Using Design Thinking to Craft Your Career: An Introduction
Design Your Career: Gather Inspiration

Design Your Career: Defining the Challenge

"Every design problem begins with a specific and intentional problem to address; this is called a design challenge."--Design Thinking for Educators Toolkit

Over the course of the next few weeks, I'm showing you how to apply design thinking and principles to your career planning and development. Here's the initial post.

 In today's post, we look at setting yourself up for success by defining the challenge.


All design starts with defining what you're working on.  What is the challenge or issue you are facing?

Taking the time to really define the career issues you want to address can be both energizing and a relief--you know exactly what you want to work on so you start to immediately feel less overwhelmed and more inspired.  This is especially true if you've been feeling stuck for awhile. 

The Well-Defined Challenge

In design thinking, a well-defined challenge is:

  • Approachable--It should draw you in and feel like something you want to work on. 
  • Understandable--You've stated it in terms that make sense to you. 
  • Actionable--You can see immediately your ability to take action to address it. 
  • "Clearly scoped"--this means it's big enough to engage you, but not so huge that you feel overwhelmed. It's also not too vague or too simple. 

Now let's take a look at the process you can use to define the challenge. It consists of a few steps:

  1. Dreams and Gripes
  2. Identifying Goals and Measures of Success
  3. Identifying Constraints
  4. Writing a Challenge Brief


1. The Dreams and Gripes Session

To begin defining your challenge, you can start with a "Dreams and Gripes" session where you:

  • Identify potential opportunities by looking at your dreams and gripes
  • Flip your dreams and grips into possible design challenges.

1. Dreams and Gripes

Often the seeds of your career challenge lie in your complaints:

  • "I'm so bored with this job I could scream."
  • "This job really doesn't play to my strengths. I'm spending all of my time doing stuff I hate and that doesn't really draw from where I do my best work."
  • "I lost my job 4 months ago and STILL haven't found the right opportunity. I'm really getting frustrated!"
  • "My supervisor is making me crazy!"

We can also see opportunities if we tune into where we wish something existed:

  • "I wish I was as a good a presenter as Jane. She always does such a fantastic job."
  • "I wish I could work for myself."
  • "I wish that we had X at our company--I would SO love to work on a project like that!"

To start the process, then, take a look at your Dreams (Things you wish where true about your career) and your Gripes (Things that could be better or improved). 

Sometimes it helps to start by just observing your wishes and complaints over a period of a week or so. When you find yourself thinking "I wish. . . " or complaining about something, write it down. You can use this log to identify your dreams and gripes. 

You can also discover Dreams and Gripes through a VisualsSpeak session. I've personally found that the images can be a fantastic way to get at some ideas or issues that you aren't able to identify verbally. 

2. How Might I. . . 

Once you have your list of Dreams and Grips, try flipping these statements into possible challenges, beginning with the question, "How might I. . ." So, drawing from the examples above, you might say:

  • How might I increase opportunities for more interesting tasks and activities at work?
  • How might I  redesign my job so that it plays to my strengths? 
  • How might I create or find better opportunities for myself now that I'm unemployed?
  • How might I develop my skills as a presenter?
  • How might I work for myself right now? 

Remember, these are the seeds of possibility. You may find in flipping these around that there is more than one way to state the issue or that you want to combine a few of these.  So, for example, you might come up with:

  • How might I use my strengths to start a side business so I can explore working for myself?


  • How might I use my desire to develop my skills as a presenter as a way to also connect with new job opportunities?

 You want to define your challenge simply and optimistically. Remember, you want to go TOWARD something inspirational, not try to escape from something you hate. 


2. Your Goals and Measures of Success

Now that you've begun to frame your issue, it's time to take a look at your goals and how you will measure success. 

Think about what you want to achieve as the result of your process. Where do you want to be when you're finished? 

Also consider how you will measure success. Often these measures will emerge as you go through the design process, particularly the Discovery and Intepretation phases. But for now, it's good to start outlining for yourself how you will know that you've achieved your outcomes. 

So, for example, if you are working with this statement:

  • How might I use my strengths to start a side business so I can explore working for myself?

Some goals you might identify include:

  • Feeling like I'm making good use of my strengths, especially in writing and planning.
  • By the end of the year, create some kind of project or event to use my strengths and make some side income.

And some measures of success you might include:

  • I've created one project or event that 5 people sign up for.
  • I have a better understanding of the issues that might be involved in working for myself, since I'm not sure I can do it.  

3. Identify Constraints

Particularly when it comes to work, most of us have some constraints on what we can do. It's crucial that we are honest with ourselves about how these constraints might fit into our process. 

Maybe there's a specific time frame for your project or you know that you only have a certain number of hours per week you can devote to it. 

You may also feel some constraints in terms of what you can consider--that whatever you do needs to take into account your geographic location, for example. Or that you need to find something that takes into consideration the fact that you have small children or an aging parent to care for.



4. Write a Brief

Once you've noodled around with the challenge for awhile, write a short brief (no more than a page) that describes the challenge you want to address. Write it as if you were handing it to someone else to design with. Capture your thoughts on WHY this is a challenge and what the opportunities for design will be. 

Some Closing Thoughts

There is tremendous clarity in taking the time to carefully define what it is you want to work on. This may change and evolve as you go through the Design process--in fact, it probably will. But it helps in the beginning to get a sense of what it is you really want to work on as you head into the next phases of the design. 

This can also be a good way to give yourself a sense of boundaries and a defined scope. Often I find that we can quickly become overwhelmed when we don't take the time to define our issues. They can all start to feel connected and we think we have to work on everything at once. Then that feels huge and we give up before we've begun. 

So start your Career Design process by clarifying the problem or issue you want to address in your design. This will make the task infinitely more manageable and energizing to work on. It will give you a clearer focus and as you move into the Discovery phase, which I'll cover in the next post. 


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