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The Beginning

“Are you crazy!?”

I was getting used to hearing that when I told my friends and family what I was about to embark on. I sold everything and bought one-way tickets to New Zealand for my wife, our ten-month-old daughter, and me. Not for vacation. Not to live, either. To work? Not exactly.

I decided to take a careercation (career + vacation) and travel around the world with my young family for about six months. After being a hard-charging entrepreneur for over a decade, I was burnt out.

In the past, I’d usually fly somewhere sunny with water, get a bad sunburn, and proclaim myself recharged. I could fool most people with that—but not myself and not this time. I realized that I really needed to slow down before speeding up again.

All About the People

At work, everything looked great. My second startup, BuddyTV, zoomed along full speed ahead. I continued learning new skills like search engine optimization, gamification, and content marketing. Andy Liu—my business partner for my first and second startups—and I celebrated a decade of working together. At this stage in our professional relationship, we could read each other’s minds, and we maintained a deep level of trust.

We assembled a great team of folks. This was crucial. Nothing feels better to me than mentoring and coaching employees to harness their untapped potential and exceed all expectations.

At the same time, I’d always assumed that as long as the business was performing well, everyone would be happy, including me. In an attempt to corroborate that, Andy and I conducted our first annual employee survey. I learned to do this from my days as a consultant at Andersen Consulting. We thought if it was good enough for a Fortune 500 company, then it must be good enough for a small startup. In December, we locked ourselves in a room, brought in pizza and cheap beer, and didn’t emerge until we concocted fifty questions for a “good” employee survey.

We implored the team to respond by the end of the year. We Powerpointed, pivot tabled, and presented the results in Q1. Then, like most managers do with almost every annual survey, we forgot about the learnings by tax day. Of course, a large annual survey didn’t make too much sense since the business—and people’s morale—change constantly throughout the year. But we thought we should pattern our practices after Fortune 500 companies.

Then one day, one of the team members pulled me aside to give me two weeks’ notice. I felt like I had been stabbed. The news blindsided me. Everyone had seemed happy when we conducted our annual survey. My first thoughts were, Why are you leaving? Can I save you? Do I want to save you? Is it something I did? Or is it something that I didn’t do?

I offered to change the role and accountabilities for this person. I discussed compensation. I tried everything, but this key member of my team left anyway, which crushed me. In fact, I not only had a mental response but also a physical response. I couldn’t sleep well, I had anxiety over who was going to pick up the slack, I was drinking too much, and I was eating poorly. I coined the phrase “34 by 34!” The whole ordeal caused me to drop into such an unhealthy spiral that I started packing on pounds and was forced to buy larger pants. After going from a 30-inch waist to size 32 in short order, I had to draw the line and rally around banning 34-inch waist pants until I was 34 years old.

This wake-up call inspired me to work out and get healthier again. I ran my first half marathon with a dear friend and fellow entrepreneur, Ben Elowitz. I also started meditating and journaling.

During these introspective moments, an important theme came to me. Managing people has been the brightest highlight and also the most maddening frustration of my experience as a serial entrepreneur. The greatest joys in my career have been watching people succeed beyond expectations. The greatest downer is having them fall short of their potential—or leave with no warning. If real estate is all about “location, location, location,” then business is all about “people, people, people.”

Feeling the Love

In 2009, after completing the Portland Marathon, I celebrated by flying to Saigon to visit my friend Dave Hajdu. Dave had moved to Vietnam to start an onshore-offshore software development company called Vinasource.

Near the end of that fun trip, my friend Simon Han contacted me on Facebook to ask if I was single. He wanted to introduce me to someone. I confirmed my single status and asked him to share more about her, since we all know about blind date nightmares. Simon responded that my potential date was an entrepreneur, also went to Berkeley, and was crowned Miss Chinatown USA. I burned into the keyboard, “YES! Please introduce me!”

That’s how I met my lovely wife Alice. Alice was Simon’s wife’s cousin. So now Simon is my cousin-in-law plus a celebrated family matchmaker.

It was love at first sight. My friends used to tell me, “You’ll know when you know.” I thought that was BS until I saw Alice. We got married in 2010 and had Keira, our daughter, in 2011. These dramatic life changes also drove me to be more intentional about filling my personal and professional life with happiness.

Feeling the Burnout

As all these changes were happening, I realized my energy was extremely low when getting ready to go to work at BuddyTV in the morning. I asked myself, Are these isolated instances of just being tired? I realized that wasn’t the case. The trend pointed towards exhaustion after over ten years of sprinting with a pedal-to-the metal mentality as an entrepreneur. I had to be honest with myself.

I confided to Andy about these feelings and my need to walk away from BuddyTV to recharge. If I couldn’t radiate positive energy at work, how could I expect others to do the same? I give Andy tremendous credit for being supportive and understanding about what I needed. We put together a succession plan and pulled off a smooth transition that enabled me to leave BuddyTV in 2012 for my careercation.

Before I left the business, one question kept me awake at night: how could I get so burnt out from a company that I started?

Living Intentionally

  • I wish I had let myself be happier.
  • I wish I had stayed in touch with my friends.
  • I wish I'd had the courage to express my feelings.
  • I wish I didn't work so hard.
  • I wish I'd had the courage to live a life true to myself, not the life others expected of me.

How many of the above themes can you relate to? If you’re like most people, there should be at least a couple of them because these are the top five regrets that people have on their deathbed as documented by Bronnie Ware, a palliative care nurse. Imagining myself near death and thinking through my regrets triggers me to live intentionally.

Alice and I took a course by Seattle relationship guru, John Gottman, who famously determined that there are seven important steps for a successful marriage. The most aspirational one is learning and making your partner’s dreams come true.

On that note, when Alice was still in nesting mode around the birth of our daughter, I sheepishly brought up the fact that a dream of mine was to go on a careercation. I shared that some of my best and most formative experiences in life were backpack traveling and studying abroad. In particular, I remembered my junior year studying at Peking University. I didn’t have a lot of money, but meeting new people from around the world and experiencing the culture on a native level made me so happy.

Alice quizzed me by noting that buying one-way tickets for a free flowing careercation was a non-intuitive approach for a maniacal planner like me. I agreed. I explained that it was exactly why I needed to do this--to break out of my comfortable Seattle structure and bubble.

She loved me and wanted to support my dreams. She wanted to model living courageously to our daughter Keira. If we’re not somewhat anxious, then we’re not pushing ourselves hard enough to learn and grow.

Careercation Goals

I was ecstatic that Alice was onboard. I give her tremendous credit for supporting me and enabling this extended break. Of course there were many heart-to-heart discussions about budgeting, safety, sanity and how Keira would fare before Alice fully bought in. She knew the trip would help me to break out of my analytical, over-planning style. Yet, I still felt compelled to shoot for two goals during our careercation.

First, I wanted to create amazing shared memories with my young family. In collaboration, Alice and I planned the places we wanted to go personally and as a family. For example, I wanted to go to the Marlborough Valley in New Zealand because I adore their Sauvignon Blancs. Alice wanted to stop by Shenzhen to visit her father and inhale yummy Cantonese food.

Second, I wanted to interview entrepreneurs and leaders about their best practices in leadership, culture, and managing people. My comfort zone in Seattle is technology-related businesses, so I vowed to talk to CEOs who ran other types of companies. The interviews would run the gamut from a winemaker in New Zealand, to the financial services consultant in Korea, to a fruit trader in China.

I was still haunted by losing a key employee out of the blue and how I became burnt out at my own business. I wanted to see if the joys and heartaches felt by these business leaders were also related to the people and company culture. I hoped this opportunity would shed light on my own challenges and somehow inspire my next journey.

The Devil is in the Details

It’s one thing to be a single twenty-year-old guy with a suitcase hopscotching around China without a care in the world. It’s another to go on a long, complex journey with a baby.

Was this trip ambitious to carry out with a ten-month-old little one? Sure. Some spouses would not be on board with this plan at all, given the many variables and unknowns. Even though Alice was in, she insisted on one condition: we needed a travel au pair as another set of hands on our careercation.

This stopped me in my tracks. My romantic ideal of traveling together with our baby—bonding and sharing moments—did not include a stranger living with us day in and out. Bringing along a nanny was not traveling light. It was also another incremental cost as we tried to live frugally. I didn’t like the idea at all.

Alice told me to take a deep breath. She reminded me that we would want to do some things just as a couple and have our own adventures. Could we find trustworthy babysitters overseas? That type of bond takes time. Taking care of a baby is a lot of work, and it’s constant. Keira was starting to take her first steps. Would this trip be about Alice chasing her around but just in a different part of the world?

She made a strong argument. I wanted us both to have fun and relax, not take our daily routine on the road. I agreed it was a reasonable requirement that made sense, and it turned out to be a great decision. (Yes honey, I admit it. You were right!)

Laying the Foundation

Alice put a lot of time and research into finding a great fit for our family through an au pair website. She filtered five hundred applications and screened fifty before finally landing on one that seemed perfect.

My job was to find accommodations. To save money and experience the culture at a local level, we would stay in vacation rentals and rental houses, eschewing hotels. We planned to dive into the culture in an authentic way, living amongst locals, shopping at farmers’ markets, and buying coffee at local cafes. Buying our own groceries and cooking our own meals would also be a huge money saver. We also saved money by planning strategic visits to family and friends where we stayed for free.

With proper planning, budgeting, and cost control, anyone can embark on a careercation. Admittedly, we went to expensive countries like New Zealand and Australia, but we could have pared expenses if we’d gone to regions like South America or Southeast Asia. I’m convinced that if you put your mind to something, you can achieve it. There are options for traveling on any budget or lifestyle.

We vowed to pack lightly, even though babies need their own battery of gear. I’m proud to say we achieved our goal with only two large suitcases, filled to—but not exceeding—the fifty-pound airline limit. And a medium suitcase. Plus a stroller, car seat, diaper bag, and Pack n Play.

Feeling the Anxiety

Wayne Gretzky said, “You miss 100% of the shots you don’t take.”

There’s always an excuse not to exercise, eat healthy, tackle a bucket list item, or in our case, travel. It’s always about leaving your comfort zone. We were determined to follow through.

To ensure that the start date of our careercation wouldn’t slip away, I anchored the beginning of our trip to an Entrepreneurs’ Organization (EO) conference in Queenstown, New Zealand. Buying the tickets to this event made our commitment concrete and real. Without that commitment, I’m sure we would have been tempted to push back for a variety of reasons.

Truth be told, I felt more nerves, anxiety, and butterflies this time than I ever had for any other trip, including my wedding! But after selling most of our things and storing only a few essential belongings, the liberation from “stuff” combined with our pending trip turned the nerves into excitement.

When the door to the Air New Zealand plane sealed shut, I finally exhaled. Along with the feeling of wheels speeding on the runway came youthful energy that cascaded over me. After living with so much structure and routine in our careers and in parenthood, a careercation would break us out of our comfort zone and push us into the flow to grow. We didn’t want to look back on our lives with longing and regret. We were going to take the shot, even while everyone was thinking we were crazy.