This simple question changed everything for me

A decade ago, I sat down on the floor of my old apartment and took out a stack of index cards. The floors were crooked, and whoever installed the carpet in the living room did it wrong — there was this harsh ridge running diagonally across the floor. There I sat, on one side of the carpet ridge, and on each index card I wrote down a goal for my life.

After I had around 10 cards, I organized them into a pyramid where the single biggest goal was at the top. Since that time, I have turned this process into an exercise I call “Clarity Cards,” and I often take writers through it in order to help them get radically clear about their priorities.

The other day, I found my original Clarity Cards. They included a mix of goals around health, time with family, and infusing my life with creativity. But one card jumped out at me:

At the time, my wife and I did not yet have kids. I was working a job at a large publishing company, commuting about an hour and a half each way to work.

With these index cards I was reassessing the distance between my daily reality and the life I hoped to lead.

The “stay at home dad” thing was my way of saying that I wanted to be present in the lives of my family once we had kids. To not always be on a train, or in an office 30 miles away from my wife and kids.

The second part of that card is what jumped out at me today: “Earn money from home.” And then the frantically written word: “How?!”

Since that time, I left my corporate job in publishing, and have run my own company for eight years. I work in a private studio less than a mile from my home, and spend loads of time with my family each day.

The question of “how?!” feels like a less frantic question nowadays, but still an important one I ask myself often. It’s astounding to look at this index card and consider the moment I wrote it, and then look at my life today which has answered that question, and lived up to the intention of that goal.

I’m thankful for this every moment of every day.

In my work with writers, we sometimes focus on similar questions. They want to define their own version of what success looks like, and how they can achieve it.

In my conversations with writers each day, they often come to me hoping to:

  1. Create meaningful connection with readers
  2. Find more time to write
  3. Define their creative identity

These people are mapping out the distance between where they are and where they hope to be. Together, we navigate that path.

In doing so, a simple question of “How?!” is turned into a structured process. I have worked with hundreds of writers in this manner. The focus of much of this work in the past few years has been my Creative Shift Mastermind program. The feedback has been astounding:

“I am inspired by the amazing folks in this Mastermind. The adage that you become who you hang out with is true and I can become a better writer and creative person by spending time with this group. This Mastermind is far more than I imagined it could be.”
– Barbara Boyd

Kimberli Bindschatel“I thought I’d signed up for the Mastermind to get my career back on track. Seems like we’ve delved into getting my whole life onto a better track.”
– Kimberli Bindschatel

Dawn Downey“This Mastermind has given me a sense of direction with the business side of my writing that I’ve never had before.”
— Dawn Downey


Simon Maple“In the Mastermind I have gone through profound creative growth. I learned new things about myself, making experiential, intellectual and emotional connections that surprised me and enriched me. That’s the secret power that Dan’s Mastermind unleashes. He is a master weaver of collaboration. Magic occurs in the Mastermind.”
– Simon Maple

KJ Dell Antonia“Dan’s encouragement and insights helped me to change my approach to connecting with my readers and my community. He helped me stay true to my values and my self.”
— KJ Dell’Antonia
Rachel Barry“I started the Mastermind because I was stuck. I thought about writing all the time–but I didn’t actually write. Dan and the Mastermind of creatives helped me get out of this tremendous slump and into the most productive creative period I’ve ever experienced. I’m writing, I’m submitting, I’m confident. The Mastermind is a priceless experience.”
– Rachel Barry

When I see the faces above, I think of the months we spent working together in collaboration. There is a richness to that experience, especially when it is focused on such wonderful creative goals.

For your own creative process, consider how a simple question can lead you creating work that matters to you and those you hope to reach.