Design Thinking for the Job Search, Part 2: Possibilities

By Anders Wallace

Design Thinking Possibilities

Photo by Arek Socha on Pixabay

Recap: Design Thinking Series

In the previous blog post, we explored how using a creative process called “design thinking” can help you find a career that matches your own skills, talents, interests, and values. In this blog post—the second part of a three-part series—we will take the process a step further to understand how you can come up with a new business in entrepreneurship.

Like the previous post, this post is adapted from advice by design thinking consultancy’s free online publication “Design Kit: The Human-Centered Design Toolkit.” If you followed the steps outlined in the previous blog, by now you’ve done a great deal of research and discovered valuable information about the priorities of different workplaces and how they match your skills, interests, and desires. Now, you’ll want to return to some of your findings and worksheets from the previous exercises in order to generate unexpected possibilities through successive rounds of ideation.

Part 2: Generate Possibilities

Follow these steps. While best done in sequence, don’t worry—you can always come back and do any given steps again to refine your results:

1. Make a List of All Your Options

First, take a pen and some post-its and write down the companies, industries, or career-tracks that stand out from the first phase of your career research. These should offer the best match between their needs, values, and workplace norms and your skills, affinities, and personal constraints (contexts in your life that you can’t or won’t change).

Write these organizations (including industries and career tracks) down on post-it’s and put them on a wall. Think about the connections between these different organizations. Try grouping different organizations into thematic groups based around similarities between them. Then, write down some of these points of commonality into separate post-its, and put them up on the wall as well. Also try writing out these commonalities as full sentences. These sentences don’t necessarily have to reflect actually existing careers, it’s perfectly fine to just capture the form of a sentence that moves you. Once you have that sentence or sentences, compare them to your personal strengths assessments (such as MBTI-Strong or Strengths Finder, which you did in the first blog post of this series). Do these sentences spark any new career ideas? Do they make you think of analogous careers you may not have thought of where these values are prized?

2. Highlight Key Ideas

Second, you’ll want to go back to the secondary research and informational interviews you conducted in the first blog post. You’ll want to highlight inspiring stories you’ve heard that move you. In performing secondary research and conducting informational interviews, you’ve gathered tons of information. You’ll want to look over your notes and capture those key ideas and stories that move you by writing them on post-it’s. Write down not only pertinent facts and impressions but also hunches. Some examples of inspiring stories include:

  • “Working to empower people in need, like Amy did in her NGO work assisting microfinance loans for rural women in India, is something that inspires me.”
  • “I want to use my creative abilities to make a message connect with its audience, like Luke does in his graphic design practice.”
  • “Personal independence—freedom to work from home, with flexible hours—is something that will allow me to take care of my aging mother and enjoy spending more time with my own kids, which is a priority for me.”

Put these post-its up on a wall, and organize them into separate categories depending on the theme or topic of the work, or the specific organization or career you’re considering. The goal here is to build a repository of stories and impressions that you can draw upon, using them to help build the narrative of your career change. This not only gives you confidence and motivation, it helps you connect with other people in your network—as well as prospective employers—by highlighting you passions, talents, and abilities.

3. Narrow Your List to Five Options

Brainstorming career choices that meet your life goals can be a challenging and heady process. This step lets you take a break from deep thinking and simply asks, what are the top five ideas or themes that stand out to you right now? This helps you uncover hidden themes, isolate key ideas, and reveal opportunities for different careers.

Looking at your wall of post-its that note inspiring stories, choose the top five that stand out to you. These must move and inspire you; they must also fulfill your goals, and fit within your personal constraints. Then, cluster together similar ideas or themes that are shared between your top five ideas. This can help you understand what’s most important to you, and reveal new or unexpected career paths. Try doing this several times, staggered after a break or at different times of day. Doing this is a great way to watch your career search evolve and to remind yourself of your priorities.

4. Create Insight Statements

Insight statements are succinct sentences that rephrase the themes you explored in step two as a short statement. This is not a solution or dream job, but rather a core insight about the connections between yourself and a characteristic of a suitable career. It’s meant to be a building block, not an answer.

For example, possible insight statements around the theme “empowering people in need” might be:

  • “Working towards gender equality and social justice is a core passion and value of mine.”
  • “I like to learn about people’s needs, and I enjoy finding creative ways to solve them.”
  • “I need a job that allows me to feel a tangible sense of accomplishment, contribution, and service in order to be satisfied.”

Also, write down insights you have when a particular theme seems to fit into a larger system, or feels related to something else. When patterns emerge, write them down or draw them (for instance, using a journey map, a relational map, or a two-by-two line graph). For example, continuing with the above theme of empowering people in need: “Working in a consultative role allows me to blend my passion for excelling in independent research with my desire to contribute to a team that is larger than the sum of my individual efforts”; or, “working as an expert consultant helps me blend my passion for creative thinking to a tangible sense of accomplishment in the real world.”

Once you’ve done this for all your themes, look back at your original goal statement. Sift through your insight statements and discard the ones that don’t relate directly to your goal. Ideally, you want five to ten insight statements about your themes.

Get back in touch with your network and ask for follow-up interviews. Pitch those sentences (from the exercise above) about kind of work that really moves you, and see what kind of reactions your experts have about your ideas. Do they think that it’s relevant to their industry? Do they think their work expresses your underlying values and ways of thinking? What kinds of challenges would they anticipate about implementing your idea in practice?

5. Develop “How Might We” Questions

Next, you’ll want to translate your insight statements into “how might we” questions. By finding themes and creating insight statements, you’ve identified challenges and topics that both excite you and reflect real needs in the marketplace. Now, try reframing your insight statements into opportunities for a career. “How might we” is a useful framework for a question because it suggests that a solution is possible, and because it invites us to answer it in a variety of ways.

Start by looking at some of the insight statements you’ve created. Try rephrasing them as questions by adding “How might we” at the beginning. The goal is to find opportunities for careers, so if your insights suggest several How Might We questions then that’s great! For example: “How might we make a career that blends my passion for consulting with my passion for baking?” Or, “how might we make a career that blends my desire for personal independence with my talent for negotiating and mediating conflicts?” Or, “How might we find work that blends my interest in social justice with my need for creative expression?”

Now take a look at your How Might We questions and ask yourself if they allow for a variety of possible career paths. If they don’t, then broaden them.

6. Brainstorm (Again)

We used brainstorming in part one of this three-part blog series, but there we used brainstorming for thinking about career paths that interest you. In this brainstorm, you want to drum up a large range of ideas about work that fit you, outside of already-existing markets and career tracks. In this phase, emphasize being open to lots of ideas. Let yourself be creative and even idealistic, rather than realistic and pragmatic. Write your ideas down on post-its and affix them to the wall.

Keeping in mind a few principles will let you have a productive brainstorming session. First, defer judgment. You never know where a good idea is going to come from! Second, let loose your wildest ideas. Wild ideas can often give rise to creative leaps. Third, let yourself follow and build on ideas that immediately resonate with you. Fourth, consider sketching rather than writing your idea on a post-it—a picture says a thousand words! Fifth, go for quantity. Aim for as many new ideas about careers as possible. Crank the ideas out quickly and build on the best ones.

7. Bundle Work Ideas Together

Bundling work ideas together takes you from strong individual concepts to solutions with substance and promise which, most importantly, reflect your personal character, talents, and passions.

Think of it as a game of mix-and-match, with the goal of putting the best parts of several ideas together to create more complex concepts. Try different combinations. Keep the best parts of some, get rid of the ones that aren’t working, and consolidate your thinking into a few concepts you can build on. For example: “Being a freelance consultant pairing non-profit social justice advocacies with funding agencies, organizations, and donors.”

One way to start is to create mash-ups. For example, what would the Harvard of agricultural extension services look like? Mash up two existing brands, services, companies, or organizations to explore new ideas. This involves layering a real-world example of the quality you want into your career idea. The trick is to isolate the quality that you’re looking to add to your dream career. Is it efficiency, speed, on-demand access, or glamour? Write it down on a post-it and put it on the wall.

Take your post-it’s on the wall, and start by clustering similar ideas into groups. Think about the best elements of those thematic or topical clusters and combine them with other clusters, if necessary. Now, start building groupings out of the themes and patterns you’ve found. Focus on translating your themes into practice, rather than just identifying similar ideas.

Now refer back to your original career goal. Are you answering it? Are there elements missing in your career idea? What else can you incorporate to come up with a great idea? This is also a great time to reach out to your network and get their feedback on your concept. They may be able to tell you about organizations that are currently doing just what you envision. They can also tell you whether they find the idea promising, exciting, or whether they see challenges with your concept that you may not have envisioned.

8. Storyboard Your Concepts

Next, you need to determine what concepts you want to test for yourself, to decide if what sounds good actually satisfies you. One way to do this is by storyboarding. This can help you visualize your career idea in a narrative format that reflects a range of time-scales: either at a close, day-to-day scale or at a longer scale over months or years. Like all prototypes, the storyboard is meant to make something very approximate to help you think the idea through. For example: “As a consultant for nonprofits, I would start my day by clearing my email; then I would spend my morning cultivating new leads for my consulting business. In the afternoon, I might spend time preparing a presentation brief or a grant application for one of my clients. Or, I might attend a lecture at the United Nations to network and generate new leads.”

9. Gather and Incorporate Feedback

Finally, you’ll want to seek feedback from others, integrate this feedback, and iterate any new ideas that resolve unexpected challenges. It’s important to capture honest feedback. Seek out and talk to those experts whom you’ve met through networking and informational interviews. Then go back and consider how it applies to your career idea.


Now that we’ve delved deeper into how you can use ideation to generate new and unexpected ideas for career paths in entrepreneurship, the next blog post will look into how you can use structured implementation to road-test an idea before committing to it more fully as a viable option.