The secrets to getting [what you want] are having done the homework to know you’re asking for the right thing, the confidence to ask for it, and the willingness to walk away when you can’t get it. — Mike Monteiro, Design is a Job

I know what it’s like to feel “stuck”.

In 2012, I was living in Portland, OR, working as a web developer. My life was easy and fun, but I was starting to get bored.

I knew I wanted to stop writing code and work as a designer, I had an itch to be in a more stimulating city, and I wanted to spend my time doing something that had a much bigger impact on the world. I was considering moving to San Francisco, the center of the tech world — I figured I might as well try something new.

One day, I got a letter from an acquaintance leading a UX team in San Francisco at a well-known company, and was looking to grow her design team. Would I be interested in interviewing for a job?

I quickly started writing a reply saying “yes!”, but I couldn’t bring myself to hit send. What if she invited me for an interview… and I got the job? I would be packing up my things and moving my entire life into a strange city. I had moved to new cities before… but something just didn’t feel right this time. I knew I wanted to do something different, but my gut was sounding an alarm when I tried to take the first step.

Maybe you can identify with that feeling. I know lots of people who do. This article is about the method I used for making that decision — and how it made me a better designer.

Let’s imagine a two-year-old named Bobby playing with toy blocks. Each block is a different shape. In front of Bobby is a box with a round hole on top.

Lil’ Bobby picks up a square block and tries to put it through the hole. When it won’t fit, he tries to force the block into the hole. After a few seconds, annoyed, he drops the round block and grab the next nearest one — and the frustration repeats itself until he stumbles on the right block or gives up.

For us adults, choosing a toy block that fits the hole would be easy. And yet, when trying to make decisions, a lot of us get stuck in a version of this classic “square peg, round hole” pattern.

Our adult problems — choosing the right career, finding the right relationship, hiring the right employee, moving to the right city, etc — are more complex than playing with toys. But we act just like the toddler, grabbing the closest “block”, trying for too long to make it fit, getting frustrated, and moving from poor replacement to poor replacement.

Naturally, some of us become resigned or even bitter, just like the toddler. But that angst manifests itself differently in adults: “Maybe work is just not supposed to be fun,” we tell ourselves. “I’m not sure I’m in the right place… but nothing is perfect.” “What could I have done differently, anyway?” “Am I holding out for something that will never come?”

When we ask for advice on these tough problems, our friends and family sometimes tell us things like “you’ll just know when things are right” or “find what works for you!” Of course, these just make us feel worse.

Eventually we may convince ourselves this is just how things are supposed to be. Life is hard, problems are hard, and others have success because they had the right “blocks” close at hand (which certainly helps, but is rarer than we like to think). Being a little sad about life is normal, right?

I think it’s wrong. The biggest parts of your life are not supposed to make you feel bad.

You might just need some help making better choices.

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 who magically summons concept cars and handbags from the mysterious depths of their creative genius.

But design 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 hard 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 life 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:

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”.

So how does all this theory work in the real world? Let’s go back to 2012, when I was considering moving to San Francisco.

Instead of emailing my contact back about the job, I ended up writing a different letter: asking for advice from my parents. I started to describe what I wanted in a job, and my list of priorities quickly grew out of control (by the time I was done, I had decided not to take the interview). It looked like this:

Actual screenshot from an email I sent in 2012

The San Francisco job would have had a good salary and benefits, exciting location, great job security and a flashy business card — all things that supposedly make for a great job, and all the things that were at the bottom of my list.

Soon after, I saw a job posting that described a really interesting opportunity: the chance to be the first designer at an agriculture tech startup. The job was far from perfect — it would require moving to Michigan (where I had never been) and the company was run by two inexperienced young founders. There were no customers, no revenue, and no investors — not even enough money to pay my salary for very long.

But looking at my list, I realized that location, salary, and risk of failure were much less important to me than growing my skills and building something great with a team I believed in. The founders were skilled and passionate, and I would have a chance to build something important. Most importantly, when I interviewed, the CEO got me genuinely excited to help create the future of farming.

I ended up getting the job, designing our product from head to toe, hiring a design team in Ann Arbor, seeing us raise tens of millions of dollars from investors, and helping grow the company to 80 people. There were lots of really hard things along the way, but I never regretted my decision for a moment (not even during Michigan snowstorms).

Finding that job was lucky — but had I never made my list, I don’t know if I would have taken it. Instead I probably would have overweighted whatever “pros” were top-of-mind, taken a random job in San Francisco, struggled through a big out-of-state move, and felt the same old restlessness once the excitement of something new wore off.

Isn’t this all a bit… analytical?

“I mean, we’re talking about jobs and people’s lives… aren’t those too important to be boiled down to an algorithm?”

Of course, this is all very analytical — and if you’re an analytical thinker, this might be a useful tool. If you’re not, consider trying it anyway, maybe on a day when you’re feeling a little lost. You might find that it’s a healthy balance to your normal way of doing things. Either way, this exercise could help you see ideas that your natural “thinking mode” tends to keep hidden.

I want to reemphasize the importance of using this process in support of your emotional compass when making tough choices. You need access to your emotions to help you find your way. That’s also what’s so beautiful about design to me — it’s never about logic or emotion alone, but about finding graceful ways of making them work together.

Form follows function — that has been misunderstood. Form and function should be one, joined in a spiritual union. — Frank Lloyd Wright

Even the design process itself is never completely prescriptive. I like to think of my process as a temporary scaffold I use while I’m build the “real thing”. The right design, when the work is over, is just whatever serves its purpose and makes people feel good. Decisions in your life should be the same.

Anyway — if you’re not convinced yet, here are a few more reasons to use this method of setting priorities first:

  1. It helps you make a choice — any choice. Often what holds us back isn’t the lack of the correct choice, but a lack of any choice at all. A short term commitment, even a “wrong” choice, means we’ll see the results of that choice more quickly than if we had waited for something better. Then, if necessary, we can change our mind and make the “right choice” now that we know. That’s what design prototyping is — just trying something (anything!) so we can learn without the high risk of full commitment.
  2. It helps you make a good choice. A good choice being one that fits your priorities (this is circular logic, but you get the idea) and makes you feel good. This one may be obvious, but it’s probably the most important reason of all!
  3. It decreases risk. Creating critical “big decision moments” in your life can feel adventurous, but these moments are far too susceptible to bad outcomes to be reliable. You probably know that big projects are best tackled by breaking them into small pieces. Following this method means that you don’t have to make big choices all at once. All you have to do is make a guess based on what you already know, try out your decision, and adjust your priorities as you learn. Choose a course, make decisions as you go, and validate them along the way.
  4. It gives you a competitive advantage over other people making similar choices. Let’s say you’re trying to buy your first house, and you decide that being able to walk around in your neighborhood is more important than having a big house with a big yard. Now you know exactly where to look: dense neighborhoods with small houses! The price and competition for those homes may be lower, and you’ll still get what you need to be happy.
  5. It helps you understand yourself. How would you describe yourself to a stranger? By telling them your age, job, hometown, and weekend hobbies? If so, you might have a lot to learn about what really makes you unique — and understanding what you value is a good start. Of course, your priorities will continue to change throughout your life (as will you).
  6. It’s a prerequisite to good leadership. Let’s define leadership as “communicating and acting in a way that helps others make the right decisions”. If you can’t clearly define what’s important to you and your organization, you’ll just be giving arbitrary orders and be perceived as scattered and inconsistent. That’s not a good way to build the trust of those who depend on you.
  7. It builds empathy. People get tempted to judge others — partners, job candidates, etc — as either “good” or “bad”. Creating priorities that precisely suit your own needs (instead of our vague ideas of “goodness”) helps us recognize that bad candidates/partners/jobs etc are only “bad fits” for us right now. They’re not “bad people”. Finding a good fit is only a matter of finding a “right-shaped” job, relationship, city, etc.
  8. It builds gratitude. People often feel a little remorse a few months after a big decision — whether or not they make a big change or keet things the same. “The grass is always greener on the other side,” as they say. But understanding what you want helps you avoid regret— and to value the things you already have. It might sound a little like this: “I don’t have everything… but that’s fine! I have what I really need.” It’s a really good feeling.

I’ll end with one last lesson from the design studio: talking, analyzing, planning, feeling, and empathizing can only take you so far. Eventually, you have to roll up your sleeves and put pen to paper. Understanding is no substitute for making.

So if you’ve read this far, why not take a few minutes right now to start your own list of priorities? Just open a Google doc and start typing—then send it to someone you love and trust for feedback. You might be surprised where it leads you.

¹ This is a really short summary of a process that’s been described by designers for decades. One classic description is the Double Diamond; the more recent Google Ventures’ Design Sprint also describes a similar process. For digital designers who want an in-depth version, I recommend Designing in the Digital Age. Designing Your Life has even more ways to use design methods (like prototyping) to make life decisions.

² Four is a good cutoff, but there’s no exact number that works for everyone. I’ve found that using fewer than three top priorities is such a low bar, you tend to make “why not” decisions which lead to poor outcomes and more stabbing in the dark (followed by decision fatigue). Waiting for more than five to “match” can create analysis paralysis and no decision at all, which keeps you from iterating through your options quickly.