Things I've totally regretted doing at work

The last time we met I was talking about some of the things I have never regretted doing at work. Which led me to open Door #2 - all of the things I have done at work which, in hindsight, were not to my benefit. So let’s put my mistakes to work for you. And not just mine! I put the call out to some friends for their facetown career regrets and received a wave of thoughtful, poignant replies that we could all benefit from. And a couple of humorous ones. With their consent, I’m sharing them here.

Long-term strategy tips

• Not considering relationship-building a part of my job. It's important to really intentionally design your internal brand at a company, including who you need strategic relationships with and how you'll build them. Particularly as you rise within an org, this may be more important than any other work you do.
• Under-preparing for a meeting because I didn't think anyone "important" would be there. Being nice instead of setting boundaries. Waiting too long to tell the truth. Not speaking my mind enough.

Confidence fails

• Not being straightforward when giving critical feedback. It's a disservice to everyone. Honest conversations are always best. Even - perhaps especially - if they are hard.
• Related: Not being more open to honest and constructive feedback. Especially from folks who, I realized much later, had my best interests at heart.
• Staying too long after I’ve outgrown a role because I was comfortable.
• Really big ideas that I failed to offer up because I was worried it could fail.
• Not selling myself better. I have more experience than some who position themselves like they are the [poo].”

There is such a thing as too nice

• Being too nice. People will walk all over you.
• I regret waiting a year too long to fire somebody, while I knew they were a poor fit all about three months in. That was over a year of frustration for everyone, including the employee, that could have been avoided.
• Not saying, "I was talking" (or similar) when a man interrupted me for the eleventy billionth time.
• I regret saying "I'm sorry" too easily, particularly in instances where something happens that, while my responsibility, isn't my fault.

Facepalm:

• Literally every email I have sent without waiting 30 minutes first. Conversely, I have never regretted waiting before sending an email, even if the topic felt urgent.
• I regret not double checking a phone number - we sent 4,000 packets to clients with instructions to call a “for a good time..." number.
• Relying on spell check instead of proper editing/review. One unfortunate result being a document sent to the CEO with the words ‘pubic discourse’ instead of ‘public discourse.” [Editor’s note: I also have done this exact typo.]
• Pulling up a YouTube video I'd never watched before, while in a client meeting. The first result link ended up being porn-like. I projected it onto an enormous screen in a mahogany-walled board room.

I know some great people. Thank you all for writing this article for me.

But back to me. My own regrets:

I have long refused to dress the part and I’m sure it impacted my reputation as a serious professional (though I do not regret wearing Dalmatian ears to my first meeting with a new VP, so I may not have fully actualized this lesson).

I have fallen for the politics and allowed it to impact my work. Longevity, progress and pride in your performance are not forged in petty sniping. 

Missing out on the big picture. I did fine, but failed to thrive in perfectly good jobs at perfectly excellent organizations by just meeting my obligations and not being entrepreneurial enough. Those are the ID badges I miss most.

The big finish

This is the part where I point out that all of the people quoted here are good, smart, successful people with active and - in many cases - enviable careers. If you're not making mistakes, you're not trying anything new. But maybe reading ours will help you avoid some mistakes already made, so you can go out and make thrilling new ones all of your own.