Failure Stories

“If at first you don’t succeed… you’ll probably fail the second time too.”

Negativity.  It’s generally frowned upon, but we all have those moments where unhappiness is duly warranted.  I’m talking about those times when “look on the bright side” just doesn’t cut it.  When there is no “silver lining”, no matter how hard you look.

Recently, I encountered two of these terribly unsuccessful events.  True failures, in every sense of the word.  These are the stories:

  1. “Ferry to Failure”


Some people like to say “Cheer up, it wasn’t that bad!”

It was that bad.

After our winter academic program in Puerto Rico, we had 5 days free days to explore the island before classes started again in Boston.  Since Puerto Rico isn’t known for its intercity public transportation (it doesn’t exist), I decided to rent a car.  I had one main destination in mind – visiting Aguadilla to see my father’s birthplace.  I found a friend who wanted to join, and I happily agreed to drive to the Fajardo Port the next day so we could go to Vieques.  In short, we each had one place that we HAD to visit – mine was Aguadilla for family reasons, hers was Vieques for research and personal reasons.

We all took the day trip to Aguadilla and had a blast.  A local had warned us that we needed to leave early to catch the ferry the next day, but it was only an hour away on the map, so we felt confident that we could catch the 9am ferry.

We parted ways and headed back to our hostels feeling quite jolly.

If only we had known that the next day would be one of the MOST UNFORTUNATE days of our lives.

It was so bad, that I have no choice but to look back on it as a crime.  However, before a man can be judged guilty, the jury needs to examine the evidence. First, some facts:

– We were staying in different hostels, hers in Santurce and mine in Old San Juan.  By parking the car in OSJ, this meant that I would have to walk 10 minutes to get from my hostel to the car and then pick up my friend before we could go to the ferry.

– I had an “emergency” tutoring lesson (I tutor over Skype) that went until 2:30am that night.

– As a result, I set my alarm to 7:00am

– I was supposed to pick up my friend at 7:30am so we could get to the dock, one hour away, by 9am

When I woke up, I was, naturally, quite tired.  But I gathered my belongings, checked out of the hostel, and drudged 10 minutes to my car.   I arrived at my car at 7:20.  This was later than I had wanted, but Google maps said it was an easy 15 minute drive to pick up my friend.


If you’ve ever driven in San Juan, then you know that the roads around the Santurce – San Juan island border are incredibly complicated.  What had seemed like a simple turn on the map ended up shooting me down a highway with no exits for miles.  Since I had no wifi for my data-free smart phone (possibly a fault in this day and age???), I had to rely on a paper map that I picked up at the rental car counter.   However, it wasn’t much help when the speed on the road was too fast to see the road signs.  After zigzagging back and forth like a forelorn lunatic, I finally managed to get back on track.

Too late.

I pulled up at my friend’s hostel at 8:10am.  I felt miserable, as if I had betrayed a sacred oath to my friend.  Fortunately, for all of my depression, my friend held onto hope like a cowboy on a bucking bronco.  “We can still make the 2pm ferry, ” she cheerfully told me.

We headed to the ferry, and naturally, missed the 9am departure.  The next four hours consisted of me bumbling about like a dodo, forgetting my bag in a shop, paying for the parking lot and then leaving again, etc, etc…  The highlight was waiting in line behind students on a class trip at Burger King.

Finally, the 2pm ferry arrived, and we got on.  I felt worse than a novel by Victor Hugo.  Now my friend would only get 2+ hours of daylight on the island (it was an hour ride), AND she felt bad because we were supposed to meet someone earlier that day.  Since I was exhausted from staying up late (my fault), I fell asleep across some seats.

When I woke up, I realized two things.  One, it was 2:45pm.  Two, the ferry still hadn’t moved.   As we soon learned, the ferry was experiencing “technical difficulties”, which, according to a local, happened all the time.  By 3pm, we decided to abandon the ferry.  “Why couldn’t this have happened this morning!” my friend asked.  She was angry now, and rightfully so.

As we drove back, my friend gave an incredible effort to try to look on the positive side – we were still in the tropics, we were listening to a fire Reggeton radio station – but at the end of the day we couldn’t escape our sour moods.  We decided to head straight back to our hostels and try to forget this horrible, rotten, no good day.

However, there were other repercussions.  First, I had to extend my car rental.  This meant an additional $60 AND a terrible hassle because I could no longer park in Old San Juan due to the enormous Festival that had begun.  Second, by losing a full day, I had to cancel my trip to El Yunque, which I was (am) pretty bummed about. And third, I now felt incredibly guilty for ruining my friend’s trip.  It was almost as if I had fallen short on my end of the deal – she had accompanied me on my dream trip, and now I had tossed hers to the wind.

We did end up going to Vieqies on the 9am ferry the next day, and we did have an awesome time.  And in the long run, $60 sure isn’t something to cry over.  But there’s no denying how terrible we felt that day.

No matter how you look at it, that day was a failure, and a painful one too.


  1. “Impossible Interview”


Last December, I applied for a part-time job at Harvard.  After sending in my applicaton, I received an email scheduling an appointment at 3pm on Monday.  I marked my calendar, and when the day of the interview arrived, I got ready (clothes, responses, position refresher) and made sure to arrive early.

When I arrived, a receptionist checked me in, took my coat, and asked me to please wait in one of the chairs.  I sat down and began waiting.  People came in, people left.  I read the flyers on the desk.  I checked my watch.  3:10.  I sat in the hard wooden chair, fingers twiddling up a storm.  Finally, the receptionist called me over.

“Hmmm, it seems you’re not in our schedule.”


In times like these, the dreaded B word always jumps out, craving for attention.


Did I misread the email, or was it a fault on Harvard’s side?

After checking the schedule, the receptionist informed me that the interviewer I was going to see was booked all day.   Fortunately, she was able to reschedule for one hour later, at 4pm, with another interviewer.

I agreed, and headed back out into the chilling wintry mix to mail a package.  After checking a computer, I relieved my conscience by discovering that I was not mistaken (curse you B word!).  The original appointment was at 3.  However, I’m not one to hold a grudge against another, and I resigned myself to the fact that the interview would just have to be at 4.

Not wanting to be late, I hurried back and arrived at 3:54 for my 4:00 appointment.

To my surprise, I found another receptionist.  “Can I help you?” she asked.

I explained my situation and that I had returned for my interview.  When I told her my name, a look of utter confusion spread across her face.

“There are no open slots now,” she slowly replied.  “But I think there are two Matthew Bakers here.”

After checking with multiple other people on the phone and in person, we discovered that minutes before I arrived, another Matthew had come in looking to meet with the EXACT SAME INTERVIEWER AT 4PM!  Naturally, after confirming that the visitor was Matthew, the new receptionist let him go by.


So long story short, I had to reschedule. Again.  Really?

As I walked away, I considered the following:

In terms of fault, I was completely blameless.  However, I was beginning to believe more and more in signs.  What if this was all a sign, be it from some higher being or elemental force or whatever, that this job was not for me?

Amidst the confusion, there was one thing that I could be 100% sure of: this trip was a total failure!


* Mr. Chan image from