Year of Discovery (Weeks 50–54): Wrapping up my YoD

Audrey Cheng
9 min readApr 25, 2022

What a whirlwind the last few weeks have been — from closing out my time in Chicago to finishing up my Legatum fellowship with innovation ecosystem tours in Miami and Boston to reorienting back in Kampala. I’ve felt so grateful for exchanging ideas with brilliant people, forging meaningful relationships, and discovering new pathways. I find myself hopeful and clear about what the future has in store.

Beautiful walkway in Uganda

The year has taken me around the world, from South Africa to France to Italy to the US to the UK to Belgium to Egypt to Kenya to Uganda, and more. I’ve refilled my bucket with much-needed quality time with close friends, built new friendships, and allowed my mind and soul to be driven by my curiosity. I had the time to deep dive into the big questions I had about the world. I reveled in my assumptions being tested, challenged, and ultimately strengthened. My mind was opened and I was continuously humbled by the unique perspectives, wisdom, and brilliance of the people I spoke with. I was grateful for the time to do Vipassana, deep-dive on climate change and reflect on comparative suffering.

Today, I’m attempting at documenting a few lessons I learned this last year. The list isn’t exhaustive but points to some of the wonderful gems I hope to carry forward with me.

What I’ve learned this last year:

  1. It takes time to allow the dust to settle

I originally believed it would take me 2–3 weeks at most to be able to feel settled in my thoughts and feelings before I was off to the races again to continue my exploration through conversations and prototypes. But the reality is that it was a continuous process over 6–9 months to sustainably bring myself to the present and find peace with the past. I had accumulated many years of unbandaged wounds that I needed to heal and tough lessons that I needed to let sink in so I could intentionally change my habits and rebuild myself. It also took time for me to acknowledge all the positives of my journey to date and to engage with my past experiences with immense gratitude.

When the dust settled over time, I was able to see myself, others, and the world more clearly than I had seen in years. The passing time was like a fading canvas filled with beautiful colors. As time went on, the canvas became less vibrant, which allowed me to highlight the parts of the piece I wanted to take forward and paint over the remainder with white, creating a bright canvas for the future.

2. Tune into yourself to know how to organize your own YoD

A number of people reached out to me to ask how I was organizing my YoD and over time, I realized that what I was sharing worked for me, but wouldn’t necessarily work for other people. So what I would recommend to people interested in designing their own YoD is to tune into themselves first:

  • Why do you want this time? Is it to discover? Is it to recharge? Is it to learn how to disentangle your identity from work?
  • What parts of life and learning bring you joy?
  • When do you feel most energized and how do you bring this understanding into how you spend your days?
  • What mindsets or beliefs do you need to actively let go of and what do you need to bring into your time away from full-time work?
  • What support do you need or who do you have to remind you why you are taking this time, especially when you start to doubt yourself?

Spending time on those questions can help those of us looking to take time away. It helped ground me when I looked around on certain days and asked myself what I was doing. It brought me clarity that I was on the right track.

3. The answers are in the questions

I’ve always been someone who is more comfortable asking questions than responding to an opinion with another one. I find more flow in trying to understand someone’s perspective than needing to immediately counter another’s perspective with my own.

I found strength in questions this past year. The most simple and open-ended questions would often lead to the most profound answers and lightbulb moments for myself and the person I was speaking with. I’ve learned that asking questions is truly an art that’s important to fine-tune through coaching courses and daily practice.

I also realized that powerful questions are grounded in the humility to realize that the other person has all the answers they’re looking for. When hearing about another’s challenge, people are often quick to judge and ‘fix’ instead of spending time listening for what’s truly on the other person’s mind and behind the challenge they’re facing. Recognizing that there is nervousness or anxiety in feeling that we need to relieve ourselves from the discomfort of not knowing is the first step and getting comfortable exploring the unknown is the next.

4. Understand deeply what stories you tell yourself

We live our lives through stories. Even more than the stories we share with others, the stories we tell ourselves about our own reality hold significant weight and impact our worldview and everything around us. I had to unpack these stories within myself in the last year. Many of them were quite negative, full of self-blame and judgment and I learned the importance of balancing my default mindset with one that’s more positive. Instead of sitting in negative thoughts, I’m practicing how to recognize when those thoughts appear and counterbalance them with kinder, encouraging thoughts. With an equanimous mind, I’ve learned that the quality of my decisions stems from the quality of my mind and my relationship with myself.

In the past when I was running on overdrive and focused on action and building, I was aware of these stories, but I didn’t have the bandwidth to create a healthier habit from an equanimous mind. Having the time to go through daily life without a primary focus on output and outcome allowed me to start to rewire these internal stories to cultivate a healthier mindset that I believe will serve my relationship with myself and others moving forward.

Understanding the stories I’ve told myself and allowing the dust to settle also helped me see and appreciate my innate strengths instead of taking them for granted. I was able to acknowledge what I uniquely bring to any group, team, or situation and how I can better leverage these strengths in the future.

5. Time to allow the mind to wander is not lost time

Throughout my YoD, I spent weeks going down rabbit holes to learn about new concepts: from carbon sequestration strategies to play-to-earn in Web3 to tokenomics to how Deng Xiaoping led China to what it is today to methods in predicting the future. I learned how economists versus humanists see the world, how personality versus cognitive psychologists understand our inner worlds, and how people who hold various, mixed identities engage with their inner and outer worlds.

I allowed my curiosity to guide me, which led to more in-depth conversations and questions that touched on the core of various subjects. I dove layers beneath the surface in ways I wasn’t able to before, broke ideas down to first principles, and formed new hypotheses. I felt like I was immersed in a liberal arts education but armed with years of experience that drove my thinking more practically.

Towards the latter part of my YoD, I began to see how the various subjects I explored and researched tied together to inform a stronger conviction of where the world is going, my role in it, and possibilities for how my own journey can look. I could recognize how the quality of my ideas increased over time as I rigorously tested my assumptions through what I was reading and who I was engaging with. As I allowed my mind to wander, my fluid exploration solidified my beliefs in some areas. I harnessed a scientific mindset that balanced comfort in the not knowing and confidence in the process of continuous testing.

6. Anxious days — whether with work or not — are normal

As I look back at the last 12 months, the time has felt — depending on the day — excruciating long or like the blink of an eye. I’ve been anxious in my boredom or energized in unraveling knowledge and connecting dots. There were times when I felt absolutely lost and wondered whether I was on the right track or spending my time wisely. These days felt unproductive, filled with dread and nervous energy. I’m incredibly grateful for the wonderful friends and partner who supported me on such days and held space for my mild panic.

While this is still a work in progress, I became more aware of and less bothered by the cycles of my mind over time. I saw my mind go in complete flow on some days with absolute confidence that my learnings were leading somewhere and on other days, my mind was completely distracted and unable to focus fully. Such as the changing seasons, I understood this as the seasons of my mind. Later on, I practiced seeing these cycles from a birds-eye view instead of only engaging with life from the eye of the tornado. I’m currently testing how to align various productive activities (reading, learning, meetings, GSD) with the mental season that I’m in.

7. Adopt a long-term mindset in a short-term thinking world

In a world of short-term results, it can be tempting to think that everything is urgent and important. I’ve fallen into this trap many times, whether in regards to my life’s mission, work, relationships, or personal growth, and it’s led me to make decisions that are more fear-based and less deliberate.

The reality is that our lives evolve over many periods and what matters more than the ‘how’ is being clear on what general, long-term direction we want to head in.

Direction = clarity of purpose + values (refined by experiments)

When I set my quarterly goals throughout my Year of Discovery, my questioning and experimentation were aimed at refining my personal purpose and values. I learned about many different industries and engaged with stakeholders and people of various backgrounds. In those conversations and in my reading, I was able to tune in and understand what resonated the most with me and why.

Achieving high-impact goals takes time. When I studied China’s accelerated rise to global power by reading Deng Xiaoping’s biography, I learned that the Chinese leader would align all of his policies towards goals spanning decades. While looking back retrospectively, outsiders can be astonished by the rapid rise of the Chinese economy, but a key component that they miss is the consistent and deliberate practice of Chinese leaders who focused on long-term goals and not the volatility of the short-term.

As I gained more clarity on my long-term direction, my short-term decisions filled with possibilities, less pressure, and less judgment. How I worked towards my long-term direction was important but it became less heavy and I could see a variety of pathways that could take me to where I wanted to go.

Moving forward, something I’m taking away from my Year of Discovery is that discovery is a mindset that can be translated into a Life of Discovery. While my values and my purpose feel more aligned than ever, I recognize that my tendency is to buckle down and build. My YoD has taught me that creating space and time to allow my mind to wander and to learn about new subjects will only enhance my ability to deliver even greater work every day. It’s a practice I want to cultivate.

I’m unsure how I’ll continue this blog as I move into full-time work again but I’ll aim to write a few more longer-form reflection pieces throughout my next few years. These blog posts have served me incredibly well and I’m deeply grateful to all the people who sent me messages, shared resources, and engaged with me as I pondered various ideas and topics. This journey pulled me in directions that I least expected and opened my heart and mind. And I’m eternally grateful for the time to discover.



Audrey Cheng

Taiwanese American. Curious about ideas and solutions that support human flourishing.