Sailing in the Present Towards the Future

Imagine you’re in the middle of the Pacific Ocean on a perfect day with sunbeams and a gentle breeze engulfing you, the captain of a majestic 100-foot sailboat with a towering mast and massive sails that can propel you to any destination on the planet. It’s just you, the boat, the ocean and possibility. The world is your oyster, so you think.

As good as it sounds (and I hate to break it to you) this isn’t a fully functioning sailboat—there’s no rudder, helm, or compass, and no sextant to navigate. You don’t even have a good set of maps on board or know how to read the stars. There’s everything required to survive and thrive on the water, except for a destination and the equipment to get there. In other words, you’re directionless, sailing blind, going wherever the wind takes you, and holding on for dear life not to capsize. Scary, eh?

Well, this has been my voyage for nearly two decades—a captain with a flawed vessel that has been at the whim of the shifting weather, winds and currents. Here’s what it’s been like to live aboard this ship.

One day, unexpectedly, I discover a far off island that energizes my ego because its shores are filled with status, money and power. Once it’s evident that island doesn’t satisfy the ego's insatiable appetite, I set sail again only to find myself lost in the middle of the ocean asking, where the hell am I, how the fuck did I get here, and where am I heading? A few months later, skilled sailors invite me on their journey, share their maps with me, and I follow their wake for some time until I lose interest because every island we pass seems like a better destination. Shortly after abandoning their fleets, I go weeks without any human interaction and paranoia sets in, believing that my safety is at threat, so I make haphazard decisions, and continue to flail in the wind. Eventually, I just believe that my life is at the whim of the wind and external conditions. Defeated and deflated, I lose hope, become cynical and pessimistic, and wonder if I’ll ever find a guiding star and be a capable captain.

These have been the implications of focusing largely on the present and reacting to whatever opportunity or shiny object grabbed my attention in a given moment.

Take it from this sailor, especially if you want to go far in your journey, it’s imperative that you focus on the destination (your vision), the shifting conditions (your present experience), and the guiding stars (your core values). They are all essential. Without a healthy balance between them, you’ll never reach the future destination that your soul is yearning for, because you won’t know what that is or even who you are.

It only took me twenty years to arrive at this realization. Here's what happened.

Blow and Go

This time last year, I made the brutally difficult decision to walk away from the VC fund that I was on the verge of launching. When I was going through that process, my coach, Dr. Josh, helped me see that I had an unconscious pattern where I’d make big decisions without much data and planning, and then I’d have to deal with the implications and consequences as they surfaced. We affectionately called this strategy “blow and go.”

As we unpacked this tendency, it made sense to me based on my upbringing. In my formative years, I never heard messages from my parents to plan for the future, set longer term goals, and save for retirement. Raised by a single mother who worked two physically demanding jobs, our family lived paycheck to paycheck throughout my childhood, so the future wasn’t a concept we openly discussed. We literally existed week to week. On top of that, my father, who didn’t pay child support but was present on weekends, spent his money with reckless abandon on clothes, drugs, and other luxuries. He lived his life like he was going to die young, just like his own father. These dynamics in my family clearly left an impression!

A decade ago, that child part of myself was activated and even validated when he discovered a new way of being in the present: Buddhism. Since then, I’ve cultivated a daily meditation practice, studied Buddhist philosophy, and tried to walk this path for a decade. The purpose of these practices, after all, is to slow down, be with the entirety of our current experience, and eventually reduce our suffering to obtain nirvana or enlightenment. These practices and philosophies, grounded in the present, deeply resonated with me from the very first session and instruction. For years they were tools to bypass my addiction and childhood traumas, and eventually they became a way of being and living more fully.

As a result of my childhood and my spiritual practice, the pendulum swung so far in one direction that my life was mostly spent in the present, slowly inching my way to a future I was blind to. This approach, which makes sense with the benefit of hindsight, wasn’t productive or truly mindful, though it may have appeared that way from the outside. For example, many big career or investment decisions were based on my emotional state, instincts, and biases, largely ignoring data, hard earned wisdom, and future implications. On other occasions, I would wonder, "Should I be thinking this long-term, who knows how I’ll feel or if I’ll even be alive in five years?” I also avoided situations lacking a clear exit just in case I didn’t enjoy the experience and wanted to pull the ripcord. I was even optimizing for a future present!

Any stability I created in my career, finances, and marriage was largely driven by fear, paranoia and anxiety in the present rather than thinking responsibly about the future. Instead of dreaming about possibilities and setting audacious goals, I focused on what was relevant in the present, like, "I have a debt payment coming up and I don’t want to be penalized so let’s make that payment" or “this is a cool job opportunity that will make me feel safe, secure and important.”

Wherever the wind took me, that's where I went, and I was ok with this existence because “blow and go” was unconsciously encoded in me. Without a destination, surviving on the ocean was all I knew.

Dropping The Anchor

Once I realized this pattern was deeply ingrained in my being, I knew that I had to shift from being reactive to proactive. So instead of quickly jumping into the next thing, which I clearly have a tendency to do, I made a conscious decision to simplify my life and avoid any major decisions for at least a year—I dropped anchor and lowered my sail to let the winds die down. I would coach, slowly grow my practice, study the craft, and lean into writing. This change would give me the time and space to discover what I really wanted and where I wanted to go.

Once my boat was moored at deep sea, the first order of business was to block and protect large swaths of time on my calendar, lease a studio in the city, lean into a Morning Pages practice, and say no to just about every request and meeting. I also walked away from Twitter, an act that would have been unimaginable a year ago. It was necessary to detach myself from the startup echo chamber and go inward, so I could locate and answer the big questions lurking in the deep water:

What’s the purest expression of who I am? What do I really want? How do I want to spend my time? Who do I want to serve? What do I truly value? What do I want to create? Where do I want to go? Who do I want to become?  

I spent the past year anchored in the same spot, trying to answer these questions and in the process discover my guiding stars and an ultimate destination. In the first few months, I grew impatient and anxious because I didn’t like being stationary, but I eventually surrendered and grew comfortable in the isolated waters. Deep down inside, I believed the answers would unfold if I was patient, positive and committed. I prepared for an extended stay. And then just last week I received an unexpected prompt that revealed a destination worth sailing towards for the next phase of my life.

Destination Revealed

Almost by accident, I stumbled across an old episode of The Tim Ferriss Show with Debbie Millman, a respected writer, designer and host of the hit podcast Design Matters. Towards the end of the conversation, Millman described a life changing exercise that she learned from Milton Glaser, the legendary designer, co-founder of New York Mag, and her former professor at SVA. For more than forty years, Glaser asked his students to write an essay exploring what their life would look like in five years if they knew for certain they would succeed at whatever they tried. My ears perked up!

Glaser’s prompt captivated me because, just a few weeks before, I began to catch glimpses of an exotic destination that was deeply authentic and aligned with my values. In other words, my senses were open and my consciousness was ready to receive a signal on the horizon. So the very next day I blocked two hours, stepped into the future, and went to work on Glaser’s exercise. I saw my future self and life in high definition. The words flowed with ease. It was me!

In the vision that surfaced, I lived upstate and co-led a thriving coaching company and retreat center alongside a talented business partner and a team of coaches. Our company helped entrepreneurs and creators elevate their consciousness and redesign their lives from the ground up. I had just returned from a book tour for my first title which was well received and reviewed! In addition to coaching and writing, I also spent my days taking care of my body and, most importantly, being with my family. The destination I saw on the horizon truly energized me—an authentic life rooted in balance, community, creative expression, and service, which are my guiding stars.

I finally had a destination (my holistic vision) along with guiding stars (my core values) to light the way!

Navigating with Balance

After a year of stillness and introspection, I’m finally ready to lift the anchor from the sea floor, hoist the sails, and hit the open sea towards this energizing destination. I can’t tell you the exact route I plan to take, and I anticipate a few detours, but I know I’m prepared—mentally, physically and spiritually—for this long, arduous, and galvanizing journey. I’ve been building towards this adventure for more than two decades.

It’s time to set sail again, but this time I’ll have guiding stars to keep me focused and steer me toward my destination every day. Because of this, I won’t be easily swayed or dismayed if the wind blows me off course, if other captains recruit me to join their crew, if I encounter choppy waters, or if powerful currents slow me down. I know where I’m headed, and I have a light in the sky to guide me. Equally as important, I have the experience, confidence, and mindset to focus intensely in the present to circumvent hazards, handle tough conditions, and readjust the route as new information arises.

A capable captain, after all, is focused, disciplined and present, knowing they must balance pursuit of their destination with the current conditions, so they can recalibrate, adjust and course correct if and when necessary. Keeping both in view are essential for a successful, prosperous and fulfilling voyage.

I’m ready, patient, steadfast, and steady! Our destination awaits!