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. 

Using Design Thinking to Craft Your Career: An Introduction


"Design thinking is about believing we can make a difference and having an intentional process in order to get to new, relevant solutions that create positive impact. 

Design thinking gives you faith in your creative abilities and a process for transforming challenges into opportunities for design. . .

. . . design thinking is the confidence that new, better things are possible and that you can make them happen." --Design Thinking for Educators Toolkit


In the past year or so, I've been exploring and writing about career resilience--the patterns of behavior we need to cultivate to deal with uncertainty in our lives, both at work and at home. It's been apparent to me that we need a new framework and mindset for how we approach our own career development, especially in an economy that is changing so quickly and not always for the better.

While working on my Youth Entrepreneurship project, I came across this fantastic Design Thinking for Educators Toolkit and something clicked. 

What our careers need is design thinking. 

Design thinking is a mindset--a systematic process and approach that we can apply to all of the places in our lives where we want to create positive change, including our careers. Once learned, you can use it repeatedly to continually address challenges and find new opportunities.

Over the course of the next few weeks, I want to walk through how we can apply design thinking to the overall career process, as well as in dealing with specific career issues. 

Today I'm going to start with an introduction to the process and some of the key principles. 

Key Design Principles

Let's start with some key design principles. These are drawn  from the Toolkit, adapted for thinking about your career.

Design thinking is Human-centered

Design thinking begins with deep empathy and understanding of people's needs and motivations. From a career perspective, this means gaining deep empathy and understanding of YOUR needs and motivations, as well as the needs and motivations of the key people in your life. This can include colleagues, of course, but also significant others, children, etc. 

You will feel the greatest satisfaction and fulfillment when you design a career that starts with your humanity--what works for YOU, as a whole human being who has not only economic needs, but also emotional and intellectual needs, important values, etc.

Design thinking is Collaborative

Success in today's economy depends on our ability to be collaborative. Multiple perspectives and the creativity of other people can open us up to opportunities we may never have considered. From a career perspective, this not only helps us build the Connecting pattern of career resilience, it also helps us develop more robust solutions to our career challenges. 

Design Thinking is Optimistic

At the heart of design thinking is a fundamenal belief that we can create change. No matter what constraints exist, there are solutions. They may not be easy (although many times they are easier than we think) and they may take some time, but we CAN create the change we need and want. 

Design Thinking is Experimental

I am a huge believer in the experimental approach to your life and career. The best way to find out if something is going to work for you is to try it out. The design process is all about devising experiments, testing things out, taking risks and letting yourself fail so you can learn from the process. 

Careers are not straight lines--they are iterative and evolving. Experimentation helps us learn by doing and gives us a way to incorporate our learning into our next steps. 

The Design Process

Now let's get into the Design process. As outlined in the Educator's Toolkit, it consists of 5 phases with associated action steps for each phase, as summarized in the image below:


Screen shot 2014-07-03 at 8.03.05 AM



Screen shot 2014-07-03 at 9.34.30 AM
1. Discovery

I have a challenge. How do I approach it?

From a career perspective, the Discover phase is when we begin to articulate our issue. It may be that we're in a period of transition--we've just graduated or we've been laid off. Or we recognize that we are dissatisfied or ready for new challenges. 

The Discovery phase is when we begin to define our issue, do some research and gather inspiration for what we want to create. 


Screen shot 2014-07-03 at 9.35.16 AM2. Interpretation

I learned something. How do I interpret it?


In this phase, we are looking at the information we've gathered in the Discovery phase and seeing what stories that information tells us--what is the meaning and what opportunities can we explore? 

We are beginning to see themes that may emerge in terms of what we want to create or things that are important to us. We start to get a sense of where we may need to create some career experiments to continue our exploration and learning. 


Screen shot 2014-07-03 at 9.35.50 AM3. Ideation

I see an opportunity. What do I create? 


Here, we are brainstorming possibilities. What is it that we want to explore further and how can we explore it? 

If we are seeing that career change may be in our future, we consider various ways to "try out" a new career. If we identify that we need new challenges, we may come up with potential strategies for bringing more challenge into our work. 


Screen shot 2014-07-03 at 9.36.24 AM4. Experimentation

I have an idea. How do I build it?


Now we're looking at ways to test out our ideas. What experiments can we set up to see what does and doesn't work for us? How can we build in a process for feedback and reflection to learn from these new experiments? 


Screen shot 2014-07-03 at 9.54.56 AM5. Evolution

I tried something new. How do I evolve it?

This is where we reflect on what we've learned in the experimentation phase and look for ways to evolve our ideas.

Often we end up back in the Discovery phase where we are learning new things about ourselves and about our opportunities and we look to incorporate this knowledge to tell new stories and come up with new experiments. 


Next Steps

The design process begins with defining the challenge--what is the specific problem or issue we want to work on? In my next post on this process, we're going to dig into how to define the challenge in ways that can help us keep focused and engaged. 

In the meantime, I want to leave you with some key thoughts on design thinking and your career:

  • You are a designer of your career. If you become more intentional about using design thinking, you will be better positioned to CREATE your career, rather than responding to external circumstances. 
  • To learn, you will need to step out of your comfort zone. You cannot create your career if you insist on remaining in your comfort zone. You need to step outside of your current routines and your current networks if you truly want to move forward. 
  • Start thinking "What if?" instead of "What's wrong?" Problems are really opportunities in disguise. But when we're focused on "what's wrong," we are not in the optimistic, positive space for real problem-solving. When you find yourself focused on the "problems," start reminding yourself to reframe so you search for possibilities. 
  • Embrace your beginner's mind--Be willing to make mistakes and to be OK with not having the "right" answer. Let yourself live in the mess a little, rather than always looking for certainty and "direction." 

Remember, design thinking is all about a mindset. It's something we can learn and cultivate and in doing so, we bring new possibilities and opportunities into our lives. 

The Real Reason You Aren't Making That Career Transition


I've been doing a lot of work lately with people who are changing their identity. They are moving from being dutiful employees who followed the rules and did what their employers wanted them to, into self-employment where they are the boss and there are no clear rules or a supervisor to please. This shift is proving more daunting than they--or I--had realized. 

I've been providing them with structure and help in setting goals, identifying the right tasks and next steps, providing them with resources to explore and what to me has seemed like a reasonably clear way forward. But each week we meet and less has been done than they had planned. 

What I'm coming to realize (again) is the extent to which identity plays a role in our shift from being an employee to being self-employed. It isn't just a matter of DOING things differently. We have to BE different--we are BECOMING someone different. 

This article from Raptitude reminds me that it's about the becoming--that when you are making big changes, you have to start seeing yourself as someone else. 

Two equally talented, equally motivated friends living in different cities decide on the same day to begin a running regimen. (Apologies for the running theme if it isn’t your thing — substitute anything you like.) A year later, Friend A has become an experienced runner, and Friend B has reverted to couch potato, and is about try to “get on the wagon” again. The difference was only that Friend B began his endeavor when his city was experiencing a brutal cold snap, and therefore much more willpower was required of him than was ever required of Friend A, in order to get to cruising altitude.

Meanwhile, both of them now believe B is just intrinsically lazy, and that A “has what it takes.” Both are unaware that circumstances ultimately made the difference in this case, because they had the same capacity for effort. Friend A goes on to run marathons. Friend B goes on to build a Blu-Ray collection. 

The real key to Friend A’s success is that, for whatever reason, he reached a place where he felt like a runner before any additional adversity derailed him. By the time he had his first day of bad weather, he already self-identified as somebody who runs, and so it felt natural for him to go out anyway even though it’s chilly.

We often regard the “baby steps” explanation as being the complete story, because we presume that success is more-or less just a matter of effort. But there’s something more important at play that we often miss, which is the change in self-image that always comes along with a successful change in habit or behavior. In every pursuit, it aids the established people and hinders the novice.

What I've been missing in the work I've been doing with people is this recognition that once you identify as an entrepreneur, you approach everything you do from that place. You SEE yourself differently, identify with different values and actions, so you approach your work in a different way.

I have worked for myself for over 15 years. I have already made this shift in identity and, in fact, could not go back to being an employee easily because I would have to re-envision who I am and what I'm about. But the people I'm working with aren't there yet. They still identify with being an employee in some deep ways. They need help in envisioning themselves differently so that the actions will come more naturally. 

This idea of how identity plays into career transition is something  I wrote about a few years ago after reading Herminia Ibarra's Working Identity, which looks at how career transition is largely about a change our self-vision. As the Raptitude article points out, part of what we have to do is start visualizing ourselves as a different person, as though we've already made the shift into that new identity: 

We tend to think of these identity changes as being involuntary consequences, or rewards, that come after the behavior change. You did the running, and because of the running and resulting fitness, your self-esteem and relationship to the world changed.

But it’s two-way relationship. This new identity, if you could somehow access it beforehand, would have made the running a hell of a lot easier. It would feel downhill rather than uphill. It would feel like an obvious and inviting thing to do, rather than a solemn self-sacrifice.

Personal development geeks have been exploiting this two-way effect for a long time. You can actually cultivate the new identity before or during your efforts, and this makes the behavior part a completely different experience. It energizes you rather than drains you.

With some basic creative visualization, you can consciously envision living life as the person who has already achieved those goals, and experience the reinforcing effect immediately. If you spend ten or twenty minutes envisioning what your present moment would be like if you already were in the habit of running at dawn every morning — including the consequences to your physique, sense of self-worth and confidence — you’ll find getting the shoes on and getting out the door dramatically easier.

Although I'm looking at all of this in the context of moving from being an employee into being self-employed, this issue of how you see yourself is at play in any career transition you make. You need the "juice" of visualizing yourself as that person you aspire to be to help you take the right actions, especially when those actions don't come naturally or they feel tedious or overwhelming. 

Maybe instead of focusing on just the "doing," you have to spend some time visualizing who you want to become first. As you do this, a beautiful virtuous cycle is created where you take different actions that feed your new sense of self and that new identity continues to suggest new actions you can take.

Spend time not just on the doing, but also on the becoming. As Amy Cuddy says, don't fake it till you make it. Fake it till you become it. 

The One Career Assessment You Need To Take RIGHT NOW!

End of competitive advantage

No matter where you're at in your career trajectory, stop what you're doing right now and ask yourself these 10 question. Can you answer a resounding "yes" to all of these statements? (h/t to The Muse for the link

  1. If my current employer let me go, it would be relatively easy to find a similar role in another organization for equivalent compensation.

  2. If I lost my job today, I am well prepared and know immediately what I would do next.

  3. I’ve worked in some meaningful capacity (employment, consulting, volunteering, partnering) with at least five different organizations within the last two years.

  4. I’ve learned a meaningful new skill that I didn’t have before in the last two years, whether it is work related or not.

  5. I’ve attended a course or training program within the last two years, either in person or virtually.

  6. I could name, off the top of my head, at least ten people who would be good leads for new opportunities.

  7. I actively engage with at least two professional or personal networks.

  8. I have enough resources (savings or other) that I could take the time to retrain, work for a smaller salary, or volunteer in order to get access to a new opportunity.

  9. I can make income from a variety of activities, not just my salary.

  10. I am able to relocate or travel to find new opportunities.

--The End of Competive Advantage, Rita Gunter McGrath

If you can, fantastic news. Keep asking the questions and keep doing the work. If you answered "no" to more than 2 or 3 of these, then you have some work to do. And if you answered "no" to most of them, you're in some serious trouble. You need to start addressing these issues NOW!

I've been doing a lot of work with people who are unemployed, many of them for years now and I can tell you that part of the reason they are in this boat is because they didn't invest in themselves and their own career management the way that they invested in their jobs and their companies.

Gone are the days when you could let the company take care of you and you could rely on stable jobs and predictable career paths. Situations are changing quickly and these questions can help you keep up. Today's careers are about being entrepreneurial and continually preparing yourself for and seeking the right opportunities. This is what career resilience is all about!

"How They Do It" Entrepreneur Interview with Dhairya Pujara, Founder/CEO of Y-Center

Yesterday I had the opportunity to do another in my ongoing series of interviews with everyday entrepreneurs called "How They Do It." This time I spoke with Dhairya Pujara, Founder/CEO of Y-Center, a a Philadelphia-based social enterprise that connects university students with a unique study abroad program where they get to participate in solving global challenges and creating social impact. 

Dhairya--or "D" as he's known around here, shared some great thoughts about how he's applied his entrepreneurial skills and thinking to a business that's having a real social impact. I think my favorite piece of advice from him is that the only way you can fail as an entrepreneur is by not trying. So true!

If you know any everyday entrepreneurs who would be willing to interview with me, please let me know. I think it's important that we really understand how to craft a career for ourselves by creating our own opportunities and the more we see how others do it, the more possible that becomes for ourselves. 


"How They Do It" Interview Series with Everyday Entrepreneurs--Melissa A. Rowe

Yesterday I posted about two projects I'm working on that promote entrepreneurship and developing multiple income streams as part of your career resilience strategy. 

To help people get a better picture of what it means to be an entrepreneur in today's economy and to help them understand all of the different ways you can be more entrepreneurial in your career, I'm doing a series of interviews with everyday entrepreneurs called How They Do It. My first interview was with Melissa A. Rowe, a Philadelphia writer, educator and innovator.

In our interview, we talk about Melissa's journey into entrepeneurship, which began after she was laid off from two jobs in two years--something that is happening to a lot of people. She shares how she's turning her skills and talents into multiple income streams and how she uses her connections and ongoing professional development to build her business. She has some great advice and tips on new ways to think about your career.

I'll be posting more of these as we do the interviews. I'm really excited about having the chance to learn more about how people do it. If you know someone you think I should talk to, let me know. I'd love to meet more everyday entrepreneurs! 

Two Projects to Support Entrepreneurship

Long-time readers know that I'm a HUGE proponent of developing multiple income streams as a strategy for career resilience. My ongoing work with people who have been laid off, often for YEARS, plus the research that I do for many of my projects has me more convinced than ever that the only path to success in the new economy is to be more entrepreneurial about our work lives. 

To that end, I'm working on a couple of projects right now that I wanted to share. 

Screen shot 2014-05-24 at 11.04.59 AM

The first is a project to promote youth entrepreneurship I'm calling Studio E. Through the website we're educating staff who work with young people in various programs, as well as young people themselves, about why it's so important to be more entrepreneurial about their careers and some of the skills and thought processes it takes to move in this direction. The video above is from an introductory webinar we did last week for Philadelphia youth development staff using Google Hangouts. 

One of the things we're doing is a series of weekly activities called Try it Tuesdays. These are things you can do with teens to help them start developing new ways of thinking that build their entrepreneurial muscles. 

Although this project is geared toward young people, it's something that all adults should be working on as well. And if you have kids, you should be checking this out and talking with them about how they plan to integrate multiple income streams into their career plans. 

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Another project I'm working on right now is called The Speedy Start-Up where we're facilitating 10 unemployed people through the process of starting up a small business. We're doing this in a group to maximize sharing and learning and to minimize the isolation you can feel when you first start exploring the self-employment route. 

The idea is that we will take them through 12 weeks of structured activities that help them formulate their business idea and then get the business up and running within that 3-month period. There's a huge emphasis on action and learning from implementation, as this is how most successful entrepreneurs get through the start-up phase. 

We're also emphasizing the need to launch with a "minimum viable product" rather than getting mired in perfectionism (a big problem for a lot of people), as well as strategies for minimizing your initial investment. I find that a lot of people get stuck thinking that they need to invest a lot of money in getting started, which is simply not true for many, many business ideas. 

Another thing we're working on is learning from your business--how do you follow what's working to create something that you didn't even know was a need in the market? 

The project itself is proving to be a lesson in all of the things we're teaching in the course. I'm finding myself going through the same steps as our participants, which is a pretty interesting process. 

Right now, I'm implementing this as a pilot for an organizational client. Eventually it might be something that we offer directly to folks who are interested, so I'll keep you posted on that. 

The deeper I'm diving into entrepreneurship and the thinking that start-up folks use, the more convinced I've become that this is key to career resilience. It's definitely impacting how I approach my own work as I recognize how I've been using certain strategies for years without realizing it. It's also impacting how I approach coaching others as I find myself explicitly discussing this multiple income stream thinking and entrepreneurial mindset with everyone I coach. 

A Career Link Round-Up

Some articles I've been bookmarking but just haven't found the time to reflect on: 

  • Is it Time to Repot Your Career?--I'm doing a lot of work lately with people who have been in the same career for more than 10 years and are getting caught up in the winds of change in a way they hadn't anticipated. This post is a reminder that at least every 10 years, you need to reinvent yourself. 
  • Purpose Workshops--I love this idea not only for young people, but for all of us. It could be a great way to revisit and repot your career. 

 Definitely worth your time this morning!

Think Outside Your Cubicle

Screen shot 2014-04-24 at 9.32.03 AM
Baratunde Thurston has a fantastic video
on how we need to think differently about our careers. We have to move beyond thinking about specific jobs or the skill sets we use at Company/Organization A and think of ourselves much more broadly than we do. A great quote:

I don’t think we’re ever going to reset to a new plateau or a new normal of any significant length.  By the time you get used to the way things work, the way things work will change because we’re on that Moore’s Law arc, because the tools that we use to connect to one another and drive everything advance far too quickly, and because we have too many minds plugged into the matrix who have a voice now, not just to consume, but to produce.

And so in a world of that much emotion and built-in volatility, clinging and calming down and saying, “This is what I do,” it just doesn’t seem like the most wise way to approach the world.  You kind of have to approach it with speed in mind and say, “Okay, well, if motion is the constant, how can I remain in motion?”

We have to find ways to keep moving, in flow with the change that's going on around us. This is where I think resilience is so critical. These are patterns and principles to build a career on--Clarifying, Connecting, Creating and Coping can guide your actions, helping you to continually adapt to the changes that are the new career normal. 

Go here to see the video, then let me know what you think. 

Clarifying the Job Landscape: Trends and Issues Impacting Your Career

For the next 12 months, I'll be working with career counselors and employment specialists who provide services through the public workforce system. You probably think of them as the people at the "unemployment office." 

We're starting out by taking a look at the work landscape and the various trends  that are impacting workers. These are issues I've talked about a lot here, but I wanted to bring them all together for this group. 

It occurred to me this morning that this info might be helpful to some of my readers here, so I'm sharing the video. I would also encourage you to take this information and really consider how it impacts YOUR career. What do you need to be thinking about and possibly doing differently?