What doesn’t work

First, let’s break down the method that’s making our toddler Bobby so unhappy. It goes something like this:

  1. When trying to make a choice, grab the easiest, closest option
  2. Put all your energy into trying to get that thing to fit (even when it’s not working)

I’ve jokingly heard farmers call this the “spray and pray” method for growing crops. Just go into the field, apply a bunch of fertilizer or pesticide, and hope that you get enough corn. Software engineering has a term called “guardrail programming”, an analogy for driving down a road without steering until you hit a guardrail — then turning the wheel randomly and hitting the gas again.

How designers deal with tough problems

You might think of a designer as a person a who magically summons concept cars and handbags from the mysterious depths of their creative genius.

But is really a fairly practical profession. Designers love to make things look good — but often spend more time on more practical requirements of their projects like making them easy to use, simple, and performant.

Designers have to make new things every day, whether or not our creative juices are bubbling and our passion is high. So we’re trained to ask ourselves “how can we systematically and repeatedly come up with good solutions to problems?” Untangling ambiguity and presenting concrete answers is what designers do.

Step one: define success

The architect Christopher Alexander describes design like this:

Every design problem begins with an effort to achieve fitness between two entities: the form in question and its context.

Chapter 1, Notes on the Synthesis of Form

Alexander uses the example of a designing a tea kettle. The “form” is the kettle itself—its shape, size, materials, and features. The “context” is the world around the kettle—the stove it will sit on, the kitchen, the person who will use it, the time of day they’ll use it. To, Alexander a well-designed teapot is one who’s shape “fits” in the world around it.

Using this way of thinking, we can judge the merit of any kettle by asking “how good a ‘fit’ is it for this environment?” Does it fit the hand of the person making tea? Does it fit on top of the stove it’s meant to sit on? Does it evoke the emotional feeling that we want to feel at 8am in the morning? Whether you use measure with qualitative or quantitative methods, the question you’re answering is always “is there a fit?”

Consequently, there is no “right” kettle for everyone. A good lightweight camping kettle is totally different from a good traditional Japanese kettle because the context is completely different.

This means that we can’t just look at the teapot itself to decide if it’s “good” — we have to use the environment around the teapot to help us make good design decisions.

Then, make something great

Now that we know what a good design looks like, how do we go about coming up with the right design? The answer is the design process.

Let’s go back to the toddler and his toy blocks. Imagine that you had to teach Bobby exactly how to fit blocks through a hole. It might sound something like this:

  1. First, look at the shape of the hole.
  2. Now, look at the shape of each of the blocks.
  3. Pick the block that looks most like the shape of the hole and try that one.

Easy enough, right?

Designers do this on a larger, more complex scale with the design process. This varies from designer to designer, even project to project, but usually follows these steps:

  1. Discovery (ie, “looking at the toys in front of you”) — First, we try to understand the context around the design. Who is it for? What are they like, and what do they want? Where, when, why, and how will they use this thing?
  2. Problem definition (describing the shape of the hole)—Now, describe everything you know about the exact problem in front of you. Based on what we’ve learned, what’s the most important problem to solve? What are the strongest emotions we need to evoke? What exactly does this design need to do, and what can it not do?
  3. Ideate and prototype (looking at the blocks you have)— Only now do designers start formulating solutions. What are all the ways we can solve the problem we defined? At this point, designers build small versions of the final product to test in the next step. (This is one place where our block analogy breaks down — in design, when no blocks fit, we can usually make our own, new block.)
  4. Evaluation (trying to fit the block in the hole)—If it fits, you’re done! At least for now. If it doesn’t fit, why not? At this stage, it’s extremely important to describe that reason as a problem (ie, “block is bigger than hole”) rather than a solution (ie “use the small block instead”). Don’t be the driver who hits a guardrail, turns the wheel, and floors the gas pedal again— just note what went wrong, describe why, then wait until the next step to invent a solution.
  5. Iteration (trying other blocks) — Go back to the discovery phase to learn more about your hold, or back to prototyping to get a better block. This step is never optional — if you think you nailed it the first time, you’re almost definitely not evaluating very well. And if you find yourself at this step over and over again (a real example: changing jobs a lot), that’s TOTALLY OK and a really good sign. It means you’re learning quickly! As long as each new decision gets you closer to what you want, be brave and keep moving.

This process is used by companies around the world to make the products and software you use every day. It’s even used in a meta sense by designers who stop doing daily product design — and design their teams, school curriculums, new businesses, and even companies.¹

To be honest, when I first read about this process as a student, I was somewhat unimpressed. “Isn’t that just common sense?” But after working with real users and complex problems, I found out the hard way that getting the right design is surprisingly tough. It’s really common for designers to jump straight to the “make something” step, stop too early, and feel almost betrayed when users, clients, and customers don’t like or use their ideas. A real process keeps you focused because it forces you to start and end with the design “context”, not the “form”.

Designing your own hard decisions

Now let’s apply this method to your own life. Next time you’re struggling with one of life’s big decisions, try this:

  1. Spend some time understanding yourself. Everyone is different. The things that make you happy are different from the things that make other people happy, the things that you really need are different from other people’s needs. What’s your personality? What puts you in flow state? What do most people find boring that you think is exciting? What daily activities are most correlated with you being in a good mood? What did you like to do as a young kid? What’s important to you at this stage of your life or career?
  2. Literally make a list of your priorities —DON’T SKIP THIS. Each answer should be named and written down. If you’re not sure what your priorities are, just take a guess (it’s not actually that important to get this right the first time around). For example, your list might read “get a lot of good job experience, help people, work max 50h/week, live on the West Coast, make $10k more than I do now, job stability, and good health insurance.”
  3. Sort the list in order of most- to least-important. Coming up with a big wish list is relatively easy; this part is hard. No two priorities can be “tied”— rank them number one, number two, etc. Technically, until you rank them, they’re not even priorities — they’re just wants. (Again, don’t worry too much about getting this perfect on the first try.)
  4. Take only the top four priorities on the list. Turns out, you don’t need to hit all (or even most!) of your list to feel satisfied with a decision. Wanting to “have it all” is an easy way to make things extra hard for yourself. The things at the top of the list are the only priorities we’ll be trying to find a fit for; these are your “deal breakers”. We’ll actually either ignore or actively work against your lower priorities. By the way, universal human needs (partners who aren’t abusive; jobs that pay a living wage) are always required and don’t count as part of your top four. ²
  5. Now, make another list of possible solutions. This could be a list of cities to move to or a list of potential jobs, for example. These are like the toddler’s blocks — or in design terms, the forms that you’re going to test against the context.
  6. Test each solution against each of the top priorities. We’re hoping for an unexpected good result here, so don’t shortcut this by labeling solutions as “good” or “bad” based on your gut. Only evaluate them based on how they suit the priority list you made. “Will this job help me learn my craft?” and “Does [city] have a strong social support network for me?”, etc. If you’re not sure if a solution “fits”, create a little experiment to find out! (Get an Airbnb for one night in a neighborhood you want to move to, for example.)
  7. Now, mentally commit to the answer that fits all top priorities. If one of those solutions fits your priorities, you have your answer! This should feel exciting and relaxing. If it doesn’t, continue to the next step.
  8. If you don’t feel excited and relaxed, thats very normal. Start at the beginning again. If nothing fits all the top priorities, don’t just shrug and compromise. Go back to the previous step, get more ideas, and keep trying until you find a perfect match for the top of your list. Where else can you move? Where else can you work? Who else can you hire? There are a lot more possibilities than you can imagine, and now is the time to expand your knowledge. Remember, your list of priorities is small, so you shouldn’t give up or you’ll be settling for something that doesn’t make you happy.

If you ever feel like you’re making a mistake, stop and reconsider your list of priorities. The problem is probably one of two things:

  • Sometimes this feeling comes from defying some external “should” that you didn’t prioritize highly because it’s not really that important to you. Maybe you assumed something was important to you because of the values of your parents (work for a famous company) or peers (date someone cool). This is great! It means that now you understand your real priorities better, and you don’t have to deal with the dissonance created by solving for someone else’s goals anymore.
  • Sometimes this is a genuine feeling that something is wrong. This is good too — it means you’ve identified some important but unarticulated need inside yourself, maybe one that nobody encouraged you to prioritize before. It’s time to put that need into words and add it to your priority list. You can always stop and rearrange your list, promoting some new priority by demoting another one, and starting again (in fact you should — I don’t think anyone gets their list “right” the first time around).

The hardest part is doing the right thing when your latest “block” doesn’t fit the list. Call it sticking to your guns or just being a grown up—but when things aren’t working, you just have to be brave and say “no”.



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