The Bigger Picture: It’s Always Worth an Ask

I have a friend who consistently lands in the cushiest situations. Ever since I have known her, she would wiggle her way out of a final exam so that she could work on a more interesting project. She could negotiate dreamlike work conditions: lots of excuses to travel, super flexible work from home schedules, seemingly unlimited vacation. She never had a traditional set up; she always had a better arrangement, something that was perfect for her. I don’t mean to imply that this friend is a slacker. Not at all. She’s actually brilliant and hard-working and passionate. She will always get the job done.

Many years ago, we were working on a school project together, and we needed special accommodations to reach our desired end result. I balked: I would never, ever, in a million years have thought that we could actually secure the special treatment. But my friend shrugged her shoulders and whipped off an email to the professor, stating, “It’s always worth an ask!”

“It’s always worth an ask.” Simple, right?

As someone who is a rule follower, who tends to stay within the lines, those words stuck with me. Ever since then, when I think of something I want, and it’s not exactly the prescribed route, I reach out and ask. It’s harder for me than it is for my friend. It’s harder because sometimes I feel embarrassed or almost ashamed if the answer is no. Why is that? Why do we feel ashamed when we are turned down for asking for what we want?

It's always worth an ask

I was reminded of this a few weeks ago, when my family was at a campsite making s’mores. My kids were using bent branches to roast the marshmallows, but the family at the next campsite had official metal rods. My youngest daughter was dying to use one of their rods but was too embarrassed to ask. I asked her why and she replied, “What if they say no?” My older daughter, fed up with the whole conversation went over and asked. She came back a moment later with five rods, lighter fluid and extra Hershey’s bars.  She turned to her younger sister and said, “They could have said no, but what if they say yes?”

When we ask, we somehow feel vulnerable and a “no” can feel like a personal rejection. But it’s not. It’s just a no. If we don’t ask, we end up with a no. If we do ask, we might feel a bit embarrassed, but there is a very good chance that we will end up with exactly what we want or even something better: s’more sticks plus lighter fluid and chocolate!

Do you want scholarship dollars at your MBA program? Do you want a raise? Do you want the chef to prepare a special meal for you? Do you want your favorite masseuse to contribute to a fundraiser? Do you need to stay in your apartment two weeks longer than planned? Next time you hit a wall, consider whether there is a way around. It might be as simple as an ask.

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