“What do you want to be when you grow up?” is a horrible question

I hate the question that we often ask kids: “what do you want to be when you grow up?” An equally obnoxious question is “what do you want to do for the rest of your life?” My objections to these questions are not based on a distaste for planning or career-focused introspection. I love to create, develop, and refine my vision for the future and I spend lots of time in my work as a teacher helping my students do the same.

Instead, the repulsion I feel when I hear these questions stems from the premise underlying this line of inquiry. Both questions suggest that there should be a single, compact answer towards planning for an unknown future. I find this ironic. I can tell you with about 50% confidence what I will be doing this upcoming weekend. Any planning I do beyond that is tentative. This is especially true for career planning, the quest for financial stability, and the pursuit of happiness.

These questions also imply that we should search for a job title to construct meaning for our future selves. It’s as if the process of constructing a career we love starts by finding a specific job title and then the rest follows from there.

In my experience, building a career that you love is often a process that happens in the exact opposite order suggested by those questions. Many people who I admire for finding happiness and balance in their work lives came to their dream jobs only after a long, nonlinear process of learning and growth. When I look at the role models I most respect for building a career that they love, I see people who create meaning in their work lives based on their own values and vision for their communities. These people are not defined by their work but instead bring their whole selves into their careers to create authentic ways of working and being while they put food on their table.

I want to reframe those two annoying questions into more useful thought patterns for anyone who is in the process of building a career that they love. Below are a series of questions designed to spur growth that may bring clarity about what the next steps in your job search might be:

• How do you like so spend your time?
• What challenges do you see in your communities? What problems do you see in the world around you that you feel strongly should be resolved?
• Fast forward to the end of your life. Imagine you are dead and your survivors are going to put a grave stone next to your remains. Now imagine that they are allowed no more than three words on that gravestone. These words represent the parts of your life you want to be remembered for and the parts of your identity that you cared most about. What will those words be? Why did you choose those words and not other ones?
• How can you create a job, career, or revenue stream for yourself where you get paid to work on problems you care deeply about and that fit into the three-word vision for how you spend your time? When thinking about this question, meditate on the quote: “how we spend our days is how we spend our lives.”
• What skills do you need to develop to be effective and make meaningful progress on the problems that ignite fire in your heart? What type of work would help you develop those skills? What type of job would pay you to build such valuable career skills and help you spend more and more time working on the problems that ignite your soul? What type of job would allow you to spend time on your three-word vision for your daily life?

I recognize that these questions are not easy to answer. I have spent over 18 years thinking about these types of questions and I continue to meditate like this every day that I work. The point of these questions is not to find concrete answers that stay static for time eternal. Instead, these types of questions are designed to get your creative juices flowing and to help you define the type of work you want to do.

Community Challenge

Creating a career that you love is a process that ends when we are six feet under the ground. I don’t believe that other people can create purpose or meaning for us that sustains long term growth, happiness, and a feeling of pride in the work we do. We are the only ones that can do that for ourselves. Because that process is nuanced, I love to encourage people in my communities who are in the process of building their vision for their work life to spend as much time as they can thinking about what it means to build work that they love. Below are a list of books that I have read (many more than once) on this subject:

• Designing Your Life: How to Build a Well-Lived, Joyful Life by Bill Burnett & Dave Evans
• So Good They Can’t Ignore You by Cal Newport
• Grit: The Power of Passion and Perseverance by Angela Duckworth
• Decisive: How to Make Better Choice in Life and Work by Chip Heath and Dan Heath
• Drive: The Surprising Truth about What Motivates Us by Daniel H. Pink
• The Power of Habit by Charles Duhigg
• Getting Things Done: The Art of Stress-Free Productivity by David Allen
• The Talent Code by Daniel Coyle

For this challenge, I ask you to find and read books on this topic for yourself. Those books might be from list above or books you find in your own research. Make a goal of reading at least two books each year on the subject of creating work that you love. At the end of each book, hold yourself accountable to making at least one substantive change to how you approach your work that will last for the rest of your life.

By the way, if you have any suggestions not on the list above, please do share in the comment section below. I’m always looking for great books to read on this subject.