This day last year, I boarded a one-way flight from Singapore to New York, with nothing but a carry-on and my passport. I didn’t know that this would be my last step on Singaporean soil, or that every part of my life would be blown open.
“So, you live in Singapore… are you excited to go home for Christmas?” my seatmate grinned, as we buckled in.
I couldn’t tell him that my doctor had prescribed my one-way flight home. That I had to convince this PhD that I was strong enough to make the long-haul alone. That I wouldn’t actually be going home, but to a ranch with five strangers to deal with my compulsion to achieve. But he wouldn’t have guessed that and neither would you.
You see, I was excellent at keeping up appearances. If you judged me by my Instagram, you’d see joyful jumps in exotic locales, beautiful friends and an adventurous heart at play. If you judged me by my client roster, you’d see a young woman (probably wearing pink pants) going head-to-head with senior executives at Fortune 100 companies. And if you considered the clean-cut, kind, and successful guys I was dating, you’d assume I was stable and healthy.
Except my days were fueled by deadlines and adrenaline rushes. My social life was halfhearted conversation, forcing a smile as we all talked about our next travel destination, while I counted down the minutes until I could return to my couch. My ideal vacation involved being put into a deep sleep for 10 days, pumped with herbs, and waking up renewed and maybe with a bit of Botox.
But what would happen after I woke up? I imagined returning to my life in Asia with the ability to not wake up in a stressed-out sweat, the vigor to make more happen and the will to hustle through work faster.
But none of this happened. I never returned to Singapore, and somehow ended up building a life in California.
“Woah! I resigned,” I texted a friend and former colleague. “And now, I’m basically living out of the trunk of my mom’s car in Venice.”
“Good for you! Take a deep breath and feel the joy of being in complete control of your destiny,” he responded.
“Good call. I was breathing in the joy of being homeless, jobless and manless.”
“The three most important ingredients of freedom, my friend! Enjoy it, own it, and live it!”
The past 12 months have been an unfathomable fresh start, and it’s all the more bittersweet when I see friends who have made very different, and sometimes fatal, choices when facing similar emotional challenges.
I’ve been reflecting on what’s helped and hindered me the most over the past year, and what’s propelled me from a life that just felt like damp gray, to an abundant existence in Venice and a successful business that is an outpouring of my passion.
So, I share this experience in the spirit that it might boost any of you guys at a similar juncture:
Being a Stepford CEO doesn’t help anyone. I’ve found that there’s a balance between projecting a positive image and having your shit together, but also being vulnerable and asking for help. Telling everyone that everything is great when you’re dying inside is exhausting. And it’s not authentic.
My biggest breakthroughs have come from sharing what’s going on with a trusted group of advisors and friends — and getting from freak-out to functional in shorter spurts.
It’s required me to change my language and my thought patterns — to go from mourning perceived lack to celebrating that I am in charge of my own destiny. To go from a wet-noodle, shanti-shanti approach to life or totally checking out because it’s too much to handle, to actively owning and driving my desires in a purposeful and spiritual way.
I still wake up at 4 am in a cold sweat (probably even more so since I’ve left the corporate world and taken the entrepreneurial route), but the difference is that today I know how to deal with it. Back in February, I was drawn to a deep meditation practice that suggests a 4 am sadhana, so now when I wake up with panic, I see it as an opportunity to get myself back to center at a sacred time of day. I re-emerge from those morning sessions balanced and purposeful — and with deep calm in what can feel like calamity. The right resources, answers and people always seem to show up — and perhaps they’ve always been there, but now I can actually see them clearly.
Following one’s heart is not for the faint of heart. I had an illusion that following my heart meant that everything would flow and an elegant dance to the cover of Forbes would ensue. But my experience is that flow comes from continually unblocking — for me, it has been about doing some serious work to shatter the doubt and fear that have kept me small.
It’s the spiritual grit and consistent inner resolve that have been the real work. It’s how I respond when the assumptions on a spreadsheet are totally torn up, how I handle starting at a legal bill that I am still gathering the funds to pay, and even how I continue diligently after a win.
In these moments, it’s easy to get into a mode of desperation and out of a mindset of trust. To take a long-term deal or sign on a partner that doesn’t make me say “hell yeah!” because I’ll earn income sooner. The real work has been holding off until it’s right — or immediately saying “yes” when it’s spot on — which means being willing to get to zero, time and time again.
It’s when I get to zero that the magic comes in — and where my character gets stronger. When I’m down to my last few dollars and a consulting gig lands, floating me for the next few months. When I can’t pay my rent and a flash of brilliance on new way to build immediate revenue comes my way. When a last-minute trip presents itself, and I meet my next partner.
This, to me, is true vulnerability — being totally in my desire to build this business, in my dedication to make it work, and in unwavering faith that I have not come this far to be dropped on the side of the 405. It applies in all parts of my life — when I’m willing to get to zero in my dating life and let go of something that’s comfortable but not working (and really let go of it — ie. not using a man as a back up plan), the next amazing guy comes in. When I’m willing to get to zero with my purpose in life, and sit in a feeling of defeat for an afternoon, something settles, simmers and sparks. I can’t explain it, but it’s what’s led to some of my boldest and most effective communication.
Now, I can’t say that I enjoy being at zero, but having been through it more than a few times over the years in all parts of my life, I now have the experience to trust that the darkest moments beget the brightest breakthroughs.
If it doesn’t flow, let it go. I truly believe that business is magical — the act of going from a scribbled note on a napkin to a product on a shelf is nothing short of a miracle. The act of someone passionately dedicating their time, money and energy to something they believe will improve peoples’ lives is beyond admirable. And it often takes the right people and circumstances converging at the right time.
It’s easy to get into the painful place of forcing it (or “hustling” as it’s often celebrated today) — and we lose the flow and magic. I’ve spent countless hours hustling hard, whether an agreement with a client whose values weren’t aligned, a relationship where we wanted different things, a life in a foreign country where I felt utterly alone. I left those situations, certainly with the experiences I needed to have, but also frustrated, exhausted and resentful.
The most fruitful, energizing and beneficial experiences have been the ones that flowed — and took unexpected turns that wowed everyone involved. This year has shaken the mindset that I have to struggle to succeed, and instead taught me that it’s okay for things for things to flow. My move from Singapore to Venice was a domino game of synchronicity: my former employer kindly covered my expenses; a new California friend suggested that I live in her Santa Monica cottage while she adventured from my place in Singapore — and oversaw selling all of my earthly possessions; a Facebook post led me to the unbelievable place I currently call home.
Getting to these “yes”es requires work — and the bravery to say “no.” I had to ask for financial support; I had to make the decision to move; and I had to post my belongings and housing requests in the right channels. I also had to let go of what I was hustling: my consulting career, certain personal and professional relationships, and even places I wanted to call home.
Finding the right “yes”es, means that I have to say “yes” to a lot, and “no” to even more. I have to willing to go with what’s flowing and to let go of what’s not — which means embracing the possibility of zero, again and again. It moves me into a mode of not hustling or forcing — just simply doing the work while being open to unexpected results, which is where I continue to meet with that magic and serendipity.
So this year has been all about vulnerability, grit and trust. It’s been about learning to make friends with discomfort and fear, and knowing that the only thing on the other side of that fear is a breakthrough — and usually one far better (and definitely different!) than what I imagine.