I Had the Perfect Excuse to Kiss My Celebrity Crush — And I Failed.

It’s Friday morning at 4 am, and I am in a random Hollywood diner eating with my celebrity crush.

But it’s not a hot Hollywood A-lister like you’re thinking.

I’ve got a thing for entrepreneurial, intense A-typers. And apparently ones who dig anchovy cleanses and turning themselves into walking science experiments.

It’s perfect: this week’s #fliplove is to kiss a stranger, and through a strange twist of events here I am, sitting next to a guy who I esteem enough to put on my very exclusive Wall of Bold. My 2016 WOB goal? To meet him. And for 2017? To break out enough to be interviewed on his podcast. (Hey, I like big goals and I cannot lie.)

Kissing said stranger would have been the epitome of a Serenflipity success story — embracing boldness and brazenness without fear. Taking advantage of ending up in the right place at the right time. Getting in front of someone who’s so influential that there’s a viral marketing effect named after him.

But I failed. I didn’t even broach it. And I actually don’t regret it.

“You should have lady-and-the-tramped him when he asked if he could have one of your sweet potato fries,” a friend joked the next day.

“Yeah, or pretended to trip, fall onto him and ‘accidentally’ pashed him,” another suggested.

“Wimp. You may have had your next boyfriend,” a mentor texted. “And dare I ask why you were eating sweet potato fries at 4 am?”

On Friday afternoon, I felt like I had missed a magic moment, with those pesky “what if”s that circle a situation of this sort. But instead, my experience with this flip taught me three important things.

First, I got a good glimpse at myself.
I hear a lot of tales about entrepreneurs making it through persistence that verges on stalkerishness.

This is not my forte — which keeps me up at night wondering whether I’m opportunistic enough or “sell myself” well enough to make it.

But I don’t want to build a business where I’m trying to sell people on me. Not that that’s wrong – it’s just not my style. I want to build an entrepreneurial life where my passion for what I’m creating is so contagious that people can’t help but join in.

“Umm, just keep living Serenflipity,” a friend reminded me the other night, as I lamented my reserve and questioned my grit.

And she’s right. When I get to know people like people instead of “networking” or trying to get something from them, I end up with awesome new allies. When I have fun with what I’m doing, and celebrate the fun that others are having, people want to hop on board. When I stay super dedicated to thinking big, going big and acting big, especially when I’m scared, the breakthrough happens. And when I get vulnerable and honest, I get to help others.

And so far, it’s working. Letting things unfold instead of forcing them has led to insane partnerships, placement with brands like Delta and TED, and offers from strangers to share my asks with rockstars. And even a workshop ahead at a sleek, chic wellness mecca in LA.

But it can be hard to trust the process and let things happen when I see peers celebrated for feats that bring the words “restraining-order” to mind.

Even at Thursday’s event, my mind started wandering to ways to engineer a restraining-order-esque run in with said A-typer, when that inner-Yoda piped in: “path yours will cross when right, time is. Make happen, there is no need.” (Translation: your path will cross with his when the time is right. There’s no need to force it.) So I let it go.

Two hours later, I was sitting next to him for two hours.

Second, it refocused me on purpose — not PR stunts.
When Serenflipity works, it’s because the flips come from somewhere real and human —whether it’s a desire to get to know someone, a hunch that the feat will put a smile on a stranger’s face, or an easy and quirky way to simply stop being bored.

“Hey, I know it’s 4 am, you’ve just done the 4 hour podcast, and are now eating with 10 strangers peppering you with questions. I’m doing these flips… and this week I have to kiss someone…” felt like a ploy.

I am pretty cute, and I did have a plate of sweet potato fries in front of me as a bargaining chip, but still… the odds that this would bring a smile to this stranger’s face in this context were slim. My chances of failure were high. And it didn’t feel authentic. (Plus, he might have a girlfriend who would have been less than pleased.)

But I could be completely wrong. It could have totally made his day, and my fear of failure could have just been holding me back. What was I so scared of? And was I really scared, or was I just following my intuition?

I choose intuition. When something’s right, I don’t second-guess it. I don’t try to emulate someone else, or engineer a situation. It simply comes together and the jolt of courage shows up to taze the fear.

“When something’s right, there’s nothing you can do that’s wrong,” my mother once told me. “And when it’s wrong, there’s nothing that you can do that’s right.”

While this was in context to teenage boy drama, it applies to relationships of all sorts. There’s no need to second-guess or continually question, whether a text message or a pitch. Questioning and stressing keep me small, and today, I have decided that I don’t have time for that.

I choose to think that not all opportunities are meant to be seized. Some are simply meant to teach us more about ourselves and where we’re going. Others are kokopellis to test us and create contrast so we know what feels right and what doesn’t. And others are no-brainers. It’s trusting ourselves enough to know the difference and believing that many more are just a decision away.

And lastly, it showed me that the unexpected and awesome are everywhere.
While I failed this flip in the smooching sense, I see it as a success. I had more fun being made fun of by my friends and all of the completely NSFW tangents that followed. I learned more about myself from not doing something that didn’t feel right instead of going heedlessly into circumstance.

And most importantly, I followed my gut and said yes at the right moments — especially the uncomfortable ones.

I said no to a free ride back to the Westside when my friends in VIP left early, and yes to using their passes to stay solo for a small Q&A.

I said no to an insane Uber fare at 2 am, and yes to a free ride to the diner, where I figured I’d wait out the pricing surge for 20 minutes.

I said no to trying to be who I thought I should be in that situation, and yes to being true to myself.

AND, I hit a 2016 goal fewer than 45 days into the year.

So, Tim, if you get off the ketones and back on the carbs, you can Lady-and-the-Tramp me anytime.


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