Designing a career: an adventure with Mair Dundon

(c) Mair Dundon

Creating a work life that makes sense and pays well is a task that most of us spend a majority of our lives focused on… Instead of having a single path, we design a WorkLife that can change and grow right along with us – a constantly renewing resource that is fueled by our life experience and the insights we’ve taken the time to gather and share. I picture us as a community of practice – supporting each other in designing our WorkLife with focus and creativity.

Being particularly susceptible to such things (and in a moment of having forgotten my New Year’s resolution, Do Less), I signed up to do this “Career Hackathon” workshop with my friend Brenda. Which meant that I spent the entirety of a gorgeous afternoon yesterday in a windowless, brightly-lit room, a design firm’s office on Market between Powell and Montgomery Stations.

Five of us made a valiant effort to keep up with our facilitator Mair’s instructions, frantically filling out a series of worksheets, marking them up, talking to one another, and doing it all over again. I was the only one in the room without a UX/UI design background, and I enjoyed going with the flow and imagining that the words “agile” and “lean” (as in “lean business,” not “lean in”) and “iterate” and “builds (as a plural noun)” were part of my everyday parlance. I was expecting this; I had signed up for a Career Hackathon, after all!

Even if you DO know what those words mean, here’s my translation of the workshop title: How To Design Your Perfect Career by Forcing Yourself to Consider All the Possibilities That Normally Freak You Out and Learning That Most of Your Assumptions are Untrue Once You Actually Start Talking To People Around You… While Also Getting Called Out On Your Shit And Frequently Being Told You’re Awesome By Very Interesting People Who Are Also Awesome.

Rather than attempt to list the many revelations from those hours — I’m still trying to remember, digest, and recover from them! — I wanted to write about one of the many tools we worked with: The List.

Now I’ve long been a fan of lists. (I’m also a fan of long lists.) While I have gotten so out of the habit of writing I needed another New Year’s resolution (Write More) to get back into it, I never fell off the list-making wagon.

One of our exercises yesterday revealed yet again how lists can help overcome that particular type of procrastination that is borne out of the feeling of “holy shit, this project is so big and so complicated that I am never going to figure out how to start, much less complete it.” Once I take the time to think through and list out all the individual steps in a project, it’s much easier to tackle one at a time, and checking each item off as I go gives me that super-motivating sense of accomplishment… to the extent that I will often add something to the list after I’ve already done it just so I can check it off.

That said, my vote for the most satisfying thing I can do to an item in my To Do List is realize that I can cross it out entirely. What if I don’t have to DO anything to fix my career? Or any aspect of anything, myself included?

When I mentioned my experiments in doing nothing to my friend Rafter, he recognized immediately what I was getting at, and yelled something about the Tyranny of Self Improvement.

He continued:

It’s somehow part of this late-capitalist Cult of the Self, this belief that we need to perfect ourselves. That Constant Growth would even be desirable if it were actually possible to begin with… sounds just like capitalism!

He probably also wove in some ecological metaphor that I have since forgotten, and I’m sure I’m butchering his actual quote… but YES.

So. In the wake of this Career Hackathon and the bazillion goose-bump-inducing insights that it evoked, I have of course added many things to my To Do List. They include:

  • Update my LinkedIn account and Twitter bio to attract the type of work I want to do;
  • Fill out more of Mair’s worksheets (Business Model Canvas, Awesome Company Picture, Research & Info Interviews, Self Persona… you can check them all out here);
  • Hire Mair to be my career coach through this latest transition; and
  • Don’t bother doing any of the above.

Which will I check off the list, and which will I cross out completely? Can’t wait to find out.