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The question we’re afraid to ask

January 19, 2021

During the pandemic, David Whyte (one of my favorite poets and thinkers) has been offering online seminars. I highly recommend them; they’ve been such a source of connection and belonging for me, even without a “community” component (maybe especially without a community component, for an introvert like me). His wisdom and poetry is good medicine for the heart.

Whyte’s most recent series is called “Start Close In,” after his poem by the same name.

Start close in,
don’t take the second step
or the third,
start with the first
thing
close in,
the step
you don’t
want to take.

Start with
the ground
you know,
the pale ground
beneath your feet,
your own
way to begin
the conversation.

Start with your own
question,
give up on other
people’s questions,
don’t let them
smother something
simple.

To hear
another’s voice,
follow
your own voice,
wait until
that voice
becomes an
intimate private ear
that can
really listen
to another.

Start right now
take a small step
you can call your own
don’t follow
someone else’s
heroics, be humble
and focused,
start close in,
don’t mistake
that other
for your own.

Start close in,
don’t take the second step
or the third,
start with the first
thing
close in,
the step
you don’t
want to take.

A throughline of David Whyte’s lecture series’ has been this idea of starting a new, truer conversation with ourselves by asking ourselves a more beautiful question. And not only asking it, but discerning what that question might be by giving ourselves space, and often, silence. We may even need to stop the conversation we are currently having in order to begin a new one. This, he says, is the beginning of saying yes to the invitation life is making to us in this moment.

So how do we find that beautiful question? According to David Whyte, it’s often the one we’re scared to ask; the one we might not want to know the answer to. The first step required by that answer may be one we don’t want to take.

Discovering that question is difficult. Often, we’re unable to see it for ourselves. Our resistance (or our denial) is too great. It could even be something anyone who gets within shouting distance with us can see, but we’re oblivious to.

So of course, I’ve been thinking about my own beautiful question. I don’t know what it is yet. But it reminds me of the question I’ve been trying to answer since taking on the CEO role at &yet (that I also wrote about during that time): How can I participate in the public conversation without being ensnared by it?

When I first wrote about my commitment to discovering how to do this for myself, I was mainly concerned about how re-entering the public sphere would impact me emotionally. I struggle with social anxiety, and in fact, in my early days on the web, the Internet was a safe haven for me. I loved being able to talk about what I cared about asynchronously with people who geeked out over the same things. But as social media took over and the Internet grew to include literally everyone on the planet (and as I simultaneously grew a business, and—consciously or unconsciously—a “personal brand” to go with it), it stopped feeling like a place where I could escape from the pressure and expectations of the world around me and be my weird self. Instead, the pressure and expectations online became even greater than the ones I perceived offline.

When I took on the CEO role at &yet a year and a half ago, it had been 3 years since I’d had any sort of regular digital presence, and I hadn’t missed it. At the same time, I felt like I was hiding from something and keeping a part of myself small. I felt like I had a responsibility in my new role to work on it. Whether that last part was true or not, I wanted to come out of hiding.

So for the past year and a half, that’s what I’ve done. Not perfectly, certainly. There was a global pandemic. Black people continued to be murdered, and there were uprisings. Our president in the U.S. proved, over and over, (and is proving still…one more day in office!) to be a dangerous egomaniac. White supremacy has become even more blatant and seems to be gaining power. In the middle of all of that, I was trying to figure out what kind of CEO I wanted to be, and how to do that job well.

But I did it (and am doing it). I worked on fleshing out a process that helped me to show up authentically in the places that mattered most to me, at least some of the time. It was (and is) a complicated process with many steps that probably could stand to be simplified, but it has worked for me. Maybe one day I’ll write about it.

So why am I still concerned about being “ensnared” by participating in this public conversation?

“Ensnared” might be a dramatic word to describe what often happens when I share my thinking publicly, but I think it’s the right one. When I’ve retreated from the public conversation, it is much easier for me to know my own thoughts and to see clearly that “small step I can call my own.” I don’t worry about how I’m perceived; I just continue learning and growing and writing about it for no one’s benefit but my own. (I have completely filled 7 notebooks in the past year; I have no trouble being prolific!)

But somehow, being online makes me prone to questioning that truth in pursuit of…I don’t know what. Relevance. Legibility. External proof of my own worth and value. It’s harder to write things because I’m fascinated by them and want to write them; that feels like a waste of my limited, so very precious time. Instead, I’m tempted to create a unifying message and to massage my writing into something that fits; something that is extrinsically pleasing, cohesive, and measurably valuable to others.

Even writing those words, the question raises itself—“What’s wrong with making something extrinsically pleasing, cohesive, and measurably valuable to others? Why else publish?” And of course there’s nothing wrong with it, not inherently. But as a writer, something in me rebels against having solely that kind of relationship with my writing. It’s why, even though I write so much, even though I’ve worked very hard to develop a system that allows me to share without a lot of friction, I still publish very little of my writing. Most of my words, I keep to myself.

I recently took a class from Clarinda Braun, a consultant focused on de-colonizing business through matriarchy. (I highly recommend learning from her. She has brilliant energy and her insight is incisive.) One principle she taught us is that the impulse of the white/colonial lens is to “extract, exploit, exotify, and simplify.” It makes me wonder: how much of the tension I experience is related to the colonizing mindset inherent in my ancestry and culture? Is some part of me trying to colonize my own self?

Start with
the ground
you know,
the pale ground
beneath your feet,
your own
way to begin
the conversation.

Start with your own
question,
give up on other
people’s questions,
don’t let them
smother something
simple.

Even though I’ve slowly, steadily built a process that helps me publish my work without a lot of friction, social media is still difficult for me. I started with Instagram; it felt safer, less self-promotion-ey, but also not quite a fit for me as a writer; seems obvious now. Then I experimented with putting whatever I had to say on one or all of The Big Four (Twitter, Facebook, Insta, LinkedIn), tailoring the content to the platform. How exhausting. Currently I’m just on Twitter, sometimes.

The problem is, I am a fish, easily hooked. An ounce of praise, and I want more of it. An ounce of criticism, and I avoid a repeat performance. I either need to become wiser if I want to be larger than I am, or I need to sidestep the question altogether.

Even if my intentions are good, when I post regularly, I become subtly motivated to use these tools more than is healthy for me. (What’s healthy for me? Small doses, batched, spaced out, and closely monitored.) If I’m feeling like people are highly engaged, I don’t want to “lose” that engagement, so I start posting more frequently. If I’m feeling like they don’t care a wit (probably closer to the truth), I spend way too much time scrolling through my feed.

I just finished reading Cal Newport’s Deep Work, one of those books I assumed I knew all about before having read it simply because it’s in the water. (Reading it felt surprisingly fresh, even for being such a popular reference.)

Newport would say sidestepping the question of social media altogether is a valid option. To his mind, we’ve been seduced into thinking network tools are equivalent to the public conversation.

“These services aren’t necessarily, as advertised, the lifeblood of our modern connected world. They’re just products, developed by private companies, funded lavishly, marketed carefully, and designed ultimately to capture then sell your personal information and attention to advertisers.”

Of course, Cal Newport comes from a place of extreme privilege to be able to ignore the consequences of disconnection. He holds a Ph.D. from MIT and is now a Distinguished Professor at Georgetown. And he hasn’t exactly withdrawn from public life—he’s built a popular podcast and blog and has written six books, in addition to his scholarly papers. I do believe that staying off of Twitter and prioritizing what he calls “deep work” helped him focus on achieving those goals, but he also had plenty of resources and connections that most of us don’t have access to.

Speaking from personal experience, I credit the relationships I built on Twitter with a great many of the opportunities that got me to where I am now. I even met my now-husband and business partner through an introduction from a friend I met on Twitter. (In fact, I regretfully find much to agree with in Vankatesh Rao’s argument Against Waldenponding, even though it initially angered me because social media hasn’t been great for my mental health. And I personally love the idea of being a hermit.)

But despite the potential benefits of Twitter (benefits which, admittedly, take a lot of time and attention on Twitter in order to gain), are these tools good for me? Are they necessary in order to take a meaningful place in the public conversation? Or would I be better served by finding a different path?

Newport’s approach to figuring this out is to get clear on your goals, and then weigh the costs and the benefits toward achieving those goals. He’s no tech moralist. For him, the decision is pure pragmatism. The only bad decision is to make a choice to use a tool that has so many potential downsides to creative work based on the potential of maybe, possibly, receiving any benefit whatsoever.

I like Dante’s approach, personally. In David Whyte’s most recent lecture, he explained that he was inspired to write Start Close In by the opening lines in The Divine Comedy.

Nel mezzo del cammin di nostra vita
mi ritrovai per una selva oscura
ché la diritta via era smarrita.

In the middle of the road of my life
I awoke in a dark wood,
where the true way was wholly lost.

Whyte went on to explain that what we now know as Italian was, then, merely a little known local dialect. It was Dante’s mother tongue.

If Dante had wanted his work to be seen and respected by educated people, he would have needed to write it in Latin. And yet, he didn’t. It was a radical choice, seemingly a foolish one. And it was exactly right. Dante started as close in as he could go.

To hear
another’s voice,
follow
your own voice,
wait until
that voice
becomes an
intimate private ear
that can
really listen
to another.

There’s something people fail to mention in their attempts to help you “find your voice.” It’s that once you find it, you might not like it all that much. You may appreciate certain aspects of it, but you will also become very familiar with its annoyances. In this case, familiarity is almost certain to breed contempt.

This is an underlying consequence of participating in public life that I have to reconcile. Using my true voice, the one that is wholly unique to me, means that I will be annoying to my own self, out loud, all the time.

I want to develop a greater capacity to be okay with the grating of my own voice, okay with being just fine at something I value highly in others. Because if I show up authentically on any frequent basis, you will see what I see every day—there are moments of beauty here, but my contribution is often average. In a world where everyone is competing to be worthy of the rest of the world’s attention, this is a scary thing to admit—what is the point of contributing something “average” to the world?

But I’m learning that this may be the most valuable contribution of all—to refuse to fall prey to the possibility of success or failure, and instead to be committed to your own path, as honestly as you can, in public.

I’m inspired by writer Winnie Lim, who has written multiple essays on this topic. (This one, this one, and this one particularly resonated with me recently.) They give me courage that my beautiful question is not embarrassingly navel-gazey, but that it is central as more of our lives and our identities are being cultivated (or at least curated) publicly.

“I wanted to find a way of living that is true: in my own definition that means being able to appreciate life and what comes with it without resorting to making myself an attractive signboard. I wanted to become ordinary so that I will know what will stay when everything else fades.”

I’ve been fascinated lately by the Eastern Orthodox monks who have lived on Mount Athos for centuries. They believe that the path to oneness with God is through the heart, and that the path to the heart is through humility.

Humility, to them, is not about believing you are small; it is about noticing that we are all fish, easily hooked. We are attached to our own egos, and without even thinking, we make them our first priority. In this way, we cannot see clearly. We cannot love fully. We can only be concerned with upholding the ego that helps us feel safe, loved, and important.

Ironically, when we are able to let go of our egos, to see clearly and to love fully, it is only then that we can experience true safety, love, and belonging. Or at least that’s what the ancient sages, myths, stories, and wisdom traditions tell us.

Start right now
take a small step
you can call your own
don’t follow
someone else’s
heroics, be humble
and focused,
start close in,
don’t mistake
that other
for your own.

So how do we develop this humility, this willingness to be deeply ordinary in our own truth? The monks do it through prayers and chanting “without ceasing” so that they become forever aware of their own need for help. “Lord, have mercy. Lord, have mercy. Lord, have mercy.”

I suspect that similarly, this kind of ongoing willingness to be both ordinary and to listen to our own voice is a forever kind of practice. Of saying what is true, noticing when and where we get hooked by praise or criticism, taking time and space to feel it, finding ways to release it, then summoning up our courage to say again what is true.

We can also keep ourselves away from situations that we know are very likely to keep us hooked. We can create environments for ourselves that support our efforts to build that muscle rather than derail them. And we can let ourselves do all of this imperfectly, trusting in our own internal process rather than holding out for some external outcome.

But you know, I’m not sure. That’s what it looks like to me right now, in my attempt to come up with a strategy. Maybe I need to question that instinct, too.

Start close in,
don’t take the second step
or the third,
start with the first
thing
close in,
the step
you don’t
want to take.

January is, of course, a time for new beginnings, but I’m more into slow beginnings these days. At &yet, we take the month of January to think about what we want in the year ahead. Our forward motion doesn’t begin until February.

I’m taking the same approach with myself. Last year was a year of searching for a process, the True Way (as Dante refers to, mournfully, as the way he has lost). This is the way that would seem to take me straight to where I want to go. But as David Whyte quoted of poet Han Shan, “there is no path that goes all the way.”

This year, I’m giving up on that perfect path. I’m keeping the benefits of what I’ve learned, but it is ultimately the conversation I am ending, in order to find my more beautiful question.

Maybe my beautiful question is, at the heart of it, “Am I enough?” “Can I trust the pale ground beneath my feet?” “Can I trust this voice, this heart that is my own?” “Can I trust the ever-unfolding invitation of my life?” “And if I do, will I be safe, will I be loved, will I belong?”

But of course, that is a question I cannot know the answer to right now. It is only the beginning of a conversation that, afraid as I may be to enter into it, requires only that I take that first small step.


I’m a student and teacher of people-first growth. Having spent the major part of the last two decades building weird businesses that tried to be good for humans, I'm now working privately on a few experimental projects and cultivating this little digital space of mine.

If you're new here, I'm working on my second book, People-First Growth (slowly, slowly said the sloth), and I’m sharing what I learn in my newsletter. If you geek out on digital gardening, I share mine publicly on Roam. You can say hi on Twitter or by email.

You can also read my first book, Gather the People, originally released in 2015 and updated in 2020 (what a year for a book release). It's a human approach to marketing for people who would rather make what they love than persuade people to buy it. If that's you, I hope it helps.