scrunchThe other day, I was looking through a bunch of old photos in my attic. I cringed at my short, poofy ’80s hair and laughed at my first pair of bifocals (yes, I had bifocals at 10, like a weirdo).

Those cringe-worthy moments are sort of a given for all of us. You thought you were so cool at the time, but later on, the photographic evidence proves you so patently were not.

Even so, those cringe-inducing memories are fantastic to wade through. Recently, my friend Laurie Ruettimann published a blog post about an experience she had with her boss as a young recruiter. Her story is one to which I’m sure many of us can relate: The boss she thought was a jerk turned out to be right, and Laurie learned a valuable lesson – not until much later, of course.

I appreciated the article because it reminded me that, just like the old photos we all have, we’ve all experienced cringe-worthy professional moments. I spend so much time teaching and leading my team now that I often forget I was once young and trying to figure out this whole “career” thing. While today’s professionals have blogs and media like The Muse and Ask a Manager, no amount of career advice will save you from having a few of your own cringe-worthy moments.

But maybe I can save you from going through the same ones I did. Here are four of my most cringe-worthy career moments, in order of embarrassment, and the lessons I learned from each:

1. The Time I Realized My State School Journalism Degree Was Not the Same as a Decade of Experience at a Major U.S. Publisher

Pride is a funny thing, and I have it in spades.

I was working my rear end off as the staff writer, ad salesperson, distribution coordinator, and photographer for a local paper – which, as you can imagine, did not have that many people on staff. The publisher and I were drowning in work and needed some help. When the publisher found that help in the form of an accomplished woman with more than 10 years of experience at a national newspaper, I was thrilled. When I learned she would be in a position of authority over me, I was not. After all, we both had journalism degrees; weren’t we the same?

Looking back at that moment, I honestly want to smack 23-year-old me. Experience matters. Of course my state school degree couldn’t compare! Of course they weren’t going to have a 23-year-old manage a woman in her 40s! Back then, though, I railed at my husband for weeks over the injustice of it all. Ah, youth.

Lesson: Experience beats youth.

wave2. The Time I Was Passed Over for a Promotion After Four Months With a Company and Responded by Throwing a Fit and Crying at Work

I had just started at an investment firm, and I thought I was the stuff. I definitely padded my resume and spent the first few months taking work home so I wouldn’t look like a moron. I worked really hard, sent a lot of emails, ingratiated myself with the higher-ups, and waited for my boss to notice that all my coworker did was complain about her husband while the rest of the marketing team did her work for her.

What happened instead was I got written up for wearing shorts to work and she got a promotion.

I thought I was a shoo-in, despite having barely a financial quarter behind me. This woman grew up in the same town as the big boss, was (as I have mentioned) quite the skilled delegator, and spent a great deal of time speaking to management in closed-door meetings. When I found out I did not get the promotion, I acted like a three-year-old. I stomped out of my office, cried in the bathroom (I am not a subtle or pretty crier), and vented to anyone who would listen.

Lesson: When someone is the boss’s close friend, has been their longer, and does not throw fits in the workplace, she is manager material. You are not.

3. The Time I Was pitching a PR Project to a Swanky Client and Said ‘Buttload’ to Prove I Was the Realest

This still makes me cringe, even though it was merely stupid rather than bratty or entitled like some of my other career mishaps were. My goal was to prove I wasn’t like all the other buttoned-up, prissy PR folks. No, I understood the customer, I got the marketing goal (but it was PR, dur).

I could see the distaste on the client’s face. I know they selected a different team, at least in part, because I presented myself poorly. I still struggle with this today. In my mind, I know my stuff and everyone in the world should just accept that sometimes the package is a little rumpled. The real world doesn’t work that way – not at 21 and not at 37.

Lesson: Rightly or wrongly, people treat you according to the way you present yourself

4. The Time I Learned That ‘Doing Things’ Is Not the Same as ‘Getting Things Done’

I have always confused “being in the kitchen” with “serving the meal” – but accomplishing tactical tasks is not the same thing as deliver strategic value. Don’t get me wrong: Both are necessary, but one is far more visible than the other.

Generally speaking, technical knowledge will be valued more earlier in your career, but savvily solving strategic problems will bring you more respect as you move into management and beyond.

I used to code sites, design one-pagers, write emails, and upload blog posts. I took pride in being a “technical founder” (at least to a marketing wonk), but that left me with little time to plan large events, speak about my experience, go to client on-sites, or create strategies that would actually impact clients’ businesses. Sometimes, I am still learning this lesson.

Lesson: Doing things may be more visible, but getting things done often matters more.

Even though incidences like the ones above make me cringe and hide from former coworkers, I’m still kinda stoked I learned so much from each one. In fact, I would wager people who don’t make similar mistakes are doomed to have little or no empathy for their direct reports, or they may find it difficult to grow in their careers.

It’s like my friend and colleague Jason Seiden says: Fail spectacularly!

A version of this article originally appeared on the Red Branch Media blog.

Maren Hogan is founder and CEO of Red Branch Media. You can read more of her work on Forbes, Business Insider, Entrepreneur, and her blog, Marenated.



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