The Things that Keep Us Safe

I write about modern finance. Highlighting injustices in the investment world has been a central theme in my work.

I’ve often pointed out the fact that many securities regulations, which were meant to protect investors, have done nothing but harm them by curtailing their opportunities to prosper.

While I don’t fault legislators for introducing well-intentioned bills, I must question the rationality in man-made laws that utterly defy those of human nature.

According to natural law, that which keeps us safe also keeps us from experiencing life.

We are surrounded by risk. It’s everywhere we’ve been and everywhere we’ll go. It’s in every decision we make. It’s in every invention that took man from the cave to the sky. It’s in the food we eat, the words we speak and in the air we breathe.

Risk is inescapable.

It is part of us.

Risk is not just the difference between winning and losing. It is the difference between living and existing. Between evolving and aging. And between love and companionship.

There are repercussions to eliminating risk from the environment – just like there are grave consequences to regulating the risk out of investing.

I have lived my entire life in fear of the unknown. Sometimes I make decisions based on that fear – other times, in spite of it. Perhaps this is why I am so vocal about an individual’s inalienable right to take risk.

If I have learned one thing, it is that the greatest risk of all lies in failing to let go of the things that keep us safe.

90 blog posts down – 275 more to go…

The Place In-Between

Sometimes change grabs us by surprise. We find ourselves propelled into newness by a sudden and unanticipated event.

We embrace it simply because we have no other choice.

However, more often than not, change is gradual. It frequently goes unnoticed until confronted by a memory. Even mirrors can be deceiving. I believe I’ve been looking at the same reflection every day for the past 20 years. But an old photograph of a, now barely recognizable, face tells a different story.

These measured changes are harder to accept. At least for me.

Then there are those instances when you sense change on the horizon. Although you detect its imminence, you have no ability to control, let alone predict, its timing.

These gaping transitions are the most unnerving.

They leave you stranded amid yesterday and tomorrow – anxiously waiting and torn between holding on or stepping forward.

Any excitement of beginning anew is tempered by the feeling of the past slipping away.

This is the place in-between black and white and the red, green and blues. It is a hazy realm where colors bleed.

When I’m stuck in the “in-between” and the weariness of waiting has taken its toll, instead of looking beyond the borders, I try to find the solace within them.

And when I do, I am reminded of how much beauty there is in the pink, yellow and purples.

89 blog posts down – 276 left to go…

This Blog. This Dreadful, Laborious, Obnoxious, Magnificent Blog.

87 days ago I made a new year’s resolution to start a new blog.

This blog.

I vowed to post every single day for one year. It was a commitment made – in haste – without much any thought.

At the time, I had a lot on my plate.

A lot.

Much more than the average bear. But that’s a saga for another time.

Let’s just say that on January 1, 2018, the very last thing I needed in my life was to add another item to my already overwhelming daily “to do” list. But for some unfathomable reason, that’s exactly what I did.

Maybe, I’m just a glutton for punishment. Or, perhaps I’m terrified of running out of things to do. I once read that it is physically impossible to die until all of the tasks on your “to do” list are checked off. Right now I am so far behind that I’m sure I will live forever.

The truth is, I felt that daily blogging might make me a better writer. My goal in writing every damn day was to get the creative juices flowing and give me the impetus to finish my book.

When I began this undertaking, I asked myself, “how hard could it possibly be to capture a random thought and throw it into a short blog post? And, would it even matter if I skipped a day or two or even four? I mean, who would even care?”

As it turns out, I would. I’d care.

It’s not in my DNA to do something half-assed. So, here I am, stuck blogging every freaking day until December 31, 2018.

Although I pretty much write for a living and even though I’ve been journaling for decades, I was petrified about bringing private thoughts to a public blog.


So much so that some posts are concealed under password protection.

But exposing myself is something that I must do, for I will never become the writer I want to be by placating my fears and holding back.

I need to reach deep – to boldly venture into places within that even I never knew existed. I need to extract whatever it is that I find and turn it into words.

88 blog posts later, I’ve concluded that this blog is far from a mere exercise in futility. This incredible inconvenience has turned out to be one of the most cathartic experiences of my life.

While I don’t know if I’m a better writer today than I was 88 days ago, I am certain that I’m a less fearful one. And maybe that’s enough for right now.

88 blog posts down – 277 more to go…

Time to Stop Chasing IFs & WHENs

I am guilty.

I am guilty of waiting around for specific events to occur before allowing myself to take action.

When the holidays are over, I will start my diet.

As soon as this next project concludes, I will finish the remaining 3 chapters of my book.

Even worse, I’ve been guilty of making present decisions based purely on future, often unrealistic, hypotheticals.

If I can only lose another 10 pounds and finish my book, my life would be perfect.

As I squander my time creating expectations, I find myself wondering, “Am I actually setting goals or am I just procrastinating – fooling myself into believing that the future will bring a more convenient time to act?”

What if I’m so preoccupied with setting milestones that I completely miss the moment?

Life doesn’t wait.

Neither will ideas.

When I was younger, and even though I had lots more time, I rarely waited. I just did.

I would have preferred to have had a lot more money in the bank when I left Wall Street, at 28 years old, in pursuit of an entrepreneurial venture. Instead, all I really had was a vision, drive and the willingness to accept defeat.

Since my ideas wouldn’t wait, I just threw caution to the wind. A decision I have never come to regret.

Ironically, now that I’m older with less time to waste, I catch myself procrastinating more. I am far more cautious. Perhaps my risk tolerance decreased with maturity.

Tomorrow is just a question mark. I know that it is fruitless to bank on question marks. Yet, I wait.

My children are a constant reminder of how fast the earth spins. There is no time to wait for IFs and WHENs. There isn’t even time to prepare for them. Life only affords us the time to do.

Yet, I still wait.

Until today.

From this moment on, I am making a conscious decision to stop chasing IFs and WHENs. Instead of holding out for hypotheticals, I’m gonna try living in definitives.

I’ll let you know how it goes.

87 blog posts down – 278 more to go…

It’s All About the Riff

I once dated a guy who didn’t like music. I refer to that dating period as the dark ages.

The relationship ended upon realizing that I would never be able to truly connect with someone who lacked appreciation of a melody.

To compensate for the months of harmonic emptiness, I began dating a musician whose obsession with music was as strong as his predecessor’s aversion to it. While I was taken with his talent as a guitarist, I admit that I dug the music much more than the guy. Needless to say, that one didn’t last very long either.

Fortunately, every relationship, no matter how fleeting, concludes with a parting gift – a cognitive souvenir of sorts that helps us uncover something about ourselves. Ironically, both men helped me recognize the need for music in my life.

In addition to opening my ears to new chords, the musician taught me about the magnitude of the riff.

A riff is a sequence of notes or chords that typically shape a song. Riffs are often repeated throughout an arrangement, making them a tune’s most indelible feature. The riff is the hook that attracts listeners to the song, keeps them singing along and playing it back over and over again in their minds.

If you are seduced by the riff, you’ll fall in love the tune. On the other hand, if the riff isn’t appealing, you’ll be switching the station every time the song comes on the radio – like most people do when this very painful tune from Miami Sound Machine is being played.

When you think about it, relationships are as simplistic as a catchy riff.

86 blog posts down – 279 more to go…

Poetic Justice

Here’s a little rhyme about how a tenderhearted poet went to sleep one evening and awoke a warrior.

You can call it a poem about a poet that personifies poetic justice.

The Warrior

85 blog posts down – 280 more to go…

Don’t Follow the Yellow Brick Road

Today’s post is inspired, once again, by my uber insightful 10 year old daughter who also happens to be my spiritual advisor.

Yesterday, completely out of the blue, my little Stoic-in-Training (S.I.T.), cautioned me to never follow the Yellow Brick Road, for it is paved with delusions and leads to a charlatan who can’t give you anything more than you already have.

Once again, her instincts are correct.

We are much better off taking an uncharted path that leads to the unknown. There is less of a chance for disappointment and so much more to gain.

84 blog posts down – 281 left to go…

Give Back the Everlasting Gobstopper

I promise this will be the last blog post containing a Willy Wonka reference – at least for a while.

But today’s Wonka lesson is arguably the most significant one of all. Even more important than, “Burp, Charlie, burp. It’s the only way.”


Life is constantly asking us to decide between right and wrong. You don’t have to be a Willy Wonka fanatic to know that the world has no shortage of liars, cheaters, and self-obsessed narcissists, and that given the choice between right and wrong, most people will side with wrong.

That is why the small virtuous act of returning the everlasting gobstopper earned Charlie Wonka’s entire chocolate fortune.

Upon being handed back the metaphoric candy from Charlie, Wonka utters, “so shines a good deed in a weary world.”

As it turned out, the gobstopper was nothing but a ruse to test Charlie’s loyalty and nobility. The riches promised by Slugworth for Wonka’s everlasting gobstopper were nothing but an illusion. But, of course, Charlie did not know that he was being tested. Nor did he know that there would be a reward for returning the gobstopper. Charlie gave it back, rejecting Slugworth’s bribe, because he knew in his heart that it was the honorable thing to do.

Meanwhile, over the last 47 years, countless millions have watched Willy Wonka and the Chocolate Factory – all witnessing the rewards of righteousness. Yet, they have learned nothing. When given the opportunity, I am astounded by how many people today cling to the proverbial gobstopper.

It’s as if the world is even wearier in 2018 than it was in 1971.


All of the chocolate or money in the world isn’t worth the price of your integrity.

83 blog posts down – 282 left to go…

So Much To Do and So Little Time – Don’t Reverse It

When you’re a kid, life is like an everlasting gobstopper.

The minute hand knows no bounds. Days are filled with so many hours, yet very few tasks to fulfill. Even play time can grow boring after a while.

At 25, you feel invincible – as if you have oceans of time and the strength to swim forever. While more has been added to your “to do” list, you feel like you have eons to accomplish it all. Wasting time is a guiltless pleasure.

When you are 35, the list rapidly expands. Suddenly, the things you want to do start dwarfing the things you need to do. You can now hear the ticking of the clock. That vast ocean feels more like a river quickly leading into a pond.

By the time you reach 45, you realize that the everlasting gobstopper is nothing but a scheme concocted by an eccentric candy maker. You wonder how you were ever naive enough to believe in forever.

It is impossible to recognize the value of something that you perceive as limitless.

Ironically, it takes time to grasp just how precious time truly is. And that is precisely the moment when you realize all that needs to be done.

This brings me to Wonka Lesson #2:

There is so much to do and so little time. Don’t reverse it.

82 blog posts down – 283 more to go…

Doubting What Nobody is Sure About

I must have been about 7 or 8 years old the first time I watched “Willy Wonka and the Chocolate Factory”.

It instantly became my favorite movie (the Gene Wilder version – not the freaky Johnny Depp rendition).

I mean, at the time, candy was the only currency I really understood. And what grown-up kid doesn’t fantasize about swimming in a chocolate river? Come on, admit it. You know you want to.

However, after having watched the movie at least a thousand more times, I realize that Willy Wonka is more than just an endless pouring of sweets, golden geese eggs and everlasting gobstoppers.

Some of life’s most important lessons can be gleaned from this eccentric candy maker and his Chocolate Factory.

We live in a world overrun by cynics where a handful of dreamers fight to belong. But, thankfully, even the most skeptical among us carries a flicker of desire to believe the unbelievable.

Without it, Hollywood couldn’t sell movie tickets. And hopelessness would plague the planet.

Wonka lesson #1: So long as there is even the slightest urge to suspend disbelief, it’s hard for even the most consummate cynic to doubt what nobody is sure about.

81 blog posts down – 284 more to go…

Advice for Storm Creators

This morning I came across a great quote by an unknown author:

“Some people create their own storms, then get upset when it rains.”

This quote characterizes so many different types of people.

There is the Firestarter. I’m sure you’ve met a Firestarter. A Firestarter is a pyromaniac who is obsessed with setting fires, but who can’t take the heat from the blaze.

Firestarters are a lot like bullies in that way. Although they are relentless intimidators, bullies cower with fear as soon as they are stood up to.

I despise bullies. But I do enjoy a good bully movie – particularly those scenes where the underdog defeats the bully. I’m pretty sure that the rewind button was invented precisely for such scenes.

No matter whether you’re a firestarter, a bully, or just a plain old troublemaker, perhaps you should think twice before starting a storm if you can’t dance in the rain.

80 blog posts down – 285 more to go…

My Inspirational Beach Chair

Today my daughter found a box of my old journals (note to self: I must burn my old journals before I die).

An entry from May 19, 1996 had us laughing out loud.

According to the journal, May 19, 1996 was a gorgeous, 82 degree sunny day that found me sunbathing on my 80th Street terrace and, of course, writing.

In 1996, I did not own patio furniture. I had one yellow beach chair that I would schlep with me to Fire Island and to the Hamptons in the summers. And, boy did I adore that beach chair – but apparently just not enough to shelter it inside my apartment.

All year long, I stored the beach chair on my terrace.

For those who don’t remember, the winter of 1996 was a historic one for NYC. That January, the city experienced one of the biggest snow storms of the last century. In fact, for weeks the city was buried under mountains of snow. Manhattanites even skied to work.

1996 blizzard

All winter long, from my bedroom, I thought I could hear strange cries coming from my balcony. But I naturally assumed that I was hallucinating and just ignored them. However, on May 19, 1996, I discovered that those shrieks had been my favorite beach chair getting tortured by Mother Nature.

Although it put up a good fight, the winter of 1996 was intent on destroying my yellow beach chair. When I discovered the beaten chair on May 19th, it was so broken that it was barely usable. In fact, the part where one would sit was completely gone.

But there was no way in hell that I was wasting a picture perfect Sunday morning combing Manhattan for a new beach chair. No. I would wait until Memorial Day weekend and pick one up in the Hamptons for three times the price like any rational New Yorker would do.

Instead, on May 19, 1996, I found a way to make use of the yellow beach chair with a giant throw pillow. As I sat on the battered – yet resolute – chair, taking in the sun, I wrote.

The following excerpts were inspired by this Stoic of a beach chair.

“I once again find myself honored to be sitting in this invincible, headstrong chair that is determined to stand the test of time. I will never throw out this chair. If it should happen that one day its arms fall off, I will rest my elbows upon my legs. I will always find a need for this broken chair. One day when my life is filled with a husband, 3 children and beautiful lawn furniture, I will still have a need for my decrepit yellow beach chair.”

Now here’s where it gets good…

“In fact, I am going to take this chair with me wherever I go. It will accompany me to the gym. It will join me on shopping sprees. I will carry it with me on my journey to the Dry Cleaners. I am even going to take it to work with me.”

Notice that the chair wasn’t joining me on dates, though. Because, now, that would be weird.

“After hanging on to dear life, dangling 19 stories during 30 blizzards, this chair is in for the ride of its life. This rusting, yet gracefully aging, yellow beach chair is my idol.”

Now, here’s where it gets a little personal…

“If I should ever fall short of my dreams, I will sit on this chair for inspiration. And from this chair, I will find the strength to chase my dreams all over again.”

But I did not stop there. No, I did not.

I concluded by declaring that, “This is the chair I want to be when I grow up.”

Now, 22 years later, through my laughter, I can feel the irony. I did indeed become that yellow beach chair.

79 blog posts down – 286 more to go…

Age is Privilege

Today’s post is inspired by my Mom – and Ralph Waldo Emerson. Although I will not disclose her age, let’s just say that I am pretty sure that she is older than me.

Anyway, my allegedly older and definitely much wiser Mother, informed me today that when you reach a certain age, you have earned the right to say whatever the hell you want.

I had my suspicions that this might be the case. I mean, I learned years ago from a Seinfeld episode that our elders are licensed to steal batteries; so unfettered, unfiltered speech only seems logical.

With age comes privilege. And the higher the birthday, the less one cares about what other people think. See chart below.

care age

The truth is, it really doesn’t matter what is said by anyone at any age. It’s one’s actions that count the most, for what people do speaks so loud that no one could hear what they are saying, anyway.

77 blog posts down – 288 left to go…

A Few Moves Away from Perfection

When I was 11, I got my first Rubik’s Cube.

As all brand new Rubik’s Cubes do, it arrived in its already solved state. Every square was precisely positioned to ensure that the colors of each of the six sides of the cube were homogeneous.

In order to play with the cube, you need to mix it up by repositioning the squares. You may one day be able to return it to its perfected condition. Or, you may not.

There are 43,252,003,274,489,856,000 quintillion ways to scramble the Rubik’s Cube. In fact, if you turn the Rubik’s Cube once every second, it will take you 1.4 trillion years to go through all the permutations.

There is a very real possibility that the unscrambled cube may stay forever imperfect. But you’ll never know unless you disrupt it.

Some never touched their cubes. For decades, many cubes have sat on shelves undisturbed and perfect.

At first, I hesitated to muddle mine. What if it remained imperfect forever?

But, if I never disarranged it, I’d never get to experience the fun in playing with it or the challenge in solving it.

Since I was only 11 years old, I had time on my side. I figured I had at least 1.4 trillion years left to figure this thing out.

So, I went for it and messed up my cube pretty badly. The colors were all over the place. No square was where it should be.

I couldn’t put it down.

It wasn’t long before I figured out how to get one side. Then two. Then three.

Then I got to four. At this point I was scared to make a move. I was fearful that in my quest for all six sides, I would destroy the accomplishment of obtaining four sides.

But, my parents promised me a Jim Dandy Ice Cream Sundae from Friendly’s if I completed all six sides. And hot fudge is a very powerful motivator.

Shortly thereafter I solved the six sided puzzle. I don’t remember the exact moves it took me to get there. It kind of just happened.

The other day, my daughter handed me her scrambled Rubik’s Cube and asked me to solve it. Although it has been a while and I now have a lot less than 1.4 trillion years left, I decided to give it another go.

When I realized that I was just a few moves away from perfection, it occurred to me that the Rubik’s Cube is a lot like life. It’s more enjoyable when you mess it up every once in a while.

76 blog posts down – 289 left to go…

The Art of the Schpiel

When I was a kid, a friend’s mom once took us to Burger King (I know, eeew).

My friend didn’t want to go inside the restaurant (if you can call it a restaurant). In fact, he was adamant about not going in. At first, he wouldn’t stop whining and pleading. But his mom just seemed to ignore him.

Then he began to pitch his case. He explained that he wasn’t hungry, that the tables were dirty and that he needed to get back home to play space invaders.

His mom was hardly convinced.

Then he started unleashing threats. “if you make me go inside, then I just won’t take off my coat.”

His mom laughed. “So, leave your coat on. Why would anyone care?”

Then he started to negotiate. “If you let me wait in the car, I’ll keep my jacket on.”

Umm. Okay.

I don’t know if it was his stupidity or what, but her patience was growing thin. She screamed, “You are going inside! No IF ANDS or BUTS about it!”

Poor little Stewie capitulated. He ended up sitting at a filthy table, with his jacket on, wolfing down a double whopper with cheese.

I learned many valuable lessons that day that I continue to carry with me.

Whining is just annoying. Pleading is pathetic. Threats are futile absent fear. And negotiations require actually understanding what the other person wants.

But the most important lesson I learned that day was: don’t ever f&ck with a Mom!

75 blog posts down – 290 more to go…

The Roller Coaster

“You know, when I was nineteen, Grandpa took me on a roller coaster. I always wanted to go again. You know, it was just so interesting to me that a ride could make me so frightened, so scared, so sick, so excited, and so thrilled all together! Some didn’t like it. They went on the merry-go-round. That just goes around. Nothing. I like the roller coaster. You get more out of it.” – Gil Buckman’s Grandmother

When it came to business or investing decisions, I always rode the roller coaster.

I never had a problem throwing caution to the wind when it came to money. Perhaps it’s because I’ve always perceived money as just something that is made or lost. And, when lost, it could always be made again if you’re willing to put in the effort and take another chance.

Sometimes I lose. Sometimes I win. But every time that I’ve ever lost financially, I always came out ahead, for any losses in dollars have always paled in comparison to the gains made in knowledge and experience.

This attitude made me a fearless trader. And it was trading that eventually gave me the impetus to take entrepreneurial risks. While there were certainly many ups and downs, there was never a trace of boredom.

My attitude towards love could not have been more antipodal.

When it came to matters of the heart, I was forever playing it safe. For a long time I stayed on the merry-go-round – continuously going around in circles. Dating became monotonous. I’ve experienced the exact same date over and over again. I’d have the same conversation while drinking the same drink. The only difference was the guy I was facing.

It all changed 15 years ago when I took a chance on the one guy who made me laugh until my stomach ached. It also didn’t hurt that he was a much better looking Richard Gere (and I’m talking American Gigolo or Pretty Woman Richard Gere – not old, present day Richard Gere).

In honor of his birthday, today’s blog post is dedicated to the guy who still keeps me laughing.

There is no one else I’d rather be riding the roller coaster with.

74 blog posts down – 291 more to go…

Stronger in the Broken Places

I used to stress out every time my kids caught a virus – until I learned that these illnesses were helping to strengthen their immune systems.

We are stronger in the places we’ve been broken.

I’ve often envied those who could let themselves fall in love so easily. I really never understood how one could give their heart so fearlessly – time and time again. Then I realized that their hearts had been strengthened by many, many breaks.

Indeed, we are all stronger in the places we’ve been broken.

Life’s setbacks can feel like a punch in the gut. But each hit reinforces one’s resolve.

Pain breeds strength, and strength is a necessary component to the healing process. When you think about it, strength is both the medicine and the cure.

That is why our mended parts are so often our most resilient.

73 blog posts down – 292 more to go…

To Whom Does the Future Belong?

Ronald Reagan once said, “The future doesn’t belong to the fainthearted; it belongs to the brave.”

While bravery is an admirable and important quality, unlike adaptability, it is not essential to survival.

Nothing – not even courage – could exist without the capacity to adapt to changing circumstances.

Have the courage to accept change. But above all, acclimate to it.

The future belongs to those most malleable.

72 blog posts down – 293 left to go…

Living Will Age You

Some people fear despise aging.

As if it’s a bad thing.

Meanwhile, one would think that growing older is much better than the alternative.

But, vanity is a powerful emotion. Almost as mighty as greed.

Narcissism keeps people lying about their age. Some are so obsessed with age that they forge their birthdays on government issued IDs. Yes, they would rather commit a crime than admit their true age.

I don’t get it.

Age is just a number. And typically the higher the number the greater accumulation of wisdom.

I truly love aging. Every birthday has gifted me with increasing confidence. Each strand of grey hair contains amassed knowledge and pride. And every wrinkle holds a lifetime of laughter.

There is nothing wrong with getting old. Now, getting fat, that’s another story.

71 blog posts down – 294 more to go…