Data Addict

Most business partnerships are a waste of time. Guy Kawasaki says so, Paul Graham says so (see the section at the bottom), and I have learned from personal advice that both men speak truth. The thing is, partnering is most appealing and dangerous to a startup early on. In those critical months and years where credibility is scarce, partnerships seem to offer a quick path to legitimacy and (your partner will lead you to believe) wealth. So it’s imperative to develop resistance and skepticism to partnership offers. But how?

Well, one method stumbled right into my lap recently. This is a spam message that I received last week:

“LET’S PARTNER INTO PROSPERITY:  Kudos!!! You’ve got a very good work going here. I’ve been contracted to develop a website and a phone application that can help people in a particular Country to learn their three different dialects. It’s a multimillion $ Project to be funded by the Government. I understand that a lot of scamming bullshit is going on online but you won’t need to spend a dime of yours, all we need is the service of a person that has the knowledge required which would be magnanimously remunerated. I don’t know much about language software design, if you do or if you know anyone that can partner with me on this please mail me now without any delay: address@yahoo.com Do you have a website? If yes, what’s your website? I’m waiting… Success!!!”

It’s got all the elements of a bad partnership: vague intentions, an appeal to the legitimacy of some large organization (the Government!), a nod to skeptics, and call to action. My advice to you: the next time someone proposes a partnership, simply tack “… Success!!!” to what they say to remind yourself that most partnerships are a waste of time. What’s scary is that many seemingly legitimate partnership offers are more dangerous than this example because they lure you into wasting time on them. At least in this case I can just click delete and get on with my day.

When I was a freshman at Oberlin College, I took a course entitled Death and the Art of Dying. It was what you might imagine: a course that addresses the issue of death and how we humans die.

The central project of the course was truly innovative: we were required to actually form a relationship with an elderly person in the town for the purpose of speaking about death. Think Tuesdays with Morie, but in real life. It wasn’t as daunting as it sounded, the professor of the course had arranged for students like me to be paired with members of nearby retirement communities who volunteered. Although not all of the elderly participants were terminal, almost all were nearing the end of their predictable lifespans.

I was paired with a woman named Gene [1]. She was in her late eighties, and despite her age was vibrant, intelligent, and active. She had white hair and a quick, irreverent way of conversing. Students were assigned small packets of information to discuss with their elderly partners and Gene and I started on page 1 of that packet on a warm fall afternoon. I was required to meet with Gene once per week for half of the semester and keep a journal about our talks. We didn’t meet on Tuesdays, but in retrospect, she was similar to Morrey in a lot of ways.

During our first few meetings, we talked about superficial topics. She was an avid collector of Asian art, with a particular interest in Japanese woodblock paintings. I was taking Japanese history courses at the time and found her collection to be impressive and beautiful. We talked about the weather, about how my school year was going, about what I wanted to do after college, and eventually, about death. For an elderly person, she was candid to a point of fault about her own death. She had few regrets, was fully in control of her faculties, and was active in her community. She recalled with particular interest stories about how she and her husband had survived the 1940s as a military family in the midst of a great war. She laughed a lot.

The semester past quickly. At the end of the assignment, I submitted my journal to my professor and received a good grade. Gene and I had our final meeting and she invited me to continue visiting even though the semester had ended. I never honored my promise to return and visit.

Several years late, during my senior year, I was asked to fill out a tenure recommendation for my freshman professor. I submitted it and made a point of stopping by his office and mentioning what a positive recommendation I had given him. I hadn’t spoken to him in at least a two years and we chatted, catching up on one another’s lives.

“Did you know that Gene died about 6 months ago?” he asked.

The news didn’t surprise me, I had met Gene in death’s proverbial shadow. All the same, the news was understandably sad.  ”I didn’t know.” I said somewhat awkwardly.

“You know that she asked me about you several times?”

“I didn’t know that.” I said. I had liked Gene quite a bit and in the few moments when I had remembered my lapsed promised to visit again, I had assuaged my guilt by assuming that her warmth towards me had been perfunctory. I didn’t explain any of this to my professor, but he seemed to understand it all anyway. I had been wrapped up in my life and it hadn’t been a priority to visit Gene.

“She was terminal when you met her and she enjoyed visiting with you, George.” he said.

I don’t recall what I said in response, only that we didn’t talk for very long after that, and I left his office feeling sick to my stomach.

Everyone has a first brush with death, some meaningful event that first defines what it means to pass on. I had lost grandparents prior to Gene’s death. Two year previous, one of my friend’s fathers and personal mentors died. Death wasn’t new to me, but I hadn’t let anyone down so profoundly before, and I regret it more than anything else.

Why am I writing about this here? Two reasons: 1) I want this blog to be not just about technology and startups but also about the life that tends to happen in between deals, investments, and launchs. 2) I think it’s instructive to work through your regrets so as to avoid them in the future. Even though she didn’t know it, Gene taught me a very expensive lesson. I think she would have wanted her death to help others learn about themselves and in my case, she succeeded more than she knew.

[1] Her name was not actually Gene, I have changed it to protect her identity.

I attended Pycon this year and had intended to post this shortly thereafter. Life got in the way, however, and it’s only now being released. This is what I had written:

I attended Pycon last week and directly after representing my company at the job fair, there was an awkward bit of time where I had my suitcase, laptop bag, and nowhere to go. So I sat down outside of the exhibit hall on the floor and started responding to some email that had built up. The kind lady from behind the now-empty registration desk came over after a few minutes and invited me to sit there instead of on the concrete floor. I gladly accepted and setup my laptop behind the modular registration table.

After no more than a few minutes, several confused-looking conference attendees stopped at the table and began to ask me a question about how they could get lunch without their badges. In mid-sentence, I suggested they talk to the woman who had invited me to sit there in the first place, mentioning that I wasn’t really a staff member. I then returned to my emailing.

A few minutes later, a couple approached and asked how they could replace their lost badges. Again, I motioned them to my benefactor, and gave a single-clause explanation of why I was behind the official counter. I was now distracted, but resolved to get my emails out.

But it was not to be, because after only a few more minutes, another gentleman came up and asked whether we had a lost and found. I resolved to move both so I get something done and so as not to make the registration team look bad, but it surprised me how easy it was to fake my credentials. Granted, being mistaken for a conference organizer didn’t take a huge leap of faith for anyone present. I was wearing a conference badge and lanyard, I was tapping away at a laptop, and I was sitting behind a desk with the other conference organizers. But it was easy to fake my role: all I had to do was move my backside twenty feet from where I had been sitting previously.

To be clear, I don’t encourage anyone to use social engineering for evil, but as this simple example proved to me, it’s important to remember how easy it is to fake it and faking it is immensely valuable. When you are running a startup, for instance, you need funding, employees, and first customers. All of them will want to see you project a certain image. It’s often not as simple as just sitting behind a counter with a laptop, but it’s often not significantly harder either. So the next time you need to influence people, remember that faking is easy.

I have been uncomfortably busy for the last 6 months. Between my startup, a monster commute, religious conversion classes, and preparing to get married, I have had to motivate myself to work more than I would otherwise prefer. This blog post is a collection of short, candid lessons I’ve learned about motivating yourself to work a lot. To be clear, I’m talking here about motivating yourself to work when nobody is forcing you to do so. Working, essentially, for your own goals, not your boss, your company, or any external parties:

1) Set Numeric Weekly Goals

I have found that this is best done hourly. I try to work 25 hours on my startup per week and I minimize my commute time by tracking it. You have to be strict about working towards your hours. Share your hourly goal with your close friends/spouse. Enlist them in motivating you to meet your goals. Make it clear that you want to succeed. If you have a support network, setup a system of prizes for accomplishing streaks of productivity. I’m on a minimalist kick right now, so for every 3 weeks that I meet my quantitative goals, my fiancee has to fill a medium-sized moving box with excess stuff from around the house and donate it. It’s a small token but it’s a big motivator!

2) Build in Emotional Accountability

Obviously there is accountability at a regular full-time job, but if you want to work 80 hours in a week for yourself, you will need your own accountability systems. In the case of my startup, I meet with my cofounders weekly and I want nothing more than to have progress to report. For my religious conversion classes there is homework with deadlines. I am going to get married on the 9th of June, so everything needs to be planned by then. All of these deadlines create immediacy that is tangible and allows me to hunker down and get things done as efficiently as possible.

3) Cut Non-Social Entertainment

This includes television, movies, single-player video games, reading, walking in the woods, and any other activity you do solely for yourself. I’ve always found absolute rules easier to live by because they don’t bring up messy grey areas, and this tip is no different: you can easily determine if something you are doing is both 1) entertaining and 2) doesn’t involve others. Sorry, but if you want to work really hard, you can’t afford to watch Community or play Skyrim.

4) Choose Your Battles

As soon as I started working a bunch, I got inquisitive about where my time went. I realized early on that eating takes too much time. Even when I rushed, it took me at least 1.5 hours a day just to put food in my mouth hole. That was time I couldn’t be working at full tilt (I know because I experimented with eating and working simultaneously). To minimize time spent eating, I started eating a lot more convenience food which is regrettably less healthy than home-cooked meals. At the same time, I made a conscience choice not to fight my rising BMI. As a healthy eater all my life, I still try to eat well, but I realize I don’t have enough time and work is more important at this juncture. I snarf organic grassfed beef sticks, cram whole wheat crackers, bust out a bowl of frozen fruit, or eat yesterday’s leftover mac and cheese and get back to it as quickly as possible. Unless you can operate for long stretches on significantly reduced sleep [1], you will need to pick the battles you are willing to fight on a daily basis.

5) Make Sure There’s An End in Sight

There’s nothing more demoralizing than being under a lot of pressure and having no feasible way to alter your circumstances. You can work 80-100 hours a week for a terrible boss, however, I have yet to find a person capable of working for themselves under equally hellish conditions without an escape plan [2]. Simply put, if you are working for yourself at an uncomfortable level, you need a light at the end of the tunnel. In my case, it’s the launch of my company’s iPhone/iPad app and my wedding date. You can push everything in your life to the brink to achieve your goals, and every once in a while that make sense, but to do so without a goal is madness.

Conclusion

I do not suggest that anyone work this much. Plenty of people do, especially when working on their companies, but I can tell you from personal experience that it’s absolutely not necessary to build a successful startup. Further, working too much damages your relationships and body. Right now my fiance and I agree that this work schedule is the right thing to do for us, but it’s no fun spending more time commuting each week than I spend with my future spouse. It’s no fun being 15 pounds overweight, unable to pursue hobbies, and stuck in front of a computer 12 hours a day, 7 days a week. In short, I don’t envy those people that consistently work this much. With that said, if you find yourself in a similar position and need to work like hell for a while, the tips above have proven very effective.

[1] I have read extensively about polyphasic sleep, I’m conducting my own sleep experiments with my Zeo headband, I have a Fitbit, and everything I’ve measured suggests that I need to sleep about 7 hours a night. If I sleep less than that, I have significantly degraded performance throughout the day. So, for those of you who only need to sleep 5 hours a night: I’m incredibly jealous, but it doesn’t appear to work for me.

[2] I suppose that a person could do this to themselves if they were neurotic, and I would readily believe there is a larger-than-average overlap between entrepreneurs and neurotics. Just the same, I haven’t personally met anyone masochistic enough to inflict this sort of pain without at least a pipe dream to work towards. The types of dreams that people motivate themselves with could be an entire blog post by itself.

When I graduated from college, I had a massive inferiority complex about my skill set.

More than anything else, I wanted to be a scientist. My father and grandfather are both scientists and most of my role models are engineers of one sort or another. So in freshman year, I took biology, chemistry, and computer science in succession hoping to find my scientific aptitude and carry on the tradition. I found the classes equal parts difficult and un-enjoyable. I was the one who struggled for a high C and hated every assignment while my peers effortlessly achieved As and Bs and seemed to be having a ball. It was demoralizing, and so by the time I had lowered my expectations and decided to major in economics [1], I had developed a budding professional self-loathing.

Founding a web startup right out of undergrad was natural for me, I had been a computer geek since the third grade after all. But being the only non-coder in a three man web startup only fueled my feelings of inadequacy. I was the business guy. I incorporated the company, talked to investors, made marketing materials, demoed our product to customers, handled feedback, and did all the tasks that don’t immediately jump to mind when you think of founding a small technology company. Someone had to do all that work, but it always ate at me that Nick and Scott could do my job as well, if not better, than me, whereas I had no such reciprocal talent.

To this day, I struggle with feelings of inadequacy, but several months ago I reached a landmark realization. Although most programmers could technically do my job, good designers, salesmen, marketers, recruiters, copywriters, and general hustlers are valuable [2]. I happen to be pretty good at filling those roles and it makes me happy. I don’t want to program, I want to work with people and technology, in that order.

I asked HN a question more than a year ago entitled “What’s a non-programmer co-founder to do?” Although most of the feedback was helpful and constructive, way down the thread, one person simply wrote “learn to program.” That sentiment seems to be rife in the tech world, but I’m here to say that just like the world needs good hackers, it also needs good non-technical professionals. As someone completely immersed in technology, it’s easy to lose sight of that fact and forget to take pride in what I contribute.

It’s liberating to finally feel that what I’m doing really does add value and helps make my tiny little corner of the tech world a better place. If you have ever felt bad about not being a coder, chin up, the world needs people like you too.

[1] A [snort] social science.

[2] I have intentionally omitting lawyers from this list.

As web business models go, content is well understood: you produce something of value and then monetize through ads, lead generation, or just charging for what you produce. I refuse to start a new business based on selling content and so should you. Here’s why:

1) It Doesn’t Pay

The web has produced such an abundance of content, and simultaneously failed to fix micro-transactions, that the expected value of any specific information has fallen to zero. There are isolated niches in which content is still worth money, but they are becoming fewer and father between [1]. As a test of this mindset: would you be reading this right now if I had asked you to pay me even $0.10 for the privilege?

The result of this change is that the average piece of content is worth almost nothing. This means that most people in the US can’t make a living wage producing content. If you are a good developer, for instance, your time is worth many times more producing code than it is producing content of almost any type.

2) Producing Content is Unpleasant Work

Some people have realized that content has become too expensive to have people keep producing it. These new content companies (like Demand Media) are highly profitable while traditional content producers (like newspapers) wither and die. Algorithms will be increasingly important in content creation, and they do it just well enough to invite a click and then frustrate you into (hopefully) clicking an ad. Sites like About.com and Mahalo flood search results with just-good-enough information at scale and it’s hard to beat companies that wield hundred of millions of links.

With that as your competition, you are forced to create bad/mediocre content as quickly as possible. Producing content is therefore a race to the bottom in which you must compete with the lowest paid global workers to produce bad content as quickly as possible. I don’t want to make anything that sucks, much less in large quantities.

3) There Aren’t Any Interesting Problems

You could argue that monetizing content in a sustainable way is an interesting problem, but I would beg to differ. Creating ever-more complex link farms at scale isn’t my idea of doing great work. And past that problem, producing content is essentially the same process as it was 500 years ago. I do not mean to imply that creating good content is easy, but the problem is well understood, labor intensive, and has reached a level of development where success is defined more by cutting input costs than by creating better outputs.

4) Piracy Exists

But just for the sake of argument, let’s ignore everything above. If you have a real itch to write the next revolutionary book of jQuery tutorials, there’s the issue of piracy. Despite misguided legislation attempting to curb the behavior, piracy is easier today than it was when I downloaded my first MP3 on Napster in 2001. If it’s easy to take from you and all you have is takeable, you are in a position of extreme vulnerability.

Again, there are content businesses that make money, but you’ll notice such businesses are almost always established B2B companies operating in specialized markets where the liability of piracy is higher than the cost of acquiring material.

This Situation Is Deplorable

I say all of this with the greatest sadness. If people can’t make ends meet producing good content, the world is a poorer place. I won’t really miss another review of the iPad 9, but I will miss proper journalism. I just finished reading the book 1491. It was both enthralling and breathtaking in the scope of research that went into it. But reading it was a guilty pleasure because I knew the author had to take a huge gamble to write the book, and his odds of making money on his investment were poor. If societies lose people that make it their business to seek truth and produce content, those societies become worse. Just as one example, Watergate was only exposed because 2 Washington Post journalists spent more than three years researching and seeking truth full time. I want to live in a world where people like that can feed their children.

At the same time, I realize I’m not prepared to devote 10 years fighting this issue, and so I refuse to start a company based upon content, and I think if you realistically evaluate the costs, you will too.

[1] I can imagine a number of niche B2B content business models in which you charge for access to highly specialized technical information that changes a great deal. Perversely, one such content business model is law, which doesn’t produce any economic value, merely re-allocating resources between parties.

Google Wave closed write access several days ago. This had been on my radar for some time, but as a heavy user and advocate of the service, it’s difficult to see it go.

This has made me realize that seeing a pet project die is a right of passage for a career technologist. It’s not just that it’s a coming of age event, it’s an important part of becoming better at building and improving ideas.

When I was young, I didn’t think about technology or specific projects as transitory. I had such a short period of reference that everything was effectively permanent. I used Altavista for search because that was the only search engine that had ever existed and I played Descent 2 because it was the best game. I spent a lot of time playing games, trying operating systems, and installing utilities without thinking much about the people behind those monoliths of time and effort.

When you don’t have an ownership stake in what you consume, it’s easy to remain agnostic about games, operating systems, programming languages, server platforms, SDKs, editors, project management styles, deployment techniques,  and a hundred other topics about which developers care deeply.  As I transitioned from being a consumer of web technology to a producer, I began forming opinions about the tech that surrounded me.

I love Google App Engine, dislike AWS, love Python, hate Java, dislike Windows, but think Mac OS is for snobs, snub Firefox for Chrome, love Winamp, hate iTunes, loath antivirus software, prefer Google hangouts to Skype, and a hundred other subjective preferences. For having so many pet technologies, I have seen remarkably few get abandoned. Among those that I have lost, Wave has been the most important.

I was enamored with Wave because of the ideals and dreams of the people who invented it. I don’t know much about the creators of Winamp [1] but I could put a face to the Wave development team and I wanted them to dethrone email, destroy chat programs, and better organize all web communication.

The fact that it failed makes me more of a real geek. I invested heavily in Wave and will now pay the price [2]. But in going away, Wave has also taught me some valuable lessons. I’ve learned that even well-funded projects die, technology doesn’t often win out against established behaviors, and evangelism can only go so far.

The pace of innovation in web technology is accelerating and there is a tendency to avoid investing in any platform, but I think that it is the mark of a mature and invested hacker to have a small cemetery of pet technologies to grieve for. Don’t hang on and be that backwards guy who wants to implement everything in Pascal, but remember what you’ve lost and use it to build better products in the future.

[1] This is because I wasn’t old enough when Winamp was disruptive and being talked about, I have heard anecdotes that suggest it is quite an interesting story.

[2] Endless exporting and unsorted data migrations await. There is a strong temptation to accept the data loss and start over on another platform, but there is data in Wave that I simply cannot afford to lose.

I graduated from Oberlin College in 2008. As liberal arts colleges go, Oberlin is considered very liberal and very wealthy. As a kid raised in a poor, middle-of-nowhere Ohio town, Oberlin was like living on the moon.

Although I was inundated with the language of liberal arts studies [1], I didn’t notice how much it had reduced my ability to communicate until a little more than a year after I had graduated. At a meal with my best friends from college, we took turns indulging in nostalgia and particularly in the rhetoric that demarcated that part of my life from the others. My friend Trina did a rousing impression of a girl in a gender and women’s studies class that had been particularly memorable:

“I feel like … you know … like women are these targets for societal redefinition and symbolism, it’s like men see us as somehow being, like, these representations and symbols of a quasi paternalistic rebellion.”

Having heard hundreds of such wishy-washy statements [2], what struck me the most was the first three words: “I feel like.” I hadn’t noticed, but Oberlin had trained me to replace “think” with the phrase “feel like” in my speech patterns. So instead of saying “I think HTML5 is going to replace Flash,” I now say “I feel like HTML5 is going to replace Flash.”

This is not a harmless alteration. As Trina pointed out, the reason people use that pattern of speech is to make ourselves immune to criticism. As Trina succinctly put it: “it’s not socially acceptable to criticize a feeling.” Since having that discussion, I’ve noticed this pattern of speech everywhere. I hear it most in situations where the speaker is unwilling to stand behind what they have said.

I don’t want to sound insensitive here, it’s no wonder that people would want to avoid being criticized, especially about tentative beliefs. During a discussion group, for instance, you may say something that only just came to you, and especially for a shy person, being criticized for such a statement could feel overly harsh.

I think, however, that it is an insidious and evasive speech pattern that reduces the opportunity for legitimate disagreement and constructive criticism. Disagreement shouldn’t be avoided, it should be sought, because it is only through disagreement and iteration that success can be obtained. I’m not just speaking about literature discussion groups [3]; any difficult and long term endeavor requires frequent and honest criticism to reach a successful conclusion.

It’s not novel to criticize the negative impact of college educations on student writing ability, but this seems like a particularly bad habit that is easy to fix. Trina was right: you can’t criticize a feeling, and couching statements and arguments as feelings is bad for everyone.

[1] Before switching to Economics in sophomore year, I was a film major and read stuff like this all the time: “Bergman’s entire film is, then, concerned with transcendence, with a transcendence of languages and of the grammar of film, of the traditional perception of the film spectator as passive recipient, of the medium conventional reliance on narrative as its formative principle, and of the historical Western concept of art as wholeness and order.”

[2] I think the cout de grais in proving how wishy washy liberal arts academic writing is comes from the Sokal affair.

[3] The idea of a “success” in a literature discussion group is slippery, but I am referring here to my startup, which would not have succeeded if not for the criticisms that hundreds of people (myself included) leveled at our idea and implementation.

Back when I was in 9th grade, I purchased my first desktop computer. I did extra chores, mowed lawns, and shoveled snow to afford my dream machine. It came tricked out with a 900Mhz AMD Athlon Thunderbird CPU, 128MB of RAM, a GeForce 2 GPU, and a Plexdor CD burner. Housed in a bleak grey metal box, it was my pride and joy. Countless hours of Counter Strike, Total Annihilation, and Starcraft were played on that computer.

Despite my fond memories of that first computer, it was never the perfect performance machine. I had made many compromises to meet my meager budget, and the hardware was out of date less than 60 days after it arrived. So around that time, I vowed that someday I would buy myself the most ridiculous performance-intensive machine that could be had.

Fast forward quite a few years and I finally have the cash to buy that no-holds-barred gaming machine. But desktop computers are no longer terribly practical. And I don’t play Counter Strike in the evenings anymore. And my middling laptop runs the Adobe Creative Suite just fine. In fact, I spend most of my time in front of productivity and office applications at my startup, and in the evenings, I try to spend time away from the computer for the sake of variety. I have the cash, but I longer want that beast computer, and it’s sad. When I explained my disappointment to a friend over lunch, he shrugged and said, “of course you wanted that computer, but dreams expire.”

He was right. Since making my vow to buy an uber gaming machine, the dream had lost meaning for me, and like a mesofact, I had not updated my list of dreams.

This caused me to not only go through that list, but to re-evaluate how I pursue and value dreams. I have kept a bucket list for several years, but I here propose a short list of reasons why you shouldn’t have one. In short, maybe you shouldn’t follow your dreams.

1) Destinations are boring.

As a society, we praise big dreams and tell kids to aspire to be astronauts. But as a society, we focus our dreams on destinations, not on the journeys that make them meaningful. I fell prey to this exact problem when we were founding our startup. I wanted to build a successful startup. For three years, we worked hard, we got some lucky breaks, and now Skritter is successful. I have become an astronaut. And you know what? It’s an empty victory, because as it turns out, what I really want is not to have a successful startup. What I want is to work hard on difficult problems with people I like. Notice the difference there: the first dream is a state, “success,” the second dream is a process “work hard.”

For all the glib discussion of life being a journey, not a destination, we overlook that fact when forming our deepest and most personal goals. Maybe you want to be a famous rapper, a skydiving instructor, or a race car driver. All of these are noble ambitions, but thinking about those dreams in terms of continuing actions rather than destinations makes them more meaningful. You don’t want to be a rapper, you want to spend most of your time rapping in a studio. You don’t want to be a skydiving instructor, you want to teach newbies how to enjoy their first jump. You don’t want to be a race car driver, you want to drive fast cars on a racetrack.

Destinations are boring, and dreams that rely on them are hollow.

2) The exotic is kinda meh.

You know what sounds cool? Getting out of a Cleveland winter and working from Costa Rica for 2.5 months. The problem is that if you value a degree of consistency, recurring familial interaction, predictable diets, stable electricity and internet, reliable transportation, and a hundred other factors you probably take for granted, then it’s actually not that cool. That was the story of my 2 months in Costa Rica.

Yet despite the disconnect, whenever I tell people about going to Costa Rica, most people said “I wish I could do that.”

Daily life constrains choice sets to the degree that most people can’t up and move to Costa Rica for 2.5 months. And for most people, that’s a good thing. Dreams often take the form of overcoming the inertial forces that keep us grounded to the status quo. But it is precisely these forces that often make us happy. So in effect, many dreams are predicated on circumstances that by their very nature would make us unhappy.

3) Dreams made in a vacuum are meaningless.

I drive an extremely economical car and I’ve always dreamed of having a performance sports car. Recently I got the chance to test drive some exceptionally cool sports cars, and coming back to my little Suzuki Aerio was a relief. Why, you might ask, would I prefer my 1600cc putsy hatchback to a Mercedes Benz E55? I won’t go into details, but in forming my dream about owning a sports car, I ignored all of my previous preferences. A Porsche looked cool, but in my daily life I prefer gas economy, reliability, and low insurance bills.

Dreamers are encouraged to think big, and that often implies “outside of our experience.” This gets back to something Paul Graham suggests about finding what you love to do: if you aren’t tinkering with computers in your free time, do you really want to be a programmer? If you didn’t sacrifice to buy a sports car when you were 17, are you really invested in performance automobiles?

We often classify our unqualified aspirations as “dreams” and then foolishly work towards them. Daily experience is often a far better judge of what you will enjoy than a groundless idea of what you want inherited by a larger society or peer group.

Summary

All of this might lead you to conclude that I think dreams are meaningless, but that’s not the case. I think dreams are extremely important, but they often grossly misrepresent what people actually want from their life experience. I am still struggling to find a good way to pursue my own dreams and would be interested to hear if anyone else has had luck better forming and achieving meaningful dreams.

At the beginning of 2011, my work schedule was light. I could stop work on the startup early without stressing out, I took longer lunch breaks, and I spent the evenings recreating. I watched a bunch of movies that had been on my list for years, I caught up on correspondences, and I thought about and wrote more blog posts. I went to sleep when I wanted, woke up when the sun rose and generally lived it up. From the outside, I was living the lifestyle business dream, if only temporarily, while other projects wrapped up.

I was, however, deeply unhappy. After the first week or two, I found that watching a lot of movies at once was kind of boring, that I could correspond with others much faster than they could reply, and that it didn’t take long to write all the blog posts I had been planning. But much worse, I discovered that for me, being productive had a large impact on my happiness and I simply wasn’t efficient when I wasn’t busy. Without hard deadlines and time limits, coworkers and customers, it was always acceptable to dally and watch an episode of Community. Or stay up late reading Reddit. Or hit the snooze button more than once.

Just to be clear, I didn’t have motivation problems at first. I found that the less I had to do, the less I had to worry about using my time efficiently, and this led to a rapid decline in productivity. The whole slowdown process took less than 2 weeks.

Starting in the summer, work started picking up again. Even though I was working more than full time, I realized I was accomplishing more on my personal projects than I had when a two hour lunch break was no problem and my days ended at 4PM.

In short, I’ve found that the right kind of productivity (as in, working on projects/work that matters to you personally) tends to increase as you get busier. There is a linear relationship between how much you have to get done in a day and how much work will get done on personal projects.

There’s an old saying that goes “if you want to get a job done, give it a busy person.” This isn’t a new or revolutionary thought, but the inverse is both: “if you want to get a job done yourself, get busier.” I can’t speak for everyone, but I’ve definitely found this to be true.

Have others found this to be true? If so, have you found any hacks that increase productivity even more?