Pivots to a Meaningful Life:

How Habits and Uncertainty Revealed My Entrepreneurial Calling

For years, I’d read of artists and entrepreneurs who found their “callings,” but never understood the power behind their visions until I had one myself. That finally happened eight months ago as I was exploring my third idea, looking to create something new from scratch. By then, I’d burned through a large chunk of my investors’ money for a startup I’d come to realize was the wrong one for me. After fifteen months of working on my own in New York, I was back at square one: facing my peers, my investors and advisers who’d bet on my success and whom I refused to disappoint, and my parents, who thought I was foolish for giving up a lucrative job at a fast-growing startup to invest in something so risky. Before my calling hit me on that cold November day, I felt fear that I’d create something new, put my name on it and announce it to the world, only to see it fail. A waste.

Illustrations by Emily May Rose

I launched and transitioned through two ideas before realizing that embracing uncertainty and cultivating a deeper awareness of my habits would lead me to the right entrepreneurial path. My startup needed to be not just something I did, but who I was, and ultimately, who I’d become in the years it would take to create a sustainable business.

This article shares the questions I asked and the philosophies that provided the answers during my two “pivots” as a new entrepreneur. If you’ve ever questioned what you’re working on, found yourself asking why you do what you do, or are trying to determine your purpose in life, it’s my hope this article will help steer you towards your own calling, the way it guided me.

My Entrepreneurial Calling Began with the Questions: “Who am I?” and “Why?”

At Bisnow Media, where I was a founding employee, the company’s rapid growth forced me to become a leader quickly. I had brilliant colleagues and was exposed to incredible creativity and innovation as we scaled from three newsletters and zero conferences, to 30 newsletters and 300 conferences a year. What started in a friend’s house in Washington, DC with 4 employees, went on to become North America’s largest platform for commercial real estate news, events, and education with 70 employees by the time I left.

After raising an initial round of seed capital, I moved to New York City in July 2013 to found The House, a thought-leadership salon that curated networking experiences in the “cool” environment of a New York City penthouse. Convening influencers around important issues of the day was one way to connect people and potentially have a small, albeit significant, impact on the world.

Photo of “The House” in New York City (Photograph by Engin Beri.), where I lived and worked. The couch on the right is where I spent most of my time with my laptop trying to get my startup off the ground.

Soon enough, however, I came to realize what I was doing wasn’t meant for me. I launched The House because I thought an event-driven company should be the natural next step for me to take. But even as The House sought to drive discussion and change, it also promoted a luxurious lifestyle and fortune. These would not be enough to drive me daily for ten, twenty or thirty years, which is the timeline needed when building a business.

The House was indeed a successful way to connect with others, but it was no longer the way I wanted to connect. Eventually, my co-founder and I decided to split (amicably). I continued operating on my own, but sadly had to let go of my employees and regroup. I thought lifestyle, influence and fortune would make me passionate. Yet, I was living and working in a 6,000 square foot Manhattan penthouse, meeting some of the most accomplished people in New York City (the greatest city on Earth!), and still I felt empty. Living in a place that large alone and having to manage all the work on my own made me realize how meaningless big spaces can be when you don’t have anyone to share them with. What I did as an entrepreneur needed to be not just something I did, but who I was. So the question became:

Who am I? And if I don’t know who I am, how do I figure it out?

I Embraced Living with Uncertainty

Becoming more deeply aware of my habits and embracing uncertainty to my advantage are what finally allowed me to inspire excitement within myself, instead of stress and anxiety.

Uncertainty = Excitement + Growth

Uncertainty pushed me to become resilient and resourceful. Today, I visualize the future and understand that things are actually more exciting when uncertain, not when you’re established and safe. Embracing uncertainty is why I believe Mark Zuckerberg said no to Yahoo’s $1 billion offer, and why Evan Spiegel, founder of Snapchat, refused a $3 billion offer from Mark Zuckerberg to sell his app. It’s more exciting to command your own ship, even at the risk of billions of dollars.

“One of the saddest things that happens with creativity … I think sometimes it isn’t expressed because of fear. Everyone is born very, very, very creative, but at some point it can be scary to try to do something new, that feels different.” — Evan Spiegel, Founder of Snapchat

Harnessing my “Flow State”

For the last two and a half years, I’ve gone to bed at 8:30pm and woken up at 4:30am Sunday through Thursday. Why would I adopt such a tough sleep regimen? Because it helps facilitate extreme flow through my work, which requires un-distracted mental space. It’s easier for me to keep a quiet mind at 5am than at 9am, when most of the country operates. A “flow state” is the feeling we get when we’re “in the zone” — a state of maximum pleasure, triggered by a release of natural drugs like dopamine, norepinephrine, and other neurotransmitters in the brain. This happens when we deeply focus on something with complete presence. It’s why “starving artists” are willing to starve for their work’s sake. I began noticing my “flow rate”, the speed of creativity and how fast or slow ideas would come to me and a “flow score”, which I consider a metric for the depth to what you’re experiencing at the moment. Consider the question: how much of you physiologically and psychologically shows up to each moment? My morning flow state and the challenge of pushing through the day when the odds were against me inspired fearless excitement, instead of stress and anxiety. My back was against the wall, but I was still able to think, create and push forward day in and day out. This inspired me to do my best.

*Watch this TED talk by one of the top researchers of flow for more details*

I Learned How Habits Work

I studied my triggers (cues) for particular routines, and understood that I craved rewards. I applied the habit loop to everything I did, and with the help of Charles Duhigg’s book, “Power of Habit,” increased my overall awareness. Here’s the “Habit Loop” below:

As I observed my habits, I noticed the cause and effect of what I did. For example, I recognized that when I shaved and dressed “for success,” I also maintained better posture, ate less and remained in a better mood overall as a result. Those became keystone habits that affected my other habits. I now use the habit loop to think about everything I do, from being aware of my intentions as I check Facebook, to whether or not I need another cup of coffee when I crave it.

I Realized How Important Mastering Presence is for Both Work and Life

The same way I used to value money and connections is how I now value being present. Presence is how we learn intuitively and how we perform our best. As my competence in being present improved, I learned how to be resilient, cope with setbacks better and to harness my attention and focus. I know, for example, not to make any decisions until I am fully present and objective instead of emotional. This applies to everything, from my startup to every time I step up to the baseline to serve while playing tennis.

Josh Waitzkin, whose life story helped inspire the film Searching for Bobby Fischer, is a world chess and martial arts champion and a great expert on the idea of presence in competition. He writes:

An Insatiable Love of Learning and Performing Well For It’s Own Sake

As simple as the concept of helping people may sound, I believe there’s a mighty reason for it. Realizing I wanted to somehow help people made me think in terms of value, rather than purely financial metrics. Strong leaders like Ghandi and entrepreneurs like Elon Musk weren’t, and aren’t, motivated by money, but by improving the planet and serving humanity. Their successes, though different, helped people in monumental ways: Elon Musk created billions of dollars in value with Paypal, Tesla and SpaceX, and Ghandi helped India gain independence.

You don’t need to be a billionaire tech founder or major global player to be a strong leader. A country’s leading accountant is also doing great work with a fundamental impact. “People don’t buy what you do; they buy why you do it. And what you do simply serves as the proof of what you believe,” says Simon Sinek in his exhilarating talk on inspiring action. Why do you think a particular accountant is the best in the country? While accountants may do similar work, leaders in the field know why.

So I challenge you to ask yourself: why do you do what you do?

That’s when I experienced my first Pivot.

Contemplating my calling on a deeper level helped me realize what made me enthusiastic on the inside and gave the greatest fulfillment were those nights I hosted industry friends in The House’s three spare bedrooms.

What I loved most were those nights when I stayed up with my guests — entrepreneurs, journalists and creatives in similar industries — chatting and brainstorming late into the night. I helped friends, colleagues, and friends of friends become more enriched personally, through introductions and in business, because those introductions often lead to long-term relationships.

These two visitors to The House were special, as I had my dad visiting while legendary artist and activist, Sir Ian McKellen, stopped by to check out the space. Sir McKellen’s visit was one of those which helped inspire my next pivot.

I decided my natural progression would be to connect hosts with travelers by industry interest. I called it B2Bnb — like Airbnb meets Linkedin — and threw myself into this new idea with fresh enthusiasm.

Within four months, B2Bnb’s website was almost ready to launch, and I’d begun matching my first beta test hosts and travelers. The potential was exhilarating. Airbnb had a raging valuation, and several other sites also had near billion dollar valuations. I believed my own space-sharing site, which added a professional networking component, could carve a unique niche for a substantial business. The space-sharing companies were raising tons of money and receiving huge valuations, and that was exciting. But then I asked myself: could I do this for the next ten years? In his bible on Mastery, Robert Greene says “in order to master a field, you must love the subject and feel a profound connection to it. Your interest must transcend the field itself and border on the religious.” In spite of the large financial potential for B2Bnb, I still felt I lacked a sense of fundamental purpose. So I asked myself:

What can I explore and geek out about to no end? What do my friends and family approach me for when they need help or advice?

Throughout the last seven years, productivity and mental fitness — from meditation to email hacks — have been topics my friends and family ask me about for advice. These were the tools I used to lead teams and guide employees, and I saw them as a natural gift. I’d read more than a hundred books on productivity, stoicism, mindfulness and habits purely for the joy of learning, and often got lost in creativity for it’s own sake, rather than just as a means to make money. My dedication to mastering presence, indeed, felt borderline religious.

I realized my mission to master presence within myself could manifest itself to benefit others. I’d never felt as excited about my career and life than at that moment. With that kind of dedication, I knew I could help people and help make the planet a better place.

Art by Emily May Rose

Being deeply curious and seeking answers provide the motivation and energy I need to do meaningful work and live a fulfilled life. These are skills that come from deep presence, elevated consciousness, gratitude and mastering attention. Being conscious enough for deep awareness made me realize how important habits are, and that learning itself made me a passionate and enthusiastic person.

Maslow’s Hierarchy Of Needs says that after food, water, security and love, come esteem and ultimately self-actualization. For the sake of those struggling to discover what they’re born to do professionally, I believe we should reverse the order and begin with consciousness, gratitude and a love for learning. Begin with what’s meaningful to you and how you’d like to serve people or the planet.

Do you love something so much you can endure “starving” to do it?

Most of us move from food to security to love, and if we’re lucky, we get a crack at self-actualization. We work away for five, ten or twenty years fulfilling the first three and four needs, sometimes for our whole lives.

Those of us lucky enough to have our physiological and security needs taken care of can reverse Maslow’s order, and begin by approaching the world with consciousness, gratitude and a love for learning. This is especially true if your ultimate goal is entrepreneurship and business.

That’s when I experienced my second Pivot.

It took me ten years of hard work to realize how resilient the mind is. The mind can handle almost any threats thrown at it, even when safety and physiological threats are present. Its ability to turn obstacles into opportunities is quite powerful. In The Obstacle is the Way, author Ryan Holiday points to legendary psychiatrist Victor Frankl, who endured the horror of concentration camps during the Holocaust, and maintained that a meaningful life comes from choice:

My Calling: Learning and Teaching the Art of Presence With Technology

My mission is to use writing and technology to teach presence and make it as intuitive and natural as breathing, for as many people as possible. Presence allows us the foundation to manage our attention, get the most from our experiences, and manage experiences better even when they feel “bad.” Today, I have so much excitement and enthusiasm about my work that I’m overwhelmed by the ideas in my pipeline.

“The more present we are in practice, the more present we will be in competition, in the boardroom, at the exam, the operating table, the big stage … Presence, must be like breathing.” — Josh Waitzkin

Work As a Labor of Love,
Regardless of Achievement

Eight months ago, I conceived what is now www.FlowApps.org. I’ve blissfully read, written and geeked out on mental fitness, and “mindful productivity,” and let my inspiration flow. As a result, I’ve conceived and created my first product that helps people incorporate habits of presence into their daily lives and routines based on principles I believe are the foundation for a meaningful life.

The Flow Button for Gmail and Outlook allow you to remain attentive while working in email. In today’s business culture, a priority has been to make everything efficient and get things done fast. It now takes serious concentration to actually work “slow,” remaining present and mindful even a midst information overload, for higher quality work.

Will the Flow Button “work”? I believe so. I’ve come to believe the universe to be a perfectly efficient place, and know all of us will “pivot” to our next step correctly if we need to.


Thank you so much for reading this piece. It wasn’t an easy one, and it took everything I had to publish my personal journey. The fact is, my journey of experiences, mistakes, and small wins wouldn’t have been possible without a group of people I’d like to thank: The Bisnow family, the Jasinowski family, the Begelman family, Doug Anderson, Matt and Judy Curry, Hooman and Cyrus Radfar, Hilton Augustine Jr., Peter Bepler, Jigar Shah, Ben Miller, Afshin Molavi, Kendall Dabaghi, Evan Beard, Fahad Hassan, Barak Sky, Michael Zolfaghari, Alex Levin, Roshanak Taghavi, Mina Lee.

The writing of this piece began as a 70 page stream of consciousness which was cut down into 13 minutes and wouldn’t have been this concise without Roshanak Taghavi, Ryan Holiday, Kate Lee, and Sophie Moura.