelings. There’s some inequality in being vulnerable and telling someone else how you feel about them. What would happen if they don’t reciprocate our feelings, if we tell them how important they are to us, and they respond that we are insignificant to them? We would probably shrivel up into a little ball and die, right there on that spot. So, we do the easy thing, and we don’t say anything. And then other people miss out on knowing how we truly feel about it. And, when faced with a loss, we finally admit to some small part of what we were feeling all along. It seems like a shame that the world works this way.

Recently, I did an experiment for a week where I told other people that I loved them. I just let myself notice all of the little times when I felt love - you know, that warm affectionate feeling in the middle of my chest. And then, if that love was directed at someone, I told them about it. With no expectation of getting anything in return - I was just feeling my own love for other people, and if they happened to have something to say to me, that was fine. Overall, the experiment seemed pretty successful. It didn’t have any overt effects in my life, but it made me feel good while I was doing it. It got a lot more in touch with my feelings, and it made me feel closer to some people who I hadn’t before. 

Another side effect was that I realized how difficult it is for most people to receive love. When I told people that I loved them, and in a way where I meant it, I could see them visibly clench up. There was that reflexive “I love you too” that people used to diffuse the situation. Less frequently, I would get a “thank you,” which sometimes indicated that the message was received and accepted. Most people just aren’t used to receiving love on a regular basis. It’s something that we get every once in a while as a reward for doing something good or trying hard to make someone feel good. But it’s a rare case where someone stops what they are doing and spontaneously gives us love. 

Then I realized something - I find it really hard to have other people love me. Like, not only do I have trouble asking for love from other people, but when people spontaneously start saying nice things about me, I feel my body tighten up. I just want it to stop, want them to tell me that I’m a stupid idiot again (that’s pretty much my baseline self-perception). It’s actually too much for me to accept that others love me unconditionally, without expecting anything in return. I always think of love as being conditional - if I’m good, I will receive love. Otherwise, I’m probably a bad person, and no one cares about me. I never really accepted that people do love me, and that it just might be too much for people to express their love in an open and vulnerable way. That we are desperate for affirmation, but mortally afraid of being rejected.

So, I’m going to propose a game (yes, blog posts can give homework). Think of three people whom you feel love for, and tell them about it. Do it however you want - text, email, or call. While I guarantee that there isn’t anyone out there who doesn’t want to feel loved, use your best judgment, and don’t call anyone who has a restraining order against you or anything. When we are down, sometimes all it takes is knowing that other people love us, and suddenly everything starts looking better. So give three people that gift today, or if that seems like too much, then just do it for one person.

Now here’s the hard one. Call someone up (or text them if it’s too scary), and ask them for love. Sure, you can give other people what they want, but how hard is it for you to ask for what you want?

What I Tell Myself When I’m Depressed

I’ve struggled with low-grade depression for about as long as I remember. It always hits its peak around this time of year, and starts to recede by March or April. Sometimes when I’m in the grips of depression, I have thoughts along the lines of, “maybe the world would be better off if I weren’t around any more.” Never to the point where I would actually do anything about it, but there is that point of despair where life doesn’t really seem worth living, and I seem to hit it once or twice a year. Fortunately, I’ve gotten better and better at managing my mental state over the years. So here’s what I’ve started telling myself when I’m in one of those moods.

First, I look at the consequences of me taking my life. In that case, a bunch of people would probably be sad for at least a little while, so that would probably result in a net negative effect. And, assuming that I the work I do has some positive impact on peoples’ lives (and I have pretty much no doubt of that), then there would be some loss of value if I made a grand exit. So, I can definitively say that I would not make the world a better place by leaving it right now.

Then, I start to do some cost-benefit analyses relative to that point. Let’s assume that I keep on living for the rest of my natural lifespan, and resolve to do absolutely nothing, other than making the minimal amount of income required to sustain myself while doing absolute nothing. This seems like it would have at the very least a net neutral impact, and would definitely be better than killing myself. But that’s pretty much just the base scenario.

Now, let’s assume that I continue to be as miserable as I am when in the grips of depression, but dedicate the rest of my life to serving others. Then, even if I’m unhappy, at least everyone ends up better off (even me). That seems like a better overall outcome than either of the others. And, when I think about that, I realize how lucky I am, and how much I have. And, once I run myself through that exercise, it's hard to keep repeating the same old negative thoughts. And, if I do find myself still running negative though patterns, I just run through the same exercise a few more times, and that inevitably works.

How I Make Difficult Decisions

There’s a decision I’ve been sitting on for the past couple months, which involved making a big change in my life. On one hand I felt like my mind was pretty clear on what I wanted to do, but at the other hand, I kept agonizing over the decision. Back and forth and back and forth. I had all the information, or did I? Every time I came to the brink of making a decision, I made up some excuse for waiting longer. Maybe if I thought about the choice for a little bit longer, I would come to a point where everything seemed crystal clear, and I could jump forward without any regrets. But, strangely, that never seemed to happen.

I feel like I spend a lot of my life in the limbo between seeing decisions and making them. The process starts when I find an important decision looming on the horizon. Do I leave my job for another opportunity? Do I take that new job that’s being offered versus remaining a free agent? Do I go to graduate school? Do I end a relationship that has some good qualities, but that isn’t working out in some way? Do I move cross-country for the promise of a new future? Do I commit to a new activity that will take a large amount of time or attention? At any point in time, at least one major decision always stands in front of me (and the same may be true for you).

There are two major types of decisions in life - the ones that have straightforward answers, and the ones that don’t. A decision with an easy answer will have a single clear upside, and any downsides will feel small and manageable. I’m pretty good with those decisions - I look both ways (sometimes a little too quickly) and then jump (sometimes in the wrong direction). The decisions that tend to trip me up are the ones that don’t have an easy cost-benefit analysis. In making a hard decision, I have to give something up, often in exchange for the possibility of a future payoff. For example, “I’m going to leave my job that pays a lot of money in order to start a new company.” Actually, the previous has been a remarkably easy decision at various points in my life, but it all depends on the circumstances.

The primary tool for decision-making is rational analysis, i.e. “choice X is better than choice Y because of information Z.” The problem is that, with a difficult decision, rational analysis probably breaks down. Choice X and choice Y seem equivalent in some major respect. So I’m not going to reason it out with the information I currently have. Which leads to a few other tactics, namely waiting it out or consulting outside sources.

My usual response when I have a hard decision is to sit on it for a while. At first, it appears that things will get clearer as time elapses, but in many cases they don’t. I get more and more information as I wait it out, but that information is often conflicting, and falls on both sides of the decision. Experience tells me that obsessing about a decision for twice as long will make me about 10% more clear than I was before. And the return diminishes over time. So, if I’m 50% clear on something after 3 days of deliberation, maybe I’ll be 55% after 6 days, and 60% clear after 12 days.

The conclusion is that it makes sense to give myself a reasonable but firm deadline to make decisions. Putting a hard deadline on it tends to work best, since soft deadlines can always be pushed off for later. So, it’s better to make it such that the decision gets automatically made on some particular date if it isn’t made by then. At the very least, that keeps me from obsessing about it ad infinitum. And, if it’s a hard decision, there’s a good chance that either opportunity 

Another common strategy is to ask others for advice (either human or spirit-based advisors). I have a few trusted advisors who seem to make suggestions based (mostly) on my interests. When I have a difficult decision, I usually consult one or more of them before putting anything in stone. But, in general, you have to consider a person's self-interest when asking him for advice. You can’t expect someone to give you advice that contradicts his own self-interest in favor of your own (although, you could make the argument that doing things in others’ best interest will yield a long-term positive effect for you). So, you would never (for example) want to rely on the advice of someone involved with the decision, or whom its effects might impact. Unfortunately, there are many decisions that will probably involve just about everyone in your life (if only peripherally), so it’s better to use other people as a sounding board rather than an oracle.

In the end, it’s important to trust your own gut. There are as many neurons embedded in your stomach lining as there are in your spinal cord, and although that may not actually mean anything to you, it sounds pretty important to me. Regardless, I’ve learned over time that my gut is pretty good at staying in tune with what I really want. So, when I get a feeling in my stomach, that probably means something important is underfoot. For some reason, a negative gut result is probably more accurate than a positive one. If something doesn’t feel right in my gut, then it probably isn’t good for me. However, if it feels good, then I may or may not have all of the relevant information to make an informed decision. I’ve made less than 100% sound decisions because they felt right in my gut, and usually I could attribute this to incomplete information. So, there’s some combination of gut feeling and rational analysis is required.

So, after much reflection, I finally decided to make a decision. I jumped, without knowing what lay on the other end. It felt kind of like jumping off the high dive after spending a long time with my toes hanging over the edge (you know that tingly achy feel). Was there anything worthwhile at the bottom of that pool, or was there just self-doubt? Regardless, with the decision made, I can move into 2014 without looking back (too much).

Happy New Years!

Don't Fight Your War on Two Fronts

One of the most common things I hear from first-time founders is, “we need to launch our new product on every platform at once.” iOS, Android, and web, and maybe mobile web for good measure. I’ve rarely seen this pan out well, especially if launch timeline is a priority. The problem with this strategy is that it’s akin to fighting multiple wars at the same time, each with their own dynamics. In the short-term, it seems somewhat invigorating to solve for multiple platforms at once, and multiple platforms theoretically increase your total user base, but you end up exhausting your resources at a geometric rate. As an early-stage startup, you have extremely limited resources with which to execute your vision. Your most valuable resources are your time and attention, and launching multiple products is going to compromise both of those. Even if you happen to be flush with cash from a monster seed round, you probably have a limited supply of engineering/design/product management, so developing for multiple platforms will take significantly longer than for one. And, if you do manage to successfully build two products at once and get them out the door with no issues, you still have to support and enhance them over time. Which is never as easy as one would imagine.

Ok, you say. “I’ll build a mobile web version. That’s almost like the web version.” Or, even, “we’ll just build a responsive version that works on all screens.” And it’s sort of true, but you are still responsible for building and maintaining multiple separate products. In the case of the responsive app, you have to optimize it for each screen size that you intend to support (go media queries). It’s easier to support two web versions than iOS and HTML5, but only marginally so. I’m currently going through this one myself. After inheriting a product midway through development, it became clear that the customer needed a mobile version. If I were building it, I probably would have gone mobile-only, but the desktop version existed, so I hacked together a mobile-optimized app. But now it comes back to bite me every time that I want to add a feature. I need to setup two different sets of pages, and the UI often needs to be rethought to work on mobile. Each time that I hack together a new feature and it’s ready to go on desktop, I realize that I need to build it on mobile as well (lest the mobile users complain). For some reason, that mobile web version always takes longer than the desktop version, perhaps because I’m resentful about it.

So what’s my recommendation? Pick one - either iOS, Android, or web, and make the experience great. Then, ignore all requests to support an additional platform until you have succeeded on the first platform (with success being defined as having enough resources to focus on the new platform without sacrificing attention on the existing platform). A mobile-only strategy is making more and more sense as smartphones become the dominant platform (if they haven't already become it). A number of hugely successful apps sacrificed desktop support to keep their focus on mobile. For example, Instagram was iOS-only for the longest time (they were acquired before Android launched), and even now, their front page is basically a redirect to the app store. It’s ok to pick iOS OR Android - although potential users will be pissed if their platform isn’t supported, it’s better to provide a great experience for fewer users than to launch a half-baked product that no one really wants. So, resist the urge to branch out - really, and focus on the things that will lead you to success.

Jumping Off The Train

Many of us live our lives as if we are required do to them. Maybe we aren’t obligated to complete our daily routines, but to an outside observer, it would appear so. Here’s a prototype that looks vaguely like my routine at various points. At some time (relatively early in the morning, but not before the sun is up), I wake up, check my emails/text messages, get out of bed, get dressed, eat breakfast and go to work. Then maybe I surf the web and read internet news before getting motivated to actually do some work. Finally I buckle down and work on a project for a while. But before I know it, it’s time for lunch, so I go out to lunch and chat with coworkers for a few minutes. Then I go back to my desk and surf the web before setting into and afternoon routine (which looks more or less like the morning routine). At 7 or so, I feel finished and decide to knock off for the day. Then I have a few hours to eat dinner and do whatever I want before going to bed (probably involving some sort of web surfing or TV watching). And then the next day it happens all over again, five to seven days a week. On some level, it feels like riding a train around and around the track. All that we can do is to keep riding the train, watch the scenery go round and round, and toot the horn every once in a while.

So, here’s a little secret. None of it has to be that way. Nothing is holding us there, other than social pressure. From the moment we are born, we are inundated with programming, coming from our families and from the media and from what we see and hear around us. “You have to have this kind of education, and take this kind of job, and marry this kind of person, and have these sort of things.” So, we continue to do things the way we always did them because that’s how the world works, and those things lead us towards the goals that society programmed into us. It’s possible for us to stop doing those things at any time, but there is a lot of pressure in place, and things get extremely uncomfortable when we try to move in a different direction.

The truth is that plenty of people live a life that looks nothing like yours. Maybe they started out with a life that resembles yours, and made a change. And it’s possible that they grew up with values that led them in a different direction altogether. Some of them follow a routine that happens to be completely different. They ride a different train round and round, and watch a different set of scenery. There are whole communities of people who live their lives completely outside of the parameters that most people would define as normal, but still keep to a precise routine (you can find many such groups in the SF Bay Area). They have goals, but those goals look nothing like the goals that you and I would set. To some degree, these are interesting, because there is so much diversity in what we would call a “normal” routine, but we can go even further.

Let’s talk about the people who choose not to ride the train at all. You need a ticket to get on the train, but no ticket is required to get off and walk. Some people choose to do that - some of them never even got on (as hard as that is to believe). Sure, you cover less ground when you are walking, but you get to stop whenever you want to smell a flower, and you also have the opportunity to notice all of the little details in life. And, whenever you want, you can curl up and take a nap in the grass. Some people don’t even follow a routine - they just do whatever motivates them at the moment. Depending on your lifestyle and choices, you may not need as much money as you think. You would be surprised by the number of people who manage to get by on 10 to 20 hours of sporadic work a week. They don’t have new clothes and cars and computers, and have living arrangements that might offend most peoples’ sensibilities, but somehow they manage to make it work. What they trade off in means they earn back in flexibility.

So the point of this story is that you can do whatever you want. Sure, your mental programming is telling you to stick with your old routine, but at the end of the day, it’s just programming, and that can be overwritten (more on that later). If you realize that what you're doing isn’t working for you, well, you have a lot more power to change it than you think (the alternative is to either stick with something that’s broken or to drop out altogether). So here’s a homework assignment (yes, I assign homework from my blog). Take one thing that you think you need to do, and change it up. Maybe you knock off work early one day when you feel like you’re not at optimal productivity, and go do something fun instead (even for just an hour or two). Or maybe you have an honest conversation with your boss or significant other, and ask for something you want. I’ve been amazed by the power of actually asking for what I want. 

A lot of times, I assume that other people will figure out what I desire and then figure out how to give that to me. But in reality, they often don’t know what I want, and their goals and motivations may be completely different from mine. So, even if they did know what I wanted, it might not make sense for them to give it to me unsolicited. By asking for what I want, I actually tell them where I am, and give them the opportunity to meet me there. And, if they can't give me exactly what I want, maybe they can get me closer. Regardless, asking for what you want breaks down a barrier that once was there.

The Story of My First Startup Failure

When I started my first company, I had it all figured out. Up to that point, things had gone relatively well for me, at least on paper. Undergrad at MIT, a software engineering job at Google, and then grad school at MIT. But the thing I had always wanted is to start a company, create something new. So, when I entered my last year of business school (in Fall 2008), I was ready to do it. I was going to found my own startup.

The first thing you need to start a company is a product idea, and one night when out to dinner with friends, an idea was handed down to me from the heavens (we had a long wait for our table). I was going to replace the restaurant pagers with a system that sends out text messages (suspend your disbelief for the next two minutes). I was in business school at the time, so I went to various mixers for the business plan competition, and found people who seemed excited about my idea. Not surprisingly, I found a few people who might be interested in helping out (one became my awesome cofounder Jeff Shi), and we started hacking together the initial concept. We came up with a decent name (InstantQ), and put together a two-page executive summary that got us to the finals of the executive summary competition. We didn’t win, but it apparently was close. I was well on my way to success as a startup founder (or so I thought).

Our next step involved building a product (your business plan competition entry is much more believable if you have a product by the final phase). So Jeff and I sat down and hacked out a quick prototype in a weekend. The next step was to find someone to sell it. My business plan required a lot of sales, and I sure wasn’t going to do it by myself (I’m a nerd. The last thing I really tried to sell was Cutco in high school, and I didn’t sell all that much). So I went out and found the schlockiest salesperson I could find (to be fair, he was actually a great guy, but he totally rubbed me the wrong way). I didn’t really like him all that much, but based on my totally flawed sales sense, he seemed like he could do the job. We went out one night and got really drunk, and I convinced myself that I could grow to like him. He more or less did his job (at first), and managed to get one restaurant in Cambridge to try out our system for one night. The reception was kind of lukewarm, but hey, it was just an early version, so we were well on our way.

We didn’t win the business plan competition, but we did make it to the semifinals, and got invited to a bunch of dinners and received $1000 to cover some expenses. We also got into YCombinator - Paul Graham actually hated our idea, but we were two nerdy guys from MIT, so we had a lot going for us (we didn’t bring the sales guy to our interview). So we moved out to California and rented a cheap apartment within walking distance of the YC office. Everything was great - we spent a lot of time coding and occasionally went out to the bar to blow of some steam. We were living the startup dream - we had crappy office furniture in our living room, and the walls were covered with shower board.

About the second or third week in California, we realized that we hadn’t actually closed any customers (or gotten anyone to even use our product since The Asgard in Kendall Square tried it for one night), and we probably needed to start working on that. Our sales guy was talking to restaurants, and they weren’t exactly giving him overwhelming feedback. It turns out that most restaurants didn’t have lines out the door on the majority of nights (the economy wasn’t exactly up at the time). So, like good little YC Founders, we went to Paul Graham’s office hours, and he had an idea. “What about a dial that restaurants can use to turn up the supply of customers?” We bought, it, and decided on a two-tiered approach. On busy nights, we replace the pagers, and on empty nights, we give you a marketing solution that you can use to bring back your existing customers.

This time, we tried to take a more customer development focused approach. We walked into restaurants with our laptops, and forced the manager or proprietor to look at our demo. They seemed semi-interested, if we could make them money. We took this as enough validation to move forward, and hacked together something that worked well enough. Or so we thought.

As we found later, the real problem was acquiring customers who would actually pay us for our product. There is a big difference between building a product and building a product that people actually want to pay you money for. It turned out that our sales guy wasn’t so good at selling a product that didn’t exist yet - he was a lot less experienced that we originally gave him credit for. After hanging out with a good friend who has been a pretty good guide over the years, I decided that we needed to let him go, and Jeff agreed. So we cut him loose - he moved back to the East Coast and has done quite well since then.

The conversation the day after we got rid of our sales person went like this. “Wait, we don’t have a sales person any more. I guess that we need to go out and sell now.” So Jeff and I spent the next couple of months going out and selling, and we slowly realized that it wasn’t going to work. Despite initial enthusiasm for the idea, neither us were passionate about selling to restaurants. And, as the rejections racked up, we became more and more discouraged. YC Demo Day came and went, and we hadn’t launched (we never launched publicly because we never had any paying customers). Investors seemed lukewarm at best - we had one or two meetings that went nowhere, and our hearts weren't really in it. To be fair, Fall 2009 was a relatively difficult time to raise a seed round, but we weren’t exactly primed for success.

We talked about pivoting to something else, but we never raised any money post-YC, so finances were sort of tight. Plus, I moved up to San Francisco while Jeff stayed in Mountain View. Paul Graham’s comment was something like “that’s too far - it won’t work.” To be fair, it seemed like we were already drifting apart. I have never taken rejection well, and having two products fail was too much for me at that point. I was pretty much ready to quit after less than a year. We met several times a week to brainstorm ideas, although I remember playing a lot of Farmville (this was right as Zynga started taking off). We initially found some consulting work to tide us over, but we weren't exactly overflowing with ideas to change the world. 

Then a bunch of life circumstances intervened. Jeff’s wife got pregnant with their second child, and he needed a steadier income. My father died suddenly about a month after that, and I was thrown totally off balance for about six months. Both of us decided to bow out of the startup game, although we dragged our feet for a while. I spent about four months working on various projects and dabbling in consulting, but my heart wasn’t really into it (I was still in shock and feeling pretty unstable). In the end, I took a job at another startup that seemed relatively promising, and we shut the company down. Jeff did another startup, and then ended up at Netflix. So that’s it - the story of my first startup. I wish I had more to talk about (like customers and revenue), but hey, that comes later (I’ll tell you about my second startup failure later).

The Power of Attention

I was talking to a stripper recently, and she told me that a lot of guys pay just to talk to her all night. That's it - they come in, talk, and give her money. Some of her clients come in on a regular basis just to talk, kind of like they are visiting the therapist every week or two.  I recently heard a similar story from a friend's trip to Vegas, where an acquaintance racked up a $1500 bill at the strip club by talking to a stripper all night. This is a good looking, cool guy who is engaged to an attractive woman (ok, she's a cold bitch). But yet something was missing from his life such that he would spend over a grand for a few hours of attention. It's interesting that people are so starved for something, and they don't know what that something is, and they think it's physical connection or sex. But once they get that attention focused on them, they realize that attention is what they want, that attention is what they are starving for.

Why can't we get that kind of attention in our everyday lives? To be blunt, most of our interactions are surprisingly shallow. I was recently at a dinner party held by a good friend, and there were only about ten people there. I knew most of the people in the room pretty well. Yet, the conversation stayed at a pretty shallow level. People were trying to say entertaining things, and not to create an honest connection with each other. I actually left feeling more disconnected than when I came, and somewhat disappointed in myself. Mostly because I had expected connection to come to me, rather than trying to create it.

A lot of our daily interactions are surprisingly scripted, with little real emotion or vulnerability.

"Hey"
"How are you doing?"
"Good! You?"
"Great!"
"Nice!"

And, in most cases, neither person is just "good;" there's always something a lot deeper or more vulnerable that we could say. But we don't say it, for fear that we will offend the other person, or seem negative, or tell them too much such that they won't like us or want to talk to us any more. So we stay in the "safe" zone, which actually just isolates even further. And then we end up "hungry," but we can't quite put our finger on what we want. Except that we feel lonely and disconnected.

So why not go to a therapist if we want attention? After all, that's what they are supposed to do; you pay to talk to them. First of all, there is still some stigma around seeing a mental health professional. If I go to a therapist, I am admitting that there is something wrong with me. Plus, whenever I go to a therapist, I feel like they are trying to fix my problems, rather than truly listening to me. "Tell me about your relationship with your parents," they say. And, sure, I want to talk about my relationship with my parents. There are a lot of things that happened while I was growing up that led to me becoming the person that I am right now, and there are a lot of skeletons in that closet. But, right now, I just want to be heard. I just want to feel like someone is listening to me, and cares about what I have to say.

So what's the solution? Our attention is constantly being diverted, and shifted, and pulled off of other people by all of the distractions of modern society. Emails, texts, app notifications, etc…. They are all great, but they constantly pull us out of focusing all of our attention on any one thing. The result is that we end up with fuzzy or diffused attention. One of the most interesting things about going a year without a smartphone was that when I was hanging out with someone, I could put all of my attention on them while we were together (or get them to focus all of their attention on me). We spend so much time "around" other people without actually being "with" them. Right now, I'm writing this blog post as I sit next to someone I know. I'm writing on my computer while he watches video on his iPhone.

So, here's an experiment to try that might create more connection. The next time you are spending one-on-one time with someone, agree to shut off your smartphones for half an hour or an hour and just be present with each other. Then try to focus all of your attention on the other person for 15 minutes, and see what happens. You might be surprised by what happens. And maybe you'll feel some real connection.

The Value of Downtime

Last night, some friends and I were having a conversation, and one person said that she needs some downtime to recover. The response from someone else was, "You don't need any downtime. Look at our friends who work for X Company, who work 7 days a week and just keep going." Unfortunately, I've found this to be mostly an illusion. Sure it looks like they can do it for now, and maybe it will work for months or years, but even the best will eventually burn out (or at least need a rest at some point). First of all, a lot of people find that they aren't at optimal productivity when working that much, and that they can often accomplish more by working less (and being more focused). But, additionally, working 24x7 puts a toll on your body, and pulls you out of the natural work/rest equilibrium. If you love and are engaged by your work, you can manage to push the biggest consequences off for months or years, but eventually you will need to pay off the debt you've accumulated.

I used to have this dream that I would find the holy grail of 100% productivity. In my vision, I would wake up in the morning, eat breakfast, go to work, and progress down my task list for 10 to 12 uninterrupted hours. Then I would go home, read a book for a few hours, and then go to bed (hopefully having lucid dreams where I would figure out answers to some of the problems that arose during the previous day). By doing some controlled experimentation where I got rid of nearly all distractions in my life (more on that in another post), I figured out that this is mostly possible (ok, except for the lucid dream part). And it worked great for about a month or two - I achieved probably 1.5-2X my normal productivity level at work. At 2 or 3PM every day, I would comment that I had already knocked off a full day's tasks, and I still had 3-5 hours left at work. And when I left the office, I have plenty of time to go on a date or read 50-100 pages of a really dense book before finally getting into bed (and I slept great). In the span of a month or two, I knocked off "A People's History of the United States," "The Singularity is Near," "No Logo," and a bunch of others. Basically my entire reading list at the time.

The problem was that it all fell apart at some point. I found myself drifting towards distractions more and more regularly. First I started losing focus at work, and then at home, until I was basically back to where I started (my productivity was essentially random on a day-to-day basis). While this was somewhat depressing, I had a number of interesting realizations about the value of downtime. First of all, it is important for recharging your "focus batteries." Just like sleep recharges your body and brain, downtime recharges your attention and willpower. It's like there is something that you are using up when your brain operates in a structured way, and at some point you will use it all up. If you can regularly go down in a planned and scheduled way, you can make the "uptime" even more productive.

Additionally, unstructured time allows your brain to operate in a much more freeform and creative way. My most creative ideas always come on the tail of a long break. When my brain is too focused on the here-and-now productivity mindset, it doesn't have an opportunity to focus on what could possibly become in the future. However, when I allow it to wander in a controlled manner, it magically use its power to generate all kinds of new things. Which is why, when I hit a roadblock, the best thing to do is usually to take some time off and think about nothing in particular (or take a nap). Strangely, the solution usually emerges relatively quickly.

So we all have two different modes, one that is structured, and another unstructured. If we engage only the structured, then we can't accomplish our highest and most creative purpose, and if we engage only the unstructured. then we probably won't get much done. The challenge is figuring out creative ways to allow both to emerge. In the end, I don't want to be 100% productive. I just want to be happy and fulfilled with what I have in my life. And, while I probably won't complete the maximum possible amount of work at every moment, I can build a life that allows me to hit a fulfilling balance. At least that's the goal.

Measuring My Words

My post yesterday got an interesting response (via Hacker News).

Maybe the whole "write a [b]log post a day" thing is not the right way to go. You can reflect without broadcasting to the world and committing to something like that. Just relax for 30 days and don't do anything of importance, just be.

I actually agree with the intention of that. In fact, the "write a blog post every day" goal is kind of antithetical to my goal of "doing nothing for 30 days." 

However, I think that there is something deeper that I'm trying to access. I currently have this perception that every post has to be an essay and a masterpiece, and I want to break that in favor of more honest, free communication. I have this deep-rooted fear that someone will read one of my blog posts and judge me as "not a good writer," or "not all that intelligent." As a result, writing a blog post becomes a project in and of itself. 

First I have to think up "the idea," and it has to be really, really good (at least in my mind). If it isn't good enough, then the post dies there. Then I need to write the first draft, preferably in the range of 500 to 1000 words. In the case that I can't think of enough to write about, I kill it. Or it sits as a zombie draft in my inbox for six months to a year, until I finally clear it out. The net result is that I've averaged about one post a month for the past four years (credit goes to one of my former coworkers for coming up with this statistic). 

And there's nothing to be ashamed of about one post per month, but one of my current life goals is to write more. I have always enjoyed writing, and have "intended" to make it a bigger part of my life, but it has remained an "aspiration" rather than an "occupation." So I'm going to try to write something every day, even if I can't think of anything better than transcribing my grocery list. And, if the quality suffers in favor of quantity, I'm going to be ok with that, and work my way through. I hope that the net result will be more honest and unfiltered communication.

And that's Day 2.

Taking a Break

Let's step back to the time when I graduated college, which would be June 2002. I landed a job post-graduation at a tech consulting company called Appian Corp. The recruiter encouraged me to begin my orientation on June 18, about two weeks after I graduated. My older and wiser friends (who were a year or two out of college at the time) suggested that I take some time off and enjoy myself before throwing myself into the working world. I took the August 5th start date, and had a great time hanging out with my college girlfriend, living in my parents' basement, and visiting some friends in Alaska. It was pretty glorious, and probably the last time that I had two whole months off.

In fact, I think it was the last time that I took any deliberate time off between jobs. When I left Appian a couple of years later to join Google, I had just a week in between, and that time was spent moving cross-country. I left Google about a week before I started grad school at MIT, and that also involved a cross-country move (and a four day long cross country drive). By the time I finished grad school, I had already started working on InstantQ and had received seed funding from YCombinator. InstantQ is a bit more complicated, because when it failed, I tried a number of other startups before giving up. But, if I remember correctly, I had a new job at Zecter about a week after I finally gave up for good.

Moving forward to 2011, by the time that I left Zecter, I had already started working with Sam on SpeakerGram/Scaffold. Moving forward to last summer, when we finally decided to call it quits, I lined up a new job within two weeks. Well, I had originally decided to take some time off to reflect and enjoy the summer in New York City, but I began to feel anxious and depressed after about a week. So, as soon as Jason called, I was pretty much ready to go.

So I left my most recent job a bit over a week ago. Things weren't working out for me, and it made sense to move on. Overall, it was about as amicable as such a thing can possibly be, and I don't feel like there are a lot of regrets (maybe I'll write more about this later). My normal move would be to jump immediately to the next thing, but I had a sense that this might not be the right play this time around. So, I decided to try something new, and pledged that I would take thirty days off before starting to think about what I would do next. 

I have noticed that whenever it comes time to figure out what I'm going to do for work, I jump to make the first reasonable choice that comes along. This has happened with jobs, but also with picking startup ideas to work on. It's just so easy to say, "that will do," rather than having the strength to wait for the thing that's actually right. Paul Graham once said something to me along the lines of "It took a lot of time and effort to kill your startup idea. You might as well take your time when deciding what to work on next." While that seemed like pretty good advice, I jumped into the next thing that came along, and the next, and the next. Until I was finally willing to listen.

What am I going to be doing during the next month-or-so? Well, the short answer is basically nothing. I've been going to a lot of Bikram Yoga, spending a lot of time hanging out with friends, and taking regular long walks to Ocean beach. I'm also resolving to write something in my blog every day (today is actually the first such day), and I'm going to come up with a bucket list of things to occupy my time. I have a trip to New York planned for the end of the month, and maybe I'll take another trip somewhere else. But, most importantly, I'm trying to commit to as few things as possible, and to enjoy every day for what it is. More on this later...