In April, I walked away from my job. In the exit interview, I stated my coworkers weren’t curious and explained that I wanted to work on new and interesting problems. It was emotional and challenging for me. I felt guilty about jumping ship and abandoning a vision I had helped create and sell. My coworkers had become my best friends and together we’d taken the business to new highs. I suspect it felt sudden to many, but my decision to exit was far from spontaneous.

This photo captures our spirit. Namibia Spring '14

This photo captures our spirit. Namibia Spring '14

Four months ago, I had lunch with my good friend, Corey, who was in town for his brother's graduation. We studied abroad together, but now rarely see each other. He is a wild man. He has tracked rhinos with drones, worked with chimps in Uganda, and now works as a park ranger at an abandoned airfield in New York City. We are very different people, yet one trait unites us -- curiosity.

We talked between slurps of ramen: “What have you been up to? Have you heard from so and so lately? Any plans to travel soon? How’s work?” He had recently returned from India and was navigating the doldrums of unemployment. I was in the middle of the longest period of work/life stability since college, having lived and worked in the same place for a year and a half. I’d quickly risen to become Director of Product at a local startup with a promising future. Yet I felt unsatisfied and was on the verge of quitting.

“Dude, do you realize how much of a pain in the ass job searching is?”, asked Corey. “Are you sure you want to leave your job? And, what are you going to do after?”

I tried my best to answer: “I have no idea, but I’m sure I can get into something interesting. I’ve asked a ton of questions and learned a lot, but I need something new to work on.”

My responses caught me off guard. The nonchalant attitude towards uncertainty and the confident way I spoke surprised me. For much of my life, I have been quiet and insecure, often intentionally invisible. Now, I felt assertive and assured. Where had this version of myself come from? How did I get here? With each question that bubbled up, an answer quickly followed. I wasn’t confident because I had answers or knew where I was going. I was confident because I realized curiosity and questions would guide me.


We paid the bill and took the long walk back to the office to allow more time to talk. My mind was working quickly. I thought about the catalytic quality of questions, their power to engage people, and the ability to unlock insights. In just a tiny portion of my life, the ability to produce one type of question, How Might We (HMW) questions, had altered the course of my career.

They had taught me to listen for negative situations and reframe them with positive questions. I could have complained or gotten upset when Swapnil, our lead developer in New Delhi, Whatsapped me with questions at 10 pm some nights, but I didn’t. I asked "How can I explain my ideas so thoroughly that he won’t have to ask questions? And can I make him smile or laugh in the process?” This resulted in a project management system centered around screen sharing and video. In under a year, I recorded 434 videos explaining designs, ideas, and tasks. Some videos had background music, some had cameos by other team members, and almost all opened with me addressing Swapnil with a new and absurd nickname (Swapnasty, Swapnizzle, and Swapdawg were my favorites).

"Hey Swapnizzle, you're smarter than me. Can you fix this?"

"Hey Swapnizzle, you're smarter than me. Can you fix this?"

If a simple questioning technique could impact my life significantly, then why hadn't I been taught this type of applied questioning before? And why wasn't it being prioritized in the workplace? My friend agreed. He confirmed his experience in college and his adult life was also void of formal inquiry training. We came to the same overly dramatic conclusion -- doesn't anyone give a shit about questions?! The thought was maddening.

That question dominated the coming months. Embarking on what I labeled a “study of questions,” I began to observe and research questions in my everyday life. I paid more attention to what questions I entered in Google, I watched interviews to see questioning in action, and I listened to the sales team take "discovery calls." I had little success searching for courses or articles on effective questioning. It seems the internet offers up advanced coursework, like “20 icebreaker questions for a first date” or “10 question to ask in an interview,” but skips over the basics -- the fundamentals of how questions work.


This growing interest interfered with work and consumed more of my time. I wanted to find an environment where people were asking questions and needed space to get there. I decided my best bet was a short career sabbatical; an opportunity to sit with my questions, or in this case, walk with them. I bought a ticket to Peru to trek for 10 days in the Cordillera Huayhuash and quit my job.

As if by fate, I read a design article that highlighted the benefits of questions for innovation just five days before departing for Peru. The article hit home, but it was the author’s bio at the bottom that caught my eye. I followed the link and landed on A More Beautiful Question: The Power of Inquiry to Spark Breakthrough Ideas by Warren Berger.

“In this groundbreaking book, journalist and innovation expert Warren Berger shows that one of the most powerful forces for igniting change in business and in our daily lives is a simple, underappreciated tool—one that has been available to us since childhood. Questioning—deeply, imaginatively, "beautifully"—can help us identify and solve problems, come up with game-changing ideas, and pursue fresh opportunities.”

I ordered it instantly with rush shipping to ensure it arrived on time. It was everything I’d been searching for and seemed like the perfect way to usher in the next chapter.

I left Denver at 10 pm and finished the book before I landed in Lima at 2 pm the next day. It felt like it was written for me and felt like I had written it. The similarity in thought was uncanny. However, I didn't have time to reflect. I was soon in a cab, darting through the notoriously busy Lima traffic. I tucked the book and it’s ideas away for another day.


It was mid-morning before the sun peeked out from behind the 20,000 ft Cordillera Huayhuash range. The first four days of trekking, while packed with novelty and awe, felt slow and unnatural. I struggled with the slower than normal (my normal) pace of the group, adjusted to life without distraction, and even felt guilty crawling into my sleeping bag before 9 pm. By the fifth day, everything had changed. My breathing was relaxed and steady, my legs felt strong, and my mind was clear. I found a rhythm and allowed myself to explore my thoughts.

Read more about my adventure  here

Read more about my adventure here

I thought back to my arrival in Lima, the day I left my job, and that February afternoon in the ramen shop. For the first time, I could view these events with distance and objectivity. I could step away and ask questions about my experiences without feeling tied up in them. I wrote them down in my trail journal during water breaks.

  • Why did I actually leave my job?

  • Could I have made it work?

  • When in my career have I felt the most alive?

  • What are the things I want from my life?

  • Could I create a business around my curiosity?

  • Could I specialize in questions and use my expertise to explore many ideas?

  • Would a business be willing to invest in questions rather than answers?

  • Would a business trust a 25-year-old?

  • Can you be confident without having answers?

  • Do I have what it takes to start my own business and lead others?

Questions have a remarkable ability to build momentum. As I focused on coming up with questions, small and powerful answers filled in the cracks.

I quit my job for the wrong reason. I made an incorrect judgment that the people I worked with weren’t curious. In reality, my coworkers weren’t expressing curiosity, and there is a difference. Curiosity manifests itself through questions. I have come to realize, questioning isn’t always instinctive or comfortable. Forming a question is expressive, and like other forms of expression, hindered by fear.

I worked hard to make people comfortable expressing ideas. I tried to create a culture of creative confidence with varying degrees of success. However, I failed to make the connection between confidence and its role in expressing curiosity. I didn't know how to get people asking questions. I didn’t know how to teach questioning.

When I returned to my newly minted bible of questions, I found Warren Berger had experienced the same thing:

“As I began to explore the subject within the business sector, I found few companies that actually encouraged questioning in any substantive way. There were no departments or training programs focused on questioning; no policies, guidelines, best practices. On the contrary, many companies--whether consciously or not--have established cultures that tend to discourage inquiry.”

His observation validated both my personal experience and a greater opportunity I was sensing.


To my left, a British expat is teaching Spanish lessons to a female backpacker. I’m seated at a cafe table in the dusty surf town of Huanchaco, Peru. My plan was to fly to Iquitos or Pucallpa and explore the Peruvian Amazon, following the trek, but I called an audible to act on my questions. The last week has been focused, introspective, and unusually routine for travel:  two egg sandwiches and a banana at the market, a full day of work at an open-air coffee shop, a break for sunset and dinner, more work, and then bed. I know where I want to go and I am putting the pieces together.

I don’t have the answers and I’m neck deep in uncertainty, but I have a newly coined philosophy to guide me -- a phrase that describes my feelings now as well as in the ramen shop months ago: confidently curious. To be confidently curious means chasing scary, uncertain situations with the knowledge that your current shortcomings or lack of expertise shouldn’t preclude you from trying now. It is recognizing you don't have the answers at the moment, but know you can find them.

We were born to question. It’s in our nature and it’s intuitive -- that’s the problem. Our questioning capacity plateaus because we don’t think about it. Take a second in your head to envision how you do a pushup, or better yet, get on the floor and do a pushup. Did it look like this? Most likely not.

This year I discovered I’ve been doing push-ups incorrectly my whole life. I’ve pumped out thousands of repetitions without thinking about form. Like pushups, questions have form, and awareness of form is a prerequisite for change. We rarely consider the nature of the questions we ask and the outcomes they produce. Is “what did you learn at school today?” the best question to ask a child every day? Or could a better question be formed? Just one example among many.

The questions we ask determine the vector of our lives. Whether in the workplace or the bedroom, a question can pull us from a place of ignorance and tension to a place of understanding and growth. In just a few months, I’ve grown immensely by learning to appreciate questions. I’ve been frustrated by the nature of curiosity but also inspired to share it.


* Thanks to my trusty editor and sister, Betsy, for helping me organize my thoughts.