My Life as a Blue Dot

Living your best life is hard enough without judging yourself.

Mid-Karaoke. Photo courtesy Shira Ronen.

Last weekend I attended an executive women’s retreat that I’ve prioritized for years. The first time I went, 10 years ago, I had just exited my startup, unsure of what I wanted to do next. I was the sole entrepreneur in a group that over-indexed on corporate tech general counsels, and yet I found my people. I joked that so long as I stayed a member of this group I could always find a good lawyer.

That first year, my membership class, or “ring,” took a behavioral assessment that plotted our individual working proclivities on a graph. Most of my ring’s dots appeared in the yellow “analyze” and red “execute” quadrants versus my one lonely blue dot indicating excessive “Explore” tendencies. This indicated I was so enamored with future possibilities that I risked floating off into occupational woo woo land and might do something crazy, like run for office, start a think tank, host a game show, or run a lifestyle business. Still, the group embraced me.

Ten years into my membership, the group has grown by a few hundred women and diversified; there are many more blue dots in our ranks. And my journey has zig zagged: I’ve returned to the corporate world, left the corporate world, advised countless startups, dabbled in new businesses, forgotten to renew my membership and, some years, been too busy with seemingly mission-critical events to attend the yearly retreat.

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But most recently I’ve clung to my membership and all its benefits like a life raft, keeping me from floating away in a sea of all my exploits. These women, while never judgmental, keep me accountable and keep me thinking beyond the crisis du jour that I’m complaining about. It feels good being with these ladies, many of whom know me as well personally as they do professionally.

It so happens, given so many of these women live in the Bay Area, that many of us flew to this year’s Las Vegas retreat and back on the same flights. I coordinated with them in advance and planned to meet them at the airport.

But I hadn’t planned on That Bitch to show up while I was among such friends.

Maybe you know That Bitch. She shows up differently for everyone. For me, she’s that high-flying boss babe who used to bring nine pairs of shoes to her company’s annual conference because she wouldn’t be caught dead appearing in a photo wearing something practical on her feet. She had no time for hobbies other than trolling Gilt Groupe for sales on luxury pieces she’d wear once (AGAIN: she wouldn’t be caught dead in a photo from two separate events wearing the same thing, which made packing for business trips as fraught as planning a Catherine Malandrino runway show).

And she fought long and hard earlier in her career not just to see the company she co-founded to exit, but in racking up enough airline miles to fly a small country, business class, to the Caribbean. 

That is until COVID hit, just short of the 1 million air miles required to earn the lifetime premier status she so justly deserved. (21,297 miles still left at the time of this writing).

Over the past 4 years my Mileage Plus account has gone dark to the point that I am Persona Non Grata to United, my app un-updated and defaulting to a long-retired credit card.

But while I was secretly happy about not having to sit on planes for a living anymore, That Bitch wanted me to book a needless trip to Beijing — business class — to knock out those last 21k miles, so I could sit like an Elite Princess for the remainder of my traveling days, mileage-god-willing.

The pre-boarding call started. And I remembered: I was no longer a 1K, or even eligible to be in Group 1. My friends started queuing up; some who were 1Ks didn’t line up at all as they knew, being 1Ks, they were the oligarchs of the plane and could cut any line to board at will.

My friend Shira, a 1K, took pity on me and offered to have me queue alongside her and see if I could get in with the rest of the pre-boards. But this wasn’t Soho House or the Battery, where I could just walk in with a member. Nor was I disabled or under the age of 2. I needed to suck it up in Group 2.

I sauntered over to the Group 2 line, feeling like Cersei Lannister from Game of Thrones doing her walk of shame, just clothed, less toned and less … groomed.

That Bitch called out, flagellating me with tags to check my luggage with the rest of the economy class.

It wasn’t a total disaster: I boarded without having to check my carry-on. Praise Be. And there was another friend in line with me. But she was a founder in pre-seed stage; I knew it would just be a matter of time before she, too, would rack up enough miles to leave me and hang out with the pre-boarders. And she had sprung for economy plus, which would mean that she and the others would get to watch me walk past their row toward the back, where I, at 5’2 and 3/4” would still complain of having no leg room, smell where my seat mate had been the night before, and would be offered whatever was left of the lukewarm tea, coffee, and sensible snacks.

Shame… Shame.

I could swear the High Sparrow and the Faith Militant were glaring at me from the toilets at the back of the plane. They were saying: Thou shall repent for those years of worshipping false gods. Thou shalt travel in eternity with no upgrades!

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The flight from Las Vegas to San Francisco was blessedly short. The drive home was decidedly more fraught, as I had unwittingly cut off someone in traffic who shared his disappointment by shame-honking at me in a three-minute long blast, followed by a staccato version of something I’m pretty sure was from Rage Against the Machine that lasted the entire length of the Bay Bridge.

I came home, dejected and shaken, to a household with documented diagnoses on the OCD spectrum who asked me upon entering to wash my hands, turn over my phone for disinfecting and change out of my “plane germs” before engaging in conversation.

Once sanitized, I returned to the kitchen and shared my angst with my husband. 

“I know it’s silly," I told him. “I thought I was past all this stuff.” 

And yet I don’t think I’ve gotten That Judgy Bitch entirely out of my system. That alone embarrassed me.

“Yeah,” my husband said. “I hope they arrest the guy with the horn.”

“No,” I said, “I mean not having that validation anymore that what I’m doing, or trying to do, is important.”

On the philosophical spectrum my husband sits somewhere between transcendental idealism and anything Nietzsche would say.

“Yeah, you should get over it.” he said. “I hope you paid for that ticket with miles."

I wish I had his dissociative powers, but I don’t. Even while taking on my dreams I diminish them. I question whether my entrepreneurial interludes are more excuses for not taking a more validated path. That Bitch loves to get the final word. 

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The rest of the week was fraught with issues. Issues with a client who could care less about my pursuit of a self-directed life; he needed leads. Issues with a tween who could care less about my hormone levels so long as she could get the phone I confiscated back. Issues with a contamination I could smell over a country that called into question every assumption I'd made about having any control over my life. 

And That Bitch kept chiming in: “You’re too good for this. Where’s that Plan A we made all those years ago? Don’t forget to get your steps in. And for Chrissakes woman, get your freaking nails done!"

But then, I also remembered a highlight from my women’s retreat. The Karaoke. It’s a legendary tradition followed every year, across musical genres and stages of inebriation. Let’s be clear: I don’t sing; even for fun. Last year, when I attempted to sing Sia’s Chandelier, I literally hurt myself and others trying to hit the chorus.

But this year I sang with my lovelies and mostly danced. And I remembered: I used to dance for hours, at clubs, in a troupe in high school. I even performed one year in an electric blue unitard with no regrets! That nihilist I married? We started dating after connecting at a Rave. I still choreograph music videos in my head for fun.

And, jumping up and down for three hours or so wishing I hadn’t stopped doing my Kegels, I remembered HER. 

Not The Bitch. The Anti-Bitch.

She was ageless, fearless, and so blissfully ignorant of all that would befall her that she just did what she loved.

She was a fleeting moment, but still a moment. And a reminder that my regrets, my shame, my success, my fearlessness are all moments too. None more valuable, though I can pick and choose which ones to make meaningful. 

And so I sit, like I used to sit in front of my closet before a business trip, deciding which moments to try on.