How to Jumpstart Your Stuck Career

Career quicksand
What happens when you feel like you're stuck in a career rut? How do you get moving in a different direction? I think we make things more complicated than they need to be. Here are three steps you can take. 

1. Admit that there's a problem.

The first step is to recognize and accept the reality of your situation. As I've written before, one of the most important things you can do when you want to make a change is to take a scrupulous, unflinching look at what's going on. Be clear about what is and isn't working and where you want to see change. The more honest and complete you can be in this inventory, the more energy you will gather to make change. (This is what some of the people in the Recovering from the Toxic Workplace course are discovering) 

One way to to do this is to simply write about your current experience. What is happening? How are you feeling about it? Who's involved? How long has this been going on? 

Another way to explore the situation is through visuals. The Career Clarity Image Sessions are a great way to get clearer about what's happening and they can help you see issues and connections you might miss through writing alone. 

2. Paint a vision of the future.

Robert Fritz, in his excellent book, The Path of Least Resistance, says that the energy for creation comes from the tension between our vision for what we want and the reality of our situation

In the first step, you looked at your current reality. Now it's time to paint a vision of what you want--what would your career look like if everything was in place?

This is where visualization can again be helpful. Michael Hyatt writes that he regularly uses visual techniques to jumpstart his creative projects. He says that creating a visual:

  • Makes it real.
  • Sparks passion.
  • Ignites creativity.
  • Forces clarity.
  • Defines a path.
  • Encourages positivity.

Your career is an act of creation and visualizing an outcome is a powerful way to create the necessary tension between your current reality and your imagined future. 


3. Build a Bridge

You have reality. You have your vision for the future. Now you just need to build a bridge from here to there. 

I encourage people to focus on taking small, daily actions that move you in the direction of your vision. Often it feels overwhelming to plan some major career overhaul, but by dedicating some time every day to building that bridge, you can start to create some real momentum. 

What kinds of things can you be doing? Here are some suggestions:

  • Keep a One-Sentence Journal--At the end of each day, write one sentence about your experiences. What did you learn? What questions are coming up for you? What was a small win for the day? This can help you track what does/doesn't work for you. 
  • Create a 6-month (or 3-month) plan of experiments--What are things you could try out? Maybe stretch projects? Learning new skills? Trying a side business or committing to reading some new books? Experiments are a way for us to learn more and to discover more about what we want to make happen. Plan these out in short increments with a focus on learning and you can start to evolve toward your new vision. 
  • Do some de-cluttering--Sometimes our problem is that we need to do some mental de-cluttering to make space for a new vision. If you're feeling bogged down by a sense of "there's too much going on!" work on doing some mental (and possibly physical) de-cluttering. You may also want to focus on creating more time for yourself
  • Schedule 50 Cups of Coffee--meet and talk with people who can help you clarify your thinking, learn more about a subject area, make new connections, etc. Relationships are the lifeblood of a career and the more we open up to diversifying our circles of connection and deepening those connections, the clearer things become for us. 
  • Ask more questions--When answers are in short supply, we may need to start asking ourselves more questions. Instead of pushing yourself to "figure things out," try focusing on getting more curious. 

Some Things to Keep in Mind

You didn't get stuck overnight. Career stagnation is something that develops insidiously, over time. So don't expect that you are going to get miraculously unstuck within a day or two. Have patience and let things evolve.

Also be aware that some of our sense of being stuck comes when our identities begin to shift and our jobs aren't keeping up. The things that used to engage us about our jobs may be changing. Or we are starting to care less about some things and more about others. Our sense of who we are and what we value changes over the course of our lives and often we get "stuck" when the personal changes and the professional realities are not in alignment. 

Finally, you will not begin to get unstuck until you are willing to try some things out that may feel risky or "out of your comfort zone." The only way to get free of career quicksand is to start pulling yourself out of  the muck and onto firm ground. At first this may feel strange. You are used to being in the quicksand. But soon, you will begin to appreciate being on firmer ground. But you have to be willing to step over to it first. 


Career quicksand

Are you stuck because you're mired in the quicksand of a toxic workplace? My new self-guided online course may be just what you need! 

Designing Your Career: Reality Checks and Evolving Into Experimentation



This is the next in an ongoing series of posts  I'm doing about how to use design thinking in your career. 

When we last left off in the Designing Your Career series, we had entered the Ideation phase where we talked about how to brainstorm potential ideas for experimentation.

In this post we're going to discuss how to do a "reality check" on your ideas and how to begin evolving your thoughts for the next phase, Experimentation. 

Reality Check

As you look at the promising ideas you've developed in your initial brainstorming, you'll want to do some "reality checks" on these ideas in order to further evolve your thinking. Remember, we're brainstorming and exploring ideas that will help you grow your career and design a work life for yourself that meets your criteria for success. 

For each promising idea you've identified, explore these questions:

  • What's at the heart of this idea? What values is it expressing for you? What real needs or issues is your idea addressing? Let's say that you're exploring the possibility of starting a "side gig." What's attractive to you about this idea? Is it a need for freedom and independence? Is it about being able to utilize and express different aspects of yourself? The more you understand what's underneath your idea, the more open to all possiblities you become. 
  • What are the constraints on your idea? What are the challenges and barriers you may face in implementing your idea? Who in your life might oppose what you're thinking? Remember, constraints or limitations don't have to be insurmountable. They merely give you a sense of where you may have to be more persistent or creative in your thinking.  
  • Brainstorm new solutions. First look at the underlying values you identified previously. Are there other ways that you could express or connect to these values? Then brainstorm ways that you might address the challenges you identified. It can be helpful if you go back to the core group of people you were working with in your initial brainstorming session. They can often offer different perspectives or ideas for how to address these issues. 

Work with each of the ideas you came up with in your initial session in this same way. Once you're finished, take a step back and see which ones feel most "do-able" at this time. Which of your ideas has the most juice and energy for you? Those are the ideas you'll want to experiment with, at least initially. 

Make sure to archive any ideas you don't want to work with at this time. It may be that at a later point, you decide you want to go back to them. I have entire notebooks of ideas that I've been playing around with for years. Sometimes it's a matter of the right time and people coming together for an idea to take on some new life. 



Summarize Your Idea(s)

At this point, your ideas will have gone through several iterations. It can be helpful to summarize and refine it as you prepare to go into the Experimentation phase. 

Take a look at your notes and field research and then try to capture your current understanding of your idea. 

  • Give it a title--try something playful or inspiring. 
  • Write a one-sentence summary--what's the heart of your idea? 
  • Describe how your idea would work--what would you be doing? What needs and opportunities do you see in your idea?
  • Who are other people involved in this and how can you get their support?
  • What value and benefits for yourself and others do you see in your idea? How will this address your career and life aspirations? 
  • What questions do you have? What is still open or uncertain for you? 

Again, it can be helpful to share this next write-up with your brainstorming team. They may provide you with additional ideas and information or point out holes in your thinking. 


In the next post in this series, we're going to look at how you play with your ideas in the Experimentation phase. This will be all about testing and trying out, pushing the edges of your comfort zone and being open to what you learn in the process. Stay tuned!



Design Your Career: Brainstorming/Ideation


Over the course of several weeks, I'm showing you how to apply design thinking and principles to your career planning and development. The series of posts so far is here

We've gone through the Discovery and Intereprepation phases, gathering information about your career challenge, looking for themes and framing possibilities. Now we enter into the Ideation phase, where you are generating ideas that you could experiment with in the next phase. 

Up to this point, your career design work may have been largely solitary. Although you may have talked to a select group of people to test out some of your assumptions or to gather information, I find that most of the time, people do discovery and interpretation on their own, especially if they are considering some big career moves. 

Ideation or brainstorming, however, is an activity that really benefits from having more minds working on the issue. Other people can bring in different perspectives and experiences and the give and take of a discussion can be very valuable. 

Here's how to tackle Ideation:

1. Invite a core group to help you brainstorm.

The first step is to gather a group to help you brainstorm. Ideally, this is 4-6 people whom you trust. These individuals don't have to be in the same industry or occupation--in fact, it can be beneficial to have some people from very different careers in your group. 

Let them know what you are doing and why you need their help and ask them to give you about 60-90 minutes of their time to help you brainstorm. This article on The Art of Asking has some great advice that you can use to plan for your invitation. 

2. Prepare for your brainstorming session.

Think about what you want to get out of your brainstorming session. Go back to your original challenge statement and to the opportunities you have been identifying and try to come up with some focused brainstorming questions to work with. For example, if you've been thinking about starting up a side business as a way to bring in income, you might have people help you brainstorm about your best options for a side business or refine a specific side gig idea. 

Next, prepare a space to work in. Pull together some flip chart paper and markers and some Post-It note pads. I've also found it can be helpful to have some Play Doh around--there's something about the kinesthetic connection to doing something with your hands that can help people think. And of course snacks--maybe even some wine or beer, depending on the time of day when you're planning your session. 



3. Brainstorm!

Once you get your group together, give them a brief overview of your design challenge, the highlights of what you've been discovering and then introduce your questions. Be careful that you don't get bogged down too much in giving your whole story--just focus on the relevant highlights that will give the group some context for your session together. 

Discuss the rules of brainstorming:

  • Defer judgement.
  • Encourage wild ideas.
  • Build on the ideas of others--think "and," rather than "but."
  • Stay focused on topic.
  • One conversation at a time so that all ideas are heard.
  • Go for quantity.
  • Try being visual--how can you sketch your ideas?

Depending on the personalities of your brainstorming partners, it can be helpful to start with a few minutes of quiet brainstorming where people write down some of their initial thoughts and ideas (good for introverts) before you get into brainstorming conversations. 

Keep your brainstorming session to no more than 45-60 minutes (minus the time you spend on the initial problem introduction and the brainstorming guidelines) so that you can maintain the energy.

Try to have fun with it. Move around, laugh, be willing to get a little crazy. Sometimes the best ideas come from what at first seems silly or completely "unrealistic."

As you brainstorm, be sure to document your ideas on the flip chart and/or Post It Notes. Don't be afraid to draw your ideas. Visualizing can be helpful. 

4. Select Promising Ideas

Once you've had a chance to toss around some of your ideas, end your brainstorming session by selecting promising ideas. In the end, of course, the path you choose will be your decision. But it can be helpful to work with your group to get a sense of which ideas have the most energy and opportunity. 

Have the group help you cluster your ideas--maybe there are several related ideas that you can pull together into a more coherent possibility. 

Then talk to your group about your sense of the ideas that are evolving--which ones seem to have some "juice" and feel exciting? Which ones don't feel like they'd work for you? Ask the group to really listen to you talk and to look for where they see you light up and feel passionate

Also ask them to push you a little on the ideas that you may dismiss--is it because they really aren't the best ideas or might it be because they would push on your growth edges and maybe seem a little too risky or terrifying? If it's the latter, then maybe they can help you explore some of these concerns. 

End your brainstorming session by summarizing everything you've discussed, being sure to capture all key ideas, questions and thoughts. 

In our next post, we'll talk about finishing up the Ideation phase with a reality check and evolving your idea for the Experimentation phase. 

Design Your Career: Frame Opportunities

Over the course of several weeks, I'm showing you how to apply design thinking and principles to your career planning and development. The series of posts so far is here

In the Interpretation phase of design, we've been looking at capturing your learning, identifying key themes and harvesting your insights. Now it's time to frame your opportunities--how do you take what you've been learning and use it to set yourself up for the next phase?

Create Visuals

One useful strategy for exploring opportunities is to create some visuals that express your key ideas. Here are some examples that could be helpful:

Screen shot 2014-07-29 at 6.27.52 AM

A Journey Map can help you look at your experiences over time. This is particularly useful if your initial design challenge is about how to make substantive changes in your career, possibly transitioning into something new. You might want to explore using the Career Stepping Stones method to map your journey. 



Screen shot 2014-07-29 at 6.32.47 AMVenn Diagrams help you explore several key themes and the relationships between them. 





Screen shot 2014-07-29 at 6.35.04 AMTwo-by-Twos are a way to illustrate tensions and create different categories. 






Vision boardAnother great career visualization strategy is to use vision board techniques to illustrate or flesh out some of your key insights. For example, in many cases this process can point us to key values we want to incorporate into our work. Through a vision board exercise, we can go deeper with these ideas and gain additional insights to use in the Ideation phase. 


Play around with using visuals to distill your insights and explore the relationships between them. This can open up new lines of thinking and fresh perspectives. 

Actionable insights

Make Your Insights Actionable

Your insights only become valuable when you can act on them as inspiring opportunities. It's important to take the time to phrase them so that they invite you into Ideation, brainstorming possible ways to experiment and make some new things happen. 

Explore your insights and turn them into "How might I. . ." or "What if. . . " questions. For example:

  • What if I volunteered to run a pilot program at work so I could test some of these ideas I'm having? 
  • How might I start using my skills as an artist to bring in new income?
  • What if I found a way to work 4 days a week so that I could use that extra day to learn some new skills?

For each insight you've gained, you want to generate several potential brainstorm questions, like the ones above. Try to make them simple and concise, expressed in plain language that feels inspiring to you. 

You may want to sit with your questions for a few days, returning to them later to see if they still resonate and to potentially revise, add or eliminate some questions. 

Ultimately you are going to select 3-5 of these questions to work with in the Ideation/Brainstorming phase. It's worth it to give yourself some room to find the right questions. 

A final note on the Interpretation phase. . .

The Interpretation phase can be both exhilerating and a little scary. If you have ignored your career for awhile, operating on auto pilot, this is often where you will find that you may be feeling the need to make some major changes. This can feel overwhelming and you may consider giving up.

Try to resist this temptation. 

Instead, use the design process to help you put some boundaries around what you will work on at this time. Go back to your initial design challenge and think about how you may want to reframe it. Set aside those insights that feel a little too difficult to address right now and look for those questions that feel more "do-able." You can always return later to those possibilities that you want to explore further after you have a few smaller successes under your belt. 

The beauty of using design thinking to plan for your career is that if you stick to the process, you will find that eventually it becomes second nature. You will naturally return to these strategies to address new problems and challenges as they arise. You will get into more of a flow, working with issues as they come up, rather than letting them fester until they can't be ignored. 

In my next post, we'll be moving into Ideation--brainstorming ideas for working with the questions you've been developing. 

Design Your Career: Harvest Insights


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. The series of posts so far is here

On Tuesday, we talked about looking for themes in the information you've been gathering as part of your design process. Today, we're going to look at strategies for harvesting insights from those themes. 

What do we mean by "Insights"?

In this context, "insights" are concise expressions of what you have learned during your discovery and inspiration process. They sum up key learnings. You may find those insights in a quote from someone you talked with or in a phrase or sentence from an article you've read. Here are some examples:

  • I need to do work that let's me express my core values of innovation and freedom.
  • I have a hard time with risk-taking, but if I want to start my own business, I need to become more comfortable with this. 
  • The main reason I'm unhappy in my job right now is because I don't trust the company or my colleagues. What could I do about that? 

Career design is a very personal experience that will go to the core of some key beliefs you have about yourself and your work. Be open to harvesting insights that may touch on areas where you feel more vulnerable or afraid, because often these are the places with the most juice for moving forward once you acknowledge them.

Also be open to insights that may force you to question assumptions that you've made about your career. You may discover, for example, that you've always felt that you "should" do certain things but those "shoulds" were hidden from your thinking. Let these assumptions come to the surface. They may point to new possibilities that previously didn't feel available to you. 

Now that you have an idea of what we mean by "insights," here's how to work with them:

Let life surprise you

1. Look for what surprise or intrigues you.

Review your themes and categories with an open mind. What surprises you? What feels inspiring and worth pursuing more? Where do you feel curious? What themes seem to spark the most ideas and possiblities? 

Pay attention to where you feel the juice, the energy. These spots contain the seeds of opportunity. 

2. Capture your insights in short sentences that get at the essence of what you're seeing. 

As you look for the insights in your themes, begin to construct some short simple sentences to describe what you're finding. If you can, word them in ways that feel inspiring and positive to you--that suggest new possibilities or opportunities, or even challenges for yourself. 

3. Reconnect to your project challenge.

Look back at your original challenge and consider how these insights are connected to it. Try to narrow down to 3-5 insights that seem most relevant and important to your initial challenge and the questions you were asking. If you have other insights that are less relevant but that you want to hold onto, create a section in your Idea Book to record those. You can always return to them later. 

4. Get an outside perspective.

If you're comfortable with this, it can be helpful to share your insights with a trusted friend, colleague or partner. See if these insights resonate with them. Maybe they have some thoughts that can add to your thinking. 


That's it for now. In our next post in the series, we'll finish up the Interpretation phase by looking at how you can use your insights to frame opportunities. 


Design Your Career: Looking for Themes


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. The series of posts so far is here

As you begin capturing your learning in the Interpretation phase, you should also begin looking for themes and patterns. This can take some time, but is well worth the effort. Here are ideas for getting started:


1. Review your Idea Book and all of your documentation to identify repeating words and patterns. 

 Look for common themes and ideas, particularly those that seem interesting or exciting to you. Write key phrases or concepts on Post It Notes or index cards so that you can cluster common ideas together more easily as you search for patterns. If you're a color-coding type of thinker, consider using different colored Post-Its for different themes.

Look for quotes that capture your ideas. If you have taken pictures or otherwise used visuals to document your research, be sure to write down the emotions or ideas these visuals evoke for you. There can be patterns in those as well.  

2. Cluster your ideas and give them a "headline. "

Organize your Post Its or index cards into clusters around the themes you are identifying. Then give them a "headline." Depending on your project, these may be things like "Skills to Learn" or "Ideas for Starting a Side Business." 



3. Look for links between themes. 

As you continue to work with your themes, start looking for links between themes. Can you group several related themes into a larger category? What contradictions or tensions do you see? What surprises you or excites you?

Over the years as I've looked at ways to reinvigorate my business, I've often found inspiration in looking at how to bring together disparate themes from different parts of my life--for example, can I bring visual art into my work? Or can I somehow incorporate my love of the journaling process into what I'm doing?

Look for serendipitous or potentially surprising themes you could link together as these could suggest potential things to experiment with later in the design process. 

4. Get input from the outside.

As you play around with your themes, try sharing your thinking with other people who might be able to give you some additional ideas or input. Talk to some trusted friends or colleagues or with your significant other. 

Often simply the process of sharing your thoughts out loud can begin to bring ideas into focus; you find yourself saying something that really "clicks." And of course, others can give you different insights or perspectives that suggest new ways of looking at your themes or different ways to organize and think about them. 

5. Be prepared to let go. 

One thing that can happen in the Discovery and Interpretation phases is that you can become overwhelmed with the information you've gathered. It can be helpful to return to your original design challenge  to remind yourself of some of the boundaries you may have set. It may be that you need to set some things aside for now to focus specifically on those things that are related to your challenge. 

You may also find that you are uncovering stories and ideas that aren't particularly helpful or that are less important to the work at hand. Be sure to set them aside, physically removing them from your design space, so that you can keep your focus on those themes and ideas that are most relevant to the work you want to do right now. 

In our next post, we'll continue with the Interpretation phase and take a look at how to develop insight into your findings. For now, see what you can do to identify and link some themes together as a way of clarifying some things for yourself. 


Design Your Career: Set Deadlines

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. The series of posts so far is here


For the past few weeks, we've been talking about how to use design thinking to create the career you want. One thing that's critical to your success in this endeavor is setting some deadlines for yourself. It's SO easy to be pulled off course by "life", as well as by the creative process itself. We can wander forever in the Discovery phase if we aren't careful. 

Although there's a certain need to give yourself some space to explore, at the same time, this boundlessness can work against you. Procrastination is a problem in any creative project, but I've found it's particularly true for our career projects. The work we have right now, combined with everything else going on in our lives can seem far more pressing than working toward an uncertain future. 

As you go through the entire Design process, it's important to set deadlines for yourself. Be clear about how much time you're going to give yourself in each phase and STICK to those deadlines. The If/Then planning process can help you keep moving. Keeping track of your small wins along the way can also be helpful in motivating you to move forward. 

Don't let procrastination keep you from crafting a sustainable career. Use deadlines to give your career project some helpful boundaries and constraints. Remember--without the "doing" your dreams will go nowhere. Deadlines can help you take action. 

Design Your Career: Capturing Your Learning


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. The series of posts so far is here. 


You've defined your career project challenge and you've been gathering research and inspiration. Now we enter the Interpretation phase of the design process, where you begin to make sense of what you've been discovering. 

This can be a confusing part of the process. You have a lot of information. Your perspective on your project is evolving and changing. In some ways your design challenge may seem clearer. In other ways it can get more muddied. This is normal. Careers are messy, especially these days, and you are in the phase where you are letting yourself be open to possibilities, so there's a lot floating around. 

We talked in my previous post about the importance of having an Inspiration Journal--your "design sketchbook" for your project. As you seek sources of inspiration, talking to other people and gathering information, you should be documenting your findings in your Inspiration Journal. Capturing what you're learning is an important part of the process, as you will be using this later to look for recurring stories and themes that can give you clues about how you want to experiment with possibilities in the Ideation/Experimentation phase of the process. 

Here are some strategies for capturing learning and keeping this phase manageable:

1. Plan For It

Set aside time each day or each week to capture what you've been learning. (This would be a great way to spend the first hour of your day!) One planning strategy that can be helpful to ensure that you do this is "If/Then Planning."  This is a simple strategy for achieving any goal.

  • If it's Thursday at 4 p.m., then I'm capturing my career project learning." OR
  • "If it's 9 a.m., then I'm taking 30 minutes to capture my career project learning."

Believe me, if you don't make specific plans for working on this, then your project is likely to get pushed to the back burner. 

2. Capture Your Thoughts, Reactions and Impressions

 In addition to documenting the content of your research--for example, recording the results of an interview with someone in your dream career--you also want to take the time to capture some of your reactions and impressions. 

  • What emotions does your research evoke? Excitement? Anxiety? Boredom? 
  • What are some of the most surprising or memorable things you're discovering? If you interviewed someone, what surprised you about about what they shared? If you're gathering articles on your topic, what aspects of these articles are standing out for you? Why do you think this is the case?
  • What questions are bubbling up for you as you gather your research and inspiration? Be sure to document these as they can be clues to potential experiments you can run later. 

3. Capture key stories.

If you're talking to other people as part of your inspiration/research process--and you really should be--it's important to keep an eye out for the stories they are telling. Document these in your Inspiration Journal, along with why these stories captured your attention. Again, these can offer valuable clues for your project. 


The idea in this part of the Interpretation phase is to ensure that you are creating space to start making some sense of your research and inspirations. In a future post, we're going to look at how we search for themes and insights in our learning. To do this, though, we need to make sure that we are actually capturing that learning along the way. 


Design Your Career: Gather Inspiration

Inspiration is the fuel for your ideas. Plan activties to learn from multiple perspectives and to explore unfamiliar contexts. --Design Thinking 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. The series of posts so far is here. 

Today we enter the Discovery phase and talk about gathering inspiration to work on the career challenge you've defined

Defining the career challenge you want to work on is an important first step in clarifying the issues and creating some focus for yourself. Once you've accomplished this, it's time to move into the Discovery phase of your project. 

The Discovery Phase

Discovery is all about being open to possibilities and to the context of your challenge. This is where you want to immerse yourself in people, ideas, and resources that can fuel your thinking as it relates to your project

From a career perspective, there are many potential projects you may be working on. You may be:

  • Considering a new career.
  • Looking for a new job.
  • Considering starting up a business.
  • Exploring how to use your talents and strengths in more creative or effective ways.
  • Looking for ways to develop particular skills or to gain experiences in different facets of your career. 
  • Seeking a mentor or wanting to create a Mastermind Group for yourself. 

To begin exploring any of these areas, you want to start gathering materials and information that can serve as a source of inspiration and potential experimentation later on. 

Here are some strategies for Discovery. I highly encourage you to try all of them because each brings its own insights and ideas. 

Inspiration journal

Create an Inspiration Journal

As you begin the Discovery process, it will be helpful if you have a place to begin documenting and gathering your inspirations. What I've found to be most powerful is to create an Inspiration Journal--a notebook I keep for the specific purpose of gathering notes, ideas, articles, etc. related to the topic I'm exploring. 

This is your "designer's sketchbook," a place where you can begin to dream and explore. 

For me, what has worked is to get a sturdy artist's sketchbook, because I like to both write and paste materials into my book. Other people have found success with 3-ring binders or even simple Composition books. 

Be sure to put a copy of your Design Challenge at the front of your book. This sets the stage for your ongoing explorations. 

You can also go digital, using Pinterest or Evernote to begin gathering your inspirations. What's important is that you have a place to document your Discovery  process that works for you. 


Do Some Research

A key part of the Discovery phase is doing some research  related to your career challenge.

  • Look for websites, articles, blog posts, etc. that relate to your topic and start to read and take notes. 
  • Watch videos
  • Listen to podcasts or audiobooks.
  • Look through magazines, professional journals, etc. for relevant articles or information. 
  • Find books related to your challenge. 

As you immerse yourself in this material, pay particular attention to where you feel excited or curious about something, no matter how "impractical" or "ridiculous" it may feel to you. I tell people to "follow the energy"--if the information is drawing you in, that make sure you document that. It may not feel immediately relevant or actionable, but you'll be surprised at how later on, you may return to information that keeps showing up and finding new ways to incorporate this into your process. 

Be sure to use your Inspiration Journal as you research. Use it to take notes, write down key ideas, paste articles, etc. 


Connect with Interesting People 

Other people are one of your best sources for inspiration and discovery. They can have insight, connections, ideas, etc. that help you expand your sense of possibilities or challenge your thinking. While reading, watching videos or listening to podcasts can certainly get you started on your challenge, you will find that your Discovery process explodes when you start getting out and talking to people. 

Who you meet with depends, of course, on the nature of your challenge. If you are thinking about starting a small business, then you want to talk with other people who have done this and potential customers who may be interested in your idea. If you are thinking of making a career change, you will want to talk with people who are in your target career area or industry and other people who have made career changes. If you are looking to improve a particular skill, then talk to people you admire in that skill area. 

Also look for ways to expand your network to new people, beyond those to whom you are currently connected. This will be particularly important if you are exploring something out of your comfort zone, like a new career or the possiblity of starting your own business. One of Herminia Ibarra's key findings in her book, Working Identity, is that new connections will add "juice" to this Discovery process, not only providing you with new insight, but also potential connections you can develop to access new opportunities later on. Here are a couple of resources that might be helpful here:

Again, document what you're learning in your Inspiration Journal. Take notes, write down key quotes, take pictures--whatever you need to capture the information that will feed your creative thinking. 


Build a Question Bank and Question Guides

One thing that may help you both in your overall Discovery process, as well as in your conversations with new connections is to develop a Question Bank. This is something you can create in your Inspiration Journal. 

To build your Question Bank:

  • Identify key topics you want to explore--What do you want to learn more about related to your challenge? What do you want to understand about your own or others' motivations, experiences, etc.? What do you want to learn about their activities? 
  • Formulate questions to explore these topics--Frame these as open-ended questions that will help you get at deeper, more powerful information. (I highly recommend exploring The Art of  Powerful Questions as part of this process). Good questions for yourself include "What do I most enjoy doing--what are my strengths" or "Why is this challenge/project really important to me? " Good questions for other people include "Tell me more about your experience with . . . ?" or "What are the best/worst parts about. . . ?" or "Can you help me understand more about. . . ?" 
  • Pay attention to questions that are percolating in your mind and keep adding to your list--As you go through the Discovery process, new questions will begin to emerge. Document these in your Inspiration Journal and use them as fodder for discussions and further research. 

Question Guides for Meeting with Connections

Use the Question Bank in your Inspiration Journal to construct Question Guides that can help you in your conversations with connections. It's helpful if you create a Question Guide for each meeting, as this will help you be able to structure your conversation and make sure that you cover the areas that interest you. To do this:

  • Review your Question Bank and identify questions that seem most relevant to the person you're meeting with. 
  • Organize your questions--Start specific, with questions your connections will be comfortable answering. "Tell me about how you go started doing this" or "Tell me about your experiences with. . . " are good examples.  Then you can move into deeper or broader questions like "What are some of your fears about this work?" or "What do you do in this situation. . .?" 
  • Create a 1-2 page Question guide for yourself--If you're meeting with someone new, it's a good idea to include in your guide any background info on the person that you have that might help you in the conversation. None of this has to be fancy or formal, but you do want to be somewhat organized about the process. 

Your Question Guides can be included in your Inspiration Journal, along with your notes from the conversations.

Get Visual

One particularly powerful way to explore is by really engaging with visual inspiration. Look for magazine photos or other images that suggest ideas about your topic. Take pictures of people, places, objects, etc. that relate to your challenge. Maybe you see an office-set up that appeals or phrases in a magazine that suggest something you want to experience. Collect all of this and include it in your Inspiration Journal. 

You can also expand your Inspiration Journal into an Inspiration Board--something to hang on your wall and continue to add to as you go through the Discovery process. This can serve as a regular reminder to you of what you're project is about. 


Give Yourself Permission to Wander--and to Wonder

The Discovery Phase is about immersing yourself in your challenge, allowing yourself to explore, wander and consider various possiblities and experiences. Tune into your emotions and to a slower pace, where you allow yourself to think about what could be and to OK with uncertainty for a few weeks or months. 

We live in a society that encourages us to be "productive," and for some people, Discovery can feel very open-ended and impractical. But giving yourself a little space and time to just do some wandering can be invaluable later on. It may open up new areas you never considered, or put your initial challenge in a new light. Don't rush yourself too much in this phase. Allow for curiosity and exploration. 


Discovery is all about being open to new questions, new ideas, new concepts and new people. Use this phase to immerse yourself in your topic and to learn as much as you can before moving on to the next phase, Interpretation. 

Design Your Career: Defining the Challenge

Colored pencils

"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


Dream walk
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.