4 Cringe-Worthy Career Moments (and what I learned)

The other day I was looking through a bunch of old photos in my attic. I cringed at my poofy short 80s hair and laughed when I looked at my first pair of bifocals (yes, I had bifocals at 10, like a weirdo). It’s sort of a given, those cringe-worthy moments. You thought you were so cool, but when you see photographic evidence that you so patently were NOT cool, well it stings a little.

Even so, those memories are fantastic to wade through. Recently my friend Laurie Ruettimann posted a blog article about an experience she had as a young recruiter with her boss. Read it here. In short, over time, the boss she thought was a jerk actually provided Laurie with valuable self-reflection. Reflection she didn’t really come to until much later.

I appreciated the article and said as much because just like those photos in the attic, we all have professional moments that are a touch cringe-worthy. I spend so much time teaching and trying to lead my team now, I often forget that once I was young and trying to figure out this whole “career” thing. While today’s young women and men have bloggers and media like The Muse and Ask a Manager, there are still a lot of potential pitfalls. When Laurie and myself (and pretty much anyone who leads and manages people) dig into the archives of our former career selves, it can be really useful for people who are learning themselves. And obviously, for us!

So here are my most cringe-worthy career moments (in order of embarrassing-ness):

The time I realized my state school j-degree was not the same as a decade of experience at a major US pub.

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 in it. Myself and the publisher were drowning in work and needed someone else. When the publisher found that person; an accomplished woman with over 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 thrilled. After all, we both had our journalism degrees, weren’t we the same? Looking back at that moment, I honestly want to smack 23-year-old me. Of course, experience matters. Of course, my state school degree couldn’t compare to this much swankier one. Of course, they weren’t going to have a 23-year-old manage a woman in her 40s! But then? Then I railed at my husband for weeks over the injustice of it all. Ah, youth. Lesson: Experience beats youth.

When I was passed over for a promotion after four months with a company and I threw a fit and cried at work.

Holy balls. 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 to the higher ups and waited for my boss to notice that all my co-worker did was complain about her husband while the rest of the marketing team did her work for her. What happened instead of that was I got written up for wearing shorts to work and she got a promotion. When the opening came up, I thought I was a shoo-in, despite barely having a financial quarter behind me. This woman grew up in the same town as the big boss, she 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 straight acted like a three-year-old. I stomped out of my office, cried in the bathroom (and I am not a subtle or pretty crier) and then vented on ANYONE who would listen. Lesson to my 26-year-old self, when someone is the boss’ close friend, has been their longer and finally, does not throw fits in the workplace, she is manager material…you are not.

That moment when I was pitching a PR project to a shwanky 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 other career mishaps. What it taught me is that rightly or wrongly, people treat you according to the way you present yourself. My goal was to show I wasn’t like all the other buttoned-up, prissy PR folks, I understood the customer, I GOT the marketing goal (but it was PR dur). I could physically see the distaste on the client’s face and 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.

The hard lesson that “doing things” is not the same as “getting things done”.

I have always confused “being in the kitchen” with “serving the meal” in a misguided notion that eventually, someone will see how hard I am working. Accomplishing things tactically is a far cry from ensuring things get completed for strategic value. Don’t get me wrong, both are needed, but one is far more visible. Technical knowledge is valued more early on in a career, but solving strategic problems and having the savvy to get things done will bring 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 what seems like a technical founder (at least to a marketing wonk), but that left little time to plan large events, speak about my experience and go to client on-sites and create strategies that would actually impact their businesses beyond the bump you get from one cutely crafted email. Sometimes I am still learning this lesson.

Even though incidences like the one above make me cringe with embarrassment 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 those mistakes are doomed to have little or no empathy for their direct reports and/or find it difficult to grow within their careers. It’s like another one of my friends and colleague, Jason Seiden, says: ‘Fail Spectacularly!’

Maren Hogan

Maren Hogan is CEO of Red Branch and general Bad@$$

Maren Hogan is a seasoned marketer and community builder in the HR and Recruiting industry. Maren started Red Branch Media and, before she hired all the smiling faces you see below, she ran it on her own. In marketing for over 15 years, she has deep experience in strategic campaigns and a long-term, results-based operational approach.