Maybe I just need a massage
Friday Reads & Recommends: the Vintage Edition

When I used to have a job (and dreaded it)

When I was out doing the kindergarten and preschool rounds this morning my old boss from 10-ish years ago popped up on my cell phone. I worked for him 3? 4? years? I should know this. And when I moved on I stayed in the same industry so I saw him often, plus he was, by then, kind of like your crotchety uncle who is secretly a big fat softie inside and gives you a giant check for high school graduation. 

It was just him and me and his dog in our tiny downtown office. He was a lobbyist and flew around and talked on the phone; I did absolutely everything else. He once yelled at me (like my DAD yelling at me, which is TERRIBLE) for getting his flight reservations wrong. Like, I was terrified to go to work the next day. He's been suspicious of Phillip ever since he didn't give me an engagement ring (LONG STORY!), but he went to my wedding, has met all my children, writes to me every Christmas, and takes me out to lunch when he's in town. But I haven't talked to him in forever. And he didn't leave a message. And he called TWICE. eep!

Anyway, when I got home I had an email from him inviting me to an industry lunch we used to go to every year, where I once won a giant television in a raffle (he paid for my raffle tickets). I am at once touched, delighted, and horrified. WHAT? No. I am not going to that lunch. Even as his now mid-thirties all-grown-up-now former assistant who can pay for her own raffle tickets this time, thankyouverymuch. 

There are just SO MANY THINGS I regret from that time, it would just be SO... I don't know! He implied that most of "the old gang" would be there, so a lot of the Important and Not So Important People I used to work with and talk to and I always felt so SUBSERVIENT to them, so insignificant and dumb and unpretty and a total utter failure at the Schmoozing that happens at those events. 

I worked super hard. Especially after I messed up those plane tickets, man. I didn't always have a lot to do there (or at my next job), but I tried my absolute hardest to get everything right the first time, to be the quickest, most efficient, most reliable, on-top-of-everything Girl Friday. And I think I succeeded, for the most part. I knew I was lacking in social graces, I knew I was easily intimidated, I knew my looks didn't exactly recommend me (this was an old boys' club, sigh), and I was just SO AWARE of being BELOW everyone else. (This is long before I knew I was a Three on the Enneagram, obvs. IT EXPLAINS SO MUCH!) So I made myself, in every way I knew how, indispensable. Like, that's what was going to make me valuable.

All of those people were SO kind to me. Some of them wrote me recommendations, some of them got me work other places, many of them gave me advice. The industry, which never interested me, was full of really tremendous, generous (and fun loving) people. When I look back I can see them affirming me, inviting me into their groups, treating me like a grown up, but I don't ever remember thinking I WAS a grown up, equal to them in any way. And to think about seeing all of them again? Errrr...

No, I think I will go. I think I will go because I love my old boss and it'd be a good time and it's a fundraiser for a great organization and because I know that ultimately all my old insecurities were bigger in my head than they were in real life. I'll go because I think it'd be fun to actually see some of those people again and while they may loom large in my memories I most likely occupy negative space in theirs. 

Besides, even if I was a very anxious, uptight, all-business 20 something, I like myself much more as a 30 something. I am more than happy in my job. I am more creative, more productive, more comfortable, more ME than I ever was working with that crowd. I have three kids, I have a sense of humor, I know now that I'm worth getting to know. 

If nothing else, maybe I'll win another TV.



Hooray! You are worth getting to know and you have many wonderful things to offer! xo


It'll be fun. Reunions are fun! :) I totally relate by the way. When I first started working I was completely intimidated and definitely felt like everyone was patting me on my cute little 20-something intern head. I felt like "NOT PROFESSIONAL ENOUGH" was written across my forehead. I stayed there 10+ years, then got another job. I still know, and see, a lot of the people from that time period, and even though I'm nearly 40 and have somewhat come into my own and have my area of expertise, I still feel the same around them. I mean, I can hold my own, I'm not intimidated anymore, but the feeling is a distinct memory, right at the surface. So I get it.


This post must have hit a nerve because I had a dream about my old boss last night.

You are so confident and fun-loving I'm sure you'll shine!


I hope you do win a TV. :-)

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