The Question That Changed My Life
May 7, 2019

Two years ago, on a cold January night, I pulled into a Panera parking lot off of Route 123 in Brockton, Massachusetts. It was only 5:00 PM but the winter darkness had already filled the air. I turned off the engine and checked the seat next to me to make sure I had my computer, journal and a pen. I grabbed everything, buttoned up my jacket and marched through the snowy lot into the Panera.

Inside, I quickly remembered why I hadn’t been to a Panera in many years. The lights were too bright, the furniture outdated, and crowd uninspiring. It was far from the cozy coffee shop vibe I had become accustomed to in Cambridge and Boston. But since I was staying at my parent’s house that weekend in the Boston burbs, my choices were limited.

I ordered a black coffee and grabbed a table over near the window. I opened the Notes App on my iPhone and checked my To-Do list. There was a mix of items for work, my blog and the tour guide business I was trying to launch. I glanced at it twice over, feeling overwhelmed. I sat back in my chair, let out a deep sigh, and glanced out the window to the dim parking lot.


I began to ruminate over my current situation. For the past year, I had been trying to escape my financial sales job for one at a tech startup but was having no luck. I had been rejected by tech companies such as Pandora, BuzzFeed, Meta and many more. No one wanted to give me a chance. On top of this, despite all the efforts around promoting my blog, it had yet to provide me any side income. I felt trapped in a career that no longer made sense to me and it weighed heavily on my mind every day I walked into the office.

Taking a sip of coffee, I turned my attention back to the items on the table in front of me. Did I want to fire up my computer and start marketing my blog again? Or maybe I’ll send out a few more networking emails to try to get another interview. Neither action inspired me. I turned my attention to my journal and flipped to the last page I had written on.

It was there that I saw a question that I had jotted down from a recent Tim Ferriss Show podcast. It was an episode in which he interviewed Debbie Millman, famous designer, author, and podcaster. The episode came back to me in a flash. Debbie had challenged the listeners to write down the answer to one powerful question. She promised that the answer to the question would change our lives. I eyed my journal carefully, and read the question back in my mind:

Debbie’s Question: What if you could do anything you wanted without fear of failure? What would a day in that life look like 10 years from now?


I blinked at the blank lines that filled the page and gulped. I felt skeptical and intimidated all at the same time. But as I took another sip of coffee and looked around me at my sad Panera surroundings, I wondered what I had to lose. Surely, there was no downside to this type of exercise. I closed my laptop, took out my pen and began to write. 

As I dove into the writing, I was able to temporarily escape the Panera, my job, and all the interviews that had gone awry. For the next 20 minutes, I lived in my ideal world 10 years out into the future. My pen didn’t stop until I filled 10 pages of my journal and I had described my perfect day in detail from morning until night. At the end, I signed and dated it 1/22/2017.

When I put my pen down, I felt a rush of warm energy fill me that I hadn’t felt before. I read back my 10-year vision and felt my face glow with hope. This is the life that I want. I remember thinking. This is a life worth fighting for.

I checked my cell phone and saw my Mom had texted me. She was wondering if I’d be home for dinner soon. I laughed as I slowly came out of my trance, and found my self once again in the Panera. I closed up my journal and headed home. I wasn’t sure if that the exercise was going to help me, but I did know that it gave me a small ray of hope on a cold winter afternoon.


A little over two years have gone by since I wrote down my answer to Debbie’s question. And while it’s too early to tell if my 10-year vision will become a reality, I can tell you that amazing things have happened in the two years that have passed. I will share two of them with you today.

First, my 10-year vision includes living in a Brooklyn brownstone. At the time that I wrote this down, I was living in Boston and had no clear way to get to Brooklyn. Less than a week after I wrote my 10-year vision, I got an email from a colleague at a tech company saying she had a spot to hire me. A few months later I was hired. This job became my vehicle to get me down to New York and I’ve now been living in and loving Brooklyn for 18 months.

Secondly, my 10-year vision includes having my own business as a coach and blogger. When I wrote that down in Panera, I had yet to coach a single person and had made no money from my blog. Seven months ago, I was laid off from my tech company and given a window to start my coaching business. For the past six months, I have been coaching full-time with plans to expand the blogging business later on.


So, with 8 years to go toward my 10 year vision I feel like I’m right on pace. The ideas I wrote down on those journal pages on that cold January night in Panera, don’t seem so farfetched anymore. In fact, it all seems within reach. I’m not sure about the science behind this stuff, but I am proof that it can work for you too.

Since writing down this vision, I have been able to use it as my compass when I make decisions in my career and life. Anytime I come to a crossroads, I think to myself, will this get me closer to my 10-year vision? If the answer is “Yes” then I pursue it.

If you’re feeling stuck and hopeless, like I was in that Panera back in 2017, then this is the way to start to dig yourself out. Your 10-year vision will give you a destination that you can then start working towards. After all, without an end destination how will you ever know you’re going the right way?

You too can find your way. Start now.





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