Afraid of making your mark?

One of my intentions for 2021 is to get back into painting. I used to draw and paint all the time when I was younger, but somewhere along the line I became afraid. I believed that if I didn’t get it right the first time, it was evidence of a more global failure.  

Even in moments when I really wanted to get crafty and creative, I couldn’t overcome my mule-headed resistance. I’d rather stare at a wall for hours than pull out my paints. Fear and longing and self-rejection, all mixed up together, shut me down for decades. 

Over the Christmas break I picked up some cheap paints, paper and small canvasses. Signed up for a couple low-commitment online courses. Started small and reminded myself it was simply play time. Gave myself permission to create ugly paintings. 

I’ve had a blast throwing paint around, making a mess, and delighting my inner 8-year old. And I’ve created plenty of ugly paintings. 

But here’s the really fascinating part. 

My first few paintings turned out more like wallpaper… low contrast and no clear focal point. The other artists in my class have the same fear when it comes to making bold marks. We’re all timidly tiptoeing around the canvas. 

What’s showing up on the canvas is our own minds. Our inner fears. Our desire to hide out in safe territory. 

Like everything else in life, the outer world mirrors the inner. 

The fear of making a single bold mark on canvas is a direct reflection of our fear of making our mark in life. We’d rather hide than be seen making a mistake… or be seen at all. 

The visual clutter, and the lack of open white space, is a direct reflection of an inability to set boundaries and a willingness to say yes to everything. 

My compelling need to add (piles of) geometric lines and shapes reflects my exceptionally fluid mind’s craving for structure. 

My tendency to exuberantly throw paint on a canvas reflects my years of failing to be intentional or to listen to myself. I’m learning that creating art is a back-and-forth dialogue of what wants to show up, and what needs clarifying.

Just like life. 

I’m able to overcome my resistance to painting now because I’m utterly fascinated by the psychological nature of this process. 

I’m starting to be more intentional about slowing down, listening, creating open space, and making bold marks. As I pay more attention in my art, I’m paying more attention to my own mind. I’m attending to what wants to be seen and heard within myself. 

And as I get more comfortable making my bold marks in the privacy of my own home, I’m also more comfortable with making my bold mark in my life and work. 

Like the Zen enso circle*: bold, simple, clear. A tall order for a brain that’s dazzled by too many possibilities, but a worthy goal. 

What about you? 

You may have never played with paint or taken an art class. But if you’re curious, I hope you’ll try it. Like the Inner Compass work that I do with my coaching clients, art is a way of externalizing what’s going on in our minds. When we externalize it, we can see it. And if we can see it, we can work with it.

And no… I won’t show a photo of my artwork right now. Maybe after a couple months of practice 🙂  

PS. I just kicked off the first cohort of Intentional Rebels, a life/work redesign group coaching program. If you’d like to be notified about the next cohort, you can sign up on the wait list here

*Image courtesy of St. Lawrence University. I have had the pleasure of being on retreat with Sensei Kaz Tanahashi, although did not fully appreciate the Zen calligraphy practice at the time. 

Seeing clearly: three life lessons from a lost pair of glasses

I lost my eyeglasses last weekend while hiking in the mountains: snazzy designer glasses that I’d worn for years, but were admittedly less than perfect. They were constantly sliding down my nose unless I kept tightening the arms; the lenses were scuffed from being dropped too many times; one of the lenses was cut for an astigmatism that had miraculously cured itself a few years back. 

Bottom line, I was long overdue for new glasses, but must have been in denial. It seemed like an unnecessary and pricey expenditure while I was in the midst of personal reinvention. They were fine… like worn and comfy jeans, quirky and imperfect and familiar. 

Fast forward to today: I’m wearing new glasses that actually fit my face. And they’re clear! Holy cow, I had no idea the world was this crisp and clean and beautiful.

These new glasses got me thinking about all the ways we don’t see things clearly, and how we can improve that state of affairs when it comes to transitions and transformations. 

What we refuse to see

For decades, I refused to see and embrace the truth of who I was: that as a gay, neurodiverse and gifted adult, I would never fit into mainstream society. It was unsurprising that my eye developed an astigmatism, getting warped out of shape and blurring my vision. It was also unsurprising when my astigmatism (and my gut issues) later vanished once I decided to love my quirks instead of hide them.

We can never effectively work within a reality we refuse to see. Seeing clearly starts with embracing our uniqueness, and then intentionally designing our lives and work to fit who we really are.  

Questions: What do you not want to admit to yourself? Without any judgment, complete this sentence: “I am ____, and I’m good with that.” Given this truth, what wants to change in your life or work? 

What’s hard to see (where’s Waldo?) 

We rebels can be dazzled by too many possibilities. Our brains take in more information than the average person, and we’re usually fast learners. And that means we have a hard time prioritizing options and taking off the table anything that’s not a Hell Yes

If the authentic path forward isn’t clear amidst the clutter, our old and familiar way of seeing — overanalyzing and wheel-spinning — doesn’t cut it.  

When federal agents are looking for a handful of counterfeit bills out of thousands, they don’t rely on their eyes; they simply pull out a blacklight and look for the florescent symbols that are printed on authentic bills. The human version of a blacklight is our gut-level wisdom, which can easily detect our true priorities.  

QuestionsWhat does your gut say? Which option feels expansive, uplifting… like a Hell Yes?  

What we can’t see

“I have no idea if I might like that line of work,” is a common refrain from the people I coach through transitions. In the absence of direct knowledge, it’s way too easy to simply sit with the question mark, waiting for an answer to appear out of thin air, or just playing around the edges of the known world. 

It would be super nice to see a clear path forward: to have the equivalent of a map or GPS system for life. But in the absence of psychic powers, our only choice is to take a small action and see what happens.  

Remember in Raiders of the Lost Ark (yes, I’m totally dating myself) when Indiana Jones steps off a ledge into thin air… and onto a walkway that only revealed itself after he took the step? 

Our eyes can deceive us. Stepping into the void requires not only courage, but also conviction and faith. We have to go through the previous two stages — accepting what is, and listening to our guts — to know the treasure we’re seeking. And then, in experimentation, fumbling forward in the darkness, the path appears… an inner vision is activated… the right people and opportunities show up.

Questions: Thinking about a possible life direction that feels like a YES, what is one baby step you can take to explore that option? Who’s knowledgeable in that space that you can speak with? 

Ok, that’s a lot of insight from a lost pair of glasses! Did you glean anything new from this deep dive into clarity and sight? Feel free to leave a comment; I love hearing from you.  

PS. I only have one coaching spot left in 2020. If you’re feeling the need for transition or transformation but can’t see the path clearly, let’s talk. You can access my calendar here. 

PPS. Want to get these posts in your inbox once a week?

Photo by David Travis on Unsplash

What do you love?

If you haven’t seen Ethan Hawke’s video on TED’s YouTube channel, you’re missing out. It’s called Give Yourself Permission to Be Creative, but it’s really about giving yourself permission to be yourself.  

My favorite quote: “What do you love?… if you get close to what you love, who you are is revealed to you.” 


Too often, we try to make decisions by thinking and analyzing instead of tapping into the wisdom in our bodies and emotions. Ethan calls it love; I call it your YES — that vast, expansive, light feeling in your body that emerges when you’re in full alignment with your truth. 

This feeling reveals who you are. It reveals your path, like breadcrumbs. 


  • How often do you feel that sense of YES in your life and work? 
  • In what ways have you sacrificed what you love in the name of an expectation or a paycheck or…? 
  • If you could do one small thing this week to create more YES, what would it be? 

Share your answers in the comments; I’d love to hear from you!

Photo by Michael Fenton on Unsplash

When failure is the best possible option

“If I’m lucky, I’ll fail.” I overheard this eyebrow-raising thought while making breakfast in my rooftop nest in Tel Aviv last summer. I considered myself lucky to hear it: usually our subconscious minds hide these heresies with Cloaks of Invisibility. But I caught mine unawares this particular morning; either that, or my subconscious finally grew tired of the years of self-deception.

An idea for a new business venture had consumed me for the previous few weeks, and it was a good one on paper. I’d missed catching the start-up wave in San Francisco, yet in Tel Aviv I’d found a new wave: a smoking hot start-up community where my particular skills could be valuable. I went to meet-ups, attended a couple VC parties, and identified a compelling white space. Boom! Here it was, my next chapter. I’d figured it out.

And yet.

Just because it was a good idea didn’t make it a good idea for me. Just because I could, didn’t mean I should. My secret wish for failure came not from low self-esteem, but rather from that still small voice within me that knew without question, “this is not the way.” I’d heeded my intuition’s call to come to Tel Aviv from Morocco, and perhaps that listening encouraged me to listen again. To not assume why I was here (to start a business!) but rather to collect more clues for my journey.

I’d experienced more than my fair share of failures throughout my career; perhaps those failures were trying to tell me something. And standing in my kitchen that morning, I can’t say I knew what that something was…. but I felt a gentle breeze coming from a window of curiosity that cracked open at the idea that, just maybe, there were other options for me to explore.

It’s perilously easy for those of us with diverse skills and interests to be dazzled by good ideas. Easy to be lured down roads that are not ours to walk, slowly losing the ability to make decisions based on our truth. Confusing “I am capable of doing this” for “I was born to do this” is how we lose ourselves, or how we stay lost.

Perhaps the root of self-sabotage is precisely this tendency to set ourselves up for failure when secretly it’s not what we really want to do anyway. If we persist in the name of should’s and expectations, failure can be the best thing that happens to us; the real tragedy would be to succeed at something that will eventually suffocate our passion for life.

The real tragedy would be to succeed at something that will eventually suffocate our passion for life.

Even if we are on the right path — if there is such a thing — we’ll encounter failure. This has been written about too frequently for me to belabor the point with more than the following observation: Failure can simply be a sign that we’re simply not there yet. Maybe we’re doing the right thing, but with an unhelpful mindset. Maybe if we change a single variable – like location, or communication style, or start saying no — a whole universe opens up. It’s usually worth experimenting and tinkering to see what’s what.

It’s so easy to want an answer, or as my friend Kate eloquently wrote, rush through the breakdown without first finding the beauty in it. Tired of the lessons, we don’t want to have to try again, and again, and again in order to get it right, or to find the treasure. Often that’s the product of thinking too small, believing that what we seek is for other people, not for us. When failure is seen as a permanent life sentence that commits us to a small cell of existence, we stop persisting. Failure becomes a blockade instead of a stepping stone.

There’s another kind of failure — not the one that we encounter when we’re on the wrong path, but the one that inevitably happens when the current chapter has run its course. Perhaps the reason we fear failure so much is because it’s a lot like death. Everything in this world has a natural lifecycle… yet instead of flowing with this truth, we fight it. This struggle against inevitability saps our life force, and drains our belief that we have the capability to change or fix anything.

When we’re “moving from failure to failure without a loss of enthusiasm,” as Churchill once wrote, that’s one thing; the sense of possibility on the horizon pulls us forward. But when the glory days have passed, when the machine is grinding to a halt, when the chasm grows wider by the day… sometimes it’s better to let failure run its course so that something new can be born out of the ashes.

Sometimes it’s better to let failure run its course so that something new can be born out of the ashes.

“Dammit, I will make this work!” is what we say when we can’t let something go. Lord knows I said it countless times during my unsatisfying career as a consultant. “Persistence is a virtue” — except when it’s not. “Failure is not an option” — except when it is. Except when we’re choosing to keep something on life support instead of allowing failure to birth an unknown future… whether that’s a career, a relationship, a company or a country. And it takes a lot of failures to finally be able to discern the difference.

What are you keeping on life support out of fear of failure or the unknown?

What failure will you create this week in order to scratch one option off your list?

What past failure will you forgive and appreciate as a learning opportunity?

What failure of someone else can you forgive as part of their own learning journey?

Don’t start with why

Once upon a time, life didn’t change much. We all had a bit more control. We could set a goal in our lives or work, and draw a straight-line action plan to get there. This approach is a bit like making a movie: decide on the plot, write the script, hire the actors, and produce. Ta-dah! A nice linear process, like an assembly line.

Of course life no longer works like this. Maybe it never did. This linear approach helped us be a bit more efficient, but it doesn’t satisfactorily deal with the messiness of reality; the constant change; the fact that there are far more interesting opportunities than we have time to chase, with new ones are emerging all the time. How do we focus?

Instead of imposing even tighter controls, let’s play with a different analogy: improv theater. Here we choose the cast, but we don’t choose the plot and neither do the actors. The actors call out to the audience to provide constraints: Tell us a character! A place! A time period! And within these constraints provided by the audience, the show can begin. The plot emerges within the bounds of an intention.

This is the power of both/and, not either/or. It’s both intentional and emergent; top down and bottom up, planned yet agile. The path becomes clear through iteration and experimentation.

how is intent best defined?

In our default mode, we choose a “what” to aim for. What do we want to do, make, accomplish? But in an uncertain world, the what is constantly changing. Focusing on a what is a bit like the movie analogy; we’ve narrowed in a bit too much on scripting the details instead of holding space for a variety of whats to emerge.

Simon Sinek says we should start with why instead of what, because why — a sense of purpose – provides a way of orienting ourselves towards what doesn’t change. But what happens when your why and my why aren’t the same? In a business context, what if our collective why doesn’t resonate with customers and partners? Focusing on why risks being rather self-centric — what’s important to me instead of we.

While I can’t fault the logic behind why, I prefer to start with who. Who is in our unique ecosystem — including myself — and what do we all care most about? Or… back to our movie analogy, there’s not much of a plot without the who. The main characters provide the storyline; the richness and emotional depth of the actors is what makes a film (or improv) a flop or a hit.

WHO defines the WHAT and the WHY

Who defines the what and the why. It makes sense that I’d focus here given my background in human-centric strategy and transformation. But I see now one critical ingredient that I’d missed in all my heady analysis; I’ll get to that in a minute. First, let’s explore the power of who.

What holds it all together?

What’s the one thing that doesn’t change? Is there such a thing? Yes… it’s our human nature: Our 12 core human needs, and how we feel when those needs are met. It’s this unchanging part of who that ensures Romeo and Juliet is still relevant 5 centuries after it was penned by Shakespeare. It’s this deep, felt experience of love or safety or freedom or creativity or belonging (etc etc) that serves as the glue (the intent) for the some of the most complex businesses on the planet.. and yes, it works magically in our personal lives as well.

I dare you to name a single wildly successful brand that doesn’t tap into one core human need or emotion. They all do. Amazon, Netflix, Uber, etc. = control (I want what I want, when I want it.) Virgin = autonomy and freedom. The largest incumbent in every category = security (“no one got fired for buying IBM.”) Apple = control + creativity. AirBnB = belonging and diversity. The list goes on. The best ones pull even more meaning and purpose (why) into this emotional container, along with more who… the sense of shared identity (rebels, creators, helpers, hosts, etc.). This focus on a Who — a tribe with shared needs and values — allows brands like Apple and Virgin to extend far beyond their original what into other categories, magnetizing customers, employees and partners along the way, without losing their essence.

We’re like plants stretching towards the sunlight, seeking the emotional nourishment that we need to grow. And the reverse is true: we move away from what we don’t want to feel: unvalued, unsafe, trapped, disconnected. Research reveals that “emotions constitute powerful, pervasive, and predictable drivers of decision making,” not only in psychology but also in consumer behavior.

Who’s the most important who?

Pre-sabbatical, I assumed the most important who in a business context is the customer; they pay the bills, after all. So I’d lay out this elegant strategy on how to orchestrate a complex global enterprise around a need or emotion that was most predictive of business outcomes, and I’d hear, “but we don’t have a Steve Jobs.” I’d reply, “You don’t need one. Simply replicate what he and others did. Here’s the recipe.” As if it were that simple.

I was wrong.

The most impactful leaders in the world magnetize global ecosystems because of who they are, not what they do. They know themselves deeply and unapologetically. They’ve doubled down on their strengths. And because they listen to their own inner wisdom, they can hear and have empathy for others. They stand on what I call the “ground of power”… the source of authenticity and individuality that allows them to balance security with flow, stability with freedom. Intent + improv… both/and. As within, so without.

This type of leader also understands the power of coherence. Coherent light is a laser that can cut through steel, while diffuse light is powerless. Coherence that harnesses the power of empathy and emotion? Unstoppable. And this requires a different way of seeing the world: connections, not compartments. Similarities, not differences.

Leaders or entrepreneurs who truly know themselves will naturally create coherence within their teams, partners and customers. A metaphorical casting call, likeminded people are drawn to their visions and identities. This doesn’t negate diversity, by the way; a mindset or emotion (what I call “motivational DNA”) serves as the golden thread that weaves through a host of differences and thinking styles.

When leaders, teams, employees, customers and partners are drawn by the same motivating force, it’s as if an ecosystem emerges from nothing. The power of attraction is activated.

How to harness WHO

Perhaps you’d like to start a business but are unsure where to begin… or you want to take your business to the next level. Or, heck, you simply want clarity in your own life… to be able to make forward progress when your what isn’t clear. My suggestion is to start with who.

  • Know thyself as a leader. Embrace your entire identity and what makes you unique. What core needs have motivated your decisions in the past? How are you wired? How do you want to feel in your life and work?
  • Know thy team. If I’m primarily motivated by freedom and you’re primarily motivated by security, we’re going to run into some fundamental sticking points: our motivational DNA isn’t complementary. That doesn’t mean we can’t work together; this is a wonderful opportunity to celebrate what freedom and security bring to the party and find the middle ground. But it could also be true that one of us is in the wrong place.
  • Know thy customer. This is the person who is responsible for paying the bills, yet too often they’re left out of the culture conversation. What will magnetize them to your brand? How do they want to feel, and how does that inform your business model, offerings, extended partnerships and, yes, internal culture?

Now it’s time to find the golden thread. In the midst of diversity, you’ll find similarity… and it’s the similarity that unifies us. That encourages to bring our whole selves to work. That breaks down silos and helps us all grow together.

The similarity provides the Intent: the stage for the improv (or to use geeky terms, the platform for the ecosystem). Now all the actors can play, experiment, and be agile without being at odds with one another. “You understand me; I belong with you” is what prospective employees and customers think as they are drawn like iron to the magnet that is our shared humanity.

Learn more

I’m a rebel with a cause who’s helping other “rebels with causes” create more freedom and impact in their lives and work (a tangible example of what I just wrote!) I’m no longer doing strategy, but I can advise, review your strategy and make suggestions, assess the motivational DNA for you and your teams, facilitate a workshop, or guide you in a 1:1 journey to gain clarity on your who, why and what (in other words, what I offer can easily evolve around the who). Learn more here.

Why New Year’s goals and resolutions don’t stick (and what to do instead)

From the archives, a post I wrote in January 2020 that’s still very relevant!

Every year on New Year’s Day, I would retreat and spend the day journaling to rehash all the things I hadn’t done the previous year, and set goals that I failed to keep for the next. After a few months, I’d beat myself up for the failures. Rinse and repeat, over and over. Not a good recipe for a healthy self-esteem, that’s for sure.

But 2019 was different: I felt no compulsive need to figure anything out. There was no puzzle to solve. Sure, I’d like to get to the gym more often and cut back on carbs, but my life is pretty simple these days. I’m a lot happier. I don’t feel compelled to make any big changes.

What happened?

I spent all of 2019 getting aligned with what brings me joy. It was an elimination diet of sorts; I literally eliminated everything from my life — stuff, job, home — and set out on a nomadic journey to feel my way back into a life that fits me like a tailored suit.

I recognize that not everyone can (or would want to) take the kind of crazy leap that I did. But I’ve made some observations from my transformation process that can apply to anyone.

  • Focus on how you want to feel. Emotions drive behavior, not logic or a list of to-do’s. When we get really clear on how we want to feel in every aspect of our lives, and start taking baby steps to feel that way more frequently, we gradually shift everything in our lives. There’s a reason why Marie Kondo’s Life-Changing Magic of Tidying Up is a global sensation; she’s simply helping people surround themselves with what brings them joy by getting rid of what doesn’t. This book was instrumental in helping shift my own life and I highly recommend it.
  • On a related note, start with releasing. We’re all operating with a finite amount of time, energy and resources that are currently allocated to other things. Most of those other things (people, activities, stuff, work, etc) don’t bring us joy. They’re simply the accumulations of life that we’ve picked up, like a snowball that grows as it rolls downhill. The older we get, the more of this accumulation gathers unnoticed and unquestioned. We all need to get better at saying no, setting boundaries, and offloading what we can. Let’s eliminate the NOs so we can clear space for more YES.
  • Then add easy YESes. It’s hard to commit to the tougher resolutions like diet and exercise if the rest of our lives are lacking joy; you’re just piling shoulds on top of shoulds. No wonder we don’t stick with them! Try this instead: start with clearing some space in your calendar by replacing a NO with a YES… perhaps a cooking class, dancing in your living room, or painting rocks… whatever floats your boat. Clear some space in your closet by taking NOs to a resale shop, and trade them in for something that makes you deliriously happy when you wear it (I just picked up some happy striped socks for Christmas!) Start your day with a routine that puts a smile on your face; I make a perfect soy latte, journal and write poetry. What brings you joy? Do more of it. Simple.
  • If it’s not a Hell Yes, it’s a No. How many of us agonize over whether something or someone is right for us or not? Let’s make this perfectly clear and simple: if it’s not a hell yes, it’s a no. Agonizing, debating, writing pros and cons… it’s all useless. Seriously. Look back over your life; can you honestly find one thing you’ve debated that turned out to be a hell yes? Ok, maybe 1 out of 100 times it might be worthwhile… but that means statistically you could save yourself a lot of time and trouble by moving on already. Make room for Hell Yes.
  • Let the process be more organic. If there’s one thing I’ve noticed by stepping off the hamster wheel, it’s this crazy focus on goal-oriented performance. Americans especially are programmed to operate in a linear fashion: set a goal and start ticking off boxes. But most human beings aren’t designed to work that way; like a blind person, we slowly sense our way a new life by making small changes and seeing how they feel to us. If they end up feeling good, we’re likely to do more of it. If it doesn’t, then we stop. So please stop flagellating yourself into performing according to some inhuman standard, and start having more fun with this process. Play. Experiment.
  • … but stick with it. If you’ve decided how you want to feel — let’s say strong and empowered — then the activities that directly contribute to that emotion – in this case, exercise – are no longer optional. It doesn’t matter how you feel in the moment; what counts is that you’re doing the thing that will help you achieve your bigger, more important emotional goal. Chances are the first few weeks are going to suck, and that’s ok. You’ll eventually hit a point where you realize: hey! I’m feeling strong and powerful right now! And boom… this whole process starts getting easier.

Dear reader, what will you say NO to this week in order to clear space for YES? How do you want to feel this year, and what will you start doing to feel that way more often?