Six Questions and the Fractal Edge of Interesting Work

Coastline fractals image

Make it a Great MondayI want to start a three-step nugget series today.

  • First, I want to talk about fractals and where truly interesting work tends to sit.
  • Second, I want to explore an idea I’ve grown to believe more deeply with age. If we are willing to listen, the world will often call us to do something much greater than anything we would plan for ourselves.
  • And third, I want to share something specific. A piece of work I feel called to pursue now. Something that will not let me go.

Today is about the first step.

Over the past few years, due to my daughters’ ages and my own, I have received more requests from young professionals seeking career advice. I genuinely enjoy these conversations. They are curious and thoughtful, often sitting right on the edge of something important.

Recently, I have been working with several bright young professionals in engineering, mathematics, and physics. Those conversations have brought me back to something I call my six questions for talking about life and career.

When someone reaches out to talk about their career, I start by sending them a short set of questions.

  1. What do you want to do with your life? Both professionally and personally.
  2. What are you good at? Your gifts.
  3. What do you most enjoy? Curiosities, interests, hobbies.
  4. Where is the intersection between what you are passionate about and what you are good at?
  5. What does your conscience tell you about how you can and should make the world better?
  6. What might be keeping you from living your most full life, and what are you doing about it?

I usually end the email with something like this:

These are just a few simple questions (-; I’m not expecting perfection or long essays. Just share your rough thoughts and send them back.

I always notice who turns these around quickly. It usually tells me something important. The questions tend to separate the pretenders from the non-pretenders. Not because the answers are right or wrong, but because the person has already been thinking.

After I get the responses, I spend a few days reflecting and jotting down some thoughts before we meet. By then, the conversation is already alive.

There is one more thing I often share with mentees at this point. An essay by Paul Graham titled “How to Do Great Work.” I use it with almost everyone, and it consistently sparks genuine, engaging conversations.

I consider this one of the finest essays ever written on work and careers. It is not a quick read and not meant to be skimmed. It deserves your full attention. Grab a big coffee or tea, find a quiet place, and set aside a couple of uninterrupted hours to read, think, and reread certain passages. (And pay attention to the footnotes.) It is the kind of essay that meets you differently depending on where you are in life, and it rewards those who take it seriously.

One of the insights that has stayed with me most is Graham’s explanation of how knowledge expands in a fractal pattern. From a distance, the edge appears smooth. But when you get closer, it is full of gaps. Uncharted, uncomfortable places that most people quickly move past.

People who do meaningful work tend to stay there. That edge can feel strange. Sometimes, even a bit lonely. But it’s often where curiosity turns into commitment, and where interesting work quietly starts.

Tomorrow, I want to linger at this edge a little longer. Because something interesting happens if you do not rush past it. If you resist the urge to immediately turn curiosity into a plan.

There comes a moment when work stops feeling like something you choose and begins to feel like something that quietly chooses you. That’s what I want to explore next.

If these questions resonate today, try them out. You do not need perfect clarity. Just honesty. And if you would like to see my annotated version of Graham’s essay, feel free to send me a note on LinkedIn.

Stay curious.

Make it a great Monday.

[Icons by youngest, Lucy Singletary Barfield @lucybarfieldcreative.]

NUGGETS began in the fall of 2010 when our oldest daughter left for college. (Make it a Great Monday; Stay Whole Tuesday; Woman Power Wednesday; Make Anything Thursday; and Fit as a Fiddle Friday.) All these years later, we have a UGA grad, a SCAD grad, a Fightin’ Texas Aggie grad, and 1500 nuggets. Plus, Mum and Dad up and moved to England. Those are my daughters above, and their guiding light – truly my every gPage Singletary thing.

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