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Get Comfortable with Awkward Situations


Right before I graduated from undergrad, one of the best (and uncharacteristically bold) ideas I had was to sit down one-on-one with people well-seasoned in their careers to get a feel of what they would do or not do again coming right out of college. I met with professors, businessmen, and even tried to get an audience with a CEO of a company with thousands of employees. (Not the one I currently work for, for those curious.)

Some of these situations had varying levels of awkwardness. On a smaller scale, the aforementioned CEO's secretary told me in so many words that he didn't have the time for me. (Fair enough.) On a more intimate level, I met with a few financial planners who tried taking advantage of the situation by up-selling me on their services. I even had one guy quickly dismiss me after he figured out I really wasn't interested in his services.

Don't get me wrong, though. There was a lot of success with this little experiment. I had the opportunity to sit down with the president of my university, several director-level leaders in the place I was interning at, and more people I never thought would give me the time of day. The advice they gave me was fantastic, and some of it I still apply to my life today.

My point is that you can't let your fear of awkward or uncomfortable situations stop you from doing something. And I won't lie: you will inevitably run into those circumstances. Period. There is no escaping them.

So how do you brace yourself for handling potentially awkward situations? You really can't. They're always going to look different. I mentioned the scenario above where one financial planner dismissed me from his office. I've also witnessed a former coworker scream at another coworker demanding a smoke break, been asked by a former associate to share confidential company information, and once confronted a superior about their brash behavior toward my team. Those were all radically different, extremely uncomfortable scenarios with no universal, one-size-fits-all answer.

What you can do is to take these situations in stride. You will encounter these unfavorable situations, so you have to be able to let that all go at the end of the day. I'm not a fan of this cliche, but it's definitely relevant here: you can't let your fear of striking out keep you from playing the game.

Don't let these things bring you down because there is a light at the end of most of these tunnels. I can say that even as a young guy toward the beginning of his career. Ask seasoned veterans edging toward retirement, and I am sure they would echo these thoughts.


Embrace the moment. If you find yourself coming out of an uncomfortable situation, take it in stride. Don't look down on yourself and instead set your sights on what's next. These things can only help to strengthen you in your path ahead.

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