Practical Imagination: An Essential Startup Skill

I was thinking today about the “soft skills” of business and particularly entrepreneurship. Much is made of the often amorphous “business skills” or “people skills.” For technical people those phrases are often heard as a euphemism for either an eagerness to take advantage of people or, just as often, moderate alcoholism.

We joke among ourselves about the starry eyed “idea guys” that post on craigslist looking for someone to just “do the code part.” As if developers are sitting in front of their keyboards watching the cursor blink on a blank screen as we curse, “If only I had an idea!”

Of course, people who know how to do stuff are biased toward the doing end of things. They know how much more difficult it is to implement an idea in the real world compared to imagining the idea in the controlled lab of your brain. A common trope among developers is the Underpants Gnome business plan that looks like this:

  1. Collect Underpants
  2. ?
  3. Profit

We chuckle at the naivety of jumping into a plan without thinking about the implementation. It’s something that we experience in real life when we’re approached by someone waving NDAs and so enamored with a half-baked idea they haven’t dared to question it. They usually gloss over the hard parts like acquiring traffic, engaging those clicks enough to convert them into customers, and, of course, writing the  software.

It’s not the idea, it’s the execution. Mostly.

But it’s the idea too, right? When we hear the folk tales of startups and entrepreneurs, we invariably hear the “origin of the idea.” Typically, amid a mess of wires and empty soda cans cluttering a garage sit bleary eyed, sleep deprived hackers who are singularly obsessed with “the idea.” The idea might seem like madness to those around them, but these visionary souls have seen the future and in a flash of preternatural insight have become obsessed with a quest to fulfill it.

Well, the good stories go like that at least.

In a more sober mood, we can perceive the other mitigating and amplifying factors like the commoditization of complements, under-exploited efficiencies born out of new technologies and their side effects, and often opportunities that arise due to luck, nepotism, political power shifts or a combination of the above.

We can thumb through back issues of business magazines and see the burned out wrecks of businesses that all started as good ideas. How many of them fell apart because “the idea” was not good enough? Often we’ll find that they failed because of personality conflicts, cash flow issues, bad partnerships, inadequate capital, a changing market or any of the million other reasons only tangentially related to the core idea.

Still, it’s the idea that gets us.

It seems like the ideas are the difference between the winners and the also rans. It seems like it should be at least. The idea is the romantic part. We love the idea because it means we don’t have to be born rich or well connected. It means that cleverness counts and that’s attractive because cleverness is fair.

Ideas also seem disproportionately  important because the founders that are left standing in successful startups are usually the sort of people that have lots of good ideas.

The ideas that they come up with to solve the problems that capsize their competitors are often not particularly novel or complicated. And they’re almost never the first idea that was tried.

What distinguishes the wanna-be from the game changer is not how big his very biggest idea is. It’s his skill in imagining practical solutions to all the little problems that have to be solved every day.

Practical imagination is a skill. Like every skill some people bring a talent to the table that puts them leagues ahead of the average joe. However, like every skill it has to be practiced regularly or it will erode and dull. If you go to work with a dull and misused imagination you will quickly get overwhelmed with all the weed-like issues that take root when you lack the ability to anticipate them.

How do you practice your imagination?

You might be hoping the answer is regular day dreaming and hallucinogens. Others will probably insist the only answer is regular exercise (I kid!) However, the only real answer is to run into a lot of problems that need solutions. The best way to run into a lot of problems is to try to do something hard.

It’s important to distinguish between hard and impossible. If you jump into doing something impossible, it’s likely you’ll learn a lot. It’s guaranteed that you will fail. Now failing isn’t the worst possible outcome. Not trying is usually worse.  At the very least, when you try and fail you learn that doing it that particular way doesn’t work.

If you want to occasionally have something to show for your efforts, you should aim for just hard. However, if you’re new or out of practice it might be difficult to tell the difference. What you do in that case is analogous to how you start lifting weights. One of the quickest ways to crash a fitness regimen is to bite off more than you can chew and hurt yourself. So what do you when you start lifting weights? You start with the empty bar. It may be the case that you’ve managed to sock away enough strength in those chubby arms to lift more than the empty bar. You’re not going lose anything by starting too low. You will definitely gain something – the knowledge of what you’re capable of.

In the same way, in business you can dream of solving the big problems. If you’re a developer, you can imagine crafting a smoothly running application with next generation features and elegant algorithms. But if you’ve never gone so far as to stand up an install of wordpress, you might want to trim your scope a bit. Start with something you can do in one iteration. Chop out every nice-to-have, strip out the clever bits, make do with the barest list of deliverables. It doesn’t have to solve every edge case. Just solve one.

Once you do, step back and take a look. You may have a rickety little jalopy of code that runs… mostly. It certainly won’t look much like what you pictured when you first dreamed it up. But it’s real and it works. I’ll bet it looks a lot more like what you envisioned than nothing does. Doing that much is more than the vast majority of wishers and hopers will ever accomplish.

The Happy Side Effect Of Doing

On top of a sense of accomplishment, one of the most valuable things that actually doing something will give you is a list of problems. Perhaps you didn’t think about saving some important data, or you realize that your sign up form is hard to use. When you have an understanding of what sort of problems need to be solved you have insight that far beyond that of even the most visionary thinkers.

On a practical level, you also have a list of opportunities to practice your imagination. Instead of idly day dreaming about how you’d solve the problems you wish you had, you have to test and try and fiddle and tweak until you graduate to a whole new set of problems.

It gets easier. As you gain experience you start to learn how to recognize problems. You’ll learn what sort of problems can be ignored, which are best beaten to death with money and which problems are worth changing your whole direction for.

Becoming familiar with problems is really just an abstract way of describing how you acquire a skill. When we say a mechanic is skilled at fixing automobiles we are saying that he knows what problems cars have and how to deal with them. The same goes for plumbers and architects and bakers and forest rangers.

For someone involved in startups and new technology, besides the practical skills of writing code, managing time, composing ad copy and the like, the most important skill you can have is a sharp, practical imagination.

You have to be able to anticipate problems early enough that you can adapt your trajectory to use them as opportunities.

I emphasize the world practical because there’s a difference between imagining what might happen and imagining what else might happen. A practical imagination is one that can be used as a tool.

Often when wedded to a big idea we fall into the trap of insisting on the original destination even after the journey has uncovered previously unimagined treasure ahead. It takes flexibility to pivot. People who aren’t comfortable solving unanticipated problems aren’t flexible.

To be flexible, you have to be good at anticipating problems three moves out or able to duck really fast. Either way you’re going to have to be skilled at guessing what might come next. That’s a practical imagination.

Squeezing The Wonder Out

Does this sound like a grumpy old man kvetching about those wide-eyed kids and their big dreams? I’m not trying to argue for limited dreams and austere ambitions.

It’s ok, even admirable, to dream big. It’s not ok to have an imagination limited to the party at the end of the road.

It’s easy to point to a mountain peak and say, “I’m going to get to the top of that.” What is hard is negotiating the bramble, rocks, gorges and poison ivy that you’ll encounter on the way up. It’s the guy that can invent shortcuts and forge new trails that’s going to get there first.

Your friends and family, the press and other on-lookers will applaud the novelty of your invention. Your fellow hackers and do-ers will applaud the tenacity, cleverness and endurance it took to implement it.

The Scrappy Sage

So what are you looking for on the “idea” side of a new business? I think you have to find a balance. Without a big vision you are unfairly limiting your ambitions. You have to have a story that people can share, that investors can grok quickly enough to read past the first page and that developers can aim for. Having a big idea is a requirement for building a business that is solving a problem big enough to warrant survival.

Balanced against that big idea is the pile of little hacks, epiphanies and pivots that you have to make as you scramble up your mountain.

The best people you can find to partner with are the ones with enough callouses on their finger tips to prove they’ve scaled a cliff or two. They know better than to gloss over the frustrating and exhausting bit in the middle.

How do you recognize those people? Here are a couple things to look for:

  1. They are suspicious of features. Every new feature of a product costs time and attention and introduces risk. People who are quick to add to the spec are often either too enamored with their own ideas or lack a healthy fear of scope creep. People who insist on doing the absolute minimum in the first iteration, on the other hand, aren’t exhibiting laziness. They are likely showing you that they understand how difficult it is to do things even when they’re simple to imagine. There will always be time to add and improve to the product.
  2. They question assumptions. If you are bringing nothing to the party except ideas it’s scary when people kick the tires of your idea. If the idea isn’t sacrosanct than what do the others need you for? People that make things want to know what they’re going to run into down the line. If someone can’t see the value in testing and tearing apart the idea it is prima facie evidence that they’ve never properly implemented one.
  3. They have finished projects that you can see. Before you commit your time and treasure to a project or business, you need to see some evidence that your partners have seen something through. Work done for other people is a good start. Things they made on their own are better.

Having a practical imagination means having the confidence to try out your ideas, the humility to abandon the ones that don’t work and the flexibility to adapt and grow. Finding people with staggering intellects or bulging business contacts is a big advantage for a startup; finding people that know how to get things done is even better.

Lance Cameron Kidwell

6 June 2011

Posted in Culture

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