Your Start-Up Failed? Go Ahead and Have Fun

Aug 25

In: Career management, Entrepreneurship, Family life, Philosophy

I chatted with a friend, who has decided to close down his start-up. He worked on it for a few years, underwent a major pivot, and, in the end, realized, it wasn’t going to work out. All this while having his first child, too.

He is closing down the company. He called me to ask for advice on various jobs for his next gig.

“None of them,” I told him. “At least, not right now.”

I then became even more blunt: “Leave the baby with your parents and take your spouse for a long weekend away. Re-connect with her, express gratitude, and have fun together.”

I think it’s very easy to leave a job behind, but it’s very difficult to articulate one’s next step unless you allow for some “simmer time.” It’s easier to articulate why you want to leave a job; it’s much harder to articulate to where you want to go next.

“From” vs. “to”: they are very different situations.

I told my friend that he was probably feeling guilty that his start-up failed, particularly as his spouse was earning most of the inbound cash and that they had a tight budget. That he was probably feeling internal pressure to overcome that guilt by finding a new job quickly.

I’ve written before that self-criticism is an entrepreneur’s biggest obstacle, IMO. We criticize ourselves, and, if we are not careful, sabotage ourselves.

So, the irony is that, after failure, giving yourself a break is usually the best thing to do. Give yourself permission to mourn the end of a company. But, give yourself permission to have fun, recharge, and relax before the next job.

I hope my friend and his wife will have a wonderful time.

About to be a College Freshman? My 2 Cents

Aug 18

In: College, Personal

It has been a busy August, and, today, I had an unusual day: many meetings, each of which was professionally interesting and personally rewarding.

For example, I connected last autumn with a local high school senior, who was accepted Early Action to Yale. Our deal was that if he chose Yale, I’d treat him to lunch. After doing his due diligence, he did so. We met today at my favorite ramen place.

He leaves for New Haven shortly and is incredibly excited and nervous. I’m envious.

He asked me for advice. Here’s what I told him:

You and your roommates should be the first ones to throw a great party. You’ll meet everyone very quickly and you’ll always be remembered for being gracious hosts.

My college roommates and I did this during the first few days of college. We ended up throwing many parties over four years. But, I still remember that first party and the people whom I met–and, who became true friends. The music was great, and we invested in a pretty impressive selection of “beverages.”

Quickly meet as many people as possible. I noticed in college that people were very eager to meet new folks during the first 30 days. They still were after, but were a bit more selective. I still find it incredible that many of the people with whom I was friendly for four years were those whom I met during the first month. So, to me, there’s something magical about the First 30 Days. So, get out there and socialize.

Meet up with your roommates for dinner every night, if possible. I had three roommates in college. Each of us is very different from the other. But, we all got along and stayed together for four years.

I think part of that is that we became friends and not just roommates. Social patterns get established very quickly. I remember my roommate, Jeff, casually asking everyone else early on when we should meet up for dinner together in the dining hall. So, we did. And, the next night and the next.

Soon, it was a room ritual to get together and share a meal together. I love those guys and miss them.

Re-create your identity, if you want. College is a great time. You no longer have to be the person typecast by high school classmates. You can be your authentic self. I went to a very “regular,” working-class, and homogeneous high school. I was viewed as “the smart Asian kid.” At college, I was just “Jo.” It was a relief and very liberating. I could be myself.

In high school, most of my social life outside of school involved other Asians. In college, I went with the flow. I noticed some Asian students nearly always ate meals with other Asians. I decided not to do that. I ate with everybody and tried to build relationships with everyone. It was really fun.

Be ready to be shocked–and to grow as a person. I told my friend that he will be meeting many people who will be very different from him. Embrace the differences. Learn from others. I told him to get ready to really change and evolve as a person. His view of the world will change radically as he meets more people different from himself.

I went to a very large all-boys school and was very naive. So, it was a “new” experience when, during the first week of college, a female friend jumped on me when we were studying in her room. I declined, and we tried our best to stay as friends. I do remember thinking as I left her room: “Well, you’re definitely not in Kansas anymore.”

Ditch your personal insecurities and rejoice in others. I told him that there will be many very smart and talented people in his class. Rather than compare himself to them and feel inadequate, take joy in their gifts. Go to the improv comedy show, football games, volleyball matches, singing jams, music concerts, and plays–and, rejoice that your friends have tremendous gifts that you may not have.


College, for me, was transformative. I felt “known and loved,” to quote Tony Jarvis. I really learned a great deal about myself. I know my friend will, too.

The Way Things Were (and, Might Be)

Aug 17

In: Cool, new stuff, Economics, Myers-Briggs, Politics

It was a fun and full weekend, as our family has moved houses. We have been living amidst a sea of boxes and strewn-about items.

But, slowly, we are making progress. It’s a joy to have more room. And, a garage. But, we will miss our starter home in which we’ve lived for over 15 years.

As I unpacked, I found some items from the past. Here are some.

Before there was Facebook, there were facebooks. I found these from my college and b-school years.

Before there were online calendars, there were paper ones. As a super-charged ENTJ, I assiduously planned my work weeks.

Before there was the Internet, there were floppy disks. Here are some from the early 1990s.

It’s interesting to see how much has changed over just two decades. I think the future will bring even more change as to how we live our lives.

I predict that over the next 20 years the following will happen:

We will have microscopic chips embedded into our skin. They will monitor our health real-time and how we communicate (imagine 2 mm chips in our collar bones and ears, that together will serve as a “cell phone”). People today are talking about “wearable” technologies. I think it’s not a leap to think about “embeddable.”

Technology makes consumer demand more and more granular. This in turns makes the supply side more and more granular. You won’t sign up for cable. You will stream shows over the top and a small chip will stream the show to the inside of your eyes. You won’t own a car. You will use a chip in your head to summon a self-driving car to take you somewhere.

International espionage will center not on nuclear weapons, but on systems. The recent purported cyber attacks by China and for-profit hackers in Eastern Europe are just the beginning. If you can disable the computers that control the nukes, that is the higher strategic ground.

The Euro will end. The EU will break up into three distinct sub-groups. Germany and France, as two of the larger Continental economies, will pair up. Countries with poor prospects, such as Portugal, Greece, and Italy will be on the outside looking in. All the other countries will be in the middle and pretty much do whatever Germany and France want.

The U.S. will continue to be a superpower. As the nation produces more oil, for domestic consumption and for exports, its economics will be more sound (oil is involved with everything produced and shipped in the economy). We will no longer be as closely tied to the vagaries of the Middle East. Oil is money, and money creates more leverage.


The future will be very exciting.

A Face Behind the Headline

Aug 16

In: Personal, Philosophy, Politics

(New York Times)

Immigration is a hot-button issue. Donald Trump is cheered in some circles for his criticism of Mexican immigrants. In Europe, political parties are getting more and more traction as they campaign against unbridled immigration.

I’m not going to write about the pros and cons of various immigration policies.

I’m writing because I just saw the above photo in the NY Times online. It’s a very moving picture. Here’s the caption:

A Syrian refugee…breaks out in tears of joy, holding his son and daughter, after they arrived safely in [Greece].

I’m writing this because I find it easy to read the news and be very detached. But, it’s another thing to find that there are real human beings behind every public policy debate.

‘The Little Problem I Had Renting a House’

Aug 11

In: Family life, Race

I think there are powerful lessons prior generations can teach us. Here is a TED Talk from James White, Sr., as he recounts his experiences as a young serviceman looking to provide for, and protect, his family. I particularly like the lessons learned he has tried to teach to the next generation, his grandchildren.

His talk is very powerful and eloquent.

Video above or click here.