Designing Your Life Using Design Thinking

Journaling: Zooming In

Although this journaling exercise seems pretty straightforward, it does take some practice—especially since most of us don’t pay detailed attention to the things we do throughout the day. While we may or may not come to the end of a day feeling like it was generally productive, we seldom sift through the particulars of what actually led to those feelings. Sometimes we need to zoom in and tease apart the nuances of an activity to really glean insights on our feelings.

Take Lydia as an example: She helps experts document procedures in manuals, and she had come to the conclusion that she hated working with people, mostly because she felt awful after going to meetings. But, after really zooming in as she reflected on her Good Time Journal, she found that she liked people fine when she met with only one or two people. She realized that what she hated was large meetings with more than six people and those that involved planning and schedules.

Getting good insights from your journal requires asking some key questions:

• activities—What were you doing? Was it a structured or unstructured activity? Were you a leader or a participant?
• environment—Where were you during the activity? How did the environment make you feel?
• interactions—With what or with whom were you interacting? Were you engaging in a new or a routine interaction? Formal or informal?
• objects—Were you interacting with any objects or devices? Which of them helped you feel engaged?
• users—Who else was there and what role did they play in creating a positive or negative experience?

What’s great about this journaling exercise is that you can use it in any type of situation where you need a better understanding of what is working—or isn’t working—in your life. Because the basis of this exercise is gathering data about what you’re actually doing, it is a fact-based, not just a speculative exercise.

This is also a great problem-identification technique, as we saw with Michael. Had Michael not completed the journaling exercise, he would have tried to solve the wrong problem—with potentially expensive, even disastrous results. In design thinking, problem identification is just as important as problem solving. Sometimes the biggest, most important challenge is accurately defining the problem.

The Value of Prototyping

As UX professionals, we know that design thinking involves creative thinking, ideation, and experimentation—trying out various ideas through prototyping, by creating not just one prototype, but lots of prototypes. In UX design, prototyping lets you rapidly try ideas that might be failures, without committing to and over-investing in a solution prematurely.

Similarly, in life design, prototyping lets you try out versions of a potentially interesting future, while physically engaging with the world around you. The purpose of these prototypes is to ask a question and gather some data about something that interests you. Good prototypes isolate one aspect of a problem and help you envision alternative solutions in a very experiential way. By definition, they also involve others, thereby helping you to build a community of people who can then come to play an important part in your journey.

So how does prototyping actually work in life design? Let’s consider Kurt as an example. He had two master’s degrees: one in design from Stanford and another in sustainable architecture from Yale. After earning these impressive credentials, he was ready to land a job in Atlanta, where he had just relocated. Using traditional job-search methods, he submitted 38 job applications and hand-crafted cover letters, along with his stellar resume. The result? Kurt received rejections from eight companies and never heard from the other 30. Kurt was dejected. Maybe you can relate.

At this point, Kurt decided to do something different. Instead of applying for more jobs, he decided to try design thinking. In design thinking, we use prototypes to learn what works well and what doesn’t work well in a solution or design we’re testing. Burnett and Evans say the easiest form of prototyping in Life Design is a conversation: the Life Design Interview, which is nothing more than getting someone’s story. It’s about talking with people who are already doing what you’re interested in doing or who have experience and expertise in your area of interest.

Key questions during a Life Design Interview might include the following:

• How did these people get to where they are? What was their career path?
• How did they get the necessary expertise?
• What is it really like to do what they do?
• What do they like and dislike about their job?
• What does a typical day look like?

A Life Design Interview is not a job interview. If you’re talking about yourself more than getting the other person’s story, you are not conducting a Life Design Interview. It is critical to distinguish the difference, which is all about mindset.

When people perceive that you’re looking for a job, what is top of mind for them has nothing to do with you. Instead, they’re thinking about whether there is a job opening—which there usually isn’t. Plus, if they aren’t influential in the hiring process, they’re thinking they can’t actually help you. Even if there is an opening, the question on their mind is: Would you fit in here? The mindset of a job interview is all about critique and judgment—and that is not the mindset that would get you someone’s story.

In short, a Life Design Interview is not a job interview. Ultimately, it’s just a conversation. Burnett and Evans equate a Life Design Interview to asking for directions. Kurt wanted to learn about sustainable architecture in the Atlanta area, hear the stories of the people working in that field, and learn what their work was like and how they got there. Kurt didn’t know his way around the sustainable-architecture industry in Atlanta. His conversations, or prototypes, enabled him to learn more about that industry and become part of the particular community in which he was interested.

In all, Kurt conducted 56 of these conversations. Yes, this took a lot of courage and a lot of work. But, as a result of this process, he ended up with eight different high-quality job offers. These offers came not from his directly seeking a job, but from having conversations about someone else’s life story—56 times.

The Cost of Not Prototyping

Prototyping is productive—and not doing prototyping can be costly. Take Elise as an example. She was ready to move on. Having spent years working in Human Resources (HR), she was ready for a change. She loved Italian food and wanted to recapture the experiences she’d had in small cafés and deli markets in Tuscany. So she decided to open an Italian deli and café that served authentic Tuscan food. Even though this took a tremendous amount of work, she opened her business to great fanfare, and it became a raving success. She was busier than ever. But she was also miserable.

Because she hadn’t experienced what it was actually like to work in a deli and café every single day, she had assumed that running a café would be similar to going to a café, an experience she had always enjoyed. But there were many aspects of the day-to-day operations of such a business that she simply didn’t enjoy. In short, she learned the hard way—and she eventually sold the business.

How could Elise have prototyped her idea first? She could have tried creating a small catering business, which would have given her valuable, hands-on experience running a business. She could have worked in an Italian deli to get a sense of the full spectrum of what’s involved. She could have interviewed deli and café owners to learn more about what running such as business takes. Prototyping is a great way of dipping your toe in the water and trying something out before diving in head first.

Failure and Failure Immunity

Design thinking is a process that requires a mindset of curiosity and a willingness to be action oriented and build your way forward. But it is important to realize that this type of approach, by definition, actually ensures failing sometimes. In fact, the authors stress that, by design, you’ll fail more often with the design-thinking approach than with any other approach. That’s why they refer to it as “failing forward.”

Therefore, it’s important to understand what failure means and develop what the authors call failure immunity. Failure has a negative connotation. No one wants to fail or sets out to fail. But it’s important to understand that how we interpret something is simply the way we think about it—how we frame it. Reframing is one of the most important mindsets of a UX designer. If you’re using a life-design approach, your life can’t be a failure.

Some of your prototypes or engagements won’t attain their goal, but always remember that their main purpose is for you to learn from them. Prototypes are part of a living, ongoing creative process. So they can’t actually fail. By design, the purpose of a prototype is to learn what works well or what doesn’t. In fact, the very reason you should build a prototype is to ensure you fail more often with the small stuff. This lets you succeed sooner in the big, important things. “Failure is just the raw material of success.”

According to the authors, designing your life is what life actually is. Life is a process, not an outcome. It’s like a dance. “Life design is just a really good set of dance moves” that let you work your way toward becoming yourself and designing how best to express yourself in the world.

Wrapping Up

All of us have problems. All of us get stuck from time to time. Although it is easy to become obsessed and lament over our problems, the authors share this insight: “Everything that makes our daily living easier, more productive, more enjoyable, and more pleasurable was created because of a problem [that someone set out to solve]. No matter where we look in our external world, we can see what happens when designers tackle problems.”

Life is not static. There isn’t just one solution to life, and that’s good. Using design thinking, we can approach our problems with a curiosity mindset and take action to dance toward the life we want, toward who or what we want to grow into. According to the authors, “A well-designed life is a life that is generative—it is constantly creative, productive, changing, evolving, and there is always the possibility of surprise.”