Changing your career is more embarrassing than you think

On constantly being humbled and learning (yet again) how to listen.

I landed my first job in journalism fourteen years ago. Well, it’s probably more accurate to say I started in digital media; I interned for a social media marketing company in Chicago and spent my days writing tweets for deep dish pizza restaurants and Navy Pier. Not so long after, I was working my way up at an online lifestyle publication, from intern to editorial assistant to staff writer. I was twenty and still in college, working full time by day, taking classes by night, and somehow surviving on four hours of sleep. I was young and hungry and ambitious, and I couldn’t be stopped. I moved to New York City and stormed through the city like a tornado until I achieved my wildest dreams. My goal was to land a major editor roll at a national magazine. I achieved that before I hit thirty.

And then I gave it all up to work in a restaurant.

I’m writing all of this because it’s humbling to look back and think about what I was like the first time I started out my career. I walked around acting like a sponge, soaking up everything I possibly could so I could make my dreams come true. I didn’t care in the slightest about being at the bottom of the totem pole, because I knew I wouldn’t be there long. I never expected I’d be back in that position, and yet, here I am. News flash that I’m sure every one of you saw coming: I’m not comfortable with it.

Being back at the bottom means you need to listen more than speak. It means messing up a lot and admitting that you don’t know everything. It means learning from your superiors and colleagues without needing to defend yourself because you’re embarrassed about how much you don’t know. (This is, quite frankly, something I am horrible at.)

The thing is, I didn’t change up my career because I hated my job. Despite the fact that it had me glued at a desk all day, I loved my job. I just wasn’t getting as much work anymore in an industry that is drastically changing in the age of generative AI, so I decided to learn a new skill, just in case. I thought maybe it was something I could write about, a new niche I could break into as a journalist. I didn’t expect to make this drastic of a change, working as a sommelier in the Union Square Hospitality Group no less.

I find myself back in this space where being humbled is a daily activity, and there is a thick layer of embarrassment that coats all of it. I partly blame imposter syndrome and my lizard brain that tells me constantly that I don’t deserve to be here. But I also blame the fact that I am still fresh into this new job, and the only way you can get good is to listen and learn.

I had this dance instructor in grade school who actually put this into perspective for me. My twelve year old self thought I was hot f*cking shit on the dance floor, so any time my form was corrected or I was told I was doing something wrong, I would crumble. It made me feel like I was failing and I didn’t deserve to be on their national team. When she saw I was visibly upset after this one class, she told me that correction didn’t mean she thought I was bad or she disliked me. It meant that she liked me so much that she wanted me to be the best I could at what I do.

It changed how I saw instruction and learning, especially in my first career when correction was a lot of literal red ink scribbled all over my work. I got comfortable with being bad, because if someone was taking the time to point out where I needed improvement, they thought I was worthy enough to teach and help grow. They saw me as an investment, not a burden.

Now someone explain to me how all of that wisdom went right out the window when I decided to change up what I do for work?

It’s probably because I feel too old to be embarrassed. I have this wealth of knowledge after over a decade of work that is seemingly useless now, and despite the fact that I feel smart and capable, when it comes to this new job, I’m really not. Sure, I have the book knowledge. But the practical knowledge? The service experience? I hate that I come to the table with a big fat goose egg.

Then there’s also the other side of things, the comments that are made or the whispers that circulate around this big, fat life change you just made. Why did she give it all up?

Thankfully, I’ve very supportive friends and family through this process. It’s the other people I worry about, the former colleagues or friends I don’t speak with much that are on the Internet watching me blow up my career to chase something new. I fear their judgement and opinions. The last thing I want people to think is that things got too hard and I gave up.

It’s rather silly, I know. Again, the lizard brain does what it wants, and sometimes it’s hard to turn it off. Let’s be clear, it has never stopped me from doing anything; I am, after all, determined and stubborn almost to a fault. I just figured it was worth mentioning, because this does play a part in the embarrassment of it all.

Needless to say, changing your career is not for the weak. You have to be okay with being humbled. You have to be okay with occasionally—or more than occasionally—being wrong. And you have to constantly remind yourself that learning from your mistakes is the only way you’ll grow.

Have you recently changed your career? Share in the comments, I would love to hear how things are going for you and your perspective on things!

Wine of the week

I had the opportunity to wax poetic about Massican Winery during lineup at work this week, and it was so fun watching our staff fall in love with Dan Petroski’s wines! This is the Annia 2023, a white blend from Napa, Sonoma, and Mendocino in California made with Tocai Friulano, Ribolla Gialla, and Chardonnay.

You can follow Dan’s winemaking and Italian culinary journey over on his Substack!

Tasting notes

• Appearance: Clear, bright, teetering on a straw-like color, medium viscosity, developing age

• Nose: Clean, moderate intensity, notes of orange zest, white flowers, honey suckle, delicate white beach. Fresh on the nose despite the color.

• Palate: Dry, high acidity, medium bodied, evidence of oak (not new), medium alcohol, creamy on the palate with a lot more of that orange and peach, long length.

Final conclusion

A delicate wine on the nose with a hint of fruit, but bursting with personality on the palate. Somehow it’s creamy and smooth and full of fruit character that makes you want to continue pondering and sipping.8

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