Seven tough lessons from ten years in bootstrapped business

When I entered the self-employment world at barely the age of 22, I had only three and a half years of industry experience, albeit in half a dozen job roles. Owing to my academic and Soviet sociocultural roots, I also had vanishingly little received social knowledge of business. Commerce was not a family tradition.

At present, my business retains a mixture of product and consulting revenue, though with a renewed focus on product following a few tumultuous years. It is what one might call a “moderately successful” business; it’s still around ten years later, and it makes a respectable, if hardly ostentatious, living for its owner, but it has not significantly grown beyond that.

Thus, in such ambivalent circumstances, the tenth anniversary of the company’s humble start as a bootstrapped concern passed largely without remark at the beginning of this year. Nevertheless, I’ve had an ample opportunity to ponder the most important things I’ve learned along the way.

There’s a school of thought out there that says speaking with candour about mixed results or outright failures, or in any way admitting or owning liabilities, is bad for marketing and bad for the business’s image. You know, it is. 99% of business-related messaging out there consists of “success porn” and proclamations of victory. No businessperson on their right mind would stray from the safety of those clichés; the image of success sells, the same way a $3000 suit and a rented Ferrari sells.

I’m out to help promote a new, brutally honest way of writing about life in the trenches. I think the social utility of publicly discussing the realities of entrepreneurship outweighs the risks. If an owner-founder out there reads this and realises they’re not alone in the obstacles they slog through as a one-man band, the magnitude of my happiness will be greater than the magnitude of my worry that someone, somewhere might think I suck at life. In short, I’m not going to take part in “success porn”; my anecdotes may paint a less rosy picture, but I’m candid about the lessons that I really did learn, and I own my many mistakes. I value reality and substance over figments of marketing imagination or self-congratulatory treacle. If you do too, that should give you some confidence in doing business with my company. So I hope.

One last thing: this article is implicitly about bootstrapping a small “information age” business from nothing, or at most a small investment of personal capital. A distinguishing trait of “information age” businesses of this sort is that the primary capital is human and the startup cost is, in principle, quite low. What I say is unlikely to apply to businesses requiring significant investments of COGS (Cost of Goods Sold) or machinery.

I started out suddenly, with $200 to my name, no revenue, no customers and no business model, and having just blown my meagre savings on a down payment for a condo. Result: two mortgages and a car payment were due the next week.

Wiser people would have avoided that kind of extreme (more on that below), but this is nevertheless possible in the business models I’ve got in mind. I suppose lesson #0 is: don’t start a business like that. If I were doing it over again, I would certainly live cheaply, save money, and capitalise the business with at least a year’s worth of runway.

If you have funding or are starting from a position of nontrivial wealth, or want to open a restaurant, a shoe store, or for that matter a backyard medical devices factory or an oil drilling rig, you might as well skip this article, as your economics and constraints are going to be entirely different.

With all that in mind, here are some other things I’d travel back in time to tell my younger self—if he’d listen, which is far from assured:

1. Consulting is not a scalable business model or a good funding strategy

As mentioned above, I unexpectedly found myself jobless, with no cash, and had two mortgages and a car payment. That means the initial conditions of my business were: do whatever generates cash ASAP. In tech, that naturally pushes one into consulting. Of all the things one can possibly do, service work pays the quickest.

Clearly, I managed and paid the bills. To those who are not so lucky in their ventures, that might seem like success. The reality is more complicated.

To make an adequate living as a consultant, you have to be rather good at many things and possess specialised skills and knowledge. Proffering relatively generic IT skills won’t work; at that point, you’ll be competing with volume operations who have made a process of this, and with offshore techies on oDesk with whom you cannot compete on price and make a “First World” living. So, for purposes of this discussion, let’s assume you have some unique knowledge of the ways and means of a particular industry, are particularly talented, and possess both wide general knowledge and deeply detailed specialisation in a few valuable areas.

This seems like a blessing, but for anyone trying to build a business bigger than themselves, it’s a curse because it’s not a business model. It’s a glorified job for yourself, with all the downsides of a salary but none of the upsides, including the “steady paycheck” bit.

First, well-paid tech consultants are paid for the fact that the intersection of many different technical skill sets is present in a single person, likely coupled with some niche domain knowledge of a particular industry. It’s near-impossible to hire anyone who is not of an identical profile to help you with that and grow the business beyond yourself. There are only so many hours in the day, and only so many hours you can bill. That is the limit of your business model and your compensation.

Even if you are somehow able to afford to pay a competitive market salary (I wasn’t), the likelihood of finding someone with the mixture of skills you need is very low, and this becomes exponentially more true as you get into rarefied niches. In IP telephony, for example, hiring most IT people off the street is of limited value; in all cases, you’re going to have to educate and train someone in the folk knowledge you use to ply the trade. That can take months, or even years, during which time you’re burning scarce cash and cannibalising your own (ostensibly billable) time.

Another peculiarity of niche consulting work is that you may have to pay these folk quite a lot, as their salaries need to be competitive with what they could otherwise command elsewhere in the market with their legitimately valuable skills. That’s a hard pill to swallow if they don’t have the specific skills you need.

As you move down the talent ladder and toward entry-level people, you can only find people who are kind of okay at one or two of the eight or nine things you need them to know well. In the best possible case, it’s going to be you and some help that will, for the value you are able to extract out of it, be suffocatingly expensive no matter what it costs, and you will spend months or even years trying to groom it. Needless to say, the help can leave any time for greener pastures where its existing skills fetch a higher return.

The second problem with consulting is that it’s custom work. The market has a seemingly bottomless appetite for custom work, but you don’t own it, and it leaves you with no residual intellectual property or, in a broader sense, capital. Yes, charging a lot can compensate for that to some extent, but there’s only so much you can bill. In that sense, it’s a profoundly linear business, no different to a barber shop. Want to make twice as much money? You’ll need to cut twice as much hair. Except you can find afford to hire people to work at a barber shop, in principle.

Yes, there are ways to optimise the process. Most consultants eventually find ways to package what they do, through some sort of reusable assets, to lower the marginal cost of doing it. In some cases, if you’re lucky, you can even get customers to fund part of the research and development cost of a product indirectly. A lot of products’ origin story lies in consulting in that sense; indeed, so does mine.

All businesses with a headcount greater than one have something in common: a real business model requires devising easily replicable workflows and business processes at decreasing marginal cost. 

If consulting in particular is your thing, there are clearly ways to scale out the business of consulting, and indeed, any other service business, as demonstrated by the existence of the professional services majors – KPMG, Deloitte, Boston, and others. But all of these businesses have solved the problem of the replicable business model. At the professional services majors, they’ve figured out how to write a three-ring binder of procedures—so to speak—that a fresh-faced Comparative Literature graduate six weeks out of school can follow just well enough without accruing years of deep expertise in a particular industry vertical. That procedure is then carried out for every Fortune 500 client that requests the services of an “Audit Associate II”. That’s still a business model, but it doesn’t work at a small scale.

That’s why I said above that being in a position to sell specialised work that one does individually is a curse, not a blessing, because it gets one out of having to solve the intellectual problem of how to build that business model. A much more enviable position is that of entrepreneurs who do not have the skills to do most of the work required to build their business themselves: it forces them to solve for how to combine labour and capital in a way that works. From day one, they have to devise a workflow and a process into which they can plug other people—other people they have to somehow afford—with the idea that more people can be added in the same way. Consulting is, entrepreneurially speaking, the laziest possible option; it pays now, but it doesn’t generalise the process of how to get paid repeatably.

Consulting is often seen as a means to an end, a short-term funding strategy until we can get the product off the ground. The idea is to do consulting at the same time as developing and marketing a product until it becomes self-sustaining. There are indeed thriving businesses and products that have got started this way, though it usually requires that the consulting be at least somewhat complementary to the larger goal.

Still, an incredible landscape of obstacles is arrayed against you in this paradigm: consulting has a way of taking up 85% of your time for 40% of the revenue. In my experience, it takes nothing less than a supernatural Teutonic discipline to properly compartmentalise consulting, and even then, by the very nature of the sort of thing that it is, it has a way of spilling outside whatever neat boxes you try to shove it into. Consulting customers are demanding and have a habit of calling.

Another widespread belief is that one can do consulting intensively for a while to build up cash reserves, then operate off that runway and focus on your real mission. This might be arithmetically possible if you’ve dialed down your personal burn rate to exceptionally low, but, if you find a way to make lucrative consulting projects arise spontaneously, exactly when you need them, and disappear precisely when you don’t, with no effort required on your part to get them, please let me know. I’ll make sure you get that Nobel Prize. In the meantime, consulting happens based on the customers’ needs, not yours, and the networking, marketing and engagement required to maintain a pipeline and get any consulting project at all will easily suck up the rest of your time.

Useless workFor all these kinds of reasons, the result is that your product development proceeds at a glacial pace, or falls by the wayside entirely, because much of your energy is spent hustling for consulting dollars. Relative to the windows of market opportunity in tech, that can be disastrous. Plus, you are likely competing with companies who are not hindered by such ballast, and can afford to focus on product 100%. This might all be surmountable if you can muster the total dedication and raw 24/7 energy of an unattached 23 year-old singleton, and have—somewhat improbably—jettisoned any expectation of a personal life, hobbies or outside interests. However,  it is essentially impossible if you have a family or other constraints that box you into a more or less 9-to-5 regime. At that point, you’re an advertising copywriter dreaming of writing the next Great American Novel. Any day now.

Critically, the friction and complexity of doing niche custom work also makes it complex and frictional to sell, particularly for someone who is not you. Sales cycles for this sort of thing are long and involve patiently nurturing consultative sales relationships which underscore you as an industry expert in the eyes of the prospect. As with business processes for employees, sales needs to traffic in simple, easy-to-understand concepts with as few moving parts as possible. It is hard to package custom work and niche expertise in a form consumable by otherwise capable and motivated salespeople. This problem can also afflict “consultingware” software products; at the very least, products which are complicated to sell require extensive sales training, driving up customer acquisition costs and prices accordingly, and limiting your ability to scale that process out.

Lastly, even if you are not in a business model that specifically contemplates a dichotomy between “consulting” and “software product”, many other models have parallels. For instance, in the IP telephony service provider world, there is a similar choice between building high-expertise, custom deployments versus prefabricated IP PBXs and trunks. Some people I know clear very respectable revenue doing the former and pride themselves in their resistance to the commoditising forces of the latter, but there are serious volume—and therefore, revenue—limits around their business model.

2. Good cash flow is more important than revenue

For my first years in business, I did only project-based consulting work and had neither a product nor significant recurring revenue otherwise. That meant I’d sometimes go more than a month without getting paid. This is the period in which I most substantially wrecked my credit and paid personal bills notoriously late, the consequences of which remain with me now.

Bad cash flow at higher revenue is worse than good cash flow at lower revenue. In fact, bad cash flow can sink even a notionally profitable and viable business. This is a well-known fact in economics, but the usual countermeasures are rarely available at an individual scale.

It is only human to suppose that if one earns a $100k (for example), one can afford a commensurate lifestyle. The trouble with that in consulting, for instance, is that a high percentage of that income is volatile (unsteady). If someone divided that $100k by 12 and gave you 1/12th on the first day of every month, you’d be set, but that’s just not how it works; if that’s what you’re after, get a salaried job.

The devil is all in the details of what you have liquid at any given moment. It is likely to be the case that $100k of unsteady income can only support a $35k lifestyle once appropriately discounted for volatility. The same logic can be applied to business expenses, and is something to think about before you commit to cutting someone a paycheck on the 1st and 15th.

Make adjustments accordingly. I didn’t; by the time I was spirited out of my last job, I had managed to buy the aforementioned condo and otherwise acquire a lifestyle that required a middle-class professional income to sustain, and have generally persisted in maintaining a relatively high personal expense base.

That’s going to create a dynamic that is substantially similar to the one poor people go through because you’re nearly always broke, only with the added irony that, on paper, you might earn a pretty sizable income. Even if that’s the case, being high-income with high expenses is about the same as being low-income. Your decisions and priorities will resemble those of low-income people. Any zeroes in your checking account will represent only a fleeting blip of happiness before they go right back out. Sizable income does nothing for you when it arrives in episodic, unpredictable chunks. You may have money once that payment clears tomorrow, but that does nothing to help you here, now, today. I can’t count how many times that has literally been true.

In principle, one can meticulously set aside cash from high points into a rainy day fund to offset the low points, but the messy timing of reality probably won’t fit whatever  savings scheme you’ve devised. The only real way to get ahead of this is to have an expense base that is vastly below your income.

In addition to deteriorating one’s ever-important personal financial history, the constant stress of poor cash flow is a major distraction from your business, and therefore an existential threat. Don’t do what I did; live cheaply and bide your time. Don’t mortgage your financial future with shortcuts.

3. Everything takes a lot longer and is harder than you think

My company’s product would be morally offensive to a young developer at first glance. It took seven years to write what is, in the grand scheme, a few thousand lines of code? Bro, I could do that in like, a weekend.

Developers are famous for grossly underestimating how long it takes to just, you know, write the code real quick. That’s not a new revelation. The real revelation is in what else you have to do to take it to market.

Overlooking the fact that the product was developed alongside consulting, with all the problems that entails as per point #1, I’d say maybe 15% of the work that has gone into this product had anything to do with writing code, and indeed, that’s not where most of the value lies.

Prototyping something is fairly easy for many minimally viable iterations of product. The real work, the dark matter of the entrepreneurial universe, is in what is sometimes called “customer development”; deploying it in the real world, painstakingly learning what works and what doesn’t, incorporating that market feedback and iterating it. Then there’s the troubleshooting of bugs and fixing of problems which only arise in production and at large scales (and therefore under the pressure of irate customers who must be placated). For enterprise-oriented software like ours, customers expect a streamlined vendor support relationship with well-considered processes. Polishing aspects of customer experience which are unrelated in any overt way to your product is a critical part of selling any product with a service and support dimension—that is, most software for enterprises and service providers.

If you multiply that out across punishingly long sales and adoption cycles which can range from months to, in many cases, years, it’s not so hard to see how it can, for an army of more or less one, take seven years to breed good product stock. Although this is not true of some products for the mass market, it is absolutely true for intra-industrial solutions with numerous moving parts.

For software development work and other intense focus-based tasks, there are also the simple economics of human task-switching. Joel Spolsky and others exposed aspects of this argument to a larger audience some time ago, but it boils down to this: development has a huge cognitive load. While Joel et al focused mainly on the ways developer focus can be derailed by distractions, development is also exceptionally sensitive to mental fatigue and to the vicissitudes of motivation — problems you’re going to struggle with if you’re juggling consulting gigs alongside product development work. “Programmer’s block” is a thing, and I’ve learned that fighting it with brute force and will power alone simply leads to burn-out.

Moreover, we’re simply not robots; one does not simply do consulting from 9 AM to 1 PM, then switch one’s mind to product coding at 1:01 PM and carry on until 5 PM. The mind needs time to unwind, recharge, adapt, and get in gear. As many of my fellow developers know, often by the time that happens, 5 PM rolls around. This is, incidentally, why developers chafe at being scheduled for meetings in the middle of the day or being burdened with errands spliced into the middle of work; the mental focus required for coding requires fairly long, unbounded chunks of time to conjure—a process not altogether reliable even in those cases. A midday meeting or a dental appointment can split your day into two useless chunks in which you can’t do anything useful.

Naive is the person who thinks software developers in large companies work on code anywhere near eight hours per day. Perhaps I am exceptionally feeble, but I don’t think the human brain can sustain that for any significant length of time. Occasional heroics are of course possible, but in general, I’d say 2 to 3 hours of solid coding per day is a banner day for a developer in the enterprise. The rest of the time is taken up with e-mail, meetings, conference calls, lunch breaks, updating internal tickets and bug reports, and just vacantly scrolling through the code, trying to summon the elusive “zone”.

If “knowledge work” were brainless piecework, it wouldn’t pay much. It’s got a lot of parasitic drag in the brain. Factor all that into your estimation of how long things really take and the resource commitments they will require.

4. Figure out what actually motivates you

Succeeding at business is quite hard, actually. If it were easy, everyone would do it. To even stand a fighting chance, you need to figure out how to keep yourself plugging away at it in a sustainable and enduring way. In my experience, generating real drive within yourself comes down to a bit of willful sleight of hand, some mental tomfoolery to trick yourself into doing work even when you don’t really want to.

I think the official party line among the self-employed is that money is supposed to be the motivation. To some extent, it surely is. To be sure, everyone wants to have enough money to solve most problems in their life and have the things, experiences and security they want, and everyone’s sense of justice is offended when they receive less of it than they believe they should. My observations suggest, however, that money is seldom the root of most drive on a long-term basis. The idealised economic free agent (“Economic Man”) is more myth than reality.

At any rate, if money were my sole motivation, I’d take the path of least resistance and find a salaried job; I’d probably make more by this point in my career, it’d be steady pay, I’d have benefits, and best of all, a narrow area of responsibility rather than direct exposure to everyday business risk. If I had stuck to the corporate career track, I’m almost certain I’d have a positive net worth and some trappings of middle-class wealth accumulation, instead of being six figures under.

When I speak of motivation, I’m not referring to sanguine or idealistic conceptions of motivation, nor grand, cosmological ideas. Many people are tempted, upon first examination, to answer this question in terms of how they want to see themselves. Some will say they want to make the world a better place. Some will say it’s all for the money so they can cash out and do what they really want. Some will say it’s all for their children, their sick brother, baby sister, destitute grandmother.

That may all be true, but it probably isn’t what motivates them in a local, everyday sense. I’m referring to the stuff that makes the work itself enticing. There are probably preternaturally disciplined people out there who are animated into everyday action by the notion of executing a long-term goal, but unless you’re one of these Terminators, you need to do some blunt and honest introspection to figure out what makes you tick.

To answer that question for myself, I have to go back to my childhood and adolescence. I started programming at age 9, and from that age until I started working, I put what I reasonably estimate to be somewhere between 8,000 and 10,000 hours into it. If you crunch the arithmetic on that, that means I wrote code almost every day, and to a degree that surely crowded out most normal teenage activities and developmental experiences, including a healthy social life. That level of dedication was certainly not sustained by a singular long-term goal that lasted from primary school through adulthood. Indeed, I had no intention of making a tech career, and entered the University of Georgia as a political science major, later switching to philosophy and entertaining vague aspirations of law school.

I spent much of that time working on multi-user chat servers called talkers, originally a UK-centric phenomenon, with a group of like-minded peers and associated social cohort of people who simply used talkers, called “spods” (verbed, “spodding”). I count some of them among my real-life friends today, but they were all online then. My programming peers were mostly a bit older, and played an important mentoring role. We frequently competed and co-opeted to over-engineer our home-brew talkers for high performance and concurrency, since we needed to support … tens of users.

Making the computer do stuff was quite interesting, but there’s no way a solipsistic interaction with the machine would have sustained my interest to this level. This was, in effect, my primary social life at the time. It was the social dimension that interested me; the collaboration, the teamwork, the feeling of watching users actually use — and enjoy — my inventions. I relished learning processes and workflows (e.g. version control) and “how things are done” as much as doing them. The journey was as important as the destination. The qualitative, human aspect of how people worked interested me. And of course, ego certainly played a big role. As my skills sharpened, my status and acknowledged expertise increased in that social group, and as I got older and demonstrated increasing maturity (in relative terms, anyway), I came to have legitimacy and respectability in that community.

From the perspective of someone self-employed since a rather young age, what I miss most is about conventional employment is certainly the teamwork and camaraderie, the feeling of contributing distinctive expertise to an endeavour larger than myself. Self-employment is a mostly solipsistic endeavour for me; my economic incentives point to spending as much time one-on-one with the machine as possible. That’s not easy to sustain for a fairly sociable person.

By and large, nobody cares what I do. I don’t really have direct colleagues or peers around due to my narrow specialisation. Certainly, customers recognise my expertise and even pay me for my work from time to time, and in capitalist society, one might say that this is the highest expression of caring about something. But I’m paid for a bottom-line result, and few people appreciate the intricacies of how I arrived at it. The resulting creative and intellectual control is liberating in one sense, but constricting in another. I have few intermediate responsibilities apart from the all-important delivering.

I’ve tried various coping strategies, such as co-working spaces (which I have written about). But I had little to say to the web economy SEO Superstars, Sales Quarterbacks and Vision Catalysts who tend to inhabit such places, and they had little to say to me. Oddly enough, this is where entry-level employees whose direct economic contributions were otherwise quite limited helped me a lot. I had people I could bounce ideas off of and show things to who also had some folkloric knowledge of our business and could put what I showed them in the right kind of context. I suppose I’m a bit like Dr. House (minus the “genius” bit); I work unsteadily in isolation and need the dynamic of a “team”. There are other people I know who seem more genuinely introverted, and really relish working at home and not having to deal with “people”. I don’t understand them and they don’t understand me, but the differences seem genuine.

Little cute caucasian girl in jacket and hat sitting alone on a seesaw swing at a playground outdoors. Loneliness mood conceptI don’t think I’m the first to say that doing small business is lonely. Much has been written by other entrepreneurs about how it can even be quite isolating even within a lively social and family life, as nobody really understands. I am not given to pity parties, but psychologically, this has posed challenges. I don’t have a good solution for my case; indeed, not all problems have solutions. Nor am I sure how I could have gone about my self-employment differently without radically altering its nature, apart from perhaps soliciting more on-site engagements. What I do know is that the solipsism of “moderately successful” small business is something the 22 year-old me failed to anticipate or consider, which I think is par for the course for 22 year-olds.

All this to say: it’s not overly self-indulgent to do some honest introspection. If you can more or less accurately deduce what really makes you tick and can find a way to cater to that in your business decisions, the returns to sustained productivity will not disappoint. While all economically useful work involves tedious drudgery, I know some people who have found their own answer to this problem and managed to solve for it, and they really do seem thrilled and energised to go to the office every day, as best as I can tell.

5. Don’t neglect proper tax planning

I have sizable delinquent tax debt that I am still in the process of resolving, and of course, the painfully injurious arithmetic of compound interest and penalties fully applies.

In my undoubtedly tendentious estimate, that’s about 30% failure to pay taxes in the aforementioned context of poor (though steadily improving!) cash flow, but 70% poor tax planning and tax-related decisions. Just by way of merely one example: I have an LLC and did not do an S-Corp tax treatment election until FY 2017. This means that for every prior year, I was assessed 15.3% self-employment tax on top-line net business income prior to personal deductions, and indeed, this represents a slight majority of my tax debt. That is to say, my taxable income for tax purposes is significantly lower than my taxable income for self-employment tax purposes. That’s tax debt I wouldn’t have if I structured my compensation differently.

Worse yet, it’s not that I didn’t know the consequences. I was just too busy trundling along with my business to attend to these things diligently.

One of the worst things about bootstrapping is that you’re always living check-to-check, leaving little time or energy for “stepping back” and thinking “deep strategic thoughts”. The strategy is “make money, pay bills”. This is also why most business advice rings hollow in this world; it’s a luxury one cannot afford.

Set aside the time to research and fully understand, with the help of a CPA and perhaps an attorney, every implication of a given business entity/incorporation structure. Don’t be like me; get ahead of it before it’s too late.

6. Lay off the success porn

By now, much has been written about research findings that social media use gives rise to depression and anxiety. This is largely explained by the fact that people selectively curate the portions of their lives they put online, leading to the impression that everyone else’s life is amazing and full of neverending vacations and rich, vibrant experiences, and you alone are struggling with the drudgery of everyday life.

This is doubly true in business, where the relentless bombardment of announcements related to other people’s success never abates. LinkedIn serves a similar function for the business-minded as Facebook and Instagram does for ordinary people. Few economic struggles or bankruptcies are proclaimed on LinkedIn, except perhaps in the “started from the bottom, now we’re here” epics that salespeople, business coaches and “self-help gurus” seem to love to write.

My earlier years invited frequent ruminations on why I alone can’t seem to hack it beyond a certain level of business development, and even making some abortive attempts to mimic the declared customs and habits of people who could. Since then, I’ve found general agreement among bootstrapped business founders that it’s integral to one’s mental health to tune this stream out, keep one’s head down, and focus on one’s own work.

7. Only hire the right people, and don’t be reticent to fire

Well, let me tweak that for my specific case: don’t hire entry-level people unless you’ve got a business model that is specifically set up to extract value from them.

That certainly does not describe my business. Nevertheless, I’ve had a bad predilection for hiring entry-level people. Those aren’t the only people I’ve ever hired, but it’s been a major theme. The first and most immediate reason is that entry level is mostly what I could afford. However, what really drove the decision in those cases was—if I can find a way to say it without making myself out to be some kind of saint on a mission civilisatrice—an altruistic impulse.

I’ve met people who were sincerely interested in learning more about technology and, in many cases, I perceived, rightly or wrongly, that they could have used the job. I have been idealistic over the years about my ability to introduce someone to this industry and “raise the floor” on their skill set, slowly but surely, until they can take over some routine business functions. If I’m being honest, there was probably an egotistical desire to disprove conventional hiring wisdom and demonstrate a civically minded alternative that spoke to the social purpose of employment.

However, I’m simply not set up to put that sort of candidate to use productively for reasons explained in point #1, and in this light, hiring them was ultimately a disservice to myself and to them. In addition to burning cash I simply did not have, I neglected to consider how bummed out people feel when they know they can’t be useful. Far from being lazy, most of these folks were quite motivated to do a good job, and it was no moral failing on their part that they simply didn’t have twenty years of broad-based IT experience that matched my needs. That did not change the reality; an unproductive employee is not a happy employee.

I think the most damage was done not by my choice of who to hire, but my tendency to keep them on payroll far beyond the point at which it became apparent, if tacitly, to both of us that this isn’t really going to work. I invariably blamed myself, believing it to be the responsibility of the manager or the entrepreneur to devise workflows and systems in which one could put other people to use. Earlier years were spent labouring under the delusion that given the right tools, technology, process and training, I can make anyone into a gainful contributor to the company’s work.

It is vital to be brutally honest with oneself about whether someone’s skills can realistically be put to gainful work. Do not allow emotions or generous impulses to override that. Big companies average together the productivity of lots of different people, and can afford a relatively unproductive team member. As a small, bootstrapped company, not only can you not do that, but to achieve any sort of “escape velocity”, your first few team members have to be exceptionally productive. Otherwise, the result will be that you will work three times as hard as you already do to keep the lights on and make sure everyone’s salaries are paid, while your employees feel useless and dejected. This is one I seem to have had to learn over and over.

Finally, letting someone go is one of the life’s least pleasant sensations. I have a pathological aversion to it, because my inner narrative about any given employment situation that’s not working out is that I have somehow failed the employee. Nevertheless, if you’ve made a bad choice, stopping your bleeding—and theirs—is an absolutely essential facility to develop as a bootstrapped entrepreneur. You really, quite literally cannot afford not to, and by not doing it, you’re leading the employee on and denying them the opportunity to move on to a more fulfilling role with better prospects for themselves.

Finally

There is a more global reflection that haunts me the most. I saved it as a bonus for last, because it’s intimately related to the conditions of “moderate success” as laid out in the introduction.

Let me start by saying that I don’t subscribe to California startup capitalism and its “go big or go home” philosophy of business, and neither to the pejorative distinction its adherents draw between “real business” and “lifestyle business”. I don’t think a small, specialised company with a small team is a worthless aspiration—it’s not a failure of $100M imagination.

I also don’t advocate byzantine, metrics-laden strategy at micro scale. There is such a thing as simply too small.

Nevertheless, the cold, hard truth is that  “moderate success” is a vast chasm that is difficult to cross. Unless you explicitly declare bankruptcy or wind down the company, nobody comes along to tell you that you’ve failed and shutter you. If you’re doing service work such as consulting in particular, you can tread water and still pay the bills almost indefinitely. You need to decide where the shuttering point is for yourself.

I’m not suggesting you should aim for Mars, nor that this shuttering point is a static quantity. It will probably need to be calibrated to the market feedback you receive and your sense of the overall prospectus. Nevertheless, it is helpful to start with some idea of where you want to be after some period of time that is more specific than “uhhh, grow?”

I’ve got my shuttering point. Fortunately, I am above it. Nevertheless, my focus on the prize over these ten years would have been sharper if I had started out with a notion of what the prize is.

What does it all mean? Should all of this discourage you from going into business for yourself on a self-funded basis, or from doing consulting work? Absolutely not! If you’re studying that option, hopefully this article has taught you something about the obstacles you will face and help you to plot your master plan in a more pragmatic way. It’s far too easy to fall under the spell of “success porn”, which is the dominant packaging of information out there for the aspiring self-employed. The only comme il faut narrative forms out there seem to be 1) “make it” or 2) “fake it till you make it”, and my aim was to shed some light on what “only kind of making it” looks like, which seems to me to be the vast middle of the bell curve. That is to say, unless you achieve meteoric, hockey-stick break-out success or you straight-up fail, I think you’re probably going to end up dealing with many of the same problems I’ve encountered.

The good news is that these problems are not insurmountable. They’re just a lot easier to surmount if you don’t spend a long time discovering them for yourself. Why play life on hard mode if you don’t have to?

Many thanks to my good friends and fellow entrepreneurs Fred Posner and Kelly Storm for their feedback on drafts of this article.


Problems and their solvers

We live in a cultural moment of what is sometimes called “solutionism” — an intellectual fixation with “solutions” rather than the problems to which they are addressed.

Some of this is ingrained in Anglo-American cultural psychology—and not necessarily all for the worse. Although this vantage point sometimes suffers from a debilitating naiveté about the nature and complexity of problems, its indefeasible optimism about man’s ability to control and master the world has made a contribution to technological and economic progress that cannot be denied.

Nevertheless, a lot of the excesses of solutionism are nowadays driven by unremittingly one-dimensional Silicon Valley groupthink of the Internet Age, a metaphysic in which all problems are reframed as a want of an app or a startup. In venture capital, code and devices lies salvation.

Nowhere is this more evident than in the worldview of TED, where the worst of 1% liberal tone-deafness meets the intellectual fraud of  facile technocracy. This has seen some public rebuke from the likes of Evgeny Morozov (who, ironically, gained notoriety through the very same TED over a decade ago for his sceptical take on the hackneyed cliché of the Internet as an instrument of political liberalisation). Although the assaults on the edifice of Apps and Machine Learning Macht Frei are muted and comes from a small renegade force, that critique has gained exposure to a wider audience in recent years. There is sufficient prior art to not warrant a recapitulation.

Business man pushing large stone up to hill , Business heavy tasks and problems concept.The bigger and more troublesome consensus I see relates to the social convention that one must provide solutions alongside one’s contemplation of problems. In America, at least, social criticism is widely deemed “unconstructive” if not accompanied by a a plan to fix the ills. It seems to me that one cannot be a public intellectual with a critical vantage point in the US unless one is prepared to offer concrete rectification, whether policy prescriptions for worldly problems or inward-looking attitudinal adjustments for personal ones. Otherwise, one’s a pathetic whiner.

The first and foremost reason this is problematic also manifests itself in the reign of the aforementioned technocracy: it posits something about the nature of problems — that they all have clear, distinct and discrete solutions. Some problems of humanity are timeless and existential, though. Not all problems are solvable, particularly in isolation. The American cultural mythos is cholerically hostile to the notion that some problems simply might not have solutions, alas. Everything’s solvable!

And maybe it is. But where solutions do exist, they are often woven into complex and interdependent systems of simultaneous equations, inextricably bound up in solutions to vast categories of other problems. The presumption of symmetry between the task of describing a problem and devising a solution is unwarranted, but if the critic balks, they are met with: “Oh, all you want to do is rant and complain”.

That explains why the “so what do we do about it?” part of socially critical books often reads like a stilted afterthought, stammered out at 5:49 AM on the day of the editor’s deadline in an eerily silent graveyard of empty latte urns and greasy take-out food caskets. After doing the rather manageable thing of identifying the problem, the writer’s now tasked with the much more cosmological burden of sorting it all out. It’s the thrill of agony and the stinging pain of defeat, all in one manuscript.

Yet the most overlooked problem ought to be the one most glaring: even where discrete solutions are possible, in principle, the people best equipped to identify and describe a problem are not necessarily the best people to solve it, and any correlation between the two is strictly incidental. Observers most sensitive to the consequences of a political problem, for instance, are rarely policy experts. They are not in a position to craft a labouriously articulated fix that is compatible with the internal logic of, for example, the legislative process.

Gun control is a timely, if random example. I can tell you in considerable detail why I think this country has a globally unprecedented mass shooting problem and that it needs to seriously re-examine its interpretation of the Second Amendment, but I don’t have the esoteric knowledge to tell you what kind of response might actually work as a matter of working law or regulation. Ironically, the people who are more qualified to do that mostly don’t seem to think our mass shootings are much of a problem.

I don’t know why we expect a competent description of a problem to signal an ability to solve it, but I do know that the demand to do so is a widely deployed conversation stopper that shuts down a lot of legitimate critical work. Conversation stoppers only work inasmuch as they capture widely accepted notions — we call it “conventional wisdom”. Conventional wisdom has it that everything’s fixable and that one must proffer a fix to get a seat at the table of criticism and dissent.

That’s something we need to solve.


No, I will not make my son a programmer

The world is abuzz with talk of “coding” lately. Lots of people tell me their brother or their cousin is “into coding”; “you know, he does web sites and stuff”. Indeed, I saw this book at Fry’s yesterday:

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(Apparently, this book, mostly a tome of basic HTML and CSS, passes for “coding” nowadays, but that’s a rant for another day.)

On the shelf below it, there was another title: “Python for Kids”. And lots of tech colleagues tell me they’re teaching their five and six year-olds basic programming.

And as I have a two year-old son, and given what I do—though it has precious little to do with web development per se, in the main—I am asked fairly often: “Are you going to teach Roman to code?” It seems to be almost rhetorical in the mind of many doing the asking, almost a fait accompli.

I’ve always found the question puzzling. I don’t know. Am I going to teach him to code? To me, it sounds rather arbitrary, a bit like, “Are you going to enroll him in karate lessons?” or “Are you going to have him tutored in oil painting?” or “Is he going to play basketball?” It depends on what he’s like as a growing person, and whether he seems interested or appears to have any aptitude for it, I suppose. He’ll doubtless be exposed to it, given his parentage; there’s probably no avoiding that. Beyond that, it’s really a question of whether he’s keen on it.

There’s an important balance to strike; when it comes to specialisations, kids don’t know what they don’t know, and one of the main reasons we have general public education (and general ed/survey course requirements at the university level, in the USA) is to expose growing minds to the range of occupational possibilities, academic disciplines and fields of human endeavour generally. Still, I’m acutely aware of what happens when parents try to remake children to any degree in their own professional or intellectual image. I got this mildly, in the form of being subjected to parental projections of Soviet intelligentsia values: mandatory piano lessons, assigned reading of literary classics, lots of classical musical concerts, ballet performances, etc. In hindsight, it probably did me some good, though my adolescent rebelled powerfully on the inside. I see much sharper examples in the lives of others, whose parents want them to proceed down some similar track — play football in college, learn the family business, or, as it happens, become a software engineer.

My own interest in IT as a child arose in a particular context, a historical conjuncture of many factors: university environment, emergence of the commercial Internet, supportive academic social community, adolescent quest for identity, efficacy, communication. There’s no reason to think the same motivations will drive others in an era in which all this is long commoditised. A lot of people seem to subject their kids to forcefully projected nostalgia for a different time and place. I know my love for computers came from a different time and place. I am not sure I’d have been lured by them as they are today.

Teenage Boy In Bedroom Writing Computer CodeI think the question about “coding” runs deeper, though. There’s a widespread awareness—and perhaps it’s fair to say, anxiety—about software eating the world. There seems to be some consensus that the foreseeable future of gainful employment in the developed world dovetails extensively with machine intelligence. Automation as a reputed killer of low to medium-skilled service jobs is a routine headline. I think what’s really being asked is, “given that we’re going to be a society of computer programmers, will Roman take part?”

I suppose don’t buy the given. It’s fair to say that use of computer technology has become routine and necessary in most full-time professional jobs. I also think it’s important for kids to have some idea of how software works so that they can make sense of the world around them; it can’t all be “magic”, and indeed, that lack of understanding is an obstacle as we rapidly leap into a very software-driven world.

But it doesn’t follow that everyone needs to learn to speak to computers in code. Indeed, one could convincingly argue that the general arc of software progress and the commoditisation of computers has been to make this less necessary over time; there was a time when everyday uses of computers required speaking an assembler, COBOL, BASIC, while nowadays a substantial portion of the digitally savvy population taps through “apps”, and frankly, so do I. I started writing socket (network-related) code in C on Linux when I was 12, but I only have the broadest idea of how my Galaxy S8 works. I’ve asked younger Millennials for Android help before.

Young friends using smartphones and drinking coffee outdoor - Group of happy people having fun with technology trends - Youth and friendship concept - Main focus on grey t-shirt man cell hand

Moreover, people learn what they need to; I know plenty of otherwise technically illiterate accountants who have conquered snow-capped summits of Excel macro wizardry, the likes of which I could not have even conceived.

My undergraduate-aged babysitter is far from a technologist, but her mobile and desktop computer literacy surpasses that of many Baby Boomer and Gen X professionals. Why? She was born in the late 1990s; she’s always known the Internet. I jokingly asked her once if she realised music wasn’t always on iPods or in MP3 format, but based on her matter-of-fact response, I don’t think she really heard the full notes of the humour. It was almost like asking me if I realised history used to be recorded on papyrus.

In short, I don’t see law, medicine, writing, poetry, music, art, or the myriad of skilled professions becoming a fancy, domain-specific branch of computer programming. These fields will—as they do—put computers and the Internet to business use, but why are we talking as if everyone’s sat in front of a PDP-11?

That leads me to the heart of what inflames me about this cultural moment of software mania and metaphysical, cosmological technocracy: technology is a tool, not an end in itself, and we mustn’t forget that. It is a force subordinated to human purpose, not the other way around. It is as lifeless and mechanical as a jackhammer, not an organism in need of care and feeding, nor a capricious god to which we must pay tribute or sacrifice our young. It does not intrinsically solve most timeless sociopolitical problems. It’s not a raison d’être, and neither is “coding”.

Speaking of sacrificing our young, while my own childhood obsession with programming and the Internet got me a well-compensated occupation in an in-demand and growing field, as well as a supportive network of likeminded online cohorts, I’m all too aware of the human costs, physical and psychological. At least ten thousand hours were spent in a sedentary pose as an adolescent and teen. I missed out on almost all social features of high school, since there was always C code to be tinkered with or someone was wrong on Kuro5hin or something. (Though, there’s no particular reason to think it’d have been epic otherwise, for reasons Paul Graham articulated better than I could). The shockingly low amounts of sleep I ran on most school days between grades 6 and 11, bleary-eyed from the blue light-soaked all-nighters of homo computatis, ought to be the subject of some kind of study, I swear. I wear multiple pairs of glasses due to eye strain. I dropped out of college because I cared so much more about my work. The fact that anyone ever dated me seems like a miracle sometimes; I somehow had a girlfriend my senior year of high school, which finally had me looking after myself more, but you, too, would ask “how?”; it didn’t (heh) compute.

I’m not saying I necessarily regret any of it, though of course we’d all tweak a few things with the benefit of hindsight and time travel. What I will say is that I don’t bill my lawyer-ish hourly rate for nothing. I got here at the cost of much of my childhood and adolescence, as we ordinarily understand those stages of life, and at this point I’ve fed for more than 2/3rds of my life span to the exacting and jealous machine. The road to being pretty good at what I do was long and arduous. Computers are addictive as all hell. It’s no accident I’m finishing this post at 4:45 AM; when you mess up your biorhythms from such an early age, old habits die hard don’t die. I’m very mindful of all that as I consider the full list of possible consequences of parentally encouraged geekery for kids.

I suppose there is one way in which Roman will be socialised in the shape of his father: he’s genetically part philosopher, and if he does take up programming, we’re going to spend a lot of time on: “But code what? And why?” In the meantime, I have no plans to plant him in front of a Raspberry Pi or “Python For Kids”.


Concerning the Heartland

Young man wrapped American flag crop field sunsetOne of the notes that the dog whistle of the Trump political machine hits is rural parochialism and provincialism, a conviction of the inhabitants of the American “heartland” that it is the essential America.

America hardly invented pitchfork-wielding country chauvinism, but it has had a particularly powerful historical current of that kind of know-nothingism, owing to its roots in a medley of dispossessed immigrant political minorities—especially religious minorities. There is ample lore in the heritage to support the popular psychological metaphor of taking a nihilistic wrecking ball to the state. There’s burning the corrupt edifice to the ground, nuking it from orbit, methodically strangling it with “starve the beast” spending legislation, “draining the swamp”—whatever form it takes.

These people don’t want to hear about big city folk and their reputedly elite cosmopolitan problems. No, it is we, on this two-lane road in the middle of southern nowhere, amidst the vestigial shells of Rust Belt industry, in the bucolic crop fields of South Dakota, who are the “real” America! It’s time to take it back! We don’t need no stinking foreigners, we couldn’t give a hoot about “diversity”, and (as was remarked to me recently) come on, show us one legit immigrant from Yemen, we dare you.

As always, the problem is that going full ostrich doesn’t work.

Like it or not, we do live in a highly globalised, interdependent world. Interdependence means complexity, and—to return to thermodynamics, as we all someday do—complexity means fragility. Fragility means that diplomacy and a multilateral approach to human affairs are necessary. Omaha mostly buys Samsung smartphones, too. Banks in Kansas are exposed to the Hong Kong Dollar and the German stock market. There are Caterpillar excavators and Boeing airplanes everywhere, and the manuals are translated into two dozen languages. Ohioans entrust their very lives to talented Japanese embedded software engineers every day, and will again tomorrow and the day after that—isn’t it nice to plug one’s ears and not have to wonder why one’s Honda doesn’t spontaneously explode or run off the road? The working-class enlisted sons of Kentucky are shipped off to places their parents would do well to learn to pronounce. The more economically privileged ones are going to discover a good Jordanian immigrant-owned falafel stand in their college towns.

(My own tech career was launched at a small-town Internet service provider owned by a Syrian Arab and his Pakistani business partner. But everyone knows devout Muslims don’t create jobs in Murrica.)

Or, more cosmologically: events in Yemen, Somalia, Egypt, South Korea, China and India, inter alia, are highly relevant to every American’s existence.

I know a lot of people who would prefer not to venture beyond the county line and like their intellectual preoccupations as they like their beer—domestic. To you I say:

Sorry, you can’t put the milk back in the cow and rewind the clock to 1802 A.D.1

Moreover, without the Coastal Mind Control Elites, this iconic heartland would have neither the government subsidies on which it extensively relies, nor markets for its products. I won’t patronise you with one of the many charts showing the geographic distribution of net inflows and outflows of federal dollars and the rural-urban trade balance. Y’all are actually pretty good at Google when there’s pervasive liberal bias and insidious Soros funding to be unearthed on the Internet, or some Julius Streicher Breitbart screed in need of scholarly citation.

Big conurbations concentrate economic opportunities and institutions. You don’t have to live in them if you don’t want to, and you don’t have to take part in the so-called Knowledge Work economy, but you can’t just give it all a sociopolitical middle finger and pretend that they, their denizens, or the larger world don’t exist. You guys just want to rap about how you’re screwed by globalisation and immigration, drop the mic, and leave hard problems of making the world turn ignored and unsolved. It’s facile, it’s petulant, and it makes you sound like an overgrown toddler

If that’s how it’s going to be, fine, but could you at least let the overedumacated, book-learned cityfolk do their jobs instead of sticking them with a reality TV demagogue and his diabolical alt-right posse?

1 This is precisely why the [seemingly] intentional deafness of the Libertarian candidates to foreign policy is a non-starter.


Questioning my relationship with The Daily Show

I am rather deeply disenchanted with and bored of The Daily Show. This has two distinct, unrelated causes I can identify:

1) One simply gets too old to tolerate its dick-and-fart jokes and potty humour. At this point in my life, I’m looking for more incisive, more subtle and less superficial political satire and social critique.

I don’t know if that problem has a solution, given that the Daily Show’s seeming target is college-aged audiences. But I find myself wishing that, in terms of sophistication, it would graduate along with the early-mid 2000s students who were the engine of its ascent.

2) Trevor Noah is a fantastic and brilliant comedian—if you watch his stand-up from South Africa and the UK.

His gift for accents and languages is uncanny, and his satire of the South African political elite (e.g. Julius Malema, Jacob Zuma) and everyday interactions had me doubling over from the stomach pain of laughter. Watch his old material; if you don’t know much about South Africa, you’ll learn.

Some of my favourite examples on YouTube (always subject to removal, you know how YouTube is) include his treatments of airport terminal announcementsthe inclusion of Chinese in the BEE (Black Economic Empowerment) programme, and this rather obscure act poking fun at the frustration of interactions with Johannesburg City Power. And his performances about cultural differences in America need no introduction at this point.

Since that was my first contact with him, that’s how I see the real Trevor Noah. At The Daily Show, I have the acute sense that he’s not being allowed to carry his artistic identity over. He’s being shoehorned into an American dick-and-fart comedian role, and to say that it’s not a natural fit for him is an epic understatement.

I understand that the logic of the show has to have some continuity with Jon Stewart and with the show’s historical inertia, audience and so forth, but he’s not Jon Stewart, and he shouldn’t be.

To really reap the rewards of Trevor Noah as an artist, an observer and a commentator, he must be allowed to be his “South African” self and to bring—perhaps it would be more apt to say, to impose—a distinctly foreign perspective to his American audience, nolens volens.

It might not be what the focus groups tell Viacom executives would sell, but there’s real potential there. Yes, there’s always the spectre of Piers Morgan, and with his demise, the idea that foreign commentators interpreting American affairs and telling Americans how things should be is a fatally unpopular formula. However, I think—perhaps naively and overoptimistically—that the younger and more malleable viewership of the Daily Show would respond better than that of CNN’s, and would have a greater inclination to stretch their brains and grapple with such a phenomenon.

I cringe when I see Trevor forced into various contrivances and artifices of a false pretense of American mass-cultural familiarity. He’s not American, and he shouldn’t be made to pretend as if he is. Low-brow toilet humour and American Millennial lore doesn’t work for him. Laundering facile Internet memes is not his competency. If he could control more of his material and delivery, and tailor it to his traditional style, there would be a show more worth watching.


Why suburbia sucks

I’ve written some in the past about how the predominant suburban design of the US of the worst features of life here, viewed from the perspective of a European immigrant like me, at any rate.

Far from posing a mere logistical or aesthetic problem, it shapes–or perhaps more accurately, it circumscribes–our experience of life and our social relationships in insidious ways. The destruction of the pedestrian public realm is not merely an economic or ecological absurdity; it has real deleterious effects. For just one small example of many: life in a subdivision cul-de-sac stops children exploring and becoming conversant with the wider world around them because it tethers their social lives and activities to their busy parents’ willingness to drive them somewhere. There’s literally nowhere for them to go. The spontaneity of childhood in the courtyard, on the street or in the square gives way to the managed, curated, prearranged “play-date”. Small wonder that kids retreat within the four walls of their house and lead increasingly electronic lives. (The virtues of a private backyard are easily exaggerated; it’s vacuous and isolated, and kids quickly outgrow it.)

However, it’s been difficult to elucidate in specific physical terms what it is about suburbia that makes it so hostile to humanity. To someone with no training in architecture, it’s often experienced as a great, nonarticulated existential malaise, like depression. You know it sucks, but it’s hard to say exactly why. The same holds true in reverse; North Americans who have not travelled abroad extensively and don’t have a clear basis for comparison can be tongue-tied when asked to explain what exactly makes a non-sprawl city street “charming” or “cozy”. It’s telling that we have no widespread cultural vernacular for why classical urban settlements, which draw on millenia of intellectual background and corpuses of architectural knowledge, are pleasant. It’s because Americans took that inheritance and unceremoniously discarded it, consonantly with the rise of the mass-produced automobile. It irks me that many of us know, on some level, that we live in a dystopian nightmare but can’t say what makes it a dystopian nightmare.

That’s how I came to spend a fair amount of time recently thinking about and researching what exactly makes suburbia suburbia. I don’t mean the abstract reasons why it sucks; I’ve pontificated on that plenty. I mean the physicality. For example, I live in Atlanta, a suburban mega-agglomeration that sucks in the same general way as cities like Los Angeles, Dallas-Ft. Worth, Houston and Phoenix. When someone asks me where I’m from, and I roll my eyes and diffidently groan, “Atlanta…” Why? It’s worth asking what specifically makes Atlanta “[groan] Atlanta”.

If one hopes to avoid broad vagueries like, “designed for cars, not humans” and instead to get specific, then there’s no single linchpin attribute that makes suburbia what it is. It’s an interdependent constellation of misanthropic zoning rules, building codes, and planning guidelines. My aim is to list as many of these as I’ve discovered and been able to formulate.

1. Single-use zoning

American zoning law (in all but its oldest cities) forecloses on the possibility of mixed-use development. This means traditional design patterns like shops and offices on the first floor with apartments above are impossible. Residences are constructed in special areas zoned for residential construction, while shopping and work take place in altogether different areas zoned for commercial development.

The idea, of course, is that the peaceful slumber of the suburbanite should not be interrupted by the noise generated by the transaction of commerce or any other public-sphere human activities. The result is that running any errand or attending to any need, no matter how small, requires getting in one’s car and driving somewhere else, in many cases several miles or more.

Since separation of commercial and residential zones by vast tracts built at automobile scale (rather than human scale) removes the possibility of accessing useful destinations on foot, it removes any practical motive for walking. Without consequential destinations that are part of normal human activity, by and large, the only people who walk on suburban streets do so for exercise. And the only reason they would do that is because their automobile-powered daily existence does not otherwise compel much movement.

2. Hierarchical traffic distribution

The chief complaint of most residents of suburban sprawl is traffic. The most obvious cause is, of course, that everything requires driving, but there are more subtle reasons, too.

The endless cul-de-sacs, winding loops and seas of parking lot in suburbia empty into larger “collector roads”, often constraining traffic in a given neighbourhood to a single preordained path.

Traditional neighbourhoods and cities are designed in a dense grid and/or interconnected web of streets, so there are many alternative paths between two points.

3. Set-backs from the street & parking ratios

Local building ordinances in suburban sprawl don’t allow buildings to directly abut the kerb. That means one cannot simply enter a building from the street. Instead, the building is set back from the kerb, requiring one to traverse a parking lot to reach it.

In the case of larger shopping centres, this means the building is set back several hundred feet, separated from the street by a large sea of parking. This is because suburban building ordinances require a generous proportion of parking spaces in relation to the surface area of the building. So, the larger the building, the more parking it must have, and, seemingly, it must be in front, not behind the building (more on that later).

4. Proximity does not mean pedestrian accessibility

On the other hand, it is not so uncommon in suburbia to live very close to a nearby shopping centre. I’ve had lots of suburban friends tell me, “actually, the grocery store is 1000 ft from me. Very convenient.” Indeed, when we lived in an apartment complex in the Perimeter Mall area in Dunwoody, the nearby Walmart shopping strip was within spitting distance. I could almost see the store entrance from my bedroom window.

But, perversely, that doesn’t mean I could walk to the store, as a normal person from virtually anywhere else on the planet might conclude from that statement. In its fanatical quest to eviscerate the pedestrian realm and make cars exclusive first-class objects, suburbia manages to make far even that which is conceptually close. Building ordinances generally require some sort of “divider” between these adjacent land parcels, like a ditch, a chain-link fence, or a concrete wall or noise barrier. In our case, that means I had to walk out of the apartment complex, go around the divider, and then cross several hundred feet of parking lot to go to the store.

It goes without saying that most normal people would choose to drive the distance. And that’s the idea.

5. Economic segregation by building type.

It does not bear repeating here that one of the things that makes interesting places interesting is variety. However, one more subtle effect of the enforced homogeneity of suburban residential neighbourhoods is economic segregation.

In older and more traditional neighbourhoods, multiple types of buildings of varying sizes coexist closely. Yes, it is a universal premise of building regulation and planning that they must be united by some sort of overarching organising aesthetic principle and geometrically agree in some way or another, but that doesn’t mean they all had to be approximately the type or size. As a result, it’s quite possible for poor, middle class and rich people to live side by side in one neighbourhood, with the difference that the rich people’s houses or apartments are merely bigger.

Local building ordinances in suburbia aggressively disallow this, and it’s the fastest way to tank property values within the logic of the suburban system. That’s why every new subdivision varies only by a handful of approximately similar house types, and the residents are all in a similar income bracket.

Suburban building codes also commonly disallow affordable housing hacks available in older neighbourhoods, such as above-garage apartments (sometimes known as granny flats). It is no mean feat to get approval for a small secondary edifice in one’s backyard–something the size of a toolshed, but habitable. Contrary to the individualist-libertarian ideology underpinning widespread suburban attitudes, even use of the space behind one’s walls, within the private sphere, is highly constrained and regulated.

6. No street enclosure and definition

The geometry of streets and sidewalks is a critical topic. Generally speaking, the reason settled streets in older neighbourhoods and European cities feel “cozy” and “charming” is because they provide a feeling of enclosure, which humans want because it gives them with a coherent sense of place, like rooms in a house.

I’m not a sociobiologist and cannot say exactly why this is, but would speculate that it caters to people’s primal need for shelter and clear directional orientation. Whatever the case, it’s an established fact that people gravitate toward places that have clear borders and relatively comprehensive enclosures; it’s a kind of axiom for the discipline of architecture. People feel vulnerable and uncomfortable in open areas with ill-defined margins.

That’s the difference between standing on Saint-Germain:

Boulevard_Saint-Germain,_Paris_June_2010_

Photo by Aleksandr Zykov.

And standing in the middle of nowhere:

sterile_suburb

Photo courtesy of New York Times.

Creating that enclosure and definition cannot happen if buildings are sparse and set back from the street. It also requires a certain broadly rectangular building geometry, with more right angles and less campy avant garde twists (more on that later). Suburban streets are notable for the degree to which they don’t provide a sense of place. Their curved, winding trajectory also robs one of a sense of cardinal direction–that’s why it’s so easy to get lost in suburbia. I am much more likely to need GPS aid in navigating through a subdivision than through a downtown.

Pleasant, walkable streets have other important features, such as protection of the pedestrian sphere from automobile traffic. This delineation is provided by architectural buffers such as trees, high kerbs, and street-parked automobiles themselves. All of these things can arrest a car about to plough into a crowd.

Another thing that takes away from the feeling of place and enclosure is large kerb radii. You’ll notice that in dense cities and older neighbourhoods, sidewalks adhere to the street at right angles, providing a minimal crossing distance for the pedestrian. However, suburban kerbs are optimised for cars, allowing them to maintain some speed while turning right–and to easily mow down anyone who is misled by the formal presence of a crosswalk into the belief that they’re actually meant to walk there.

7. Useless, ugly and wasted space

When quizzed about the advantages of suburban life, the most common answer is “space”. But even if you like lots of space, you’d have to agree that the quality depends on what kind of space it is.

Suburban development ordinances are replete with requirements for useless frontages, pointless greenspace between compatible land uses,  as well as chain-link fences, concrete barriers, and drainage pits. Space is still inhabited by humans, and has to be articulated to match their specific uses for it. A lot of open space in suburbia lacks that articulation; it’s neither pristine forest nor a particularly usable surface. It’s just kind of there.

The absurdly large width requirements for inner residential streets are a special case of their own. Small, low-density streets don’t need to be so wide that one almost can’t see his opposite neighbour’s house because of the intervening curvature of the Earth, especially given that street parking is generally not done in these places because, evidently, everyone needs their very own [expensively and unnecessarily] paved driveway. The formal reason for large width requirements is generally something comical, like to accommodate a full-size fire engine or other large emergency vehicle in case tragedy should strike. Well, sure, conceivably you might need to land an A380 there, too.

8. Parking-first aesthetics, garage façades, no alleys, no interior yards

It took me some time to consciously realise it, but one of the biggest differences that makes traditional neighbourhoods more appealing is that parking typically happens behind the house, reached through an alley. One is not likely to see an alley approved in suburban construction; that’s where robbery happens, right?

Instead, suburban houses are set back to make room for a driveway. Much of the façade of many houses is accounted for by a garage. This telegraphs the impression that the primary function of a house is really, above all else, to provide parking for one’s car.

Considering that suburbia is reputedly sterile and safe, there ought to be many other uses for alleys and common interior courtyards located at the rear of buildings, away from the street. In addition to being the proper place for cars, those are good places to put trash and recycling bins. Instead, the suburban street is surreally dotted with plastic trash cans at least weekly. So much for the pretense of civilisation.

What this says is: we have such a delapidated and depressing public realm, so few memorable places and things worth seeing, that we truly don’t care. This tension also accounts for the kitschy, farcical schizophrenia of the suburban home façade:

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It’s a castle, a veritable homage to collonades! But wait, there’s more: there’s a front porch–and if you’re a toddler, you can fit on it! Seriously, what is this thing? It looks like it’s trying to be a lot of different things from the annals of written history.

It’s not a house. At best, it’s awkward and unsettleed eclecticism, and at worst, it’s a caricature, as Kunstler would say. The form of normal houses much more closely follows their function. The problem is, when there’s nothing else worth looking at, developers are maximally exposed to the charge of building “sterile” suburbs if they build a merely functional house, the sort of thing that would be thought attractive for its simplicity and cohesion elsewhere on the globe. And that’s how we get to the neurotic potpourri of superficial ornamentation above.

The same dialectic is often a driver of the infamous suburban NIMBYism. When the public realm is so depressing and demoralising, describable mainly in terms of the car traffic it generates, it’s understandable that nobody would want to see more of the same built nearby. It ultimately comes down to the fact that we don’t value our public realm in America, and, no surprise, we’ve not built a public realm worth valuing but instead retreated into escapism in the private one. All escapists, ranging from readers of fantasy literature to video game players to drug addicts, are generally irritated by any effort to somehow disrupt or meddle with the ongoing process of their withdrawal from reality.

9. No street life or visible human activity

Periodically, people will ask me: “Well, if you’re so committed to walking, why not just … do it?” They mean right here, on the highway, next to six lanes of traffic, in 90F heat.

Well, in actually-existing psychological reality, people aren’t going to walk where it’s neither comfortable nor interesting to walk. Contrary to popular Republican-type mockery of the notion, “interesting” doesn’t require a hipster paradise of airy-fairy, frou-frou creature comforts like street cafes (though they do uncannily arise in interesting places). “Interesting” just means there’s some intimation of human presence and activity expressed in the architecture and scenery.

There’s nothing about a treeless six-lane highway that conveys this. I’m going to drive, not walk, because to walk would be boring, tedious, uncomfortable, dangerous, and, in a sprawling geography designed at automobile scale, impractically slow.

10. No public transport

Aside from its superior efficiency and ecological footprint, the primary value of public transport is not in being able to commune with the armpits of your fellow man, but in being able to spend your time in some way other than chained to one’s steering wheel cursing the traffic. You can read a book, catch up on e-mail, or just close your eyes for a while.

In suburban sprawl, you’re doomed to spending vast amounts of time at the wheel–time you cannot do much else with, and which you won’t get back. The nature of low-density automobile sprawl cities is that everything is insanely far away from everything else, so no matter what you do, you’re doomed to driving vast distances to see most friends, to commute to work and so on.

Clearly, it bears mention at this point that self-driving cars could address the chained-to-steering-wheel factor. But it remains to be seen to what extent they can shift the larger paradigm. I can envisage self-driving cars doing very little to change the overall blight (and environmental costs) of suburbia, or I could see them evolving more rationally into a kind of semi-personalised public transit. It’s a phenomenon that has the theoretical potential to either greatly further our atomisation into the pathetically sybaritic techno-pods of a WALL-E type world, or to turn into a moderately pleasant band-aid.

Whatever the case, they don’t solve the more fundamental problem of our vicious contempt for the idea of a public realm.

11. Improper interface between city and highway

In most places in the world, one will find that high-speed highways run between cities, not through them. You’ll also find that intercity highways don’t have a lot of commercial development along them, allowing unadulterated views of the countryside.

In places like Atlanta, interstate highways are something like main thoroughfares. Three of them converge downtown, along with numerous other high-speed roadways.

The effect is to induce lots of derivative traffic within the city. Freeways breed on-ramps and car-centric development along the corridor. At the same time, the city, especially its most important historic parts, is partitioned by an ugly exoskeleton.

12. Lack of regional planning vision

Turning back to Atlanta: Decades of unbridled free-for-all building in Atlanta have led to a widely dissonant, fragmented patchwork that cannot deliver a coherent thesis for future development in the city.

Some individual neighbourhoods in Atlanta, like Midtown (where I live), have made great strides over time to become walkable and present viable in-city living options. The problem is, as soon as you need to leave such a neighbourhood, you still have to get in your car.

The same problem can even play out on the block level. I’ve been to some downtowns of suburban sprawl cities and found them to have a number of blocks or sectors that are actually quite pedestrian-friendly, well-designed and interesting. The problem is, these blocks are like a chessboard; they’re not contiguous! Want to go more than 500 ft? Better start the car.

The point is, Metro Atlanta covers nine counties and untold municipalities, incorporated and not. With all the resources and initiative in the world, there’s nothing the City of Atlanta can fundamentally do to alter the reality of life in 95% of Metro Atlanta. I haven’t seen anything inhabitable constructed in America through a laissez-faire approach to building across such a patchwork. Charge has to be taken at the regional level.

As far as I can tell, the same holds true almost everywhere, since everything in the US that is–gallingly–called a “city” consists of fragments scattered across unconscienable stretches of freeway. I have a special place in my heart for Dallas-Ft. Worth, much of which should be reclassified as a rural area outright if one is to judge by density. But the need for a regional approach to development priorities and transportation probably applies almost everywhere, including places like St. Louis, Indianapolis, and Omaha.


This post draws in part upon the work of James Howard Kunstler, including his widely disseminated TED talk, as well as upon the data and ideas in the well-known New Urbanist title Suburban Nation by Andres Duany, Elizabeth Plater-Zyberk and Jeff Speck.


More lessons from my twenties: surviving as an amateur literator in tech

My upbringing and extraction unquestionably lie in the liberal arts and humanities. I’m moderately extroverted, and always leaned hard on the side of verbal, expressive and linguistic capabilities. For the time I was in university, I was a philosophy major with vague notions of law school. My parents are philosophy professors, and most of my relatives have an academic pedigree. I also had the unique intercultural experience of coming to America at age six with no knowledge of English and subsequently learning it in an academic social setting (my parents were graduate students). I carried that formative experience, and the globally conscious, relativistic outlook on language and people that it fosters, forward with me through life.

That doesn’t mean I’m a great writer, but I can write. Great writing, though, is really hard. As with many other things, if you plot a line from “can’t write at all” to “great writer”, you’d have to plot it on a logarithmic scale. Having a broad vocabulary, a firm command of language, and adroit self-expression will get you to the table stakes of “can write”, but that last bit, on the right, is a hundred, a thousand times as hard as what precedes it.

You know great expository writing when you read it; the thoughts and ideas are scrupulously organised, yet presented in a compelling way, with varied transitions and entertaining use of language, at once colourful and precise. Come to think of it, it feels pedestrian to anatomise it this way. You know great writing when you see it.

My writing is far too disorganised and repetitive to hit those notes. I’m verbose and can write a lot quickly and easily, but quantity is not quality; organisation has always been a struggle amidst my desire to relate a lot of details. If you read this blog with any regularity, you’ve seen that battle play out.

Though I’ve got better at condensing my thoughts and communicating ideas simply with age, I’ll never write like my friend Alan. His writing is incredibly brief and terse, but his gift is succinctness per se, which is not the same as brevity, though the two are very often confused in contemporary minimalistic fashions in communication. He can say much with little where many others merely say little with little.

As far as I can tell, the real gift there is the ability to accurately foresee the details and connections that the reader’s mind can work out for itself. Then you can say only what’s necessary to anchor the conceptual tent, cloth not included, avoiding most of the potential redundancy that makes verbose text tedious. This post would be about six times shorter if Alan were writing it, yet say every bit as much–if it’s truly important.

I tried, for a time, to emulate his style growing up, but the results were farcical, much more along the lines of saying little with little. Not everyone’s intellectual output can be compact and tidy. I have to ply my version of the craft, such as it is, differently.

Anyway, I lay out all these concerns not to be pompous, but rather to say that the kind of stuff I spend a lot of time worrying about doesn’t typify the STEM personality one commonly finds in the software engineering profession, nor the pragmatic, utilitarian–and often Spartan, at least when it comes to writing–communicators in the business world. There are exceptions, of course, but as a whole, my life experience is that it’s a valid generalisation about engineer types and MBAs thumbing out curt txt spk on their Blackberries. And this is the environment in which I’ve spent almost my entire adult life, having dropped out of university to seek the exalted heights of corporate America.

BUCHAREST, ROMANIA - OCTOBER 23, 2013: Unidentified lonely thoughtful retired man on his 60s rests on a bench in a park, autumn scene. The retirees represents 22% of the Bucharest's total population.

As you can imagine, this occasionally leads to amusing and infuriating conflicts of style and culture, and in general doesn’t make for an easy professional life. It’s not easy to talk to people when you have completely different psychological priorities than they do. The curse of being somewhat better-rounded is that my mind often takes detours not travelled by fellow Professionals. To their mostly utilitarian sensibilities, idle musings and the cultivation of an inner life beyond the immediate task at hand are, above all else, a waste of time. It’s not enough to just write this e-mail; it must be a good e-mail, at once brief and useful, but also poignant, articulate, maybe even with a dash of wit, or clever and original use of the English language? They’re thinking: get to the point, Alex, because business. There’s money on the line, or action items or something. Never mind the existential why! Business

Being wordy didn’t make for an easy childhood, either. I don’t think I came off overtly as bookish, being mostly chatty and rarely seen with an actual book per se. All the same, I can’t remember how many times I was called “Dictionary” or “Thesaurus” in school, or otherwise suffered social opprobrium for… well, for using words like “opprobrium”.

Outside of the liberal arts wing of a university environment (which I forsook at age twenty), the rest of the world offers a pretty steady diet of hostility to aspirant wordsmiths, and, as far as I can see, more generally to broader combinations of the intellect. There’s the automatic, default hostility of idle, unemployed kids in school, and the studied hostility of busy professional grown-ups. It’s easy to get depressed shouting into a waterfall, or, more accurately, pissing into the wind. I often feel an impostor, not quite sure what I’m doing here donning the regalia of tech entrepreneurship. When almost everyone I mix with expects small talk, being the guy always keen to start some big talk is demoralising and lonely.

And yet, as I pass the thirty mark, I’ve noticed something interesting. As more and more friends, colleagues and classmates move up the career ladder or otherwise evolve higher-order life needs, they’re coming to me for help in formulating thoughts: delicate requests, polite demands, cover letters, biographies, dating profiles, admissions essays, crowdfunding campaigns, petitions. All of this and more has landed at my feet in the past year.

“You always know how to say this stuff just right.”

“I don’t know how to say this – help!”

“You can put it a lot better than I can.”

Every once in a while, I’ll even get a note from a customer: “We always appreciate your thorough explanations and your going the extra mile.”

So, good news from our own “It Gets Better Project” for fellow closeted English majors in their twenties and thirties: keep your head up. As folks who know you move up the value chain into managerial realms requiring them to flex their communication muscles for the first time, you’re going to be more in demand.

Moreover, through my own experiences in hiring and being hired in the technology sector, I’m firmly of the impression that the most valuable candidates in the long run are those who both possess raw skills and can communicate well. There’s a lot of bottom-line value in clear analysis, disentangling messy ideas, and presenting esoteric information in an accessible way to outside stakeholders. Wordy missives may always be ignored by MBA frat boys as a matter of course, but effective and engaging communicators have more influence and audience.

The point is, as you gain confidence on your professional ascent and increase your leverage, stop taking shit from philistines. Don’t shy away from selecting aggressively for employers, customers and partners who realise that better-rounded people bring more to the table and appreciate you for who you are. Much has been said about how the customer is always right, and while compromises are necessary in life, you don’t have to concede everything and always. The fibres most integral to your self-actualisation should be armoured. The rightful sense of self is not for sale.

Evaluating potential hires for “culture fit” is all the rage in human resources now. Why not evaluate them for culture fit? What’s the culture like at the new gig? Neverending arguments about last night’s Steelers vs. Cowboys and the impact on Fantasy Football picks? Spirited discussion of the pros and cons of sundry brotein shakes? A thriving marketplace of World of Warcraft items? Hackneyed memes about bringing democracy to Syria? Either way, fire ’em. Sounds like bad “culture fit”.

Finally, choose your cohorts and your spouses wisely. Your true friends will help, not hinder you in leading an examined life.