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Any place where you spend 40 hours a week, you’re bound to make some mistakes. So forgive yourself for that big work blunder, but don’t forget—the trick is to learn from your missteps. Enter these five Chicago women, who share their big boo-boos in the hopes of sparing us all a little workplace pain and suffering.

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saying yes to everything chicago career advice
Comedy Central

The Mistake: Saying “Yes” to Everything

“My first job out of college was at a start-up, so we were understaffed and overpromising at every corner, which meant I was doing probably the job of three people. The leadership team was all about driving that ‘culture’ home, and for awhile I bought into it…until I landed a job at a more mature company and realized that as much as I love my job—it’s a job, not a hobby, and I should be getting compensated fairly for the work, or extra work, I do. So now, I’m very careful before I take on major things outside of the job I signed up for and that best serves my career. Oh, and also, if you say ‘yes’ to everything, you will miss a deadline at some point, and people might not be as understanding as you’d expect.” - Shondra, account manager

not asking for help chicago career advice

The Mistake: Not Accepting or Asking for Help

“I don’t really know why, but early on in my career I had a hard time asking people for help—probably because I thought it made me look bad or I wanted all the credit. So, because I refused to ask a colleague to review an email that we were sending to all of our subscribers, I wound up sending something with major errors—the dates for the event were wrong. It wound up being a much bigger deal, going up the chain of command, and made me more self-conscious. So yeah, don’t let your pride get to your head—working by committee can save your butt.”- Maria, publicist

over crtiquing others work chicago career advice

The Mistake: Over-Critiquing Others’ Work

“I got a new job that felt like a major promotion—I was finally managing other people. Big step up for me. So I think I felt like I had to act more critical of my reports than I think I naturally would have been. I would nitpick literally everything I possibly could—on a big email thread—to make it seem like I was doing my job. In retrospect, it obviously wasn’t a great management style—people transferred off my team and I started to feel really isolated. Lesson learned. Compassion goes a long way in the office.” - Pia, graphic designer

trusting everyone chicago career advice

The Mistake: Being Naïve and Trusting Everyone 100 Percent

Not that the world is evil, but people have different goals at the office and most of the time it’s not ‘to make friends’ unfortunately. At my first job out of college, making friends was, admittedly, my goal. I moved to a new city and I thought work would be where I could meet my new clique. So…basically I told who I thought was my best friend at work that I wasn’t going to the doctor during lunch, but another job interview…and she told my manager! I wound up not getting that other job and had to stay at the current one for an awkward amount of time. So be cautious of what information you share….very cautious.” - Danielle, sales rep

toxic environment chicago career advice
20th Century Fox

The Mistake: Getting Too Comfortable in a Toxic Environment

“I absolutely loved my job when I first started…but it literally changed overnight with a new hire who wound up being my boss and things went from amazing to awful. I really, really wish that I had taken my dad’s advice, A. B. I. (Always Be Interviewing), so that I wouldn’t have had to wait so long to jump ship. Interviewing is a skill, and even if you don’t necessarily want a new job, you might as well go on the interview for practice. Worst-case scenario: they offer you the job, which you politely turn down for timing reasons. Then, when you do want to leave, you’ll have some contacts.” - Genevieve, executive assistant

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