Escaping from Alcrataz

May 23

In: Career management

When I was sitting where you are, back in 1989, I would’ve told you that I wanted to be a lawyer. I didn’t really know what lawyers do all day, but I knew they first had to go to law school, and school was familiar to me.

I had been competitively tracked from middle school to high school to college, and by going straight to law school, I knew I would be competing at the same kinds of tests I’d been taking ever since I was a kid, but I could tell everyone that I was now doing it for the sake of becoming a professional adult.

I did well enough in law school to be hired by a big New York law firm, but it turned out to be a very strange place. From the outside, everybody wanted to get in, and from the inside, everybody wanted to get out.

When I left the firm, after seven months and three days, my co-workers were surprised. One of them told me that he hadn’t known it was possible to escape from Alcatraz. Now that might sound odd, because all you had to do to escape was walk through the front door and not come back. But people really did find it very hard to leave, because so much of their identity was wrapped up in having won the competitions to get there in the first place.

There’s a lot of wisdom in those sentences above. I took them from a transcript of a Commencement speech that Peter Thiel gave. He is a co-founder of PayPal.

I’m writing this for a few reasons, First, the speech made me think about the Jeff Bezos view that “we are our choices.” The road you don’t take, in Peter’s case, a high-powered law firm job, is often more important than what you do take.

Second, choices have costs. To “un-brainwash” yourself and get off a corporate track requires a great deal of inner strength. Some family members and friends will think you’ve lost your judgment, and some may even judge you for your lack of wisdom and being a quitter.

Third, it reminds me of my own choices, such as leaving my investment banking job, quitting Bain & Co., and starting Kepha. Those were excruciatingly difficult, but I no longer cared about what people thought.

Fourth, difficult choices can cover career topics, but, also, they can cover decisions about relationships. Has anyone ever agonized about initiating a break-up? Sometimes, relationships can be as suffocating as career choices that don’t mesh with one’s values.

There’s a lot there in Peter’s speech. I encourage you to read it. Here again is the link.

May 12 and My Mother

May 12

In: Family life, Personal, Spiritual


May 12 is “one of those days” on my calendar.

Fifteen years ago today, my mother passed away. It was Mother’s Day then. My mother also was born on May 12. She was only 60 years-old when she died.

I’m amazed by how quickly 15 years have transpired. So much in my life has changed, yet so much feels the same.

As I’ve blogged before, my mother had a very fulfilling but challenging life. She and her family were war refugees; they lost everything they owned in a few hours. She and her siblings all died young, the results of long-term stress and malnutrition. My mother suffered from kidney failure and two bouts of cancer.

Yet, she every day tried her best and put on a good face to the world. She was a very giving person, the life of the party when healthy, and had an insane work ethic when her body allowed for it.

One of my favorite pictures of her is up top. We were in a rough part of Brooklyn then and were visiting the Brooklyn Botanical Gardens. My mother loved being outside and she loved flowers. I remember that day well: a cold hot dog for lunch, my mother happy and healthy.

My mother was frugal. She bought very little for herself. All of her clothing was from discount stores. Her most prized possessions were shoe boxes filled with our greeting cards to her over the decades, which she asked to be placed in her casket.

Later today, I’ll be at 12 noon Mass. I’ve asked that it be celebrated for her. Catholics pray for the dead. We hope that they have found rest.

I’ll be praying for my mother. I will pray that she is at rest and has found complete joy and peace.

A Connecticut Weekend and Imposter Syndrome

May 8

In: Brain hacking, Fly fishing, Personal, Philosophy

Our children are in schools with different spring break schedules. This year, Mrs. T. took trips with various children, while I stayed at home with the others.

So, I just took a belated spring break of sorts over a long weekend. I fished.

I went to a river in Connecticut and stayed at a cheap room on the water. It is at a very working-class part of the state, pretty rural, and it’s an interesting change of pace. Many pickup trucks. Just a few stores.

My routine was:

  • Awaking before dawn
  • Eating nuts for breakfast
  • Hitting the river at daybreak
  • Fly fishing 10 hours+ a day and eating a PB&J sandwich for lunch while standing
  • Eating dinner at a restaurant’s bar and finally sitting down
  • Tying fly fishing flies in my room, while I listen to podcasts
  • Lights out at 9 pm

I couldn’t have been happier.

I fished for 3.5 days, and it felt like just a few hours. I landed many fish, double digits every day. On one interesting day I landed a few dozen.

It’s silent for me all day, except when I chit-chat with the bartender during dinner. It’s very meditative. Almost like a religious retreat. It’s funny that a few dollars worth of hooks and feathers can catch such beautiful fish.

I’d pick this low-cost weekend over any luxury trip any day. I don’t need fancy toys. Just my fly fishing rod and some trout are more than enough for me. There’s something very pure about being outside all day, in a moving body of water, with fresh air and natural beauty all around you.

I think taking care of yourself is really critical, particularly for someone like me, who has Imposter Syndrome. I one day will write more about that.

In the meantime, here are some photos.

Redemption and Shaka

Apr 30

In: Books, Brain hacking, Philosophy, Race

It has been an interesting week. Serendipities about writing and choices.

First, I read Frank Britt’s article about how we write our own life stories and have the ability to change our paths. Then, Anne Mitchell wrote a comment in response, mentioning a Jeff Bezos idea that we are the sum of the choices we make. It reminded me of a conversation with him many years ago.

Then, I picked up a New York Times bestseller, Shaka Senghor’s Writing My Wrongs. A convicted murderer and former drug dealer, Shaka served many years in jail. It was riveting. Anne had heard Shaka speak at the MIT Media Lab and Lab director Joi Ito wrote the book’s forward and how he met Shaka.

Such a small world.

Shaka’s book is about the power of rewriting your life story to find forgiveness and resolve to improve one’s life. He wrote numerous letters in prison, including one to the murder victim’s family.

He also wrote about all of the horrible abuse he experienced as a child and while in prison. He wrote about being in solitary confinement for over four years and the complete madness that overtakes some prisoners in that situation.

Shaka unflinchingly named all of the bad decisions he made. He started to forgive the abusers. All that gave him the resolve to change his life.

And, he most certainly has. Redemption in spades.

His book is important. Please read it.

‘Top 5 Regrets of the Dying’

Apr 29

In: Books, Personal, Philosophy

When my friend Mike Connell told me he was going into hospice, my heart broke. When my mother started receiving palliative care, everything changed.

I know, I know. This is a morbid post. But, bear with me.

Ever since’s Jeff Bezos told me about his desire to avoid life regrets, I’ve been trying to find the survey to which he referred. Apparently, there is a survey of the elderly that asked about their greatest accomplishments and regrets. I cannot find it.

But, this morning, I found online this book. A palliative care nurse wrote it. So, below, are the “Top 5 Regrets of the Dying,” via an article I found (here).

There is much below to contemplate. We truly become the sum of our choices.

1. I wish I’d had the courage to live a life true to myself, not the life others expected of me.

“This was the most common regret of all. When people realize that their life is almost over and look back clearly on it, it is easy to see how many dreams have gone unfulfilled. Most people had not honored even a half of their dreams and had to die knowing that it was due to choices they had made, or not made. Health brings a freedom very few realize, until they no longer have it.”

2. I wish I hadn’t worked so hard.

“This came from every male patient that I nursed. They missed their children’s youth and their partner’s companionship. Women also spoke of this regret, but as most were from an older generation, many of the female patients had not been breadwinners. All of the men I nursed deeply regretted spending so much of their lives on the treadmill of a work existence.”

3. I wish I’d had the courage to express my feelings.

“Many people suppressed their feelings in order to keep peace with others. As a result, they settled for a mediocre existence and never became who they were truly capable of becoming. Many developed illnesses relating to the bitterness and resentment they carried as a result.”

4. I wish I had stayed in touch with my friends.

“Often they would not truly realize the full benefits of old friends until their dying weeks and it was not always possible to track them down. Many had become so caught up in their own lives that they had let golden friendships slip by over the years. There were many deep regrets about not giving friendships the time and effort that they deserved. Everyone misses their friends when they are dying.”

5. I wish that I had let myself be happier.

”This is a surprisingly common one. Many did not realize until the end that happiness is a choice. They had stayed stuck in old patterns and habits. The so-called ‘comfort’ of familiarity overflowed into their emotions, as well as their physical lives. Fear of change had them pretending to others, and to themselves, that they were content, when deep within, they longed to laugh properly and have silliness in their life again.”