I’ve spent the last 15 months on a deep journey of introspection — learning and questioning many of life’s most basic assumptions. This was in part motivated by the desire to find fulfillment, and in part, to find equanimity.

Coming off of a 14 year career in Corporate America, I realized that while I was extremely deliberate in my professional life (skill acquisition, productivity, “networking,” fitness, and reading, to name a few), I was very much a passive participant in my own life.

This journey has taken me to many fun and unexpected places and I’ve learned a tremendous amount. The learnings have taken place in a variety of mediums: books, podcasts, videos, coaching, discussions over wine, self-reflection (much captured in the RadReads newsletter.) They’ve also drawn from a cross-section of disciplines: philosophy (eastern and western), spirituality, psychology, anthropology, mindfulness, sports, literature, and more. In the words of Oliver Sachs, it’s been a tremendous exercise in neuroplasticity — the brain’s ability to create new pathways.

Recently, I’ve started to synthesize this information, creating a loose framework to help organize some of this thinking. I’m excited to share it with all of you:

It’s early days, but I view these as pillars that form the foundation on my journey towards Being My Best Self.

Compassion

“Love and compassion are necessities, not luxuries. Without them, humanity cannot survive.”
~Dalai Lama

It starts with compassion, first with yourself. We tend to be our harshest critics — we self-judge, critique and sabotage, oftentimes in the name of motivation. But much of this is a Useless Worry, an unnecessary narrative emanating from the toxic cocktail of Fear and Scarcity-based thinking. Self-compassion unlocks resilience (to loss/failure), decision making clarity, empathy, and inner happiness.

Once we are compassionate towards ourselves (“We cannot give, that which we do not have”), we can then become a vessel of compassion and love and impact the lives of others.

And our world needs this more than ever, whether it’s in politics, our communities, and in business.

Uncomfortable Introspection

“My mind is like a bad neighborhood… I don’t want to go there alone.”
~Anne Lamott

This is where it gets ??? AF (spicy as fuck, for the unacquainted). I want to draw a direct comparison to many of our workout regimens.

We are so deliberate about our workout routines — whether it’s Ironmans, Crossfit, SoulCycle, the ungodly hours at which we wake up and the limited scope for excuse (hangovers, business travel). When it comes to working out, as a group, we don’t fuck around. This is a deliberate choice that many of us make, with an acknowledgement of both the long-term benefits of exercise and the positive way in which it makes us feel. And we rarely question the cost or time commitment.

We approach exercise fully knowing that it’s going to be challenging, not always fun, painful (at times), time consuming and logistically complicated — but it’s worth it. It’s a deliberate choice.

Why don’t we exercise our minds? Meditation and mindfulness are starting to creep into our routines (see below) but where is the Crossfit for our minds?

Introspection is hard. It’s not fun. It’s uncomfortable at times, as you look and engage with your fears. These Fears often revolve around death, being broke, and failure.

There’s a misconception that you can compartmentalize these fears and they just go away. That’s Dead Wrong. It’s actually dangerous thinking, as they tend to resurface towards your family, your employees, or other people who just get trapped in the collateral damage, when you’re least expecting it.

And if that wasn’t enough there’s this complicated thing called our Ego. We do need an Ego, it’s our Drive, our Identity, our ?. But it’s a delicate balance — too much Ego, and we know how those stories end.

Prior to this journey, I faced a tremendous imbalance — my “Outer self” was a well-honed-tactical-machine (say, a Ferrari) yet my “Inner Self” was a scared, confused, and lost child.

I was a Ferrari being driven by a five-year old.

Presence through Stillness

“The quieter you become the more you hear.”
~Baba Ram Das

There’s a lot of noise in our minds. There’s also a lot of noise out in the world, much of it driven by technology. It is hard to connect with ourselves amidst this noise.

While I have a committed meditation practice (200 hours over the past year), I do not believe that it’s the panacea to all of our suffering. It’s just another tool in a very broad continuum of finding Stillness. On one end of the spectrum you have good smartphone hygiene and on the other you have Vipassana Retreats.

“With one foot in the past and the other in the future, we’re pissing on the present.”
~ Dan Harris

Personally, I’ve always been very afraid of the present moment — in fact, prior to this journey, I’d been much more accustomed to living for tomorrow. I’d be drinking a beer, thinking about the next one. On vacation, fantasizing about the next trip. The present moment can be uncomfortable — which is why our default mode is to pick up our iPhones. Why? The present moment forces us to look within and see the elements of the Uncomfortable Inquiry described above.

Yet, from this stillness emerges reflection, creativity, trust, compassion, equanimity, and clarity — who wouldn’t want that!?!?!

Living your Truth

“There is a time in every man’s education when he arrives at the conviction that envy is ignorance; that imitation is suicide; that he must take himself for better, for worse, as his portion”
~ Ralph Waldo Emerson

Imitation is suicide. Wow.

What is your truth? What is your definition of success? (Mine used to be selling a company for 50 mm.) What is your purpose?

As children, we are carefree, curious, and unconstrained by the pressure of society and its expectations. Over time we become hardened, there’s a resignation that there is only one path.

We get lazy — we default to societal benchmarks of “success” and often become passive participants in our own lives. We punt on the question, by striving for our “Number” without questioning what we would actually DOwith our time, specifically, once we hit that number.

There’s a misconception that happiness is a series of Step Functions — you get a promotion, bonus, vacation home, fancy watch and happiness increases. These extrinsic factors provide very short-lived bumps to your happiness, but you quickly converge back to your baseline level. Sustained happiness really comes from Hundreds of Small Wins — a good night’s sleep, meaningful relationships, the ability to love and be loved, self-compassion, and a sense of purpose.

We all have our truths — we just need to listen to our hearts and inner voices — and give ourselves permission. By NO MEANS does this mean we should quit our jobs — the change is usually incremental — more time with family, volunteering, restarting a long lost hobby, reading a book for “fun” rather than for “work.” But we need to listen. We need to have healthy conversations with our Fears and Ego. We need to give ourselves permission.