When You Know You’re the Underdog

  • Posted by: Chaloner

A guest blog by Samantha Beach

The term “underdog” comes to us from dogfights of the 19th century where, at the end of a battle, one dog would end up on top and one underneath. The dog that lost bore the shame in the books where it would read “underdog” beneath his name and number. Though the next fight had not yet begun, he was already defined by the improbability that he would win.

I have just finished reading Malcolm Gladwell’s David and Goliath (about a year after the rest of the world) which challenges our traditional concept of the underdog. Gladwell argues that having a plethora of desirable resources, ability and experience is not always helpful; that in fact, the creativity and boldness that limited resources produce in a person might be more powerful than we realize.

It is easy to feel like an underdog in a job search. There will always be someone who went to a better school, has a wider breadth of experience, speaks more languages and is having a much better hair day. Sometimes you hand over your resume and feel like it might as well have the label “underdog” beneath your name. But I wonder if we might use underdog status to our advantage and embrace the possible benefits of being against all odds.


Maybe you’ve just moved across the country and are looking for work in PR without any local media connections to boast of. Maybe you spent much of your career at a small and relatively unknown company and are struggling to translate that experience to a larger organization. Or perhaps you made your mark in the paper industry of yesteryear and are struggling to adapt to the new skills and strategies of the digital age. Gladwell asserts that this may not be the disadvantage we believe it to be. “We spend a lot of time thinking about the ways that prestige and resources and belonging to elite institutions make us better off. We don’t spend enough time thinking about the ways in which those kinds of material advantages limit our options.” What skills have you had to develop that might have otherwise lain dormant? How can you turn this apparent disadvantage into a type of experience that might actually set you apart from the competition? I.E. “My time at small company X forced me to problem-solve with limited resources, and that experience has made me more innovative and savvy.” If you can do a lot with a little, chances are you can do a whole lot with a lot.

Desirable Difficulty

Perhaps it’s a deeper issue or perceived weakness that makes you feel like an underdog. A learning disability, crippling anxiety with public speaking or interviewing, a mental disorder that affects your work habits- whatever it may be, it can feel like you’re starting the job search with a disadvantage. Gladwell spends more time unpacking the idea of desirable difficulties than I have room to do here, but he advocates for the kind of learning one is forced to do to when one must compensate. He says most of the learning we do is “capitalization learning”. If you are very coordinated and tall and find that you excel at basketball, you practice and get good at it by building on natural strengths. But he uses the example of dyslexia to introduce “compensation learning.” If you are a terrible reader, you have to scramble and create some kind of strategy that lets you keep up. He says, “Those who can are better off than they would have been otherwise, because what is learned out of necessity is inevitably more powerful than the learning that comes easily.” Consider the possibility that your Achilles’ heel has made you stronger. And let the knowledge of what you’ve had to overcome embolden you as you enter an interview or important conversation.


Underdogs know failure well. They’ve experienced it firsthand and people have even come to expect it of them. If you can rise above the negative line of thinking that can accompany this track record, consider how incredibly liberating it is to be free of the fear of failure. Gladwell says, “Courage is not something that you already have that makes you brave when the tough times start. Courage is what you earn when you’ve been through the tough times and you discover they aren’t so tough after all.” My work in the arts has given me a taste of the freedom that comes from having nothing to lose. Because I walk into every audition with about a 1 in 300 shot of getting the job, the more auditions I go on and don’t book, the Iess nervous I get and the more courage I feel to make bold choices and take risks with the material. Why not? If you find yourself deep into what seems like a never-ending job search, you may be in the exact right position to surprise someone as you feel the freedom to try things no one else has dreamt of.

There is no denying that it is difficult to walk into a room knowing you are not expected to succeed. But all around us, Davids are slinging down Goliaths. And Gladwell would tell us these aren’t just lucky throws; the dog that’s been on the bottom enough times has learned something the favorites never can.