Ideation: How to come up with ideas for your career when you feel stuck

Charlota was in the fourth year of her Master’s in industrial design, yet she didn't feel prepared at all to enter the workforce. The school assignments felt too abstract - no actual client behind them, no access to customers, no business constraints. That's probably not what it will look like in reality when I leave the school. Am I building the right skills? she thought. Charlota was worried that she would waste several years in school only to realize later that the degree didn’t equip her to do what she wanted. A big question was hanging over her:

Should I drop out and find a job to practice my craft in real scenarios?

Yikes, this is a big question! To Charlota, dropping out of school felt like a scary leap to make. However, staying put with the very real concern that she’d graduate without enough experience to get a job felt equally scary. It was a binary question with seemingly only two options. You’d better make the right choice, Charlota found the voice in her head saying on repeat. The weight of the decision was becoming too much, and Charlota felt stuck. One night she went for a walk, and the fresh air triggered a small new thought: there must be other options…

So she sat down with a pen and asked:

How might I gain more real work experience in the design industry while still at school?

At first, it was hard to think of things she could do as a student, but soon enough the ideas started to flow.

She could...

  • Ask a design professional if she could shadow that person on a project
  • Apply for a summer design internship
  • Ask for mentoring from someone more experienced
  • Gather a group of design students and start a self-initiated project
  • Create an online portfolio and try to get her first freelance project
  • Do a series of interviews with designers to ask them about their work
  • Dedicate every second weekend to working at a local design studio
  • ...

Charlota was stuck looking for the one answer but through her first brainstorming session ideated multiple paths to try. In the end, she decided to pause her program for a year and did three different internships in different industries to gain more experience and information about what the jobs entailed, what she could offer employers, and what excited her.

Everyone feels stuck at some point in their career

It's natural.

Often in careers, we get stuck when we’re fixated on one single solution to solve our current problem (like waiting on a promotion at work to feel like we’re achieving).

Sometimes we feel stuck when we’ve listened a bit too closely to external voices telling us what they think the right job for us is (this is often parents, or the pressure we feel from seeing other people’s careers on social media).

Sometimes feeling stuck comes from a lack of inspiration and getting outside our small work bubble. 

And sometimes we feel stuck because we keep rushing to quick answers without taking time to deeply investigate the root causes of our unhappiness. For most of our lives, we’ve been encouraged to be problem solvers. We feel rewarded when we get to answers quickly. However our desire to solve something quickly creates a habit of coming up with obvious answers to surface level challenges. If you are going to take the time to ideate and brainstorm, make sure you’re tackling the right question. Check out our previous post for ways to reframe challenges into the right problem to solve.

So, how do designers get unstuck?

We ideate. Ideate is a designer word for coming up with lots of different ideas to solve a problem. We also call it brainstorming. In the last post, we learned how to reframe career blockers into career design challenges. By reframing, we can move from problems that seemingly only have one solution (“I’m stuck here until I get my promotion”) to opportunities that have multiple solutions (“how might I grow in my career?”).

The reason we do this is that in both design and in careers, there is always more than one right answer. In fact, designers never accept the first idea or answer that comes to them. We thrive on coming up with a large number of ideas because by forcing ourselves to let our minds wander and generate lots of ideas (including many wild and wacky ones), we choose better.

How do you generate lots of ideas for your career?

The first tool we use is actually the question itself. 

1. How Might I?

In order to focus our ideation efforts, we need to frame our chosen challenge as a question. In design, we start all of our questions with the words "How Might We …" This question is purposely constructed to help us switch to a different way of thinking.

“How” implies that there are many possible ways to solve the question.

“Might” creates a safe space in which we know that a potential idea might or might not work (both are okay at this point).

“We” reminds us that we solve the problem as a team.

In career design, we do things slightly differently. We keep the "How" and the "Might" but to take ownership of our own careers, we swap out “We” for “I”. We still recommend brainstorming with other people, but the solutions will be personal to the person asking the question. 

There's a right size of How Might I question to ask. Sometimes the question can be too narrow, meaning it implies one answer and stops you from coming up with a lot of solutions. For example, “how might I get a job in the Disney marketing team?” is too narrow, there’s only one job idea in that question. Sometimes a HMI can be too broad, meaning it is trying to fix everything, causing you to feel lost when confronted with the challenge. For example, “how might I work in a creative sector?” is such a big question it’s hard to think of a starting point or specific ideas. A better sized HMI could be “how might I enter the consumer marketing field?”. This question sets you up to start brainstorming different types of roles, companies, and projects that could be an entree into this space. You'll know you have the right level of a question when you immediately want to start generating ideas around it.

2. Brainstorming (and rules for brainstorming!)

There are no hard and fast rules in design thinking, except when it comes to brainstorming. Here we have several rules that exist to ensure we protect the creative and nurturing nature of the process. Here are the rules we use at IDEO:

  1. Defer Judgment - there is plenty of time later to evaluate the ideas, but now is NOT that time. In this phase, ALL ideas are good ideas. 
  2. Encourage Wild Ideas - it’s much easier to take a wild idea and make it more practical than to take a safe, small idea and make it more ambitious. The wackier the better when we’re ideating. Have fun with it!
  3. Build on the Ideas of Others - we often do brainstorms as a group, and we rely on each other to take one idea and turn it into a second and third idea by adding to it.
  4. Stay Focused on the Topic - brainstorms should be done in short, structured time blocks. If you wander off-topic, you risk moving into discussion and generating fewer ideas. Stay disciplined.
  5. One Conversation at a Time - Good ideas come when everyone feels listened to, respected, and valued. 
  6. Be Visual - the stickiest ideas are ones that are captured in a simple visual. This could be a drawing, a photo, or something copy/pasted from a website.
  7. Go for Quantity - The more ideas the better. Quality can be improved over time, and therefore the goal of brainstorming is quantity. We need a big number of ideas to start strong.

3. Mad Libs 

Have you ever play the game Mad Libs? It’s a game of sentences with missing words that you fill in to make silly stories. Turns out it’s also a fantastic ideation tool, and something we use all the time in design thinking to let our brains get expansive at the start of an ideation process. 

Once when Mollie was working on an urban mobility project, the team used Mad Libs to push the boundaries of their thinking. They created a Mad Lib sentence that read:

How might we help__________(sub segment of target customers) to _____________ (job to be done) in ___________ (environment)?

They also created a list of customer sub-segments, a list of potential jobs-to-be-done, and a list of environments. They then mashed up different combinations of the three lists using the above sentence, and brainstormed ideas for each. For example, one Mad Lib read “How might we help van owning tradespeople to save money on fuel in dense urban city centers?”

The team brainstormed answers to this question and then tried swapping out different words from their lists to see if it sparked more ideas. Changing the environment from dense urban city centers to sprawled suburbs led to new ideas, including ideas that could benefit city centers but hadn’t been thought of until we tweaked the question. 

There are lots of Mad Lib structures you can come up with for career ideation. One thing we like playing around with is the mode of work, which can include things like “in my current job”, “in a new job”, “as a side hustle” or “as a volunteer gig”. It looks like this:

How might I try __________ (area of interest) as/in a ______________ (mode of work)?

If one of your interest areas is brand management, your HMI’s could look like this:

How might I do/explore brand management in my current job?

How might I do/explore brand management in a new job?

How might I do/explore brand management as a side hustle?

How might I do/explore brand management in a volunteering gig?

By playing with the mode of work, we can come up with several different ways to pursue an area of interest. There’s never just one way!

There are several categories you can play around with when writing your career Mad Libs:

  • Your career criteria: These are the things you’ve identified from your Looking In work and your current career constraints (which could be things like, I need to stay in my current location, or I need a job that lets me pay off my student loan).
  • Timing: What new ideas do you come up with if you change the urgency of the question. Try using words like “today,” “this week,” “this month,” “this year” to generate more ideas.
  • Collaborators: Sometimes the most important part of work isn’t what we’re doing but with whom we’re doing it. Include a blank space in your sentence for “with whom” and swap between “with my current team,” “with my partner,” “with my family,” “with a different group at work,” or “by myself”

A few more examples:

How might I ________(career criteria) if I did it ________ (time option)?

How might I ________(career criteria) if I did it with ________ (collaborators)?

How might I explore _________ (interest area) if I need ___________(career criteria)?

Now that we have some great activities to help us generate ideas, it’s time to get ideating! Block some time on your calendar (weekends are great because you gain some distance from work), invite some friends, and generate lots of ideas. 

3 more tips for successful ideation

  • Write every idea down (or better yet, capture it with an image). It’s easy to forget ideas as we go, and seeing all of your ideas in one place will keep you organized, inspired, and moving forward.
  • Bring in collaborators. Ideation is best done with a group. Invite your friends or mentors to join you for a creative ideation session. Remember to share the seven rules of brainstorming with them before you start.
  • Get concrete. Ideas need to be specific enough that you can test them in the real world. We sometimes see ideas that read “something that lets me teach”. This is not an idea, it’s an interest area or a career criteria. An idea would be “creating and leading a course on public speaking within my company”. This is something specific that you could immediately go do.
  • If it’s hard to generate ideas for a HMI question then it’s probably too big, too narrow, or too vague. Try rewriting the question or revisiting your career criteria. This is an iterative process. It’s common to circle back and update your criteria (usually by making them more specific) once you’ve “tested” them in this step of the career design process.

We hope these techniques enable you to generate lots and lots of wild and wacky career ideas. We’ll need all of these ideas as we move into the prototyping and testing phases of career design. Stay tuned for those upcoming posts!

Back to Blog

Explore the Crew Membership