Make Me Work for It: Challenge Psychology

Fifth-degree black belt.


Rocket scientist. Triathlon competitor. Fighter pilot. Franciscan Monk. Astronaut. World-record holder. Five-star General. Firefighter. Navy SEAL. Everest scaler. Antarctic explorer. Olympian.

What comes to your mind when you read these titles?

For some, these titles were the answer to “what do you want to be when you grow up”, before they grew up. For others, these titles represent an obvious demand for respect. What’s invariably true is that none of these titles is easy to attain. In fact, quite the opposite; to earn any one of them, one would have to invest an enormous amount of energy and commitment.

What’s more – we attach a sense of elitism to these labels. Perhaps that’s why we wanted to be one of them when we grew up. We naturally have an appreciation for the difficult-to-attain. But why?

Our Addiction to Simplicity Ignores Our Affinity To Challenge

As designers, entrepreneurs, developers, etcetera, we often believe it is of utmost concern to make everything “simple.” We have taken Rams’ principle of “as little design as possible” and over-extend it to mean that anything difficult is evil.

This is not the case.

In fact, Rams’ idea of making something simple should be reframed: design should be easy to understand. Actions should be clear, but not always easy to accomplish.

Let’s take P90X as a ubiquitous example. If you haven’t heard of P90X, you probably don’t watch TV at 3AM… but if you do, you know Tony Horton quite well. He’s that guy reminding you how lazy you are, but also letting you know there’s a path to no longer being lazy via his infomercial.

It’s not an easy path. It’s not a short path. It will take a lot from you, but if you commit to it, a lot of other people who have committed and followed through show you proof that you’re likely to see results. You can get ready for the beach, but it’s going to take putting yourself through 90 days of hell.

I am in no way affiliated with Beach Body, but I find this phenomenon fascinating.

Why would somebody commit to something that is so difficult? Why would they pay a significant sum of money just to hear someone tell them to push themselves harder than they are comfortable pushing? Haven’t we learned that people only do things that are easy and obviously rewarding?

People have the capacity and drive to do hard things. We have that natural affinity to the hard-to-attain – an affinity to challenge that causes us to pick up the phone and order those P90X DVDs, not just because we want to lose our soda-and-Cheetos-weight, but because Tony looks us in our collective faces and gives us a challenge worth engaging.

Challenge: Competition, Achievement, Worth

I believe we have such an affinity to challenge for at least these three primary reasons.

1. Competition

I’ve been watching the College World Series this year. (In fact, it’s playing in the background as I write.) I’ve never watched baseball until this season, and it’s my new sports addiction.

We watch sports because we love competition and collective identity. We even mindlessly attach ourselves emotionally and face-paintedly to a team, without any logical connection, because we identify with competition and create an identity space for ourselves by joining in the highs and lows of fanhood. Why is so much energy, emotion, and resources put into a game? Because we fundamentally are wired for competition. We self-actualize by competing, giving definition to our place in humanity and in our individual communities by adding the dynamics that come with winning and losing, and the excitement of the tension of the game.

2. Achievement

The psychology of Flow (as defined by Mihály Csikszentmihalyi) requires two things: a high skill level and a high challenge level. Furthermore (directly from the Wikipedia summary), flow requires these conditions:

  1. One must be involved in an activity with a clear set of goals and progress. This adds direction and structure to the task.
  2. The task at hand must have clear and immediate feedback. This helps the person negotiate any changing demands and allows them to adjust their performance to maintain the flow state.
  3. One must have a good balance between the perceived challenges of the task at hand and their own perceived skills. One must have confidence in one’s ability to complete the task at hand.

In other words, challenges aren’t really challenges if they are impossible, but they need to be at the edge of our skill set. “Flow” state gives us a sense of movement and achievement.

3. Worth

When we can compete with others, we understand who we are in relation to our competition. When we experience achievement, we naturally develop self worth. We recognize that we have done something significant.

Design Challenge

Perhaps we have an inappropriate amount of value placed on simplicity. Maybe we should take a chance to challenge those engaging with what we create – to ask them if they are willing to do something harder. To invest in doing something: time, money, energy.

Did you set your pricing strategy based on making it easier for the user? Consider the worth your users attach to something they invest in versus something free.

Does your sign up form let anyone with an email address register for your application? Consider requiring users to justify their membership by asking them why they want the membership.

What classes are worth taking? What weights are worth lifting? What walls are worth climbing? Trails are worth hiking? Miles worth running? Time, money, energy worth spending?

Ask this question of yourself: Are you taking away the opportunity for your users to face a challenge worth facing, and trading it for “simplicity?”

What does this say about the worth you place on what you create? Most times, the most rewarding things require challenge. Open a conversation with your users. Be clear, and make it simple, but don’t lower the barrier to entry by making everything easy to accomplish.

Your new marketing pitch:

This is going to be very difficult, but once you’ve gone through it, it will have been worth it. And we are here with you every step of the way.

Create Small Things

Great things are done by a series of small things brought together.
– Vincent Van Gogh

Rule of Parsimony: Write a big program only when it is clear by demonstration that nothing else will do.
– The Unix philosophy

How many of your successes came from complex, massive projects?

The world is made up of simple things, and when we try to create our “big” ideas, we have a tendency to fail. The idea of making something simple does not mean making something easy – it means putting more concentrated attention into fewer details.

WhatsApp. A brilliantly simple concept. I don’t care to discuss the valuation – I care about the fact that it’s used and validated widely. I care about the fact that the design and conceptual approach worked, and all it does is… something small.

At Whiteboard, some of our most effective work has happened over the course of afternoon sprints. This happens because good ideas don’t necessarily rely on a complex network of supporting features, but stand alone. Good ideas often, perhaps almost always, directly address a small, simple problem.

This isn’t to say that we don’t give time to research and fermentation of ideas, but rather to say that we focus on a few ideas intently, and the execution of a solution often occurs very rapidly.

Build Small, Lose Small

Building small means failure is less painful. Building small leads to a higher volume of ideas and more intentional, deep exploration of single ideas, leading to highly predictable outcomes. Building large, on the other hand, usually means a plethora of poorly executed remixes of previous ideas with little predictability.

Building small means your ideas can easily be combined. It means you can test earlier, and rebuild from ground zero with little to no loss, as the value of your efforts is on the knowledge, not the product.

Small Means Easier…

When you build small, you build less maintenance overhead. It makes debugging easier. It makes testing easier. It makes marketing and the road to profitability clearer (maybe not easier). It makes scaling easier. Ultimately, the things that should be easier become easier with a smaller idea.

Small Means Harder…

Because you have to be good at what you do. Really good. You have to win at making fundamental ideas come to life, because when you build small, there are no bonus features. When you build small, transparency and purity shove your work out into the open. Every small detail is in plain view, because there’s less to get lost in. If you build small, you take on a challenge of creating boutique, focused experiences that ultimately get at the core spirit of the problem you’re solving.

Do Less, More Often

The challenge I present you with is to execute smaller ideas to perfection, and do so repeatedly. Small, beautiful, proper nouns are still in high demand, so make Small Things.

Getting Past Writer’s Block: Break the Rules

One thing I’ve been able to do in my writing career is… well, write. Perhaps the better way to describe this is to say that I have a knack for not getting stuck in writer’s block.

I didn’t realize this was a skill until a coworker recently asked me about my writing process, and inquired into how I get from zero to finished without many hitches.

(He should see how many unfinished articles I have in my Svbtle queue, but nonetheless…)

I started explaining my process. Usually, my ideas come from a conversation (as an example, see the article you are currently reading). Next, I write what I’m thinking.

I don’t marinate on the idea for very long. I don’t try to fully construct my argument. I don’t map out the sections. I just write, unadulterated and usually raw.

Most of the time I make many references to things that others don’t understand. I’ll make some strange comparisons and synthesize fairly obscure meaning out of thin air. But I write.

Then, I go back, check my headings, rewrite the things that don’t make sense, and if something good comes out? Publish. Iterate.

The truth of the matter is, so many people get caught up on their inability to write cohesively. To write something compelling. We all think a major amount of research is necessary, probably because we’ve been poisoned by academia to believe our own thought isn’t legitimate – that we can only speak from anecdote.

But no one is grading these papers. People read anecdotes. You don’t need to formulate the perfect argument every time you sit down to write. Instead, you absolutely, without fail, must tap into some kind of core human emotion inside of you, and let that emotion inform the flow of your words. Perhaps this is why my best writing comes from conversational topics. My emotions are peaked in conversation, and things that move my emotions are often likely to also move others.

There’s no pride in that necessarily – we are human. Emotions are powerful, and starting your writing in emotion is perfectly viable.

Of course, that doesn’t mean you shouldn’t edit. And edit again. It also doesn’t mean you can rely solely on emotional appeal to prove your argument.

This isn’t about whether or not emotion is a viable alternative to logic or reason, as it certainly isn’t. Emotion guides you towards intuition. When you tap into emotion, words become fluid, and writer’s block seems to stay at bay. You stop second guessing and examining the idea – practices which kill your output – and instead you focus on the fact that you have something to say. Ultimately, if you are a writer, having something to say is the most important skill you can achieve.

Think of your writing as an architect thinks about a new building plan. If you first approach your writing by constructing the technical requirements, toiling over the debate-style point-by-point inspection, you are effectively trying to build the schematics for a building first. Instead, you should cast your vision for the building by painting what you feel it should be. The details of that approximation are fleshed out in editing phase.

Write without the rules in mind. Contradict yourself. Commit every logical fallacy in the book. Allowing your human tendencies to be present in the first phase of writing is incredibly important.

Why does this work?

I strongly believe the reason this works is because “writing” isn’t one discernible practice. Instead, it is a collection of practices that should be treated as separate, distinct skills that are combined into a singular super-skill.

Writing is:

  • Output: This is what we’re talking about in this article, for the most part. This is where people end up getting “writer’s block”, and is absolutely the primary, most essential part of the writing process.
  • Research: Research occurs in so many different ways. For me, research isn’t purely academic. It’s coincidence, experience, and consumption all in one. Research performs two roles as it relates to your writing: informing and validating.
  • Editing: Editing occurs throughout the process. We do both simple editing (wherein we correct our “alright”s to “all right”s), as well as complex editing (wherein entire sections are nixed, and the necessity for new sections arises). Editing is informed both by your output and research, but will also affect your output and research significantly.

If you can do the three of these things well, I believe you can write well. What’s more, it takes a massive amount of fluid output to be able to effectively research and edit. If you are experiencing writer’s block, ask yourself these questions:

  • Am I trying to over-validate my idea?
  • Have I hit a roadblock because I’ve lost my argument along the way?
  • Should I start fresh, or should I shift modes into editing to re-align myself on the emotional track?
  • Am I trying to fast-forward to a post-output stage?
  • Am I actually invested in the idea I’m writing about? Where did the idea come from, and do I care enough to keep writing about it?
  • Do I believe in my own writing enough to be authoritative on the subject I’ve started authoring?
  • Am I just trying to avoid a longer editing process by writing it “right the first time”?

Answering these questions should help you find a shift in thought that will put you back in the output stage. Never write without authority. Don’t trade emotion for logic. Write with your feelings. Paint your buildings first.