The stupid embarrassing thing I did and the email I finally sent about it

Embarrassment isn't the same as shame and we need to stop confusing them.

A while back, I read advice from the wonderful Gretchen Rubin about “sending one hard email a day” and it really resonated. Especially as someone who tends to put off uncomfortable things.

(I’m not confrontational at all, which often surprises people who know me. I’m opinionated! But not confrontational.)

For me, however, the goal of sending one hard email a week is a lot more attainable than each day and I’ve been doing it ever since.

It’s one of the most productive routines I’ve stuck with in a long time.

I suppose we could sort the “hard emails” into categories of sorts.

• The overdue personal email (perhaps in lieu of making the phone call)

• The overdue business email

• The pitching your work email

• The asking a favor email

• The fan email

• The apology email

• The tough love email

• The relationship repair email

• The email saying, “I’m sorry I can’t help you with that right now

• The email saying, “Yes I’d love to help you with that, let’s find a time.” And then you schedule it — and put it on the calendar and keep it. (Which might be the actual hard part.)

• The calling out the elephant in the room email

• The come-to-Jesus email

• The love letter

(Just don’t quit your job or break up over email. I’m old-fashioned that way.)

Just one hard email.

If not every day, maybe once a week.

Last week, for me it was the embarrassment email I’d been putting off.

And here, my face flushes just thinking about it.

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Come on, don’t you have one incident you wish you could take back? Something utterly mortifying, something that still fills you with discomfort or panic; one that makes you go all red-faced and sweaty-palmed, so you bury it deep for as long as you can?

(In fact, you might have even buried one such incident until oh…say today, when some jerk writes a Substack essay asking, “Do you have one super embarrassing moment you think about a lot?” — and now here it is again.)

Embarrassment differs from shame in that shame has the essence of a moral failing. Embarrassment is the feeling of a social failing — a disconnect between the way we want to be perceived and the way we think we are perceived.

I would like to be perceived as someone who is thoughtful and says the right things the best I can. I would imagine most of us would say the same.

And so, when we fail at this… embarrassment.

Photo: Braydon Anderson on Unsplash

Early last year, I wrote a loving and effusive Facebook remembrance honoring a friend who had passed, and posted it on the feed of their spouse. I described a wonderful memory of this friend from decades ago; something sweet and quietly admirable, something other people didn’t know that I thought they should.

The thing is, it wasn’t my friend who did these things.

It wasn’t from a period of my life that I even knew this friend.

For some reason (stress, sadness, overwhelm, momentary break from reality), I conflated multiple people from my life and fabricated an amalgam of them, thereby describing a “memory” that never existed.

In the retelling here, it may not seem like the most horribly embarrassing thing ever. And it’s not. (I mean, I didn’t accidentally attach naked photos to the post or anything.) But imagining mutual friends laughing about what the hell drugs I might be on, that I could make up a memory out of whole cloth and express it with utter confidence — that truly weighed on me, the way I’m sure some “not the worst thing ever” things weigh on you.

Last week I took a deep breath. I sent the hard email.

You know what?

I’m so glad I did.

The exchange we had was more than worth it. My friend’s spouse was gracious (again) and happy to hear from me. I was happy to have the chance to reconnect, to hear how the family was doing, to learn a little more about the friend I had lost.

I feel better.

It’s over.

And now I can put my energy toward something more positive.

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I’ve always heard that we tend to judge ourselves harder than others judge us — at least if we’re not sociopaths — and one day, the piles of evidence will finally compel that lesson to stick with me.

One day.

Interestingly, I’ve learned that embarrassment can be a projection of your most positive traits. If you forget the name of your colleague’s husband at a party and feel bad about that; if you forget a birthday; if you misused a word; if the waiter says “Enjoy your burgers” and you respond, “You too!”— it’s okay. It’s more than okay. They’re not moral failings and they’re not shameful. Just embarrassing because you want to be the kind of person who says and does the right things.

It’s the not feeling embarrassed about those things that would make you a little sketch.

Maybe consider sending an embarrassment letter this week. At minimum, it will get something off your chest. At best, it will remind that person a relationship with you is one completely worth having.

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Gratitude Notes

To activists and lovers of democracy like Mark Elias who are working their butts off every day to save our country; and reminding us to spend less time on absurd media narratives and incomprehensible SCOTUS decisions, and more time getting out the vote in November.

To all of the incredible humans who make ours a blended family, and to the grandparents, cousins, in-(ish)-laws who just treat us like a family. Happy 11th to us!

Also, to all of you who have been patient with a lighter-than-usual publishing schedule in February and still renewed your subscriptions. It was…a month. This one should be better.

Read it Forward

I first got to know the extraordinary

Katherine Goldstein

when I interviewed her on my podcast about working mom guilt several years ago about her viral NYT article about anti-mom workplace bias. Just last week, she officially brought her newsletter and active community

The Double Shift

to Substack and I think you’ll love her! She’s an award-winning, solutions-oriented journalist dedicated to changing the status quo to make work — and society as a whole — more equitable for caregivers.

Kind of Obsessed

…with parchment paper. Jon realized that baking everything on parchment paper (vs foil or a greased tray) makes it all come out perfectly. That includes crisp bacon, which we are now making in the oven with a lot more frequency. So I guess good thing we accidentally bought a ginormous Costco-sized thing of parchment paper instead of foil! Happy accident!

P.S. The cool phone cases and tech accessories I mentioned a few weeks back? My AirPods case finally came and I am so happy every time I look at it! I’m getting a new phone case next. Something happy and springy.

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