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by Julia DiPrete | October 25, 2022


Up until now, we’ve discussed design thinking as a somewhat abstract concept. To borrow the definition from the Interaction Design Foundation, design thinking is “a non-linear, iterative process that teams use to understand users, challenge assumptions, redefine problems, and create innovative solutions to prototype and test.” 

In this final post on design thinking, we’re going to explore what applying design thinking to career decisions looks like in practice. The goal is to help you identify paths and opportunities that can lead you to deeper career satisfaction, but that you may not have been able to see. 

Step 1: Free Your Mind. 

Many of us get in our own way before we even begin thinking about a next career step, because we begin with a set of preconceived ideas about our careers that can severely limit our thinking. 

Begin with a blank slate. Completely blank. Throw away the list of career options you got in law school. Stop Googling “what jobs can I get as a lawyer,” because most of what you’ll find looks a lot like the list we just told you to throw away. Maybe even sit down with a big, blank piece of paper in front of you. Grab a pen, some colorful post-its, and you’re ready to get started.

[As a side note, did you know that writing by hand actually engages your brain differently than typing? Neuroscience research has revealed that you write more thoughtfully when you write by hand, because physically drawing letters activates a distinct neural pathway that is linked to overall success in learning and creativity. And there’s more: When we write a letter of the alphabet, the process of producing letters involves pathways in the brain that go near or through parts that manage emotion. Helpful for creative career brainstorming, perhaps?]

Step 2: Empathize With Yourself. 

Empathy is the first “space” in design thinking. (I say “space” because describing design thinking in “steps” or “stages” suggests a defined linear process, and that goes against the whole iterative point of it all. That being said, it’s easier to follow if we talk about steps, with the caveat that it’s potentially misleading.) In more traditional design settings, like trying to design a consumer product, empathy means getting to know the consumer and understanding their wants and needs. In the context of your career, empathy means getting to know yourself. 

You might be thinking, but I already know myself. Do you really, though? 

Far too many people have a perception of themselves not as they are, but as how they want to be—or if insecurity plays a role, how they fear they might be. Empathizing with yourself means being honest with yourself about your strengths, weaknesses, passions, and limitations. You have to be able to let go of assumptions; one great example of this is assuming that because you are good at something, that must mean you like doing it—or even that you should be doing it. (Or, to jump ahead a bit, assuming that just because you were successful in law school means that you should be a lawyer.) 

This is where the colorful post-it notes can come in handy. Start writing down things about yourself. “I’m a strong writer.” “I’m not very organized.” “I really want a more flexible schedule.” “I’m a night owl.” The list can go on and on. 

It’s also important to write down things about your current circumstances. If you’re at a career crossroads, say because you’re unhappy in your current job, it’s essential to identify, with specificity, exactly WHY you’re unhappy. 

Step 3. Define The Problem You’re Trying To Solve. 

In case you were thinking that the problem is obviously finding a job, you’re going to have to be more specific. In design thinking, defining means taking all the information you gathered in the empathy stage and looking for patterns and trends. Ultimately, the goal in this step is to redefine the problem with specificity, to ensure that you’re trying to solve the right problem. 

One important thing to realize is that there are some problems that can’t be solved; in other words, they are not actionable. In design thinking, these are called “gravity problems.” Here’s an example of defining the problem in an unactionable way: A law firm associate who took on 200k of debt in law school is unhappy at a law firm, and realizes that they should have followed their early passion to write poetry. It’s not exactly actionable to simply say, I want to quit BigLaw to write poetry, if you can’t afford to make that jump.

Instead, reframe the problem. Take your colorful post-it notes and look at why you’re unhappy in your BigLaw job: is it the hours? The office culture? The work itself? Then look at the things you’ve identified about yourself as strengths, and/or that make you happy. “I’m a very creative person.” “I like expressing my voice.” “I’m a great writer.” 

With all this data, you can see that a more actionable way to think about your career is to say, “What kinds of jobs could I find that offer me more chances to be creative and write, without such long hours, but that still pay enough to afford my loan payments?” 

Step 4: Ideate. 

This is when you start brainstorming. But here’s the key to brainstorming in design thinking: Throw EVERYTHING at the wall to see what sticks. 

Too often, we limit our creativity by imposing parameters around our thought processes. This means that we dismiss ideas out of hand that don’t obviously fit within our parameters. Unfortunately, we run the risk of dismissing ideas that might offer promising insight, even if they’re not exactly right themselves.

Going back to our example. Even though we’ve defined our problem statement with specificity, we need to dismiss parameters when tackling ideation. One way to approach the ideation stage is to say, “If money, power, and time were no issue, how would I solve my problem?” Then write down EVERYTHING that comes to mind, no matter how far fetched. 

Of course, many of the ideas you come up with really will be unrealistic. That’s not the point. Even an unrealistic idea might have elements that you can use, but you might not have seen those elements if you had dismissed the entire idea. 

Step 5: Build A Prototype. 

After you’re done brainstorming, design thinking asks you to prototype. In traditional design work, this means actually building rough models of the product you’re designing to identify successes and flaws. But how do you prototype a career move? 

Obviously, you can’t really build models of careers and test them out before committing. But what you CAN do is learn more about the potential roles you’ve identified in your process. Maybe you’ve identified legal content creating roles as a potential path. Do more research about what legal content creators do. Find some people to talk to. Gather more information and prototype that information into your own life to see if the career move could be a good fit. 

Step 6: Test Your Plan. 

Maybe you’ve decided that legal content roles are the ideal next move, based on your design thinking process up to now. In true design, this final testing phase would mean building a model based on your prototype and testing it with consumers. Based on their feedback, you can either tweak your model or, in some instances, go back to the drawing board. 

Unfortunately, the reality of career moves is that they’re not entirely up to us. We can’t just decide to test out a new career and step right in. After all, we do have to actually get hired. 

In the career context, the testing phase of design thinking is to start applying for jobs and see where you end up. Prospective employers end up in the role of the consumer, and you’re the model. One way or the other, you’ll get feedback from prospective employers about whether your career move is feasible, and you can use that feedback to tweak your plan…or develop a new one. 

Sure, it might sound incredibly discouraging to get to this final stage and then discover that you have to start over with a new plan. For design thinking to lead you to an optimal outcome, you CANNOT be afraid of failure. Every process is valuable in what you learn, so that your next process will be closer to success. 

Remember: Design Thinking Is Iterative, And Careers Are Long 

If you take nothing else away from this post, take this: Design rarely goes from point A to point Z, and neither do careers. Products almost always evolve over time, becoming better and better as designers gather feedback and technology allows improvement. Similarly, a fulfilling career path is often similarly iterative; with each career move, we learn more about what we want from a career. 

Don’t be discouraged if your early career moves don’t take you to your “dream job.” After all, you may not even know what your dream job actually is, until you start the process. Keep an open mind, don’t be afraid to act, and a fulfilling career can be yours.