Doubts

• 02 Apr 2013
• reflecting,
• work

It’s not easy to write or talk about doubts. The things we have doubts about are often precisely those things that are most important, both to us and to those around us: a relationship, a job, a major life choice. If they weren’t important, our ambivalences and worries wouldn’t reach the level of real doubt.

But those things are often so important that even feeling a little bit of doubt around them (did I make the right choice? is this going to work?) can become a crushing weight. Doubt in those cases seems tantamount to betrayal, especially when it’s clear that acknowledging those doubts would create anxiety in the people around us. How can you possibly admit to feeling doubt? It would only let everyone down.

Or, if it won’t disappoint someone else, doubt can feel like an admission of error — and the stakes of such error can be too high to countenance. (Having spent ten years preparing for a career, for instance, experiencing doubt about the choice not only feels like failure, but like a failure so long-term that it raises the possibility that one can have wasted one’s life tout court.)

So the doubt gets suppressed, stuffed into the corners of our lives that we ignore. And sometimes that works, and in the busyness of the day-to-day, in the daily struggles and triumphs, the doubt fades. But sometimes it festers in those corners, and feeds on itself and everything around it, becoming much worse than is necessary.

Finding the sweet spot between allowing doubt to metastasize and infecting others with it is an enormous challenge. This is the kind of thing that people rely on trusted advisors, therapists, clergy, and really close friends for — airing doubts with someone who won’t freak out, someone who can act as a reality check and reflect the doubt at an appropriate size.

I find myself, however, wanting to write about my doubts, to air them publicly, in part as an attempt to demonstrate — as I have found myself doing over and over with a range of professional fears and failures — that we all experience this pain. I’m confident, in fact, that we all^[1] feel painful levels of doubt, precisely because that doubt is a core element of the intensely self-reflective careers that we have chosen. Not-knowing, uncertainty, insecurity, second-guessing — without them, we wouldn’t have questioning, investigation, development, growth.

So here’s the admission: I have doubts. Big honking doubts. Now more than ever. I’ve been asked more times than I can count over the last two years how my career transition has gone, how I feel about the change, and my standard response has been to say that 90% of the time, I’m absolutely certain I’ve made the right choice. And I think that’s all anybody can ask for.

What I don’t tend to say is that 10% of the time, the doubt can be all but paralytic. And I also don’t say that it’s gotten more intense lately, now that I’ve taken down the safety net. In fact, though, it’s been particularly acute for the last few weeks, as I’ve felt myself not getting done the things I want to do, and not doing well at the things I need to do, and as I’ve been left wondering whether I’m really cut out for this new gig at all, and what if I’ve made a horrible, terrible, irreversible mistake.

It’s not at all coincidental, I think, that my doubts — indeed, my self-doubts — have become so much more painful and pronounced just as I’m inching up on closing the largest financial transaction of my life: I’m buying an apartment in New York.

(That sound you hear is me hyperventilating.)

It’s not just a transaction with huge financial implications. It’s putting down roots. It’s not just saying “I’m not going back there,” as I did some months back. It’s saying “I’m staying here.”

And on a day when, for one reason and another, I just don’t feel like I’m good at my job, the weight of those doubts becomes unbearable.

I had a dream over the weekend that I think is about all of this doubt. I’ve been dreaming about work more or less non-stop for weeks, anxiety-filled dreams about trying to get stuff done and being unable to keep the details from skittering off everywhere. But this one was different: I dreamed I quit. I told the people around me that I just couldn’t handle it anymore.

Right in the middle of that, I remembered a couple of my projects — in fact, the biggest, scariest projects that are actually on my desk right now. I realized that I wasn’t going to be involved in seeing them through. And I was suddenly, crushingly, disappointed.

I wanted to be involved in those projects. I wanted to be the one who would get to see them through.

And so I ran off, trying to find Rosemary (hi, Rosemary! Don’t worry; it turns out well) to take my quitting back, to tell her I’d changed my mind. But I couldn’t find her, and I was horribly afraid it was too late.

And just as I told someone that, a huge airliner^[2] came flying in right overhead. Way. Too. Low. And it pulled up hard, but too late, and it clipped the top of the building across the street, and flipped over, and fell to earth upside down.

Everything else I was thinking just stopped, and I stared at the upside-down plane. Literally: the upside-down plane. It wasn’t wreckage. It wasn’t on fire. It was just sitting there. And all the passengers, who I had been sure were dead, were filing off in an orderly fashion.

And I thought, Huh. It’s all okay.

Which is when I woke up, thrilled beyond belief that I hadn’t in fact quit my job, no matter how stressful it can be at moments. Certain I could work through the doubts.

I started writing this post on the subway yesterday morning, feeling as though I needed to do some public thinking about the nature of doubt and what it means for the choices we make. Got into the office, put it aside, and took care of business. And proceeded to have a day utterly full of win.

The doubts will — undoubtedly, ha — come back. But even if I crash, it doesn’t mean I have to burn. It is really possible, even when it doesn’t seem so, that it will all be okay — maybe because being willing to embrace the doubt means that I’m ready to do the impossibly scary things ahead.

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