Learning to date myself

As 2017 comes to a close, I’ve been reflecting on a transformative twelve months — my hardest, worst, and maybe most meaningful year. Here are some of the experiences and lessons I’ll be taking into 2018.

Fall into Winter: December 2016

Saturday, the 17th of December was supposed to mark the start of a happy holiday week. Having buried myself in work for many months, I was eagerly awaiting some time with friends and family. My boyfriend and I had made a plan: We would celebrate my birthday early (which is on Christmas Eve), fly to spend the Christmas week with our respective families, and reconnect in San Francisco to ring in the new year together.

My boyfriend Ted (not his real name) had mentioned his office’s winter clothing drive, so I had planned to spend the afternoon Kondo’ing before my early birthday dinner. Unexpected, Ted texted me:

Ted: What are you up to? I’m nearby.

Me: Hey! I’m cleaning out my closet.

Ted: Can I come join you?

Me: Aww, of course you can.

In my mind, I saw Ted staring at me lovingly while I struggled to part with old clothes. I’d hold another shirt up to the light, explain memories tied to it nostalgically, and he’d jokingly ask me whether it gives me joy or not. I’d end up tossing it into the growing pile, laughing.

But then Ted stepped into my apartment. With teary eyes, he seemed a bit anxious.

“What’s wrong?” I asked, worried.

“Let’s sit down” he said.

After a painful pause, he continued, “Koun, I don’t think we’re on the same wavelength.”

Oh. God.

We climbed aboard a roller-coaster. First it was him saying we should break up, then it was me in shock, then it was us both crying, then me rambling, then us both crying more, and finally me in a puddle. When we couldn’t find anything else to say, we talked more. Over two hours later, I was so emotionally drained that I barely noticed when he walked out the door.

Was this really the end? Could this really be happening?

Amidst discarded clothes, I curled up in a ball. As someone who prides herself upon being rational and in control, I was completely out of my element. Not only heartbroken, I was shocked. I couldn’t begin to imagine what came next. All I could do was hurt.

Our breakup came as an utter surprise. He’d been so sweet throughout our time together. A week earlier he’d asked me to join him on a weekend trip with his friends because he “didn’t want to be without me.” A month earlier, he’d told me he loved me for the first time, given me keys to his apartment, and taken me house-hunting. He’d been my best boyfriend. I recalled zero negative memories of him. Now, my world was upside-down, inside-out, and twisted beyond recognition.

There’s never a good time for a breakup, but this seemed downright cruel. The worst birthday, Christmas and New Year of my thirty-five years. I couldn’t sleep. I couldn’t eat. I could barely remember who I was. The person I had learned to trust the most had broken my heart with no warning. My mind wandered aimlessly, seeking answers.

What was wrong with me? What was wrong with him? What was wrong with the world?


Spring 2017: Sadness into Self-Awareness

By March, the clouds outside had begun to clear and the sun was shining more often after an unusually rainy winter in San Francisco. But in my mind, there was still mostly darkness.

My sadness felt all-encompassing and at times I was inconsolable. Well-intentioned friends reminded me that the passing of time would help, and I knew they were right. But adding insult to injury, time was passing SOOOO slowly. Could the world be less humane? I scraped up what motivation I could muster, and tried to avoid spending too much time idle or by myself. I journaled. I spent time with friends. I read dozens of books.

One book that resonated in particular was Sheryl Sandberg’s Option B: Facing Adversity, Building Resilience, and Finding Joy — chronicling her path forward after her husband’s unexpected 2015 death. To be sure, I wasn’t mourning anyone’s death, but the loss of my future life with Ted had left me feeling empty, and what’s worse, I hadn’t given myself permission to grieve. But I learned that however small or big one’s loss, grieving requires time and honest reflection, and also empathy for oneself. For months, my life had been way out of balance, and it wasn’t balancing itself back out. For the first time, I realized that I needed professional help, so I started weekly counseling with a therapist.

At work, I tried to keep myself together but I found myself crying in many 1-on-1 meetings. Although I’m a proponent of bringing one’s whole self to work, this was too much. My seasoned can-do attitude was nowhere to be found. My supportive manager and colleagues suggested that I take a few weeks off to take care of myself. They offered to pick up the slack.

It bothered me immensely that I didn’t know when I’d be better. A few years prior, I’d recovered from a ruptured appendix (with the doctor’s prescribed 6 weeks of rest), and though I’d been anxious about slowing down for so long, I’d done fine with a timeline to give me context. Grief was a different animal; I had no prescription to follow. Slowing down at work didn’t sit right with me, especially as the product manager on an impending product launch. It had been three months since the breakup, and still I lacked the mental capacity to handle otherwise normal work stresses. I realized that I needed to take more drastic actions.

I embarked on week-long trip to clear my mind. I spent the time mostly disconnected, on a boat — mostly reading, reflecting, and journaling. Just after I set foot on land again, I submitted my notice at Square and set about transitioning my responsibilities over the next two months.

Quitting work to focus on myself was very hard for me. But along with seeking professional therapy, it was my first honest admission that I needed and deserved more. Foreign as the concept of being unemployed was, I made the commitment to do it in hopes of turning myself around. Perhaps I could return stronger, wiser, and more resilient. My colleagues were sad to see me leave but they universally called my decision brave. I remain incredibly grateful for their support and encouragement.


Summer 2017

Planning for No Plan

Transitioning my responsibilities would take several weeks, but the process was relatively straightforward. Rather than enjoy the absence of chaos and look forward to my impending time off, the idea started to give me anxiety. To quiet my inner critic, which didn’t know how to process the concept of unstructured life, I started to plan my time off. My first urge was to set an end date and an end state for my break. In my mind, the clearest way to do that was to lock in the future start date…of my next job.

After speaking with a dozen companies, I was fortunate to receive several offers. My internal critic urged me to make a decision quickly and objectively. But as I went about my normal planning routine, a less familiar, kinder and more subtle voice spoke to me in my quiet moments. And that voice kept getting louder as I was trying to make a decision. It took a while, but through honest introspection and encouragement from friends who were worried about me, I finally admitted that I wasn’t ready to consider a new job.

My old playbook had told me that first, I should check all the professional boxes. Then and only then, I could devote time and energy to myself. In hindsight, what I needed was the opposite. I needed to actually close the current chapter of my life and open a new one. This wasn’t just a pit stop to get back on track. I needed to live with the discomfort of not having a job to define me. I needed to wrestle with the possibility that when I was ready to go back to work, I might not be able to step right into a job I’d love.

So in June, with no specified end date, I began my break. My goal was simple: to take care of myself. I felt excited and nervous — nervous because it was unfamiliar territory, and excited because I could feel deep down that this was right for me.

When I talked to people about taking a break, they’d often ask if I would spend the time traveling the world. I love traveling. I once took a sabbatical from Facebook and traveled adventurously for nearly three months. This time, rather than travel to new lands, I wanted to explore the hills and valleys of my own life. I basically wanted to learn to date myself.

How did I adjust to having no responsibilities and no plan? Terribly at first. For a few weeks I sat and milled around restlessly in San Francisco, worried that I wasn’t maximizing each day. Work had provided me with social interaction, camaraderie and a sense of belonging. Absent those default interactions, sometimes I unintentionally spent days without talking to a soul.

Yearning for a semblance of structure and human connection, I wrote a list of things I wanted to do and roughly how often I wanted to do them. Thankfully I fought off the urge to set quarterly goals.

  • Daily: exercise; meditate; write down 3 things I’m grateful for and 1 thing I’d learned about myself; have 1 meaningful social interaction
  • Weekly: try something I’d never done before
  • Monthly: volunteer; host a happy hour/dinner party
  • General: take art classes, cook, research and learn about topics of interest, binge-watch TV shows without guilt, spend some quality time with mom, get certified as a Pilates instructor

Mindfulness and Self-compassion

In case it’s not obvious: I am a “do-er.” It’s generally a positive trait that’s served me well professionally. An ex-colleague told me that she coaches her team to “channel your inner-Koun” when something seems too hard. Historically, you could find me either doing something, figuring out how to do something, or planning something to do.

Early in therapy, I asked impatient questions: “How do I get out of this grief? How I do I shake this off? What can I do to speed this up?” I was assuming that emotional and mental issues could be “solved” like a product could be built. Turns out, you can’t solve life just by doing or planning — sometimes you just need to let things be. It sounds so simple, but it wasn’t easy.

Being fiercely independent has been a central tenet of my life. Through therapy, I learned how I’d come to be this way. When I was fourteen, I’d emigrated to the US from Korea without my parents. By reflecting on this experience, I came to understand that it had cemented in me an uncompromising self-reliance: If I wanted something to happen, I must do it myself. As a teenager in a new world — without familiar friends, without parents to help me, fumbling with a new language, struggling to assimilate to a new culture — I’d had no one to lean on. Over time, I’d come to believe that I never should.

As a strident and solo teenager, I’d set my ambition to eleven and never looked back. Twenty years later, I came to realize that while climbing hill after hill, like so many of us, I’d failed to smell the roses and enjoy the view.

Per my therapist’s suggestion, I enrolled in a Mindfulness Based Stress Reduction (MBSR) program at UCSF’s Osher Center. Over eight weeks, the intensive program taught me how to practice mindfulness: How to be, how to stop all the doing, and how to relax into the present, without trying to fill your days up with anything in particular. It wasn’t easy to make meditation a habit, but with their help, I was able to take small, noticeable steps. Even unremarkable actions like brushing my teeth, enjoying a morning coffee, cooking a meal, listening to others, or working out, became an opportunity to notice my thoughts and feelings. My definition of “doing” became more generous. Even “non-doing” became a practice.

Something else I learned in therapy was that I‘ve been very hard on myself. Not only had I been struggling with the emotions from a breakup, I’d been scolding myself for not shrugging it off and I’d felt embarrassed about being so distraught. My inner critic was ruthless:

Do you deserve to feel this badly? So selfish to let your team down. How can you feel so sorry for yourself when your life is so full of great things, when you’ve never gone hungry or without a roof over your head?

Though I’d achieved many things, I’d never taken care of my emotional self. I’d been busy learning English, adapting to life in a new country, getting into a good college, getting a good job, launching products, supporting my parents. The list never got shorter, so dealing with feelings was a nuisance and a luxury I couldn’t afford. Finally, emotional negligence had caught up with me.

I am slowly learning self-compassion. It is ok for me to feel sad and to grieve the end of a relationship. It is ok for me to give my 14yr-old self a pat on the back and to acknowledge that it must have been hard for her. It is ok to be angry at my ex for the way he broke up with me. It’s ok to devote time to getting my life back in order, even if it inconveniences others. It’s ok not to accept the weight of the world all the time — It’s ok not to take myself so seriously.

Relationships

It took me six long months to muster the strength to face Ted. It took a while for me to truly come to terms with the fact that no matter how deeply I wanted a relationship to work, it wasn’t something I could do by myself. And though it saddens me a bit to admit it, romantic love isn’t enough to make a relationship last.

I also learned a lot about myself in the process. In relationships, I had been ignoring my own needs in order to support my partner. In fact, long-lasting relationships require mutual vulnerability. Each person must trust the other to honor their most authentic self. Though I’ve tended to be the “giver” in relationships until now, being more self-aware will help me to find a better balance. Although I did love many qualities about Ted, I have a new respect for emotional maturity and seek a partner with whom I can communicate more openly and consistently.

This past year has made me think a lot about other relationships in my life as well — colleagues, friends, and family. Something that surprised me was that the people who are most empathetic when you’re struggling aren’t always those who are closest to you when you’re succeeding. Nonetheless, gratitude was the most dominant feeling by far.

The night of the break up, some friends immediately drove an hour to keep me company. Another friend called from Berlin to console me. One friend who was visiting family in India sent a DoorDash delivery of flan! Other friends admitted not being able to relate personally but offered whatever they could. My younger cousins took care of me during the holidays that terrible winter. Colleagues at work cried with me when I told them I planned to quit and take care of myself, and many of them supported me knowing that my quitting would make their lives harder in the short term. I was only ever able to heal because of their kind words, understanding and support.

All the people who supported me inspired me to be more authentic, so that I too could be a better friend, colleague and human, and to support people when they needed me most.

Finding Work: Round 1

Although I had made peace with not treating my time off like another job, I found it rewarding to use my new flexibility to explore different areas of opportunity with an open mind. I referenced a list of criteria I’d used to find a new opportunity after leaving Facebook:

  • Great people and culture
  • Mission driven; Solves a real human problem
  • Builds products I can relate to and love
  • Early → growth stage: opportunity to make impact, learn, and grow with the company

Initially I narrowed in on early-stage, hardware<>software integrated companies only. Quickly I realized that it was too limiting, so I decided to include software-only companies as well. I also considered tech non-profits, to see if I could find a way to more directly do something good for the world.

I reached out to an ex-Facebook employees group and asked for recommendations and insights, explaining my thoughts on the search for my next meaningful job. It must have resonated with many of them; the post received dozens of comments. I met privately with about a dozen people and explored various ideas. These explorations helped me learn a bit more about myself and refine my criteria:

  • I preferred the opportunity to work as a PM at a for-profit company
  • Mission-orientation was not enough for me. I wanted to work on a product that I could personally get excited about.
  • I should be open to smaller companies within larger parent companies, where a promising new technology had been germinated.
  • Very early stage was probably not for me. Given that I enjoy working cross-functionally, working within a very small, homogenous group might feel stifling.

Finding Work: Round 2

As I continued to hone my preferences and self-knowledge, self-driving car companies kept popping up on my radar. Outside of Tesla, there were many whose size and stage seemed perfect: Waymo (Alphabet), Cruise (GM), Level 5 (Lyft), ATG (Uber) and others. The more I researched the industry, the more energy I gained. I knew I was onto something.

Getting self-driving car companies to consider me for a lead PM role was challenging. I literally had no colleagues in the industry, and generally they were seeking someone with more relevant or more technical expertise than me. At Square I’d been entrusted with flagship hardware products without prior hardware experience, because I’d had the good fortune of proving myself capable in other arenas. Self-driving car companies generally couldn’t take that chance on me, a noob and an unknown.

As I began to lose hope, a former Square executive, who knew nothing about my search for a role in the self-driving car industry, reached out and asked me if I would consider a PM job at a rather stealthy self-driving car startup. Through several chats and interviews, I grew increasingly impressed with the team and their vision. The company culture and role also seemed like strong fits for me. I’m so pleased to say that I’ll be joining Zoox in December. I am thrilled to be a part of the self-driving car revolution with an amazing team who I can learn from and grow with.

What did I learn from this search? Again, when you let life be, the right opportunity might just find you.


Autumn 2017: A Year Later

Autumn is harvest season, and a time of thanksgiving. Thankful is exactly how I feel. Although this year began with what felt like unbearable sadness, I’m now as ready for the world as I’ve ever been. Although my time-off was triggered by an unpleasant event, I am thankful that I had the opportunity to get to know myself a bit better. Armed with many lessons, recharged with a full heart, gratitude, and love — I am stronger than I was a year ago.

By no means am I the first person to have gone through a hard breakup, and who knows — perhaps this won’t even be my hardest emotional trial. But what is most personal to each of us has the strongest potential to resonate with others, so I am sharing my deeply personal story with the hope that someone else might gain strength from it.

I am very aware that taking an extended break was my privilege. Not everyone can afford to take a few months off, enroll in classes and therapy, or to be picky about employment. Not everyone has a wealth of supporters to call on. I certainly don’t take this for granted. But I too would probably have said that I couldn’t afford the time or money but now that I’ve done it, I know it’s an investment well made.

As my time off comes to an end, I’m pleased to have kept generally to my commitments. I’ve journaled regularly, kept to my physical routines, started watercoloring, and have been diving deep into interesting new areas. I am sure it will be much harder once I start working full-time, especially learning the ropes and getting acclimated to a new industry. No doubt the learning curve will be steep. But I hope to bring both a renewed enthusiasm and the benefit of a beginner’s mind to my new professional challenges.

For my friends who are reading this, please help me maintain my balance. I’m sure I will falter and I will continue to need your support. I still want to excel and achieve professionally, but I also want to be there for myself. And I want to be there for you.

Now finally, I can see that even in my darkest hours, I was blessed. I offer one of my favorite blessings to you:

May you be safe and protected.
May you be happy the way you are.
May you be healthy in body and mind.
May you live with peace and well-being.
May your heart be open and free.