March 2018

The Humbling Truth About Starting Over at 60
Sometimes you just have to laugh.
At yourself.

A few months ago, I decided to imitate entrepreneur, vlogger, public speaker and Internet superstar Gary Vaynerchuk’s video releases. For months, I’d watched this over-caffeinated dude in a dirty t-shirt strut around his driveway exhorting his followers to reach for their dreams. I loved the way he spoke directly and authentically into the camera. There was no studio lighting, no hair or makeup person trying to make him look perfect. There was just his message.

To me, Vaynerchuk’s videos are the apotheosis of modern Internet communications: raw, unpolished, real. They are also the total opposite of the careful, studied media world in which I grew up–where not a hair is out of place. Since I’ve always been an early adopter, and now am a full-fledged entrepreneur, I decided to try his approach myself.

At that point, I was six months late producing the beta version of Covey and I was becoming increasingly anxious that my potential members–some of whom had signed up way back in February 2015—would start to feel I had left them dangling. I was dying to reach out and communicate. And one day, I just knew it was V-Day (as in Video). That Thursday, I was headed to New York City for an event, which meant I had dressed nicely and was wearing mascara. (So, yes, although Gary Vaynerchuk’s authenticity spoke to me, his dirty t-shirt did not.) I had 10 minutes before I needed to leave for the train, so I walked out into my yard, held up my phone and pressed record.

Three minutes later I tried to post the vlog but noticed that, while I could hear myself perfectly, the only thing I could see was a bright orange wall. I looked around my yard: no orange wall there. Did I push the wrong button and download an orange filter? (Pushing a button that blows up the world—or just everything on your phone—is the chronic fear of those of us like me who were born on the wrong side of the Digital Divide.) I Googled “orange filter on iPhone” but found no answers. I Facetimed my daughter at college. “Can you see me?” I asked. “No, Mother,” Lake said huffily. “I’m running to class but all I see is orange.”

Where was that corporate IT guy when you needed him? Maybe I wasn’t cut out for this entrepreneurial life after all. Maybe. This. Was. Just. Too. Hard.

Panic constricted my chest as I realized that instead of coming home after the event and chugging through my list of To Dos, I would now have to spend the afternoon at the Apple store fixing whatever was wrong with my phone. Experience has taught me that nothing in tech takes just a few minutes to fix, so I knew that this meant the whole day would be shot. I despised this fend-for-yourself world the Millennials had invented. I would start looking for a new corporate job—with an IT department!—immediately.

But wait. What train was I taking again? Since I no longer commuted into the city on a set schedule, I no longer had the train departure times memorized. To stop myself from constantly checking the Metro-North app, I’d come up with an ingenious solution: I’d write out the time of the train I was taking each morning on a sticky and paste it right onto the phone.

The note said I was catching the 8:58.

The bright orange note.

That I’d placed over the camera eye.

Geez. I’d gone from sharing the podium with First Lady Michelle Obama at a big More event to becoming a techno-idiot. I posted the video anyway, blank orange wall and all, hoping you all would laugh with me instead of at me.

But I want points for at least trying!

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