Category Archives: theory

Why It Pays To Be A Misfit

Photo: Amanda Jordan via Unsplash

About five years ago I attended a party that a friend was throwing in celebration of her new clothing store launch in downtown Los Angeles.

I spotted the host off to one side and walked over to say hello. As I approached, she looked around, then behind me.

“Did you come alone?” She asked in a high pitched voice, the end of the sentence curling up into an extra-squiggly question mark. “Yep,” I cheerfully replied, holding up a pair of neon-yellow drop crotch trousers to my waist. She grinned. “You’re such a lone wolf! I love it.” She touched my arm in a way that maybe she thought to be conspiratorial before turning to walk away.

I get it, I’m independent. I live alone and traverse social circles fluidly, dipping in and out of various groups while enjoying time spent alone immensely. Still, her comment stuck because the tenderest part of me felt like a misfit for being this way, an outsider even — as though by being independent I was somehow doing something wrong both socially and in life.

I began paying closer attention to those around me who I considered to be independent. I looked for cues and commonalities in both their actions and in the traits they expressed. I noticed that some of them are misfits in the most admirable (and even lovable) of ways, and that those traits can translate to big moves in business.

Misfits can be brutally honest, for example they say things like “Great story, thanks for sharing.” They yawn loudly at dinner. They are masters of the chat and cut.

What I discovered was a treasure trove of traits that make a certain type of independent person unique, uncompromising, and at times terrifically entertaining.

I also found that some highly productive and creative people — including many successful business founders and leaders —are all misfits in their own way and share some of the following traits.

1. They play big.

Misfits think beyond their perceived set of limitations. They take big risks because they understand that the long term reward outweighs any immediate risk. Some misfits live for the possibilities — they proactively seek opportunities and double down where they think they can win. This is sometimes effectuated to set an example, and other times pursued for personal gain.

2. They speak their mind.

I once met a very successful female entrepreneur in a line to board a bus at a wellness retreat. We got to talking and as we boarded, she casually said something to me about her business that I’ll never forget. “I’m not going to do that, it’ll hurt my soul.” In that moment I had laughed, but secretly I was also relieved. I respected her ability to unabashedly voice her concerns — it made her relatable and human, and gave me permission to think about adopting a similar philosophy to my own life.

3. They are relentless.

While their actions don’t always seem logical, over time they might become crystal clear. In business I’ve noticed that many misfits are often relentless in asking for what they want. They are also unafraid of rejection and will be persistent enough to keep asking — or find another way — until they get what they want. A friend of mine is a band manager. Every time we go somewhere together she manages to find a way to get in the door, behind the rope, onto the stage, and into the after party. When I asked her what her secret was she simply winked and said “You have to find a way to weave your web around them.”

4. They do whatever it takes.

Independent people tend to be focused on their own priorities. At work, they look for the end goal and do whatever it takes to get there. At one former job, my boss at the time knew that in order for us to land a critical new business partner our odds were greater if we met with the decision-makers in person. We scored a meeting, and before I knew it we were boarding a plane from San Francisco to New York where the winter storm season was at its worst. We pulled an all-nighter polishing up our presentation for a twenty minute meeting with someone who had zero vested interest in our company. There was no guarantee of a favorable outcome, but my boss had demonstrated the importance of doing whatever was necessary in order to take the opportunity as far as it could go.

5. They break the rules — and don’t look back.

For many misfits, there simply are no rules. Rules can be seen as a distraction and their actions often reflect this. I once had a colleague who came barreling into the office at seven in the morning each day and left at four in the afternoon. She knew that those were the hours in which she was most productive, so that’s when she showed up and left for work. It took someone boldly breaking the rules to demonstrate how efficiencies could be made.

6. They are quirky and memorable.

I once worked for a very successful entertainment executive who was a sought-after speaker. Often times he’d bring a squirt gun to an event with him and shoot water at speakers who started to sell their company rather than speak to the topic at hand. (He also had an electric cattle prod in his office that was given to him as a gift, and subsequently my desk was zapped a couple of times but that’s for another story.) I know many executives who surf, skateboard, or deep-sea scuba dive. Many have large personalities or distinctive character traits that aligns them on a level to any central character from a Wes Anderson film.

Misfits are important to business and society because they’re unafraid to carve their own path, which is necessary in business for making considerable progress and change. It can be lonely at times to be an independent person, but in other ways can be extremely beneficial. When we march to the beat of our own drum, we follow the paths available only to us. This leads towards alignment with our goals and personal definition of success — even if at times we need to show up alone.

This post has been syndicated from Thrive Global

Becoming Antifragile – How To Gain From Disorder


Image Credit: Andre Faria Gomes

Image Credit: Andre Faria Gomes via Slideshare: Antifragile: Lessons Learned

“Wind extinguishes a candle and energizes fire. Likewise with randomness, uncertainty, chaos – you want to use them, not hide from them. You want to be the fire and wish for the wind.”

-Nassim Taleb

Last week I gave a talk at the monthly Catalysts Collective event here in San Francisco on the topic of antifragility. The following points are highlights from my talk.

To understand the premise of Antifragile – Things That Gain From Disorder there are three key areas to consider.

We know what it means to be fragile – to be easily broken. Another way to interpret it is to be damaged by disorder. The world’s banking system is a good example – something left vulnerable to chaos, randomness, and uncertainty.

After the state of fragility comes resiliency. Things that are resilient have the ability withstand disorder. Imagine a structure built to withstand earthquakes. When an actual earthquake occurs, the building (hopefully) remains standing. It does not change.

A great story of being resilient is the phoenix. The phoenix may rise from the ashes, but he rises only to become what he once was before. 

The final state Taleb focuses on is the state of being antifragile.

Antifragility is when something benefits from disorder. While startups are known to harbor an improbability of success, when viewed in increments success happens as a result of randomness, chance, volatility and instability. 

When viewed from the macro level, the startup economy benefits society as a whole. It creates room for opportunity and innovation. Things like volatility and instability are required in order for them to achieve the point of contribution at scale. This concept can be applied to the contribution of individuals too – organic things, like muscle mass, require some level of instability or challenge in order to grow.

I believe that being antifragile is essential for personal revolution.

Some benefits of being antifragile include:

  • Increased confidence
  • Welcomeness to change
  • The allowance of discomfort
  • Possessing a growth mindset versus a fixed one.

Here are  ways to become antifragile:

  • Think of perceived failure as opportunity
  • Lean into fear
  • Embrace community
  • Listen to yourself and to others
  • Seek opportunities
  • Build a strong baseline
  • Use the barbell strategy.

The barbell strategy is a method presented by Taleb. Consider the image of a barbell. The maximum amount of risk you’re willing to take goes on one side. It’s balanced by Maslov’s basic needs (food, water, safety) on the opposing end.

This is a very basic introduction to the basic concepts of Antifragility. If you’d like to learn more, I recommend checking out the book itself or visit the following blogs that present nice summaries and applicable tips for becoming antifragile.

Taylor Pearson – Antifragile Book Notes

StartupBros – How You Can Profit From The Unknown: Becoming Antifragile

Buy – Antifragile: Things That Gain From Disorder (Amazon)

Summertime Reads: The Element, at Work


There are many books written and released around this time of year to entertain us on a hot, sunny, leisurely day at the beach with an ice-cold bevvy at hand. Some of these are written to educate, examine, and create dissent around current affairs, while others are written to inspire, entertain, or encourage us to think outside the box to better make sense of the world around us. Some books even manage to move the reader on a deep and profound level.  I recently devoured a book that for me, accomplished all of these.

The Element, by acclaimed speaker and thought leader Sir Ken Robinson, discusses the basic desire for us as human beings to connect to our individual “element.”  The Element, in essence, brings us to the core of our talent and as unique individuals, what we’re most optimized to do as a productive member of society.

The theme, admittedly au courant, is reminiscent of authors like Chris Guillebeau who encourage a similar aesthetic that our prime place of happiness and productivity exists where passion meets purpose.

In a reverse Marxist twist, Robinson taps into the education system and breaks apart the very formulaic systems created to educate, take stock of our talent, and train us for the job market. He explains that our element cannot be established with the current systems in place. He explains why standardized testing is a fluke on so many levels and convincingly provides reasons why the system’s measurements of strengths and intelligence are broken.

According to Robinson, unlimited variables exist that we do not acknowledge. From the importance of creative intelligence along with other possible “senses” – kinetics, intuition, and balance, to start – we cannot possibly come close to ascertaining a true path for each of the six billion human beings on earth with the methods currently employed.

What struck me repeatedly were the similarities between the flaws in our education system — and the unaddressed flaws in the construct of the present day working environment.

Robinson says:

“The current processes of education do not take account of individual learning styles and talents. In that way, they offend the principle of distinctiveness.”

In the prevailing 21st century business model of start-up culture and the race to IPO the next product, how does this fit in?

In many ways.

We hire programmers as modern-day line workers. They serve as mechanics, tasked with developing solutions and moving repeatedly in a reactive basis rather than a proactive one. Little regard is given to the creativity and underlying passion that this person may have as an individual.

We do not inspire our programmers, developers, managers, salespeople, and even designers to be proactive, to be curious, to learn, challenge, and be challenged. At a hot organization today’s talent is underpaid, uninformed,  yet highly in-demand for the technological advancement they afford.

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V. Context and Supposition

Hand-delivered meaning courtesy of air status-quo.
We secure it in boxes making sense of the world.
Those who find a fit win the best prize.

Is this an excuse for particular behaviours?
I hold dearly to a thread of paths undefined.

Independent thinkers awaken outside of the box.
Circumstantially we’re at risk to lose – or to have  – everything.
I choose beyond measure, unsure if this includes us or boxes.

Creative people seek a place at the table through craft.
In diluted form of luck it drips to the masses.

I saw a photo I shouldn’t have seen
and whip back full of piss and vinegar
upset from the displaced context of things we see online.

I’ve outwardly changed my tune to cancel the noise.
No one will ever know the box I’ve built.

Shiny object or person of affection
game changer or playing games
I’ve since grown tired of hustlers and find no amusement in deriving deduction.

Gray is nothing until it is something, a social acknowledgment signed by both parties.
Until this is proven, we independently choose a path for truth
whomever the guide may be.

Time vested in nothing is a devaluing shade of assumption.
I ask why we burn through people, but maybe I’m the one who does it.
We want it all.

PS I’m not crazy

IV. Symmetry and Sundials

Special principle of relativity: If a system of coordinates K is chosen so that, in relation to it, physical laws hold good in their simplest form, the same laws hold good in relation to any other system of coordinates K’ moving in uniform translation relatively to K. — Albert Einstein: The Foundation of the General Theory of Relativity, Part A, §1

Suspended in time we stand still on a relative moving plane with little regard for rule. In the blank spaces of what hasn’t been said, we each silently regard the potential for the stuff legends are made of.

Two-dimensional reality runs parallel to virtual flesh and blood. We’re composed of blinking synapses that fire on small, colorful cupcakes and the idea of (someday) playing chess in the park.

Oh, the games we play.

Your opportune moves have small meaning on which to be assigned.

I’m a dreamer trapped in fighter’s form, shaped by invisible steel filled on the inside with melting glitter and gumdrops.

Somehow the game intensified along the way, making me feel lost. In our alternate reality the tricks and motives became unclear. Did the broken rules betray us?

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