The Fine Art of Opportunism

There are four major approaches to decision-making: deliberative, reactive, procedural and opportunistic. The first three are well-understood. Academics study them, business and military leaders practice them, self-improvement gurus teach them and hippies protest them. Ordinary people understand them in common-sense ways. Opportunism though, is both the least-understood and highest-impact approach to decision-making. Here is my immodest 101.

An Example

Let’s say you run out of coffee one fine morning. “Damn!” you say as you hurry out the door, bleary-eyed. “I need to get coffee.” How might you deal with this situation?

  1. You could plan a trip to the grocery store and implement that plan. This is the deliberative, or goal-oriented approach. Stephen Covey preaches it. Your grandmother drilled this option into your decision-making toolkit with “measure twice, cut once.” Business leaders deploy it via Gantt charts and the much-derided waterfall planning approach. Most of the academic field of AI Planning obsesses over this approach.
  2. You could view the observation that you’ve run out of coffee as an error-feedback signal that tells you that your Universe is Out of Balance, and run it through a mental process that repeatedly asks the question “What action might reduce the Severity of the State of Being Out of Coffee?” and implement the answer, repeatedly, until your senses report, “You now have coffee.” Rather than planning, you take a first step, which might be “get in the car.” Then you take another. And another. Until your Universe is In Balance again. David Allen preaches this approach. “One Step at a Time,” your grandmother says. Business leaders wrap up meetings with this philosophy by demanding, “Who has the action items?” Most of the field of control theory obsesses over this approach.
  3. Maybe you don’t miss a beat. You put it on that grocery list magnetically attached to your refrigerator and head to work as usual. Come Saturday, at precisely 7:30 PM you embark on your weekly shopping trip, and Presto! magically your lack of coffee is corrected. Entire shelves in the self-improvement section are available to fill your life with such procedural “systems,” that help you avoid the problem of making case-by-case decisions entirely by automating your life. To the point where you’ll never need to overtly worry about coffee. Our prototypical guru here is Benjamin Frankin of early to bed fame. Lean Six Sigma coaches drive organizations towards this ideal of Proceduralize Everything. Most of the field of operations research is concerned with this approach.
  4. Finally, you might just file away the no-coffee observation as a casual background thought rather than a “get coffee” intention. The next time you happen to drive past a grocery store, you remember, “Oh, that reminds me, I need coffee!” and you detour to grab some. No gurus preach this. Besides Shakespeare (pop quiz: which quote am I thinking of? For answer read to the end) little about this approach is in our database of common proverbs, and businesses do very little (the SWOT analysis is the only one that comes to mind, and it is not particularly good) with it. While there is some academic work on opportunistic decision-making, it is a minority concern fragmented across disciplines.

A subtle point: many people just see opportunism as reactivity in a different guise, but the two are in fact radically different. Why? Think about it. If you still don’t get it, click “the buy me a cappuccino” link and I’ll email you an analysis.

Deliberative approaches are high-effort, custom-solution beasts. They also require a LOT of thinking and even when done well, are very brittle in the face of changing realities.

Reactive approaches deal better with changing reality, but can easily get lost in a series of knee-jerk next-actions that head nowhere. You get into your car and drive a block towards the grocery store. You realize you forgot your wallet and head back. You notice you forgot to feed your cat just as you are heading back to the car, and now that supersedes your coffee intention. You will also be late for work.

Procedural approaches can be very efficient over time and low-cost, but at the expense of built-in inefficiency for particular instances (i.e., “go till the weekend without your morning coffee”). Clutter your life with enough procedure and your life will creak to a standstill, overloaded with all those “Just 15 minutes a day” routines (exercise for you: why does the infomercial formula of “just 15 minutes a day” lack believability even when it is true in a nominal sense?)

Now for the magic solution. Opportunism delivers coffee with low effort (say a 2-step detour instead of a 15-step deliberative plan), high reliability (since it is invoked closer to the goal state than reactive approaches, with fewer distraction/failure modes) and high responsiveness (no waiting for the weekend). Not only does the opportunist not get disrupted by the changing world, she actually takes advantage of it. It is often a she. Women seem to think this way more naturally than men. That’s why, even among working couples, wives call husbands more often to pick up stuff on their way home from work.

The bad news: opportunism is a probabilistically effective way of getting things done. While on average, you will replenish your coffee supplies faster, more cheaply, with less thinking and less bureaucracy, there is a chance opportunism won’t do the job. Unlike the others, a non-zero failure probability is built into the model, as opposed to being an unmodeled externality. The perfect opportunist may never get her coffee. You may never catch that perfect wave.

The Importance of Being Opportunistic

Here is why opportunism is so under-appreciated. Suppose you have your deliberative, reactive and procedural games in order. You’ll get through your weeks, quarters and even years. You’ll survive. You don’t need opportunism. But year after year without opportunism in your toolkit, and a scary, frightening thing will happen to your life. It will become ordinary. You’ll achieve nothing remarkable. In purely decision-theoretic, Las Vegas terms, you will fail to “beat the house.” This is because the rational incentive structures of the world are designed to pay off less than the investment of rational players. Salaried jobs take more out of you than they pay. Non-financial rewards work the same way.

Opportunism is about working with and manipulating luck, not waiting for it. It is about engineering your path through life in such a way that the probability of disproportionate-returns events in your life is increased. You actually navigate by steering towards uncertainty and positive disruption because you know that your life is otherwise headed for ordinary outcomes. Here is a brilliant articulation of the point by a very smart scientist, Richard Hamming (he of Coding Theory fame) in his famous speech to Bell Labs titled You and Your Research.

And I will cite Pasteur who said, “Luck favors the prepared mind.” And I think that says it the way I believe it. There is indeed an element of luck, and no, there isn’t. The prepared mind sooner or later finds something important and does it. So yes, it is luck. The particular thing you do is luck, but that you do something is not.


Great scientists have thought through, in a careful way, a number of important problems in their field, and they keep an eye on wondering how to attack them… You can’t always know exactly where to be, but you can keep active in places where something might happen. And even if you believe that great science is a matter of luck, you can stand on a mountain top where lightning strikes; you don’t have to hide in the valley where you’re safe. But the average scientist does routine safe work almost all the time and so he (or she) doesn’t produce much. It’s that simple. If you want to do great work, you clearly must work on important problems, and you should have an idea.

A word to the wise is sufficient. Enough motivation. Let’s talk about how to become an opportunist.

The Prescription

Perhaps the single biggest barrier to opportunistic behaviors is a sort of puritanism drilled into us by most cultures that an outcome is not won fairly if it is won without an effort proportionate to its value. Gamblers are not respected in any culture. Not even smart gamblers who learn to count the cards at blackjack.

The skills that mark the opportunist — a sense of timing and leverage, adaptability and willingness to rapidly shelve existing plans and disrupt procedures — don’t add up to what any culture views as an honest citizen. It doesn’t help that our prototypical model of the opportunist is the politician. It also doesn’t help that by all rational calculations, opportunistic behavior looks insane. If Outcome A is worth 4 months of planning, and you abandon it in favor of going after Outcome B, shouldn’t Outcome B take 6 months of planning, by virtue of being more valuable than A? Does it not seem insane to shelve months of planning and pretty Gantt charts to act on hours or days of hasty paper-napkin scribbles? Yet that is often what opportunism looks like. It takes serious thought to understand that this is the reason opportunism works.

It works because opportunists are humble enough to realize that the random forces of nature are more powerful than themselves. That these random forces often conspire to make things ridiculously easy just as often as they conspire to create hurricanes and earthquakes. Most people realize that a lot depends on being in the right place at the right time. Very few realize that this situation is not the outcome of hard work or trying to identify and move to hotspots (visibly “happening” places are actually not, a phenomenon known as the El Farol Bar paradox, which is why hopping on bandwagons rarely pays). It is the outcome of a cultivated ability at recognizing when you are randomly in the right place at the right time (which also implies that there must be a certain amount of deliberate randomness in your wandering through life).

The cure begins with a sense of context and history. Week by week, very little happens that marks the importance of opportunism in the real world. Paychecks get delivered, tasks get done, plans play out as designed, reactions play out as learned, procedures chug along. But zoom out to decades and centuries and you’ll notice that with almost boring predictability, the course of the world was altered by somebody taking advantage of an opportunity. Probe further and you’ll notice that almost anybody (or any organization) with an episode of wild success or growth got started by spotting an opportunity and acting.

Once you’ve calibrated your mind right about the importance of opportunism, you can start learning specific behaviors to increase the degree to which opportunism shapes your life. Turn John Lennon’s observation around: if Life is what happens while you’re busy making other plans, make more room for life by planning less (and learning fewer reactions and installing fewer procedural systems in your life). And no, this is not about being spontaneous. That’s for romance novels. Opportunism is a deeper and more fascinating attitude than spontaneity of the maudlin romantic variety. Here is a 7-step program.

  1. Start by training (untraining?) yourself to be more of a daydreaming, idle, idea person. Put more unrealistic, unachievable desires in your head. Things that you know are going to be too difficult to attain from where you are now. This is how you prepare for luck.
  2. Become aware of, and start cultivating, your ability to recognize opportunity. This is NOT the same as trend-spotting or trend-prediction. You are not trying to sensitize yourself to happenings in the world at large with a “listener” mindset. You are watching with a motivated bias for connections to things you’ve already thought about in some depth.
  3. You’ve started noticing the right things? Good. Time to start probing. Probing means idle playing and dabbling. If something catches your eye, poke it with a metaphoric stick. Click on random ads, connect with people who intrigue you in unclear ways, act on impulses. Do not get sucked in and get addicted only to small, idle experiments. The key to probing is to drive towards yourself more information about opportunities you might be able to act on, and less information about stuff that will not yield opportunities. The reason this works is that most people just manage a deluge of zeroth-order information broadcast at everybody, and filter out what they don’t want. To such people, it seems silly to actually go after even more information than comes at you naturally. But that’s the key: information coming at everybody, no matter how sophisticated your filtering, is of limited value. Until you probe to discover first-order information that is available to all at low effort, but which few bother to poke out, you don’t have much of an informational advantage. Think of it as using your stick to clear away fallen leaves as you stroll through the park. No more complex than that. No high-effort digging. Just more information than the guy without a stick.
  4. Start developing a sense for leverage. Leverage is what creates disproportionate returns. Opportunists aren’t lazy, they just act in focused bursts and get more returns for every ounce of action. But this only happens with a lot of idle watching. Leverage is a combination of timing, selection and energy bursts. You develop your instincts for leverage by pushing with varying amounts of intensity on the opportunities that your constant and restless probing will reveal. This will gradually lower your resistance to agile action, lower the inertia of your planned, reactive or procedural thinking, and prime you to act in bigger ways.
  5. Act. If you’ve cultivated your opportunistic instincts in time, when an actual opportunity comes, you will recognize it faster, be more prepared to act given your background ideas, more armed to act, given the extra information your probing will have delivered you, and finally, more willing to act, even at the cost of disrupting well-laid plans, ingrained behaviors and ponderous rituals. Your sense of leverage will tell you how much you need to do. If you’ve accepted my religious preaching, you won’t be held back by an unnecessary sense of guilt about trying to steal a bargain from Mother Nature when she isn’t looking. But at some point, you’ll actually have to start placing your bets, so learn to tell yourself in no uncertain terms, pure black-and-white terms: this is it; I am going for it. The worst thing ever is not knowing when you are committing, and paying the high cost of a ‘dip’ without realizing it. I did it once. It wasn’t pleasant.
  6. Burst. If all your work disciplines were acquired through a moral ethic and a sense of static work-life balance, you won’t be able to do this. Within an extremely short period of time you have to bet a LOT. Not just direct effort (as in staying up nights), but relationships, earned trust, all your brownie points, money.
  7. Rinse and Repeat. Here is the fun part. More often than not, you’ll lose. Watch leopards hunt on the Discovery channel. You’ll see burst after burst trail off into lazy ambles. That’s how you live the opportunist life, like a hunter. Which means after every failed burst, you go back to your laid-back, droopy-eyed-but-watchful life, waiting for the next window of opportunity.

Even if you never win, that’s one hell of a rewarding way to live life, as Sisyphus found. Kipling said it pretty well, towards the end of If.

If you can make one heap of all your winnings
And risk it all on one turn of pitch-and-toss,
And lose, and start again at your beginnings

–you’ll be a Man, my son!

But Shakespeare said it best of all in Julius Caeser (which I had to memorize in High School. I am glad I did. This quote is burned in my brain, and has served me well.)

“There is a tide in the affairs of men, which taken at the flood, leads on to fortune. Omitted, all the voyage of their life is bound in shallows and in miseries. On such a full sea are we now afloat. And we must take the current when it serves, or lose our ventures.”

Fail to live this way, and you’ll pay a high cost. The opportunity cost of your life. Carpe Diem!

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About Venkatesh Rao

Venkat is the founder and editor-in-chief of ribbonfarm. Follow him on Twitter


  1. Hi Venkat,

    I reckon you’ll find that most good managers do, in fact, adopt an opportunistic decision-making style. They may rationalise it after the fact, putting it into one of the other three categories, but I think most managers have a list of things on their mind that they’re keeping an eye on/looking out for a potential solution for/a way around.

    It’s actually quite similar to the findings of Mintzburg’s and Kotter’s diary studies of managerial work in the 70s and 80s, especially Kotter’s idea of agenda setting.

    If you haven’t read them, they’re a great read:

    Kotter, J.P. (1999) “What effective General Managers really do” Harvard Business Review, March-April, v77:2

    Mintzberg, H. (1975) “Manager’s job: folklore and fact” Harvard business Review v53:4 July – August p49-61



  2. Interesting post! You should also check out Marc Andreessen’s post on ‘Luck’ that touches on similar things:

    I don’t have much to add except that it perhaps works best as a portfolio strategy. (for repeatable low-return parts of life e.g. bills, groceries, TPS reports, use procedural etc.). Pure opportunism applied across all facets in life probably devolves to chaos.

  3. Hi Rob: I agree that most good managers do adopt this approach; the question really is what proportion of managers are good :). Thanks for the refs. I was also thinking more of opportunism in individual decision-making about personal work than about managerial decision making about others. But yes, the approach is particularly visible in management roles.

    A — I do agree with portfolio comment. Pure opportunism will lead to chaos as surely as pure proceduralism will lead to a grinding, rusty halt.

  4. Hi Venkat,
    I generally agree with most of what you have written and feel that many people would benefit from pursuing this kind of opportunism. Working in a “large company”, a lot of the people I see around me fall into one of two categories:
    1. The focused executers: they focus on doing their “job”, and plan everything, and execute it well, and do reasonably well in their jobs. If they get a new idea, they go around with proposals getting appropriate permissions/buy-ins from the powers that be and more often than not end up dropping their best ideas due to lack of support. These guys need to do more of #1, #2 and #3 from your list.
    2. The dreamers: these get all kinds of crazy ideas and get passionate about the ideas. What is missing is steps #5 and #6. They rarely act upon any of their ideas with anything more than a cursory, short-lived effort.

    However, the part that I don’t necessarily agree with, is #6. I think that you can achieve substantial things even without all-consuming bursts; i.e. without giving up on the work-life balance, without sacrificing the relationships. In fact, I’m putting my time where my mouth is – I just quit my job to pursue some of these opportunities (starting today in fact!) , but I intend to confine my bursts to a 9am-to-6pm time-frame. To be sure, there still are bursts. And it is really, _really_ difficult to drag myself away from the computer at 6pm when it’s time to go home during one of these times. But the energy is back again at 9 the next morning. I intend to find out if it works.

    It is likely that you and I differ in our idea of what constitutes a substantial achievement. (I got the same feeling while reading your post on How to be an Idea Person. I felt that you were far too negative about the possibility of idea people achieving success.) Basically, I am not interested in coming up with, and successfully executing, the next world-changing idea. I would be happy with more modest achievements. And those, I contend, require less of an effort than you seem to be implying.

  5. Hi Navin: Good points. I’ve definitely seen scenario 1 play out a couple of times at least. There is a delicate balance between getting enough buy-in to enable ideas and getting so much that you get a godawful mess that attempts to satisfy everybody. My approach has been to develop a very right-brained sense of the “conceptual integrity” of anything I am trying to promote and then work hard on consensus building, but work equally hard to gatekeep out anything that messes with the integrity of the concept too much.

    Interesting that you differ on #6. I wouldn’t say what you are trying to do is modest. Quitting a day job to go full-speed on an idea you believe in quite a phenomenal opportunistic commitment of the Kipling-ian variety, and I am going to predict, from my observations of other entrepreneurs (you became one this morning whether you admit it or not), that the thing is going to take over your life beyond 9-6. So it would be an extended burst of energy :)

    If you manage to pull off your “modest” job-quit-worthy ambition on a 9-6 balanced schedule, hats off… I’ll be trying to ferret out your secret!

    But yes, I guess there is a romantic side to me that does get attracted to world-changing ideas, but I am pragmatic enough to maintain a portfolio with some modest ones too… let’s see if any of them work out.

  6. Not sure if I agree with your description of opportunism. The woman might already be on her way to the store to fetch coffee but along the way sees a coffee stand or something…

    I myself have often wished I could improve my ability to recognize opportunity. In hindsight, it is so much more visible.

  7. Great post. This reminds me of the advice Eric Ries gives to startups (his Lean Startup concept) and the OODA loop of John Boyd. It also reminds me of what I accidentally did when I self-published a book that was in the intersection of two very buzz-filled areas at the right time…

  8. P.V. Narayanan says

    Opportunism in my opinion is practised by most people — and often with mixed results if applied at random. It cannot be applied where the stakes are high. The second point is that a lot of us who work in institutional setting with accountability to people other than ourselves, will do a great disservice if we become ‘opportunity’ focused instead of looking at a viable Plan B. The best opportunitists will probably go with a plan. I think the most effective way of using it is to make it part of the plan and use it when the random ‘opportunity’ presents itself.

  9. Venkat,

    Great post!

    Do opportunists on a plane need a reminder “Please note that the nearest exit may be behind you” ?

    Looking forward to your new posts.

    Kind regards,