Alex Payne

Letter To A Young Programmer Considering A Startup

2013-05-23T00:00:00-07:00

Letter To A Young Programmer Considering A Startup

I regularly get emails from young people, usually those with an interest in programming, who are trying to make decisions about school and/or their professional futures. This post is for those young people.

If you’re in your late teens or early twenties, you’ve grown up in a world that has come to idealize startups, their founders, and the people who go to work at them.

If you’re in school, maybe you’ve felt pressure or been incentivized to drop out and join or start a company. If you’re already out in the working world, perhaps you feel that your non-startup job is in some way inadequate, or that you’re missing out on valuable experience and potential wealth.

The generation you’ve grown up in has, for the past few years, teetered on the brink of being “lost”. Jobs are scarce, and going to university offers no assurance of landing one. Big, old corporations are no longer guaranteed safe havens in which to build a career. Startups seem, through the lens of the media, like the only sign of life in an otherwise dying landscape. I understand their appeal.

Everyone’s path is different, and your choices are your own. That said, you aren’t making your choices in a vacuum. Here are some things to consider that, in my experience, you’re less likely to hear about working in startups.

A startup is just a means to an end.

I recently interviewed a young man. I asked him where he wants to be in four years. “Running my own company,” he said without hesitation. I asked why. “Because entrepreneurship is in my blood,” he replied. There was no mention of what his hypothetical company would do, what problem it would solve for people. His goal was business for the sake of business. That’s what he had gone to school for, after all.

People are fulfilled by their work when they operate with a sense of purpose. So much of our understanding of the psychology of success is around setting goals and keeping those goals at top of mind: visualizing the moment of accomplishment, tracking our progress towards it, having others hold us accountable to reaching it. Goals give shape to our individual futures.

Maybe a startup is the best way to meet a goal, and maybe it isn’t. If the goal of the young man described above is to run a business – any business! – then perhaps a startup is indeed his best path forward. For others, though, I often wonder if they’re fitting their goals into the format of a startup because it’s an approach that’s lauded, admired, and easily understood (if not easily accomplished).

Maybe the best way to meet your goal is starting a non-profit or going into politics. Maybe it’s doing research at a university or making art in a squat. Maybe the answer is joining a large, stable company with formidable resources that you can leverage to meet your goal. Maybe your goal is best met by building a stable yet undemanding career that leaves plenty of time for family, friends, community, and self improvement.

A startup is just a means to an end. Consider the end, and don’t seek to revel in the means. What do you care about? Who do you want to help? Does a startup make meeting your goals easier or harder? Where will it leave you when your goal is met? Where will it leave you if it isn’t?

A startup job is the new office job. Startup culture is the new corporate culture.

Startups are portrayed as an exciting, risky, even subversive alternative to traditional corporate work. Startups are thought of as more free, more open and flexible. Some companies surely begin that way, but a few interviews at later-stage startups will make clear just how quickly they ossify into structures that look very much like the organizations that came before them.

As there was in the first dot com bubble, there is a current proliferation of startups, incubators, accelerators, angel/seed funding, and so forth. In order for the “startup community” to replicate itself, nanobot-like, the mechanics of “doing a startup” have been reduced to an easily transmitted sequence of actions accompanied by a shared set of values, norms, and language. As a consequence, the culture of most startups is blandly uniform, right down to a style of dress and grooming that helps “startup guys” – and all too often are they guys – stay with their herd (lest they be picked off by cougars).

Business school graduates like the young man I interviewed are going directly from college to startups, if they even finish school at all. Business majors, traditionally risk-averse, now say they don’t want to work for big companies. But startups are the new big company. They are, as I’ll describe below, the field offices of a large distributed workforce assembled by venture capitalists and their associate institutions.

There’s nothing inherently wrong with an office job. Just realize what you’re signing up for. When the company-provided keg runs dry, the free lunches are making you fat, and playing the Xbox in the break room is no longer as fun as it used to be, what then? When you find that you now report to a politicking middle manager and not the inspiring CEO who interviewed you, will you still want to be there? Is a supposedly novel working environment enough to sustain you? When everywhere you might consider working looks more or less the same, is the novelty even there?

Startups have been systematized, mythologized, culturally and socially de-risked; reduced down to formulas and recipes. Yet, there is no enduring formula for creativity and rebellion. When we attempt to factory farm innovation we breed out the very thing we’re trying raise: the creative destruction that stokes and re-stokes the fire of capitalism.

Startups are part of the system, not a rebellious wrench in the cogs.

The funding for startups – that is, the money that pays your prospective salary – comes from somewhere. Wealthy individuals and institutions invest in startups as just another asset class. The futurist Bruce Sterling recently quipped that “start-ups are full of [young] people working hard to make other people rich – Baby Boomer financiers mainly”. While that might be an overly general and cynical take it’s by no means untrue.

In broad strokes and excluding areas like biotech, venture-backed startups are a machine into which relatively small amounts of capital are inserted in one side and, ideally, quite a lot more comes out the other. (In actuality, this machine doesn’t seem to work anymore, though the effectiveness of VC as an asset class and VCs themselves is certainly up for debate). The salient point, though: what’s in the middle of the machine is you. You make it go.

The machine doesn’t care about you. In fact, the machine is designed with the understanding that most startups will fail, or at most offer unremarkable returns to investors. The majority of the companies in many VC portfolios are acknowledged duds. One or two “10x” companies prop up most portfolios. At best, startup founders who fail get another pull of the slot machine. At worst, their failures drive them to desperation.

There is nothing inherently disruptive about a venture-backed startup. The startup system is just another system; an alternative to the corporate ladder with just as many rungs to climb. Some startups may end up dramatically reshaping a market, but then so might an incumbent player or an active regulator.

The now-perennial celebration of startup-driven disruption raises the question: if we accept that disruption is even happening, are we better off in the resulting disrupted market? Have we solved a problem, or have we shifted the problem elsewhere? Have we created value while furthering justice and equality, thus yielding enduringly positive change? Or have we merely made one group of wealthy people slightly more rich at the expense of another group of wealthy people? Are we creating a better future or just scrambling up the present?

Startups have an ongoing interpersonal cost.

No story of a startup is complete without a scene or two of macho heroics: nights spent programming to exhaustion, weeks away from home trying to raise money in pitch after humiliating pitch. Startups appeal to a desire for daring that’s lost in many forms of modern work, and we’re told stories of the rewards waiting when personal lives are sacrificed on the altar of the launch schedule.

Less frequently do we hear about the damage that startups do to people’s lives. In extreme cases, as with the entrepreneur whose story of failure and suicide was linked to above, the “community” might take a day or two to reflect and mourn in blogs and tweets. Then it’s back to “grinding it out”, and more importantly, making a public show of just how hard you’re working to appease investors and intimidate competitors.

I’ve seen firsthand the damage that startups can do to relationships. I’ve watched marriages and friendships fall apart, seen children and partners pushed aside, and failed those in my life in all kinds of ways when work came to the fore. I’ve listened as people who are the very picture of startup success – visible in the press and social media, headlining conferences, forever founding and exiting – have confided their utter loneliness despite being seemingly at the social center of the entrepreneurial community.

When you’re young, relationships seem like a renewable resource. Friendships are plentiful and come easily. Just out of the house and out in the world, you’re eager to escape the heretofore-constant presence of family. Being pulled into work makes you feel important, independent, and adult. Work itself can provide a new community and new friendships, and the bonds formed during intense collaborative work are strong.

I’ve made such friends through work at early stage companies. Ironically, those relationships are easier to maintain and enjoy when I’m not working at a startup.

Parting thoughts.

I’ve worked in startups on and off for over half my life now. That work has brought me some financial freedom, and I’ve put money I’ve made back into other startups. If there is, as I argue above, a modern “startup system”, I am a part of it.

I won’t equivocate: I am deeply skeptical of this system. I’m skeptical of this system’s slavering, self-congratulatory fetishization of “disruption” while so obviously becoming the sort of stolid institution it seeks to displace. I’m skeptical of the startup community’s often short-term outlook. I’m particularly skeptical of its callous disregard for both the lives of the people who participate in it and the lives of those who live in the world that startups seek to reshape. Let’s not even begin to discuss how commonplace collusion, price fixing, and other market-corrupting activities are in the world of VC. The point being: it’s a bad game and a rigged one.

And yet. There are startups I wouldn’t want to see disappear. There are people working at and funding those startups who are good, kind, balanced in their personal and professional lives, thoughtful of the impact of their work. Just as we might cast aspersions and accusations of corruption on other systems like politics, mass media entertainment, and professional sports, we must admire those who operate ethically and efficiently within them. We should further celebrate those who are pioneering new and alternative systems, for they work in the shadow of a community that has a constant hand on the crank of the hype machine.

Now, you could say that I’m laying too much responsibility at the feet of the startup world. Though this system daily broadcasts itself as the savior of everything from capitalism to culture, surely we can accept that business is business and ideals are best left at the door. As a VC at a top-tier Sand Hill Road firm told me during a pitch several years ago when describing a conceptual feature in Simple that would let users easily and regularly donate a portion of their savings to charity, “let’s not waste time on that stuff; we’re here to make money”.

You could take this tack, but I hope that your idealism hasn’t been worn down at such a relatively young age. I hope you want your work to be imbued with meaning, purpose, and value no matter what form that work takes. More than that, I hope you want your life to be defined by more than work.

Young programmer, I urge you to consider both sides of the startup coin. There are so many ways to make a dent in the world.

A note on feedback.

If you’re part of the intended audience of this post, I’d love to hear your feedback and answer your questions, preferably over email. My address is easy to find on this site.

If you’re not part of the intended audience and are very very mad that a stranger on the Internet has a different opinion than you, I encourage you to direct your energy into an alternative argument that a young person (or, really, any person at a point of career transition) might benefit from reading. They are your future employees, coworkers, or founders. It’s them you need to convince, not me.

Alone Together, Again

2012-11-11T00:00:00-08:00

Alone Together, Again

The following was written in August, 2012. It was published a month ago in the first issue of Marco Arment’s iOS-only publication The Magazine. Marco has generously allowed his contributors to retain copyright and the option to share their work on their own sites after a time. If you have an iOS device, please consider supporting Marco and The Magazine by purchasing a subscription.

· · ·

I am in a stranger’s apartment in Reykjavik, and for the first time in almost five years, I am truly alone.

Two months ago my life was as per David Byrne’s enthusiastically confused yelps: beautiful house, beautiful wife, not one but two large automobiles. I had a job that seemed like the job I should have at a company I was proud of. I lived in a city that I had carefully chosen to live in, a city that I thought was going to be my home for some time.

Nobody’s life ever really falls apart, exactly. Lives unravel, thread by thread. First, I came to realize that the job wasn’t the right job. Then the city wasn’t the right city. Two threads loose, easily stitched back in; there are other jobs, other cities. Our house went on the market. I resigned.

Then, a month ago, the person I thought I was going to spend the rest of my life with came home from a neighborhood-scouting trip to a place we were intent on moving back to. “We need to talk”. Never good. “I can’t do this anymore. We’re just too different”. The seam, ripped.

That was Saturday evening. There was no going back and no way forward. By Tuesday afternoon we’re in a lawyer’s office, drawing up a settlement. The court moves quickly when there’s no children and no disagreement over who gets what. The divorce should be final by the time this is published. I will probably hear about it by email, wherever I happen to be. I will look at my iPhone, wince, hit “Archive”, close my eyes, and breathe.

The next four weeks disappeared like a long weekend spent sick. I went to the other side of the country while she moved out. Family and friends did their best to hold me together as the stages of grief washed over me in no particular order. The last listed stage of grief in the literature is Acceptance. It didn’t take long to accept that this is all for the best. A gift, wrapped in barbed wire. I just wish I had seen it being wrapped.

Teeth gritted, I went back to the city that was no longer our city, back to the house that was no longer our house. I packed up what was left, put all but necessities into storage. Sold my car. I could have stayed, but I couldn’t stay. The whole city was our life together, brief as it was. Coupled a little over four years total, just a bit over two of which was spent married. We moved mere weeks after the wedding, bought the house not long after. Friends have been engaged longer than our entire relationship lasted. It was something small that we foolishly made into something big, and it’s already receding into the distance. I’m filling my vision with fields of lava, mossy valleys steamed by hot springs. Trying not to look back.

With my life in that place done, I got on a plane, and then another plane, and now I’m alone in an apartment in Reykjavik. Now, this is my life. Not the apartment or the city or travel, but the laptop I’m typing on. We are alone together, again.

· · ·

I owe my life to technology.

I first realized it in my early twenties. Everything important around me at the time, I’d found on Craigslist: my girlfriend, my job, my apartment. It was a powerful realization: I could sit down with my laptop and, in a matter of hours or days, change my world in both superficial and fundamental ways.

That was years ago. Technology specializes over time. The life I just finished packing up wasn’t courtesy of Craigslist. It wouldn’t be, now. The modern web has six sites for everything, branded and polished and localized and full of options. House from Redfin. Cars negotiated online before ever walking into a dealership. Wife from OkCupid. Wedding invitations by email. Date-night dinners booked on OpenTable. Fast and friction-free.

I spent four years telling anyone who asked how we met that OkCupid’s matching algorithms must have been off. “We were only a seventysomething percent match, with like a twelve percent chance of being enemies. Guess they need to work some bugs out!” The joke’s on me, of course. I emailed the right person at OkCupid to apologize for the years of disparagement.

I could blame technology. Maybe stitching together a durable life takes physical work, needle callouses. Maybe technology made it all too easy to slide into a life I wasn’t meant to have. It would be so convenient to think that way. Marriage didn’t work out? Blame the dating site. Bad experience at a restaurant? Blame Yelp.

Technology is just people, though. People like me. We get it wrong. And even when we get it right, people are people: they ignore the algorithms and recommendation engines and scores and weightings. People do what makes sense to them, then and there. What else are we to do? All the specialization, all the options, and we still have to choose. We still have to make our way in the world, alone, save for our technology built from other people’s frozen choices.

· · ·

I will owe the next part of my life to technology, but I will owe it more to experience.

I tried to imagine what my life would be like in the wake of all this if I had been living two hundred years ago. Most likely, I would be trapped. I would be living in the scraps of the life that had unraveled around me. I could not seek the support of friends from around the world at any time of day or night. I could not book passage to wherever I felt I needed to escape to. I couldn’t work from wherever I happen to end up. Trapped.

I am grateful that I live in this time. For all the loose threads in my life, I don’t feel trapped. Technology allows me to make choices that can shape and reshape my world. I don’t yet know what I will do, where I will live, or who I will love. For each of those decisions, though, there are tools, and the tools present options.

The trick, of course, is having the experience to inform the selection of the right options. For that, we have no technological substitute. You simply have to live, work, love, explore, fail at all of those things, and learn.

From Reykjavik to Berlin. Then on to New York City, maybe for a month, maybe for a lifetime. Airbnb, Hipmunk, TripIt. Messages in my inbox suggesting new ventures, new possibilities. Choices. Threads to be sewn together, making something whole again.

· · ·

Postscript, November 2012. A stranger’s apartment in Brooklyn.

I thought long and hard before submitting the above to Marco. Divorce is a subject that, despite its sad prevalence, remains taboo. Divorce is generally discussed behind closed doors, on long phone calls, or via whispers in crowded restaurants. I do not regret my decision to be public about my experience, though. I received many responses, often from people who are going or had gone through something similar. Those people found comfort in knowing that they were not alone, and that is justification enough.

My parents divorced just as I was on the cusp of adolescence. There was nothing in the world that I wanted less than to experience that again, much less firsthand. Some months on, though, I stand by my statement that this was a kind of gift. I do not live with shame, for I have nothing to be ashamed of; I was true and honest, and that was not enough. I do not live in misery. My life today is not at all what I imagined it would be, but it is wonderful and strange and exciting.

It is taking time to make things whole again, as it should. I’m in no rush. I spent so much time trying to organize the life that I thought I wanted. It wasn’t the same as living.

Moving On

2012-07-25T00:00:00-07:00

Moving On

Over two years ago, I flew across the country to spend hours in a basement in Brooklyn talking with two guys I barely knew. Those two guys were Josh and Shamir, respectively CEO and CFO of Simple (then BankSimple). When we first sat down, they had already put in months of work figuring out how to start a new kind of banking service. Josh and Shamir were ready to turn their vision of online retail banking with stellar technology, design, and customer service into a reality. I was ready for a new role and a big challenge.

During those first conversations, I asked Josh and Shamir where they saw themselves in ten years. Neither hesitated to reply “running this company”. Since then, I’ve witnessed their perserverance and dedication firsthand. Over the past two years the product has evolved from rough prototypes and a list of features on paper to a working, growing banking service. Today, Simple is bringing on customers by the thousands and rapidly becoming the center of their financial lives. It hasn’t been an easy thing to launch, but working on a product that addresses real problems at the intersection of economics and technology has been a fascinating opportunity.

While I’m extremely proud of the work everyone at Simple has done on the road to launch, I’ve come to recognize that the role of CTO isn’t right for me at this point in my career. Part of my motivation for joining Simple was to explore what it’s like to be a founder and executive at a startup. Being CTO afforded me the opportunity to work with and support a number of the most talented people I know. In that and many other respects it was a great experience. As with any job, though, there are tradeoffs.

The biggest tradeoff for me is that this role has taken me further from learning more about the craft of programming. Simple offers many great career opportunities for engineers, but not in some of the areas I’m most passionate about, particularly programming languages and developer tools. I feel that I have an enormous amount left to learn as a programmer, and hopefully a few things to contribute in that capacity as well. For that reason and some personal ones, I’ve stepped down as CTO at Simple.

My relationship with the team at Simple remains strong. The engineering organization there is in extremely capable hands. I have every confidence that the team will continue to do exceptional, industry-leading work. For my part, I’m staying on as an advisor to the company.

My next steps are to take some time off, relocate, and to consider my next move. This will be the first time in my adult life that I haven’t immediately gone from one job to another, and I’m looking forward to the perspective that a breather will lend.

I’d like to extend my thanks to Josh and Shamir for taking a chance on me, to the exceptional people who came to work with us, and to everyone who’s helped Simple along the way.

What Is and Is Not A Technology Company

2012-05-08T00:00:00-07:00

What Is and Is Not A Technology Company

When I was a kid, I had a morning routine with my family. Over breakfast, we’d divvy up the newspaper. I’d go straight for the Business section, and from there to the back pages with yesterday’s stock prices. Scanning down the lines of tiny text, I’d look for SUN, ORCL, MSFT, AAPL, SGI. Then back to the front of the Business section, reading whatever I possibly could about the silicon giants of the day. Then, finally, the funny pages. I was a weird kid.

Today, like many, I no longer get a physical newspaper. Most mornings I sit down with my iPad and pull up Techmeme, which more often than not leads me to several different “tech blogs” that deliver a mix of rumor, opinion, gossip, rehashed press releases, and, very occasionally, actual news.

There’s a striking difference between the technology news I grew up with and a lot of what I end up reading these days. The difference is something I only recently cemented for myself: most so-called tech news isn’t about technology at all anymore.

Confusing Startups for Technology

There was always something that bothered me about TechCrunch, and it bothered me more and more over the years that the blog rose to be the sort of force that could wipe a site out with a tsunami of traffic just by linking to it. For a publication with “tech” in the name, technology only ever seemed ambiently present in TechCrunch’s reporting. Software and hardware are background music for the site’s real interests: money and power, success and failure, who’s up and who’s down. TechCrunch often read to me like the parts of the Business section I used to skip as a kid, the boring ones with “merger” or “acquisition” in the headline and a picture of two suits shaking hands.

TechCrunch’s popularity urged on a slew of imitators, and now the majority of “technology journalism” consists of blogs that operate in the same general mold. Even newspapers have adopted TechCrunch’s overall format and pace of publication for much of their writing on technology. This has shifted not just the tone and the depth of technology reporting, but the subject matter as well. Where newspapers tended to focus on established technology companies, TechCrunch has always primarily been about startups. With everyone following in their footsteps, startups have become synonymous with technology journalism.

And why not? Startups are exciting. They’re often headed up by interesting people who want to take on big problems. Startups seem somehow rebellious and alternative, but in a way that’s safe and accessible enough to read about at the breakfast table. Startups have drama. Will they survive? Get bought for a billion dollars? Fail spectacularly? What’s more, startups love to talk about themselves, which makes life easier for reporters. What founder, save one who’s already well-established and cagey, is going to turn down free publicity?

Startups, however, are not inherently technology companies.

It’s now accepted-going-on-cliché to say things like “software is eating the world”, which is an aggressive way of assuming that every company now has to be at least a bit of a technology company, and those that want to grow rapidly even more so. Many new companies targeting industries as diverse as eyeglasses and baby food are, at the outset, leveraging technology for everything they do: supply chain management, marketing, recruiting, internal communication, product development, and so on. This makes these businesses look like technology companies, if you squint. But, of course, they aren’t. They’re eyeglasses and baby food companies.

Somewhere along the way, we confused “startup” for “tech startup” and “company” for “technology company”. Now that every growing business requires significant competence in technology to succeed, the distinction is even blurrier. Is a company that has staff members with “programmer” or “engineer” in their titles a technology company? Are they a technology company if they were funded by venture capitalists who have previously funded businesses that we think of as technology companies? Are they a technology company if their founder was using a laptop when she came up with the idea for the business?

A Definition, But Not a Value Judgment

These questions are pretty easily resolved. You are a technology company if you are in the business of selling technology. That is to say, if your product – the thing you make money by selling – consists of applied scientific knowledge that solves concrete problems and enables other endeavors, you are a technology company.

By this definition, most of the companies that dominate the “tech blogs” are not technology companies. They’re just, well, companies. These businesses might use technology, or develop technology, or even be run by people who used to work at technology companies, but they don’t exist to create and sell technology.

IBM is a technology company. Basho is a technology company. Boundary is a technology company. Apple is a technology company thanks to some of its lines of business (hardware, software), but is not a technology company in all of its lines of business (music, movies, books). Ditto Google and Amazon, which make money both from selling technology and from leveraging technology to sell things like advertisements and socks.

Simple is not a technology company. We use and develop technology, but we are a banking service, and we make money through banking. Zappos, likewise, is not a technology company. They use and develop technology, but they make money when people buy shoes from them. Technology might make our respective businesses run more effectively, or give us a competitive advantage, but it is not our product. An interest in technology might shape our corporate cultures, but technology is not what we sell.

Put more crudely: sticking feathers up your butt does not make you a chicken, and having an engineer or a data scientist on staff does not make you a technology company. Having people in these kinds of roles just makes you a company that has to do business in a world that requires code to be written in order to operate efficiently.

This definition also doesn’t suggest that only “enterprise” technology companies are “real” technology companies. There are plenty of companies that make money by selling technology to consumers. But there are also a lot of businesses selling actual things to consumers who get lumped in with technology businesses simply because they sell products via the web. That might have been an important distinction in 1995, but no longer.

What I’ve spelled out is a definition, but not a value judgment. I’m not saying that technology companies are good and other types of companies are bad, or vice versa. What I’m saying is that they are different, and that they require different approaches for investors, executives, and particularly for the press. Because technology companies are trafficking in applied science, an understanding of that science is required in order to reason about and report on their operation with any kind of cogency.

New Terminology Needed

“Tech company” and “tech startup” are over-applied labels that have outlived their usefulness. Calling practically all growing contemporary businesses “technology companies” is about as useful as calling the enterprises of the industrial era “factory companies”; it accurately describes an aspect of what they are (or were), but it doesn’t really capture the totality of their operation. It certainly doesn’t tell you anything substantive about how they’ll behave in the market over the long term, which is probably the most useful reason to label a business at all.

What’s more, this mis-labeling results in the conflation of companies in totally different industries applying totally different business models, all being funded and staffed and reported on by the same pool of people. If we remove the label of “tech startup” – and with it the hypothetically stellar trajectory we like to imagine such businesses are on – we’re forced to confront the reality of a business’s model, independent of the reverberations of the echo chamber.

That said, what TechCrunch and other sites often cover is clearly something distinct: companies that have information technology so close to their core (“in their DNA”, if you can still stomach that phrase) that they seem to have acquired the essence of this thing that they use to get ahead. But in confusing how these businesses make their product and what their product is, we introduce a whole set of assumptions and biases and information gaps that, by the looks of it, have resulted in a distorted market for companies and their equity, salaries, publicity, office space, and so forth.

I’m not sure what the ideal terminology is for today’s burgeoning companies. At startup showcases, terms like “disruptive businesses” are thrown around, but they presume too much to be useful. The word “startup” itself presumes too little, and has become overloaded. In time, a new word will present itself. Or maybe we’ll have to learn to be satisfied by talking about businesses that leverage information technology in creative ways as, simply, “businesses”. But clarifying our language is only the outward expression of clarifying our thinking.

Really, nobody but sociologists and historians should be running around talking about “technology” in the large. It’s a vague word for an even vaguer set of ideas about how humans operate in the world. Our current culture sprinkles this word around like faerie dust, blinding us to the truth of what things are, how they work, and who’s responsible for them. Broad cultural change takes time. As a starting point, the business world seems as good a place as any to wipe away the magic dust and start seeing clearly.

The Game

2012-04-09T00:00:00-07:00

The Game

A few years back, I lived and worked in Northern Virginia, a sprawling collection of suburbs just outside Washington, DC. It’s a place of malls and strip malls, office buildings and office parks, a territory inlaid with and surrounded by perpetually packed freeways carrying government workers and contractors home to planned communities. It’s a place people live because of a job.

At the time, I had a job I liked very much, and so did some people who worked across the highway-wide street. We all got to do challenging things with computers and we had a lot of freedom as to how we went about it. We became friends.

Some evenings, after work, we’d gather at one or another of the area’s strip mall Middle Eastern cafés. We’d order big plates of kabobs and rice and hummus and pita and try to best one another at the ideal combination of flavors of shisha to share in the hookahs that are the cafés real draw. On warm nights we’d sit outside and watch the sons and daughters of wealthy diplomats preen for one another in an endless contest for the nicest car, the chicest clothes, the most beautiful partner on your arm. Farsi music videos blared and the suburbs around us were all but gone in the hanging smoke.

And then, when the plates of food were replaced with mint tea and Turkish coffee, we played a game.

The game is called Zendo. It’s made by a company called Looney Labs who, like many clever small game companies, reuse a set of universal pieces for a number of their products. Zendo is played with signature plastic triangles called Icehouse pieces, as big and as varied a set as you care. The triangles are hollow, allowing them to be stacked. They have a small “pip” on each side that designates a point value. The triangles come in just three sizes, but are available in a whole variety of colors and opacities.

A round of Zendo begins by designating a “master”. In her mind, the master comes up with a rule that describes multiple configurations or structures made up of the triangular pieces. A rule might be: “blue triangles must always have a red triangle stacked atop them”. Or: “the total number of pips in the structure must be divisible by two”. The master builds one structure that satisfies the rule alongside one structure that does not, and the two structures are marked accordingly with white and black stones respectively.

Each turn, a player who is not the master builds a structure from the shared pile of spare triangles. Each structure a player builds is marked with a stone designating its adherence to the master’s unspoken rule, just as with the master’s original example structures. If a structure fits the master’s rule, an additional green guessing stone is earned by the player that built it. A player can trade a guessing stone for a guess at the rule, asked of the master in front of the other players. Play proceeds until someone correctly guesses the master’s rule.

That, modulo some details, is the game.

Zendo and Understanding Programming As A Collaborative Endeavor

Zendo is a game of inductive logic. Anyone can enjoy it, but programmers take particular delight in it. In broad strokes, a round of Zendo mirrors the intellectual process programmers engage in when debugging. You know there’s a rule in the machine undermining the task you’re trying to accomplish, but you don’t know what the rule is, so you build and rebuild and think and observe and rebuild again until you understand the rule, and then you win.

Zendo’s process of becoming gradually un-blind could even be said to be a metaphor for how many of us learn to program, particularly if you’re self-taught. You’re thrown into a black nexus of thousands of unknown rules and made to reason in the dark. With each rule you discover, a little less dark. (I’ve been programming in earnest for sixteen years and presently find myself in a sort of early-evening twilight, plus a couple of sconces in the corner and maybe a night light.)

For me, the interesting thing about Zendo is not its parallels to the task of programming as an individual, but thinking of the game as a model for collective problem-solving.

One strategy for Zendo is to hole up in your mind, obsess over the structures you’ve built, and try to crunch through every possible permutation on your own. This approach works well if you’re a genius, I’d imagine, but most of us are not. It’s also a good way to lead yourself astray, convinced that you can see the general shape of the master’s rule when in fact you’re thinking along entirely the wrong lines.

A more broadly applicable strategy is to throughly observe the plays of your opponents and treat “solving” the round as a kind of computation distributed across all the players. Together, you and your fellow players are brute forcing the problem of discovering the rule. Every (motivated) player at the table decreases the time it takes to win.

The best rounds of Zendo I’ve ever played are ones in which the master has chosen a devilishly hard rule, a rule so difficult to guess that the players cease to be in competition with one another and are instead in a collective war against the inscrutability of the master. When one player finally wins, it’s due to the combined efforts of all the players building structures, making guesses, exploring the solution space. That shared victory is a wonderful moment.

Flashes of brilliance are few and far between. Even when they strike, turning a brilliant insight into something reproducible is almost always an effort beyond just one person. Programming lore is full of stories of lone-hacker-in-the-night heroism, but the reality of what we do is one built on collaboration: between pairs, amongst teams, amongst companies in the marketplace, amongst universities and laboratories, amongst contributors to open source projects.

I write this by way of encouraging you to:

Play a round of Zendo. It’s out of print, but you can still buy Icehouse pieces.
Remember that people are everything. It’s easy to get caught up in a problem, particularly if you aren’t a naturally collaborative person. Don’t forget that the people you work with – peers or partners, managers or interns – complete your work and vice versa. If you don’t at least observe the successes and failures of their work, you’re going to be that much more in the dark.

One last thing about Zendo: it’s not much fun to be the master until someone guesses the rule.

Are We Experiencing an Information Technology Fin de Siècle?

2012-03-06T00:00:00-08:00

Are We Experiencing an Information Technology Fin de Siècle?

It is a strange and interesting time for information technology.

For every example of technology dominating both markets and mindshare – Apple as the most valuable company in the world, Groupon and Zynga accounting for 31% of all IPO money raised in 2011, Facebook’s own massive upcoming IPO – there is an equal amount of nay-saying, second-guessing, and soul-searching. It’s easy to find people who are excited about making money off technology-driven businesses. At the same time, it’s becoming harder to find people who are unreservedly excited about the overall state of information technology and its impact on our lives.

Nick Bilton, the New York Times technology writer, thinks today that the fun is leaving technology. Malcom Gladwell thinks networks aren’t the tool for political and social revolution that they’ve been built up to be. Jolie O’Dell, another technology journalist, lamented two years ago that technology companies aren’t solving real problems. Hermione Way, a British tech PR consultant and journo, argued much the same last year after spending some time immersed in the Bay Area technology community. Meanwhile, Silicon Valley technology journalism itself is under fire as a pay-for-play ‘cesspool’ run from the pockets of venture capitalists.

Peter Thiel, one of the more notable figures at the intersection of technology and finance, has argued very repeatedly that technological innovation, particularly in America, is decelerating. The business press echoes this sentiment, having spent the past several years questioning Silicon Valley innovation (when not celebrating the apparently un-innovative but business-savvy people making piles of money there, inclusive of Thiel). We’re in a technology bubble, they say, but not one that’s likely to directly produce technologies with much lasting social good. The claim is that wallets are expanding, but our list of big unsolved problems is not shrinking proportionally.

Moving into longer form writing, the world of books is full of voices that are at least as critical of the state of IT today, if not more so. Nicholas Carr is worried about what the Internet is doing to our brains. Sherry Turkle thinks technology is undermining our relationships. Jonathan Zittrain is worried that the coming corporatized, locked-down Internet will end a cycle of innovation. Jaron Lanier thinks social technology undermines humanist values. Eli Pariser thinks collaborative filters are narrowing our world. Evgeny Morozov is suspicious of the promise of digital democracy. Interestingly, several of the aforementioned authors spent the earlier parts of their careers as staunch technology advocates and innovators.

I’ve only carved off a sliver of the tech-whinging of the past several years. The summary is basically that people think we’re both not innovating enough and innovating in the wrong directions. Regardless of what you think of the individual arguments, the sheer volume of the chorus of voices criticizing the state of IT today is interesting.

There are any number of possible interpretations of all this criticism, questioning, and doubt:

Technology really is going down the wrong track and these critics are picking up on that first. Or:
People are always critical of new information technologies, and they’re usually wrong. This is just the latest round. Or:
Technology has become so commingled with the rest of our lives that we can’t see the forest for the trees anymore. See Sequoia, don amongst technology venture capital firms, funding a chain of grilled cheese restaurants. Or:
Technology is about to head in a new and different direction, but we’re not yet sure that what that direction is, so there’s a lot of tension and malaise and last-gasp profiteering as we milk the last fifty-plus years of research for all they’re worth.

Or something else entirely.

At any rate, it’s interesting right now. Interesting and strange.

How Not To Sell Software in 2012

2012-02-29T00:00:00-08:00

How Not To Sell Software in 2012

Though most of our stack at Simple is based on open source software, we occasionally try commercial software. Mostly, we don’t end up buying it. A big reason why is the incredibly time-consuming, aggravating sales process that most commercial enterprise (that is, non-consumer) software vendors insist on. I’m between vendor calls today and channeling my irritation into this post.

It’s 2012. Practically everyone who’s paying for software is doing so through an app store: one click or tap and you’ve got what you want. Heck, even free/open software people have an app store these days.

Similarly, more and more people who are paying for remote computing resources, whether servers or software, do so through instantly available, transparently priced cloud services. I can give Amazon my credit card number and have everything I need to run a growing business without ever talking to a salesperson. I like it that way.

Today’s startups are tomorrow’s enterprises. Many of the other startup folks I know share the same expectations about how software should be sold. Basically, if a given software package or service isn’t free/open, it should be as easy as humanly possible to try it, pay for it, and start using it in production. If it isn’t easy to get started with your product, I’m going to find another vendor.

The List of Don’ts

If you’re in the enterprise software business, you’re going to be dealing with more and more potential customers like me as the demographics of our industry shift. So, if you’d like to keep making money, here’s what not to do:

Don’t require that I waste my time on a sales call – or, worse, in a “webinar” – before I can give you my money. Instead, provide all the information I need about your product on your website.
Don’t make it hard for me to try your software. If I can’t play with a trial version or sandbox immediately, I’m moving on.
Don’t hide your pricing behind a sales process, and don’t play pricing games. I can find and talk to your other customers basically instantly in order to determine what they paid for your product and if they’re getting the value they expected from it. I will do this. So just put the price of what you’re selling on your site and skip the games.
Don’t make me read a whitepaper in order to get essential information about your product. Put it on your website. In HTML. Not in a PDF, not in Flash, not in Silverlight or ActiveX or whatever. What your product does, on your website, in HTML.
Don’t automatically sign me up for a newsletter about your company or product when I give you my contact information. Ideally, don’t request my contact information at all until I’m giving you money.
Don’t make it hard for me to talk to a technical person at your company about the nitty gritty details of how your product works. If you don’t provide a forum for those discussions, someone else will, and you won’t control it.
Don’t make it hard for me to pay for your product. I have a credit card. I also have a PayPal account, a Google payments account, and an Amazon payments account. Any of those are fine (although PayPal is not ideal). Any other billing process is not.
This should go without saying, but don’t cold call or spam me. If your product is good and meets my needs, I promise that I’ll find out about it.

Basically, the farther away you get from being like an app store or Amazon Web Services, the less likely it is that you’re going to get my money.

Examples, Good and Bad

I’m sure some vendors think that they’re special and unique snowflakes whose products couldn’t possibly be sold without high-touch interactions with potential customers. Yet, somehow, a new generation of companies is managing to meet the above requirements, and I sincerely hope they eat everyone else’s breakfast, lunch, and dinner.

Beyond aforementioned Amazon, here are some companies doing it right:

Urban Airship – transparent pricing, get started immediately.
The Resumator – ditto.
PagerDuty – ditto.
Expensify – ditto.
Duo Security – ditto.
Skype – their Manager product for business is actually really handy, and the information on their site about it is clear and to-the-point.
Google Apps – their dashboard is a mess and their customer service is abominable, but pricing is straightforward and you can get started immediately.
Datameer – not perfect, still a lot of whitepapers and salesy garbage on their site, but I was able to get up and running with a trial version in minutes.

And, some companies doing it wrong:

Five9 – your site says “cloud”, but your sales process says “1970s mainframe”. Every possible sin: forced sales call, forced webinar, getting set up with a demo requires yet another phone call, pricing is hidden. Just awful.
GitHub Enterprise – it looks like their sales process has improved somewhat from when the product was called GitHub:FI and it took them days and days to take our money. That said, “trial licenses are subject to approval” in the current iteration, which is kinda weak. I really love GitHub and I hate to talk mess about them, but I’m only mad because I care.
Yodlee – pricing games galore.
Karmasphere – I don’t want to “request a trial”, I just want to try it.
Metamarkets – lots of good product information on their site, but everything else is hidden behind a contact form. I filled that form out and never heard anything back, not even an automated reply. (Updated: they got back to me and set me up withe a demo; apparently they had a bug in their marketing site come up while migrating from one domain to another.)
Basically everyone else in the business intelligence market.
Basically everyone else in the VOIP/virtual callcenter market.

Conclusion

I want to give you my money. Your sales process may be a bigger barrier to you getting my money than your competitors. Please join us in the year 2012, where software is available instantly and transparently priced and the word “webinar” is only used ironically.

On Business Madness

2012-02-12T00:00:00-08:00

On Business Madness

I am not intentionally a business person.

Over the course of my career to date I’ve worked at companies of various sizes, and have been situated at commensurately varying distances from the concerns of running a business: funding, sales, forecasting and planning, marketing, payroll, legal matters, and so forth. In that time, I’ve developed an interest in the mechanics of business. It seemed prudent to know where my paycheck was coming from. Still, I got to keep my distance from the “business stuff”.

Being now a co-founder of a startup has made it difficult to stay impartial when considering how businesses work, how they succeed, and how they fail. I’ve made a couple of angel investments, and I advise a couple of other startups. It’s hard to spend one’s time and money this way and not develop an opinion about what is a “good business” or a “bad business” and the practices and decisions that support such outcomes.

But, as I observe discussions of business matters in the startup community, I can’t help but think that none of us – for all the blustering blog posts, crowing keynotes, self-published manifestos, and chest-beating sound bites fed to hungry reporters – have little more than the slightest idea what we’re doing.

We mistake dumb luck for a machine that produces success. We rely on induction when we should rely on deduction, and then, having realized our mistake, we lean on “data-driven decisions” in lieu of common sense. We chase patterns that aren’t there and miss eager markets right in front of us. All this while projecting the confidence, real or manufactured, that’s necessary to play the game.

This madness takes many forms.

Pattern Matching

There is a term that venture capitalists use: pattern matching. My ears perked up the first time I heard this from a VC, because in the world of computer science, pattern matching is a well-defined concept and a feature of more interesting programming languages.

To a programmer, pattern matching is a slick way of looking for a needle in a haystack of data. The haystack must be a known quantity: a thing, or maybe a collection of things. The needle, too, we must be able to describe: a particular value, a type of thing, a collection of things grouped in a particular way. Once we have our haystack and describe our needle, the computer does the rest. But pattern matching is not fuzzy logic. It is clean-shaven logic. Logical logic, of the sort programmers tend to like.

For venture capitalists, pattern matching is a way of saying: “I’ve seen this result in people making money, but I haven’t seen that result in people making money, so you should probably do this and not that if you want to make money.” I have to admit, I was somewhat disappointed when I realized how the term was being employed at the negotiating table. I thought maybe VCs had access to some brilliant new software that evaluated prospective investments in startups. But no. What we’re talking about is good old fashioned experience, which is what you get to call induction when you’re making money and what you say you earned instead of cash when you were losing money.

Many firms make their venture capital investments with a “shotgun” approach: fire chunks of money at a bunch of companies and hope that a couple of them make it big. That is to say, the VCs who operate this way make their money from anomalies. Talking to some such investors, though, you wouldn’t know it. If they haven’t seen it before, they’re not interested. They want something new from something known. They rely on exceptional outcomes from circumstances that align with their experience.

Apparently, experience hasn’t worked particularly well for the last decade.

Location, Location, Location

Startup founders love to obsess about location. Worrying about where in the world to start your company is a wonderful way to defer the terrifying prospect of working really hard on it and potentially failing.

To wit: as I type, one of the top articles on Hacker News is a guide to where you should locate your startup in the Bay Area, down to the neighborhood level. Read now, lest you lease an office on a block that hasn’t been visited by the talent acquisition faerie!

People outside of the Great Silicon Valley-San Francisco Startup Sprawl also love to talk about location, but defensively. “Hey, we matter too!” they shout from Boston, London, Seattle, Iowa, Berlin, and most anywhere else that a person with a laptop and the eagerness to fill out incorporation paperwork can live. Certainly, a fair amount of agonizing about local startup viability goes on in my adopted home of Portland, Oregon.

A cursory look at the data shows that location pretty much doesn’t relate to the long-term success of a startup. Which, if you think about it for even a second, makes perfect sense. How many of our corporate behemoths have their home offices in unlikely towns and cities? How many of those towns and cities have grown up around companies, and not the other way around?

There are good reasons to start a company in a particular place, or to move your company from one place to another. “Because everyone else has” is not one of them.

Process Cults

Running a business means making many, many decisions. Decisions can be hard to make. Having a framework in which to make decisions greases the wheels, but coming up with said framework is even harder than making decisions. Thus, the wide world of business books.

No, I’m not going after business books as a whole. What interests me is a particular form of Business Madness that often ends up in book form: the Process Cult.

Process Cults form around a set of business practices that, when judiciously applied, are supposed to yield a profitable, successful business run by shiny, happy people. The startup segment of the business book market has its favorites:

Eric Reis’s lean startup and associated book.
Steve Blank’s customer development and associated book.
37signals’ methodology, as expressed in the books Getting Real and REWORK.

I have read all of the above. I don’t necessarily agree or disagree with their contents. What I disagree with is the notion that anyone should start or operate a business in the explicit mold of someone else’s experience, as reduced to a couple hundred pages padded with illustrations and diagrams. It’s a bit like starting a fad diet without considering the particulars of your health and lifestyle. It may be hard to subsist on kumquat juice when your neighborhood grocer doesn’t sell kumquats.

The ultimate use of such books is not so much for the advice they contain, but for the social signaling that comes from adopting one as scripture. Lean Startup people go to Lean Startup meetups to find co-founders. The term “customer development” is dropped in pitches to knowing nods from investors who believe in the approach. Those who have Gotten Real leave supportive comments on blog posts by their brethren, railing against the inanity of whatever venture-funded company is this afternoon’s big story. Bonds are formed and reinforced. Process Cults emerge, putting more faith in ritual than in ideas.

When I look around the world, the businesses that dominate don’t seem to be the ones that formed around process as a rallying cry. Rather, they adapted processes to bolster world-changing, market-creating ideas. The world doesn’t need a lean startup, or a developed customer, or a REWORK’d business; it needs solutions to problems, magic where previously there was darkness. How that magic happens is interesting and maybe even useful as a basis for other people running businesses to compare to, but it’s not a recipe for success.

Conclusion

Given some preparation and calibration, you can bake the same cake from the same recipe the same way every time. But a business is not a cake – not even a cake-making business. You can retrofit “success factors” to businesses that made it big, but you can’t then reapply those factors to another business and expect the same results. Every new business is an experiment with too many variables to possibly control for: the concept, the execution, the stability of the people working on it, market forces, political turmoil, the weather, and on and on.

The factors that appear to make a business successful change from week to week, article to article, tweet to tweet, blog post to blog post. This week, everyone is trying to figure out how to replicate Facebook’s “hacker way” because that’s where the money is going. But eventually, the money moves on, and with it goes our idea of how to manufacture success. It was Taylorism in the 1880s. It was Japanese management theory in the 1980s. A few weeks ago, before our collective attention shifted to the Facebook IPO, it was whatever Steve Jobs had done, from hallucinogens to yelling at your employees. Next week, it will be the philosophy of whoever seems likely to make the most money right then.

How can we be like the successful ones and not like we are: tired, confused, scared, not-rich? Just tell us the secret. There is a secret, right? There must be. They make it look so easy.

I am not a business person. I don’t know what makes a good business. It seems like it helps to have a good idea, great people, the willingness to work hard, and an absolute shit-ton of luck. Being certain about much beyond that seems, well, a bit crazy to me.

On the Welcome End of a Black Year

2012-01-09T00:00:00-08:00

On the Welcome End of a Black Year

At the beginning of 2011, all I wanted was a year of single-minded focus on our work at Simple. 2010 was a frenetic year for me, full of change and excitement, risk and commitment. I had made a number of life-altering choices in 2010 that I was eager to see through in 2011, and work was foremost amongst them.

Around this time last year, I remarked tone day that things were going almost too well. I was loving my new home in Portland. I was loving the excitement of getting Simple off the ground alongside the brilliant people I get to work with every day. The other shoe had yet to drop.

Then, just as I was about to leave the office one night in March, I got a call from my mother.

“[Your step-father] is dying”, she sobbed.

And there went 2011.

Memorium

My step-father, Rodney, was a remarkable human being. Born in South Africa, he got his start in the forestry service, engaging in early conservation efforts and planting forests in Mexico as well as his home country. Diplomatic work later took him to New Zealand. Eventually, disgusted by apartheid back in South Africa, he moved his young family to the United States and found work in the decidedly niche field of nuclear transportation. There, he excelled, ultimately co-founding Transport Logistics International, which he ran until its effective sale in early 2010.

Think about this for a moment: like it or not, the world has many nuclear weapons, plus a number of nuclear reactors used for power, medicine, scientific experimentation, and so forth. In the last several decades, most of the world has decided that nuclear weapons are bad, but that nuclear reactors can be quite good and useful when operated correctly. To that end, there are international cooperative efforts, like Megatons to Megawatts, that turn nuclear weapons into fuel for power plants. So, who moves the actual nuclear material from those weapon sites to places where it can be used for good? Who moves nuclear material to and from reactors? Who keeps it safe in the process?

Well, Rod did. Which, whatever your opinions on the safety and efficacy of nuclear power, you have to agree is a phenomenal thing: moving potentially planet-destroying nuclear material around the globe safely and predictably while billions of people simply go about their days.

In many ways, Rod was my model for entrepreneurship. Throughout my teenage years, I watched him start a company, grow that company, cope with its with ups and downs, handle politics both interpersonal and international, and ultimately exit TLI successfully after more than a decade of hard work. His surprisingly small team performed their critical task from a modest office in suburban Maryland. He demonstrated every day that it’s possible to run a company ethically, do good and important and meaningful things, treat employees fairly, and still make a profit. Before knowing Rod, I never would have considered the world of business. Having known him, it’s hard to imagine doing anything else with my life.

Fighting and Dying

With most of my extended family living across the country, death was always a remote event, something that happened “over there”. Our relatively small family hasn’t been free from loss, but we’ve also had fewer funerals in our past than many other clans I’ve known. Upon receiving my mother’s call, then, my immediate reaction was to outright dismiss the distant – in all senses, distant – possibility that what she was saying was true.

My step-father had been diagnosed by his general practitioner with pancreatic cancer, a type of cancer that’s recently seen a lot of press in relation to Steve Jobs’s death. There are several main varieties of pancreatic cancer; some are operable and some are not, but the overall survival rate on a not-particularly-long time scale is not high. If you have your choice of cancers (and you don’t), this is not the one to choose.

Rod had been told by his doctor, bluntly and unkindly but ultimately truthfully, that he wouldn’t live to see Christmas (2011). We, of course, refused to accept that. We searched every available resource, contacted everyone we could who might have some insight or direction, considered every experimental option. Rod was quickly enrolled at the Sidney Kimmel Comprehensive Cancer Center at Johns Hopkins, which we deemed to be both the best and the most practical option for his treatment, as my mother and step-father then lived less than an hour’s drive away.

That was early Spring. Over the next several months of in-person visits and frequent phone calls, things went up and down repeatedly. One week, Rod would be feeling better and numbers on tests would be interpreted as saying good things; you wouldn’t guess from looking at him that he was dying from cancer. The next week, he’d be a wreck, and the numbers were now telling grim stories. Then it would all shift around again. Surgery wasn’t an option in his particular case, so our hopes of spending more time with him rested on drugs and chemotherapy.

It’s hard to say how much time the treatment bought us, and if it was worth the pain and time and expense. As summer drew to a close, I got on a plane yet again. I knew from the grim tone of the doctor I had spoken to that I wouldn’t be coming home until my step-father was dead.

The man I saw when I arrived at the hospital was a faint shadow of the man I had known throughout my adolescence and early adulthood; a pale gray crescent of a person who had always shone brightly with determination and conviction. We talked for as long as he could manage, and after he fell asleep, I wept at his bedside until I could physically produce no more tears.

That seemingly endless week in August was the conclusion of our family’s personal tragedy. Rod had sold his company a little more than a year before his diagnosis. So here, dying in barely-contained agony, was a man who had worked tirelessly his entire life, only to be felled mere months after his retirement. His regret was palpable, never at having worked hard, but for having worked too hard, sometimes putting the wrong things first. It was a final lesson.

After

Reading an article on how doctors choose to die some months later, I found myself nodding sadly along. For as far as we’ve come with medical treatment, diseases like pancreatic cancer still have the best of us. For the future, we need to aggressively fund and remove barriers to research. For today, we need to acknowledge that simply managing pain for as long as you’ve got may well be the best option. I wish Rod had spent less of his final weeks in a hospital being filled with hopeful poisons and more with us, doing whatever he damn well pleased.

I was happy to see 2011 go. The remainder of the year was filled with unpleasant reminders of death as Steve Jobs, John McCarthy, Dennis Ritchie, and Christopher Hitchens – all men I revered – passed away one after the other.

With the my friends, family, and my unbelievably kind and understanding coworkers and board at Simple, I feel ready to make 2012 the focused year that I hoped this past one would be. Life, after all, is for the living. Rod taught me how to live better and work better. That’s what we’re here to do.

Obligation

2011-06-27T00:00:00-07:00

Obligation

Back in March, I wrote (and subsequently removed most of) a ham-fisted post about the obligation that smart, privileged people should feel to work on things that might make a difference to other people. This was discussed in the context of questioning whether so-called lifestyle businesses are a good idea for entrepreneurs and society at large.

I’ve mulled over the idea of obligation and how it relates to entrepreneurship off and on in the intervening months. That thinking has changed my tune pretty significantly.

There are several obvious problems with obligation as it relates to work:

Some people don’t feel obligated to do much of anything.
Most people don’t like to feel obligated to do something, even if it’s the optimal thing for them to do. We like choice, or at least the illusion of choice.
If what you’re doing isn’t making you happy, you probably won’t do a good job at it. You might even subconsciously sabotage yourself.

That final point, on happiness, is by far the most important of the three. Even if we had a magical machine that told us the optimal, most societally beneficial job for every individual – that is, the job we should be obligated to do – it wouldn’t matter if we were all assigned jobs that we hated. Fulfilling a sense of obligation isn’t a substitute for actual unqualified happiness, and it’s certainly not a recipe for good work.

At the end of the day, the best thing you can do is to figure out what makes you happy and then do the hell out of that thing. You’ll probably do a great job at whatever it is you’ve decided to do. Hopefully, your passion for your work will result in positive outcomes that benefit you and your community. Maybe we’ll all luck out and the job that makes you happy ends up benefitting a large number of people. If not: hey, at least you’re not miserable.

Problem is, it’s really really hard to figure out what makes you happy. It’s way easier to guilt yourself into a sense of obligation which you then use to rationalize the decision to do something you don’t actually enjoy. (Other popular happiness-avoidance tactics include doing nothing, trying to make a lot of money, bad relationships, and over-education.)

The type or scale of work you do doesn’t really matter as long as you’re happy. Some people are made happy by running a lifestyle business. Some people are made happy by running a Fortune 100 multinational. Doesn’t matter. Do what you love. If you don’t, you’re not going to make things better for anyone, very least yourself.

This advice is so completely and utterly not new, but it’s repeated over and over again because so few of us actually seem to remember it. Or maybe people do remember it, but they never create or are afforded the opportunity to do what they love. I’m not sure. All I know is that trying to do what you love as a guiding principle makes a helluva lot more sense then acting out of a sense of obligation. That, and I was pretty damn wrong.