Soft Confidence

Between arrogance and meekness is the constant calibration of confidence

Illustration by Stephanie Davidson

When my startup was in Y Combinator, the prestigious startup incubator (which I recently wrote about here), the head of the program sent an email to about seven hundred current and former founders with the subject line: don’t be arrogant. In the brief email, this leader said that he had heard from some investors that YC founders were showing signs of arrogance, like demanding higher company valuations because they were in YC. Don’t do that, the email admonished, it’s bad for all of us.

Anyone familiar with (but not indoctrinated into) YC will understand the irony here—this is somewhat like Narcissus himself sending an email with the subject line “don’t be narcissistic.” The lack of self awareness was stunning and the approach laughable—what type of leader thinks he can just send a brief email commanding a massive cultural change and it will be done? Well, um, an arrogant one.

But even at the time, and despite my disbelief at the gall required to send an email like that to so many people, it did get me thinking: what is the role of arrogance in entrepreneurship? And was there any room for humility in the entrepreneurial game? It seemed to me then that arrogance was much more an asset than a liability for an entrepreneur—so many of the men who won the game possessed the quality—and humility was rather a beta characteristic. For my own part, I would have placed myself somewhere on that spectrum even further to the right of humility, possessing qualities that seemed the total opposite of arrogance: meekness and crippling self-doubt.

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I have been thinking about this whole theme again recently after reading a quote from Carl Phillips via

Lisa Olivera

:

…a career in writing maybe most requires…a constant calibrating and recalibrating of arrogance and humility. You need the arrogance to believe not only that you have something to say but that the world must hear it; and you need the humility to recognize both that not everyone wants to listen and that no one is in fact obligated to do so.

Reading this provided me with one of those precious moments when I could see for an instant the evolution of myself and the distance between who I am now and who I was then. In writing, unlike in starting a startup company, I do not feel meek and submissive. I also don’t feel (and actively try not to be) arrogant, I instead feel…confident. I feel like I have a lot to learn, I feel like there are plenty of much more skilled writers out there from whom I want to learn, and I also feel like I belong here with them, like I am on the journey I want to be on. Not to say that every day I sit down with confidence and happily click out the next work and feel immediately great about it…very far from that. Rather, there is the “constant calibration” that Philips suggests: I feel challenged and I feel proud and I feel beat down and I feel lifted up and I feel hopeful and I feel hopeless and I feel motivated and I feel like slamming my fist into the wall and I feel respected and I feel insignificant…and the whole group of these feelings, in the best moments, kind of average out to a certain soft confidence.

So now I’m envisioning a spectrum with a personal ideal: Soft Confidence

That I could live in or around this ideal for even a fraction of my day is a huge development for me, the kind of immense but gradual progress that can get lost in the long slog of life, so I want to take a brief moment to acknowledge and celebrate this. And also to explore a bit, how did this slow, meaningful shift come about?

1. I’ve been writing a little bit for a long time

I’m only thirty-five, a baby writer, since our kind tends to evolve and marinate for decades before reaching any kind of maturity, but I have been writing more or less seriously since I was sixteen. It didn’t feel like that along the way: I didn’t feel like “a writer,” I didn’t ever feel like I was doing enough writing, I didn’t feel like I was learning enough about writing, I didn’t feel like I was serious about it when my life was involved with all the other projects of growing up. But the fact was, and I see this now, I was doing it. I was doing it once a month in my journal. I was doing it every morning for two weeks before work and then burning out and feeling guilty about stopping. I was doing it in an adult ed class here or there. I was doing it in a short-lived blog, in a half-finished essay, in professional writing that I deemed uncreative, in a book that was never published. I was doing it before I started a company, I was doing it (a little) while starting a company, and I did it in spades to process the whole experience after it was all over. The point is: I was doing it, and any given year it didn’t feel like I was doing much writing, but add together twenty years and I see that I’ve got some accumulated experience. For me, experience brings confidence. Sure, I can be a quick study, anyone can, but there is a depth that comes from focusing on a skill or topic for a decade or four decades.

For writers: this is not to say that if you didn’t start writing at 16 you’re screwed (and by the way, I wouldn’t have said at 16 that I was really “writing,” just keeping a mandatory journal for English class; it’s only clear in retrospect that it was part of a broader life theme). This is to say that this year, whatever writing you’re doing is adding up. It’s the thinnest little tree ring added to the trunk, hard to see in one year but certainly visible in twenty. And this type of experience lends itself to soft confidence: you’ve done this. You’ve done it over and over. You don’t have to prove you can do it. You also know from experience that there’s always more to learn.

And I think this applies outside of writing, too. Whatever those activities are that you seem to do and do and do, less or more, year in and year out, I suspect that these are the wellsprings of soft confidence. It could be developing an area of professional expertise, it could be nurturing decades-long friendships, it could be holding space for pain, it could be managing a team, it could be growing a vegetable garden.

2. I’ve failed completely and returned to it

Another source of my emerging soft confidence about writing is my total, complete, horrific, epic failure in the category of writing. As I’ve written about before, when I was in my twenties I spent three years sporadically writing and editing a nonfiction book about hitchhiking with truck drivers through central China. God, how many hours went into that project, how many frustrated, groggy mornings, how many stomach aches, how many tears. I got an agent after more than sixty rejections, and we spent two more years editing the thing. When she finally sent out the manuscript, the rejections rolled in until, as I understand it, every single publishing house said “no.” Man, that was rough. WTF had I just done wasting all that time for the last five years?! Dumb, dumb dumb. When you’re twenty-seven, five years is like one fifth of your conscious life. I had spent one fifth of my life on this shit.

The extra salt was that I didn’t really like the book enough to self-publish. I wasn’t really proud of the work, I had written it amidst a lot of “should’s,” and I think this was the source of its downfall (a topic for another time). Needless to say, I stopped writing for awhile. So there was really nothing to show for all of that.

Or was there? Eventually I picked up my journal again. Eventually, I signed up for a personal essay class. In other words, I couldn’t stay away.

And this is very powerful. I’ve already failed spectacularly at the ultimate culturally accepted threshold for “being a writer”: publishing a book. And I still kept going, not grudgingly, but (eventually), willingly, because the desire to continue was so strong. So really, what more is there to fear? Though I am somehow able to still conjure plenty more things to fear, I recognize too that this failure and return has endowed me with a certain level of serenity towards the whole endeavor. I have internalized the lesson that whatever the outcome of any individual effort, the grander arc will bend towards me becoming a better writer.

3. I’ve had the experience of making something from nothing

Finally, I must give credit where it is due (and how I dislike crediting Silicon Valley for anything, but…): the experience of starting a company from thin air, is undeniably empowering. Though I constantly struggled through it, and never felt like a girlboss even a little (ugh, that word), I did play a big role in creating a thing that employed people and served customers and collected accounts receivable and eventually got acquired. That certainly had an impact on my current confidence, though it also took a huge toll on my health and wellbeing. I do believe there must be less painful and personally damaging ways to build that muscle of creation—please share your story of creating something from nothing if you have one!

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So to conclude this exploration: I like the spirit of Philips’ assessment that writers need to balance arrogance and humility, but I disagree slightly. I can’t endorse arrogance, or “having an exaggerated sense of one's own importance or abilities.” This is the quality I saw so often in Silicon Valley Man, and which I found so abrasive and off-putting. However, I very much can get behind confidence: “a feeling of self-assurance arising from one's appreciation of one's own abilities or qualities.” Yes, building and appreciating one’s own abilities rather than exaggerating them, that seems right. And even more, I love the idea of mixing in a little humility with confidence, bringing an acknowledgement that there is always more to learn and other people have something to teach us. And so we have soft confidence.

Let’s talk!

💡 What do you think of soft confidence? Does it help clarify anything for you?

✍️ Have you gone through fits and spurts of writing in your life? What does your rhythm look like lately?

🙈 What’s been your biggest writing (or another craft) failure so far? (Trust me, we can all commiserate.)

I’ll meet you in the comment section!