The two scariest things I’ve ever done
Here’s the story about the first.
This article is cross-posted from my weekly newsletter, The Sunday Soother, a newsletter about modern spirituality and useful tips for creating more meaning in your life that goes out every Sunday morning. To get more content about how to infuse your life with thoughtfulness, reflection, and meaning, subscribe here. I am also a holistic personal development coach. You can learn more about working with me here.
Happy Sunday, friends. After a hiatus, a fresh look, (and a fresh me!) and a lot of August adventures, I’m back.
And I’m here to talk about fear. The kind of fear that has you clutching your stomach and taking in stabbing breaths. The kind of fear that dominates your entire thoughts for days, if not weeks. The kind of fear that keeps you in one place, convincing you the situation will never change, and that you are powerless to do anything about it.
I’ve experienced every single kind of fear on that list. The idea of getting on a roller coaster causes the first — the accelerated breathing and stomach-sinking sensations. The second fear, the ones that roils around in your head for ages? Thinking about the future of our planet and our country does that to me.
But it’s the third kind of fear that, I would say, has been a primary driver of my life. Fear that I didn’t deserve audacious things I wanted; fear that I couldn’t change the outcome of any given situation; fear that kept me on the straight and narrow, the prim and proper, and most of all, that kept me silent and small.
It was this kind of fear that I came face-to-face with this summer in a midtown Manhattan karaoke room, where, buzzed off Sapporo, the trailing remnants of “Bittersweet Symphony,” and wild, heart-shuddering adrenaline, I told one of my dearest friends that I liked him.
Like, liked-liked him.
Like, REALLY liked-liked him.
And had for years.
But let’s back up.
(I was an English major. Let it never be said that I don’t know how to build a sense of suspense.)
I think today we mask a lot of fear as caution, or wisdom. We should only do things if we’re sure of the outcome; if we’ve erased risk; if we’ve calculated out success to the Nth degree.
But I get a feeling that a lot of the women I work with are tired of operating in this manner. They sense that the story they tell themselves, of how or why they shouldn’t do something because it’s too scary, because it doesn’t make sense, because it’s a big risk, because they might “fail” — well, that that story may not be as factual as they were led to believe in the first place.
They’d like to try something different. To indulge whims, to trust their intuition, to take leaps.
So how do you start living that way? And how do you stop operating from fear?
Here are a few tips (and I’ve learned these myself the hard way). Journal on the following:
- Observe how often you say you “shouldn’t” or “can’t” do something. “Shouldn’t” and “can’t” are often just words to mask something you’re afraid of, and you can learn a LOT whenever those words start showing up. A “shouldn’t” or “can’t” can generally indicate a fear. Note those fears. (I mean, be realistic and practical, too. If you say, “Hey, I shouldn’t jump off that cliff!”, “Or no, I can’t send you a check for $1,000 so you can buy a pet tiger,” that’s pretty fair.)
- Next, note what these fears may have in common. Are they related to your body? To money? To emotional needs? To romance? I find, often, the fears have an underlying theme.
- Work to discover the source of these fears. Generally, this starts in childhood. Say your fear is around money. What was your caregivers’ story around money? What lessons did you witness as a kid around money?
- Start questioning your old story’s validity. Consider, having become more conscious of the invisible story you grew up with that may have led to your fears, if there’s a new story you can start telling yourself.
This past summer — really, the past year, in my own work — I went through each of these steps. As I meditated more and journaled more and became more present and observant of my patterns, I noticed how often I lived by the credo of an invisible “should” or “shouldn’t.”
These fears were never really goals, or physical things or experiences — I would happily train to run a marathon, or travel by myself, or set a goal to read 52 books.
But I began to realize the fears had to do with two main themes — not “rocking the boat,” and not speaking up for my emotional needs. I started to realize I had learned somewhere along the way to never take risks, to always play it safe, for reasons of stability and security, and also to think that emotions were a burden rather than a song to be sung for the rooftops for my loved ones to hear and respond to.
And then I came across a quote — and I cannot remember the exact quote, or the source, and it is killing me — but it went something like this:
A feeling is still true whether you choose to say it out loud or not.
It was at this time that my dear friend (let’s just call him MDF from here on out), on whom I’d had a MASSIVE crush for years, and I reconnected at a wedding. (And by reconnected, went out for beers a bunch like we used to a week ahead of the main event, danced up a storm at the wedding, and laughed our asses off. Platonically. Like always. Sigh. Pine.)
A brief bit of backstory of MDF: We’d met about three years ago, and from the second I knew him, I knew I liked him. We developed a wonderful friendship. I felt fully myself with him, and I know he felt the same. And neither of us could make the other laugh like we did.
But it literally never crossed my mind to say anything about my feelings, to give them air. First, it was clear he was still healing from a breakup, and not ready to date, and I respected that. But second — and the crazier one, perhaps — I felt I didn’t have any right to ask for anything romantic. To say, “Hey, I like you — maybe let’s try this thing out?” I felt comfortable in my friend lane, and hoped I could eke out the following years on the meat of the friendship and shove my pining in a corner.
I didn’t really have a longterm plan for the whole thing. But the friendship was so fun, and so nourishing, and I cared so deeply for him, that I sort of just hoped we’d be friends forever and I’d figure it out at some point. OR — even easier for me — HE would be the one to buck up and do something and I’d never have to risk myself at all!
Turns out, feelings don’t really work like that (and, take note, neither does the hoping somebody else will step up to the plate so you don’t have to take your risk). At some level, I became frustrated with just the friendship, and drifted away from him. He moved to New York. We didn’t talk for over a year, never having really discussed why or how that happened. I dated other men. He started a masters program. Life went on.
But the wedding. After the wedding, I kept rolling around that quote in my head: “A feeling is still true whether you say it out loud or not.”
This feeling was still there, despite my best efforts to move on. It was clearly going to keep being true for me. And I owed it to myself to say it out loud. I owed it to myself to be brave, to take a risk, to show up for my emotional needs.
I owed all this to myself, while still having no idea of the outcome (and in fact, believing I would be rejected, and lose my dear, recently reconnected friend). I had no hopes of it working out.
And yet. The feeling was so deep, and so beautiful, and so urgent, I knew I would be filled with regret the rest of my life if I never even gave it a shot. Donald Trump is president, y’all. One thing I have learned: Now is not the time to give space for future potential regrets.
After such a lovely reconnection at the wedding, MDF and I planned a visit up to him to explore his new-ish neighborhood. We had a wonderful few days in NYC, my heart breaking every time I looked at him, knowing that at the last possible moment (to reduce my inevitable humiliation as much as possible) I was going to drop this bomb on him and our friendship was likely to be over, this time forever.
And I was still willing to do it.
(An important aside: I knew, also, that even if it didn’t work out — even if I was rejected in the most horrible, humiliating, soul-crushing, friendship-ending way — that I would be okay. I had become enormously resilient in the past year. I knew, though there would be a lot of crying, drinking wine with my sister and sniffling, and sad feelings in my chest — I would still. Be. Myself. I had worked at this.)
Anyways. At the close of our visit, somehow, we ended up in a karaoke room by Penn Station, at some level, neither of us really wanting the weekend to be over. An hour before I had to leave for my train, I gathered my strength. I closed my eyes and prepared myself to step off the cliff. I asked him to turn the music off. I had something to say.
My words, inelegant and hurried, tumbled out. They went something like, “I hate to do this because I don’t want to lose our friendship, but I’ve had feelings for you forever — romantic feelings — and it’s so hard to be friends with you because of that. I’m sorry. [Even in my blaze of courageous emotional glory, I am apologizing. Sheesh.] I don’t expect you to reciprocate. But I had to say it.”
There was a pause. The room was quiet. The music was off. He took a deep breath, and, (MEN!) started to make a joke, speaking into the karaoke microphone.
“MDF!” I absolutely SCREECHED. “THIS IS NOT THE TIME TO MAKE JOKES!” I literally slapped the microphone out of his hand across the room and glared at him. “Do you have anything to say?”
He took another deep breath and looked at me.
“I feel exactly the same way.”
PS: That second scariest thing I did this summer? I made plans to leave my full-time job. You’ll hear more about that soon.
PPS: Are you interested in learning more about how to trust your intuition and stop operating out of fear? That is the focus of my upcoming retreat in Shenandoah, Virginia, 9/27–29. It’s small, cozy, affordable, and intimate. And we only have a few spots left. We’ll be doing exercises, meditation and journaling related to learning to discern and trust your mind, body, and heart, and you can find out more details here.
PPPS (last one, I swear!): My podcast is returning in October, and I’m looking for questions about life to answer and dish advice on. Submit yours anonymously here.
