The joy of carving your own path

Last night, I stood with a mic in front of a large room of maybe 30 or 40 people, many of them my friends, and shared with them this list of 24 questions to connect authentically. I walked them through why I created it, how to use it, and we proceeded to break into groups of 3 or 4 and share ourselves with each other. To tell our stories, reveal ourselves, and to do so with open minds and—hopefully—wide open hearts.

This was a night of magic for me.

Many of my friends (and strangers) who attended this event in the heart of the city came up to me afterward and told me they felt uplifted, that they loved it. I also made some seriously great new friends in a very short amount of time. New projects and collaborations (involving me and not involving me) were also born amidst the constellation of connections. But these, as affirming and lovely as they were, weren't the reason behind my everpresent afterglow.

Most importantly, this evening of pouring my heart into organizing a (last minute) event of real meaning for me, of sharing a message I think the world needs, and of being my full self through speaking and facilitating deeper conversation—these things are the very things I left my prior life to pursue. I left Google and all the solidity, the certainty of that initial life design for wild, radical commitment to these values. I was scared shitless in some ways, but some tiny part of me had this steadfast faith I couldn't explain. 

Despite the faith, though, when things come together in ways that hint at the ideal future of meaningful work and projects I want to design for myself, I feel unutterably grateful. It feels like my blind faith is proving to not be so blind after all. 

I like to think when you follow the tugs of your most idealistic and wide-eyed curious self, stars align and magic happens in a seamless way. So far for me, this has been invariably true, to the point where I rejoice in how lucky I am to be experiencing these creative and connecting moments at all, randomly and often throughout the week. It feels like the universe has invited me to dance, and I took her hand, grimaced with trepidation but said yes anyway, only to find the doors open to experiences that unfold with a momentum of their own, as if they were just waiting for me to take the first step.

The mechanisms of our world, our universe, the spiritual dimension (and whether or not spirituality has anything to do with it at all) are not nearly as interesting to me as the encouraging function of this kind of faith in something that guides and supports me. I am generally very willing to discard my beliefs about what's true of the unseen, but there's one thing I can't refute and that is the deep feeling of gratitude I have for all the beautiful friendships, experiences, creative outlets, and opportunities I've encountered at every turn, even during the rocky and confusing moments of the journey so far. 

In short, I feel lucky. I was scared to make a big change (perhaps rightfully so, only time will tell) but things have unfolded beautifully. I'm not a typically positive person, nor am I especially negative, so this daily and effortless gratitude isn't something I ever experienced before now. And some part of me feels obligated to share it, to indicate that if there's ever a part of you that feels pulled by what seems trivial or delayable, that you might want to consider giving it the attention it's been asking of you starting now. 

I don't want this blog to be a broken record of the same brand of encouragement. But I do want it to document with full honesty my entire reckless and adventuresome pursuit of fulfillment, meaning, and service. And a core part of this truth, I'm discovering, is that this pursuit leads to magic. The small but very real courage it takes to step into the shoes you tell yourself you will dare to fill when you are older, more secure, more successful, more confident should be acted upon now. 

This is the only life that makes to me. And last night was just one evening of warmth and novelty of the kind I live for, but to me it represented how joyful the journey itself can really be, how glad I am to have surrounded myself with people and places that facilitate this more whole-hearted and intellectually curious living.

I feel, now more than ever, like I'm home.

How to be successful

“[All highly successful people] treat life, business, and success… just like a nightclub.
There are always three ways in.
There’s the First Door, where 99% of people wait in line, hoping to get in.
There’s the Second Door, where billionaires and royalty slip through.
But then there is always, always… the Third Door. It’s the entrance where you have to jump out of line, run down the alley, climb over the dumpster, bang on the door a hundred times, crack open the window, and sneak through the kitchen. But there’s always a way in.
Whether it’s how Bill Gates sold his first piece of software, or how Steven Spielberg became the youngest director at a major studio in Hollywood — they all took the Third Door.”

— Alex Banayan

How to fall in love with anyone, the 36 questions redux

One of life's great pleasures for me is good conversation. To cut through the thick of inane small talk straight to the heart of what's real and important.

What makes you tick? Why are you here—in this bar, at this event, in this city, in this life? What last moved you? What do you wish you had said?

And what a blessing that I've surrounded myself with friends who have the curiosity, courage and depth to explore these soulful conversations with me. This has continued to nourish me during a pivotal growth period in my life.

I sincerely believe that a prescription for a happier, saner world lies in more true connection and less fluff. More heartfelt reaching out, and less of the passive or unuttered desire for bonding that traps us in loneliness.

Inspired by a New York Times phenom from last year, I've made a remix of 36 questions to ask to fall in love with someone. Slightly shorter (24 questions). For fun, for use, for the hell of it.

I've plucked the questions from my mental catalogue of some of the best real conversations I've had (I'm brazen like that); from questions I've always wished were appropriate to ask in lieu of "What do you do?"; and from the crowdsourced megabrain that is my group of Facebook friends.

The result is this mash-up of what I like to call deepeners. These questions let you skip the niceties and dive into the substance. Have they made me fall in love with a stranger yet? No. 

But they have made me fall in love with my friends.



Here's where you get to map out the contours of their life, their personality. It's discovery, with playfulness. The curation of their thought and how they present it to you will reveal plenty, and the exploration, if the chemistry is right, can be a fun romp into rapid mutual acquaintance.

  1. What do you wish you could help people with?
  2. What do people most often compliment you on?
  3. Describe your perfect Saturday.
  4. What would you do more of if you had more time?
  5. What do you never get tired of talking about?
  6. What’s one thing you have strong opinions about?
  7. What's something you've always wanted to try? Why?
  8. Why are you standing here right now? Start at age 10.

Hors d'oeuvres.

Now, substance. Depth. The beliefs and the feelings beneath the facts begin to emerge, slowly uncovering the unique shapes and colors of who they really are.

  1. Tell me about your greatest accomplishment.
  2. What’s your favorite quote and why?
  3. What’s one book you think everyone should read?
  4. Who most deserves a thank you letter from you? Why?
  5. Who do you most want to write a fan letter to? Why?
  6. What’s one quality you wish you had more of?
  7. Who or what inspires you lately?
  8. What three qualities do you most value in a person? (My personal favorite when meeting people I find interesting.)


Here, the truth. The stuff people won't share without a loving, present, explicit invitation. Here, you get to give someone the life-giving permission, finally, to put their truth, their uncensored stories into words. The privilege and intimacy of these journeys into someone's inner world can be enthralling, frightening, revelatory—and always humanizing.

  1. What experiences have been the key turning points in your life?
  2. Tell me about a time when your worldview really shifted.
  3. What would be too good to believe, if someone were to sit down and tell you what’s coming next in your life?
  4. What makes you come alive?
  5. What would be the highest compliment someone could pay you?
  6. What’s one thing most people don’t know about you?
  7. What do you still need to forgive yourself for?
  8. What do you most wish someone would have said to you in a time of struggle?

This is what it's all about. Because falling in love with someone by seeing who they are and giving them the truest version of you is among the most beautiful experiences we can have.

Allow this list to be your starting point to craft your own.



Anything that does not bring you alive is too small for you

You must learn one thing. You must learn one thing.

The world was made to be free in.

You must learn one thing.

The world was made to be free in.

Give up all the other worlds

except the one to which you belong.

Sometimes it takes darkness and the sweet

confinement of your aloneness

to learn

anything or anyone

that does not bring you alive

is too small for you.

—Excerpt from "Sweet Darkness," David Whyte

The real reason you should do what you love

You should only leave behind what you knew if an idea has enchanted you so thoroughly that not engaging it would hurt more than letting the steady ground slip out from beneath you.

The thrill of the free-fall must be greater than the comfort of keeping your feet planted. The very act of daring — regardless of victory — must bring you to life.

So you leap.

You soar, and you realize: you had wings.

And tentatively at first, but with growing triumph you spread them wide and see at last that the vast open air has a glorious, unobstructed view from 10,000 feet high whose beauty alone makes the flight transcendent.

It’s a fallacy to think you should only leave what was working if you have a guarantee of success awaiting you. There will never be a guarantee.

There may be no net to catch you when you fall.

People who tell you it’ll all work out if you chase your dreams shouldn’t be trusted (especially if they’re selling you something). Nothing always works out. Many, many things don’t.

Does that mean you shouldn’t ever have leapt? That you shouldn’t dare venture out beyond the trappings of comfort?

Maybe. (You didn’t see that coming, did you?)

Who knows? You may be better off cocooned in safety.

The pressures of having vast, open possibility in front of you may become burden rather than adventure; the paradox of choice can be crippling. You may not like heeding the imperative to design your own life from the ground up, carving your own path instead of following a well-worn trail. It may be one of the most painful things you do.

But just maybe…

The act of stretching beyond your limits becomes the reward itself.

Maybe if you hadn’t danced with reckless courage now, you would never have dared again.

Maybe the risk of falling flat on your face for something poetic, stupid, and wildly creative is something everyone should do once, just to say they did.

You cannot know what’s on the other side. But do you need to?

In fact, can you ever really?

Even your safest moves on the board are just calculated bets in a game where we can never truly know when the final checkmate signals the end.

The leap will teach you about yourself.

It will force you to think about what’s important and why. It’ll show you your true colors: how disciplined are you? What are you chasing? How much reverence do have for hard work? Who matters in your life? Who sticks around when your old world collapses? And what can you give up to sustain the lifestyle you’ve chosen?

These are questions most people take great pains their entire lives to avoid. Usually if they’re asking them, it means something bad has happened; they were forced towards the big questions.

But if you are one of the 1% who dares to tend to these questions, to step towards knowing instead of waiting for it to corner you, you will unlock self-discovery.

And this — the insight behind the question mark we fear makes us skirt around — is worth every risk of falling with no net in sight.

I don’t know what’s on the other side of the leap for you. But I do know what’s on the other side of self-discovery:


The silence between the notes makes the music

One day, life will beckon you to retreat.

It will call upon you to become completely still, and to temporarily withdraw from the noise of life and its tumult. It may even strip you of the things your heart had clung so tightly to—like a new career, an entangled relationship, financial security, friends you loved—just to empty out the space you had been scrambling so compulsively to fill.

It’ll take, take, take, wrenching from your grip what you thought was all-important, just to get you to sit quietly and finally listen.

We live in an age in which movement is akin to survival, and action is the glorified state.

But we can’t fight the natural way of the world, which depends on the dance between rest and activity; between the void and the material; between silence and substance. Our social conditioning may equate doing with worth, but the most sacred of all “doing”—the act of creating—emerges, inspired and alive, only from the spaces between the doing.

What does this look like?

This looks like standing on the edge of what you knew, facing the dark velvet abyss beneath you, shimmering from a distance with unknown promise, and knowing that you have to leap into the void to find what you’ve never had.

It feels like death; either through the relentless subtraction by a forceful unseen hand of all the things you had used to prop up your identity, or by an inner stirring that grows increasingly restless, impatient with the abrasive noise of all that is lifehungry for otherness.

It’s the craving of nature as refuge from the city. The yearning for quiet in lieu of cheap pleasantries. The complete disenchantment with the very things that had fueled your frantic race towards some ever distant goal post.

It can creep up on you gradually, an exhaustion that slowly takes over.

Or it can descend in one fell swoop, knocking you off your feet and leaving you blindsided and agape on the floor.

However its arrival, it will hurt. It’ll bewilder, and it may feel utterly alien. And this exact moment of confusion and panic is when I invite you to lean in.

When you want to step back to the warmth of familiarity, step forward. When you want to distract your thoughts with an unending stream of outward focus, go inward. And when you want to claw at the comforts of yesterday, I implore you: forge ahead into the engulfing silence.

This is the space where all possibility lives.

This is the rest that your soul needs to revive.

This is the unfolding.

The wisdom formula (or how to get better at doin' stuff)

I'm convinced of my own cluelessness, especially since I hold enthusiastic but loose & agile positions on everything on principle. But I do follow a lot of great speakers and writers with a gift for sharing inspiring and useful ideas. Our modern epidemic of self-help gurus & life coaches notwithstanding, I think there's some real wisdom out there as signal amidst the noise.

Some of the people whose words I enjoy for their useful insight tend to be in business (Seth Godin, Paul Graham, Gary Vaynerchuk, James Altucher, Warren Buffett to name a few off the top of my head), personal growth (Steve Pavlina, Steven PressfieldDanielle LaPorte, Cal Newport), and spirituality (Martha Beck, Tara Brach, Eckhart Tolle, Charles Eisenstein).

This begs a key question: what is wisdom? From years of observation, here's my take.

Wisdom is the synthesis of knowledge into insight.

To gain wisdom is fundamentally a practice of accurate pattern recognition: you are faced with input (facts, experiences) and you apply awareness and analysis to tease out the insights, a distillation of value from volume.

The other characteristic of wisdom, besides that it is derivative from fact and the outcome of an actively intellectual practice, is that it's useful. By its very nature, it takes input and converts it to insight that can then be applied to relevant future scenarios.

You have situations A, B, and C. They all have X in common, which allows you to generate insight Q. You then are faced with scenarios D, E, F and notice that they also exhibit signs of the pattern X. You extrapolate, apply Q, and are able to take some shortcut to more efficiently think about or do whatever those scenarios require, this time with better external outcome or with a smoother internal (mental, emotional) experience.

In short: find patterns, generate insights, do better. And maybe even live a little happier as a result, as life becomes faster and easier over time.

If human personalities fall into archetypes, and I believe they do, I'm a hardcore perceiver and thinker (if you couldn't tell). So I try to apply this process to my life at all times, in both the inward and outward directions. I'm both a deep-sea diver of my own psyche, exploring my inner workings with the zeal of a scientist set out to disprove or prove a hypothesis, and I'm a keen analyzer of the world, constantly studying humans, societies, and businesses to find the core insights hidden in the seeming chaos of cause & effect. This process also involves consuming the wisdom of others to iterate my own constructed models of understanding, which is an efficient and personally enjoyable way for me to optimize the optimization process. ;-)

In other words, I like hacking life. Finding better ways to do things is extremely gratifying for me, and I especially like to apply this process to the inner human emotional-psychological landscape, because I think it's harder to study but just as replete with interesting patterns awaiting discovery.

But while hacking your biology, your startup, or your social life are more straightforward processes with more tangible moving parts, the process of hacking your own thoughts & feelings is definitely more parts art than science, and often this constitutes the core of wisdom. It involves a finely-tuned sense of awareness being applied to how we think, feel, decide, and relate. It also tends to require more patience, I think, since becoming a baseline happier person with patterns of thought and feeling that serve you instead of obstructing your life experience and goal attainment is fundamentally tricky.

Living life with skill—that is, with the maximum net love and happiness, which we fundamentally seek—requires knowing how to think, feel, decide, and relate better. And this demands an inward gaze towards our own nature, a constant (and compassionate) study of what we're doing and how we can do it better.

There are ways to strengthen the pattern recognition muscle (meditation comes to mind), but I think starting with the intent is enough. And always being open to the lessons that are there is another key, especially when faced with undesirable outcomes. Given an existing scenario, to persistently react with negative emotion or thought is futile and self-defeating. Instead, to maintain a constant mentality of learning, I've found, is the best way to always get the most out of life. In this orientation of receptiveness to feedback, no negative experience is a source of regret, nothing is without its lesson, and everything becomes progress towards a more accurate model and system of living. This, I think, is the art of living skillfully.

When you're stuck in fear, just keep moving

If you've read my previous posts about creativity and the big risks I've taken recently, you know I'm struggling with this idea of inspiration in the face of fear. When an idea strikes, do you seize it? Can you ease into it gracefully and overcome the paralyzing fear? How can you minimize the terror of putting yourself out there, or of eschewing conventional a career path for a more inspired one?

I follow this one beautiful blog, and the curator and purveyor of #girlboss wisdom who runs it posted this in response to a similar question. 

And it is beautiful. (I've bolded the parts that especially moved me.)

In 9th grade I had a creative writing teacher who told the class not to write about love. The next week she read us a poem about love that one of our classmates had written in defiance, called: You Told Us Not to Write About Love. It was a really good poem. The teacher was delighted with the irony, but all this taught me was that you can break the rules, but only if you can swing a good outcome.
I see examples of this everywhere. Like the woman who pursues a writing career and is regarded as courageous and inspiring if she gets a multi-million dollar book deal, but if she fails is called idealistic and irresponsible. Even worse, called ‘lucky’ when she does succeed. Or a male who leaves his high-paying corporate job, couch-surfs and spends all of his (and his parents’) money while developing an app that everyone says is stupid, then ends up selling it to Google and is celebrated on the cover of Fortune Magazine. I read these articles and think, what about the people whose shitty life chapters aren’t absolved by a happy ending? Of course, what I’m really worried about is my life. That I’m going to get stuck in the trying-really-hard-and-risking-everything part and not come out the other side. Just like how you read about these women who look like they’ve overcome so much and think: how will I ever do what I want with my life if fear is stopping me from even starting?
There are so many articles and endless advice about how failure is part of success, that fear is healthy, that it’s a sign you’re doing something right. This is all true. But then I think, am I messing up the right way? Instead of learning how to improve this site’s SEO and figuring out how to get people to come to our events, all I really want to know is, am I making the right mistakes? And while I’m worrying about the fact that I’m worrying about the wrong things, I do this:
Keep moving.
You can try to ignore the voice that says you suck, or scream over it with positive affirmations, but this doesn’t work for me. What does work is staying busy. I tackle small things and by doing one thing means I have to do the next thing. I focus on what I have to do instead of what I have to worry about. Fear festers when you stay still, but it doesn’t like being forgotten about when you are busy doing other things. Even if you are just pretending to forget about it. Start moving and stop worrying.
Learn to live with it.
When OKREAL was just an idea, I was so worried that no one would let me interview them for a website that didn’t exist. Some people didn’t, but some people did. Then I was scared that no one would come to my site once it launched. It didn’t end up on the homepage of a monolith website and get a million hits overnight, but people started coming. Then I was scared that no one would come to my first event, but when they did, I was scared that they wouldn’t enjoy it. And now I am scared that I need to keep growing, and mostly that I will get in my own way. I’m scared that I’m writing this while lying in the sun in New Zealand, because if I’m not working every night until 3AM in New York City and surviving off ramen while growing my business, I can’t be serious about it, right? Fear does not go away, it evolves. Sometimes your fears will come true. And then you will get over it and be scared of something else.
You get to choose what you’re scared of.
You mention bravery comes in many different forms. People might say I am brave because I am choosing to launch a startup instead of working full-time. But one of the reasons I’m in this position is because I am afraid of working for somebody else. Just thinking about it gives me anxiety. For me, bravery is a nice way of saying I was too scared of doing one thing, so I was backed into a corner of doing another. There are fears that come with working for someone else, and there are fears that come with working for yourself. You get to decide what you’re most scared of, and what you’re willing to sacrifice. OKREAL might not work out, but I am more scared of regret than I am of being poor and making a fool out of myself.
Do things before you’re ready to do them.
I used to waste so much time over-preparing. Like perfecting my pitch before I scheduled a call, coming up with an answer for every potential question, safety-netting myself against every possible situation. I had a nice collection of excuses to keep me in my safe place, too. And then I looked around and saw everyone getting on with shit, and became more afraid of being left in the dust than having my media kit ready before I scheduled a meeting. If you spend your time getting hung up on the details of how everything is supposed to pan out, you will never get anywhere. And you will annoy the hell out of everyone while you talk about this thing you’re going to do one day, but why you can’t do it just yet, but as soon as this other thing works out, you’ll be able to start. You need to have enough humility to iterate and learn as you go. Claudia Batten likens this to kayaking:
You know you are getting in the kayak and heading downstream, but exactly the twists and turns, how you will navigate through the rapids, is something you need to be in the moment for. Planning in advance is the basic element but not the whole. We know how to plan and it’s comfortable—but we risk getting caught in trying to make something perfect and never doing.
Prepare enough so that you don’t look like an idiot, and then schedule the call. Buy the ticket. Book the trip. It’s amazing what you can figure out when you don’t have a choice.
When you ask yourself: ‘What am I so afraid of?’ what is it, exactly? If it’s about creating, I’m guessing that it’s the same as what everyone else is afraid of: I’m going to look like an idiot, I’m not capable, people will criticize me, no-one will care, I don’t want to take on too much, I’ll spend all of my time and money on something that has no guarantees. I’ve talked about writing a list of the worst things that could happen, and then what would happen, and so on. But if rationale doesn’t work, I try humor. I tell myself to lighten up, to get over myself. Am I really going to spend my short time on earth worrying that someone might not like a website I made? That some random person won’t agree with something I wrote? Or stay working somewhere I hate because I’m too scared to see what might happen if I try and do what I really want? We are here for the most minuscule flash, for who knows what reason, and we get to choose how we spend our tiny slice of time. There is nothing like a mortality reminder to realize that you’re being ridiculous.
I’m glad I’ve finished writing this response. I kept putting it off because I was scared I didn’t know how to answer it properly. Because much like writing about love, writing about fear is so universal it’s hard to say anything original. You might become an embarrassing cliché, or you might become a good example for how things work out when you take a risk.