Explaining Your Unconventional Background

From having to eat fried chicken every day, to working with a boy who was raised by wolves, I discovered how unpredictably life can be. My story is one of the many that could never have been possible without being set in an unconventional background. There are countless people out there like me – and all we want is for our stories to not just end after high school.

Vintage young Man job interview wrestling alligators.

Do you ever find it difficult to put into words your distinct background? Do you find it difficult to describe a specific unflattering job history in a manner that seems credible? If that’s the case, you’re not alone.

Perhaps you skipped college to open a coffee business. Perhaps you dropped out of college to join the army. Maybe you spent a few winters as a ski bum. Maybe you spent a few years on the road with your band, waiting for a ska revival (good luck with that).

People who live basic vanilla, cookie-cutter lifestyles are rewarded in today’s workplace. Anyone with a “abnormal” history is often written off, or at the at least, has an uphill struggle in explaining their background to prospective employers, landlords, and future in-laws.

So, what do you do if you come from an unorthodox family yet live in a traditional society?

Let me tell you about my buddy Colin if you can relate to this.

Colin dropped out of college to join the United States Coast Guard, where he became part of an elite team tasked with retaking ships captured by pirates. I asked Colin to tell me about the most bizarre encounter he could recall without killing me. I almost expected him to reply that the first rule of fighting pirates is that you can’t speak about fighting pirates, but he didn’t, which is lucky for you and me.

Colin recounted an event in which his team had to reclaim a stolen cargo in the Gulf of Mexico. His Coast Guard cutter sped through the darkness in the middle of the night, straight up beside the hijacked ship. Because both boats were bouncing up and down in the water in full darkness, Colin and the rest of his crew had to throw a rope ladder over the side of the deck and climb up the swinging ladder onto the ship’s deck.

Oh, and did I mention that as they were attempting to mount the ladder, the pirates were firing machine guns at them?

The team had to travel room-by-room around the ship using special night vision and thermal imaging goggles to see through walls and identify where the pirates were hiding after they were back on deck and retook the bridge.

I can’t watch The Goonies without clutching my wife’s hand, yet this was simply another day at work for Colin. So you’d assume his background would help him advance in his job, right? Guess once again.

Why Is It Bad to Be Unconventional?

Colin’s story may seem incredible now, but it was difficult for him to speak about his time in the Coast Guard before 9/11.

“No one knew how to connect to me,” he said. Worse still, “it had a significant detrimental influence on my ability to obtain work.” It seemed like I’d been jobless for five years.”

In a society driven by traditional expectations, Colin had to find a method to communicate about his unusual upbringing. He eventually came up with a way to express his odd employment history. “To get people to listen to what I have to say,” he adds now, “I constantly try to utilize empathy and analogies.” “Respect, empathy, and context are the most crucial variables.” You must ensure that the audience comprehends what you are saying.”


The irony is that Colin ended up working in information security, which entails defending organizations against digital pirate assaults. He claims that his career “discovered me, not the other way around.” And it couldn’t be a more perfect match.

Do you have a similar story to Colin’s? Have you found it difficult to speak about your unconventional upbringing in today’s world?

Do you know how to describe your experiences in a manner that others can understand and connect to?

Hold your breath if you haven’t figured it all out yet. Here are seven suggestions on how to discuss your odd or unorthodox past in a conventional setting:

1. Don’t Ignore the Subject

We’ve all seen the TV detective dramas where the character who is most hesitant to discuss his background always seems to be the guilty culprit, even if he isn’t. Attempting to avoid discussing your past might have a surprisingly comparable impact. To put it another way, being hesitant about the topic might do more damage than just being honest about it.

Even though he had no experience with television, James Swanwick, an Australian print writer, earned an interview to be an anchor on ESPN’s SportsCenter. Swanwick was well aware that his lack of anchoring experience may be a deal-breaker for ESPN, but he didn’t shy away from discussing it.

“I acknowledged I had no experience with television,” Swanwick adds. “However, I said that I had meticulously studied [the previous SportsCenter hosts] Stuart Scott and Scott Van Pelt.” I showed initiative and zeal.” He was offered the position, and he accepted it.

You don’t have to tell everyone everything about your life, but if someone asks, be open and honest with them. If it isn’t a major matter to you, it isn’t likely to be a problem for anybody else.

2. Communicate in everyday language

What’s the fastest method to lose someone’s attention in the middle of a conversation? They’re talking over one other’s heads. Remember that others may not have had the same experiences as you, therefore you may need to clarify crucial ideas or terms.

Dov Gordon, a friend of mine, is a superb marketing expert. You’d never guess he never went to college. He is, in fact, a voracious reader. He never employs huge terms or language while discussing marketing topics. Similarly, my pirate-fighting friend Colin doesn’t speak in jargon that only his fellow Guardsmen understand, but instead shares anecdotes from his military days in layman’s words.

When discussing your history, be aware of the terminology and lingo you employ. Make an effort to simplify things so that everyone can understand and appreciate your story.

3. Make a joke

Humor is a fantastic technique for discussing a strange history. Your audience will be more receptive to your message if the ambiance is casual and the tales are amusing.

David Nihill knows a thing or two about having an unconventional upbringing in a traditional environment. Nihill, a former stand-up comedian, has worked as a financial consultant for PricewaterhouseCoopers as well as for Silicon Valley firms.


“A smart salesman, marketer, leader, or business development person establishes a relationship,” says Nihill, author of Do You Talk Funny? To Become a Better (and Funnier) Public Speaker, Follow These 7 Comedy Habits. “The quickest method to do this is to make someone laugh.” According to Nihill, the easiest method to make people laugh is to come prepared to every discussion with amusing anecdotes from your unusual past. “Write these [stories] in the simplest and most effective way possible,” Nihill advises. “Cut away any unnecessary words and recall Shakespeare’s wisdom: Brevity is levity,” says the author.

You don’t have to be a stand-up comedian to accomplish this. However, we all have amusing anecdotes from our pasts, and your unique history might be a terrific place to start.

4. Concentrate on your accomplishments that are relevant to you.

Joshua Jordison is a successful entrepreneur headquartered in Los Angeles, whose firm creates live music events and provides music licensing advice to businesses. He does not, however, hail from a traditional middle-class family. Jordison was homeschooled for most of his schooling and grew up in a rough and crime-ridden area just outside of Los Angeles.

Although others may be self-conscious about his background, particularly when rubbing shoulders with Hollywood’s elite, Jordison claims that his unconventional schooling doesn’t come up too frequently.

“In the last five years, I’ve been asked where I went to college fewer than six times,” Jordison adds. “People are usually interested in learning more about what I’ve done and don’t think about my school background.”

When Jordison does speak about his unusual upbringing, he attempts to keep the conversation focused on his professional achievements. Jordison adds, “I simply mention what I’ve done and don’t inflate or exaggerate anything.” “All you have to do is be genuine and connect on a human level with others.”

5. Share Your Insecurities and Be Vulnerable

When you tell others about your uncommon history, they may get defensive, particularly if your background is so extraordinary or odd that boasting about your accomplishments seems like bragging. If your adventures look incredible (particularly in relation to others’ ordinary lives), you may arouse envy.

There is, however, a simple solution to this problem. Simply demonstrate that you have made errors in the past. Talking about your personal flaws might help you demonstrate that you’re still human. Whether you’ve leapt off of aircraft or caught legendary criminals, you’ve almost certainly locked your keys in the vehicle at some point. (Just remember not to lock your keys in the vehicle when handcuffing a criminal.)

Others may be able to connect with your tale and experiences, and relate to you as a person, if you admit your flaws.

6. Describe your transferable abilities

Even if you come from an uncommon or unorthodox background, there are certainly some transferrable abilities you earned earlier in life.

Josh Parkinson can attest to this. After earning a master’s degree in English, he took the next natural step and flew to Europe, where he worked as a street musician for the following five years.


Isn’t it difficult to identify transferrable talents in such experience? Wrong. In fact, you might claim that five years as a street musician has given you a wide range of transferrable talents. You must be scrappy, inventive, diligent, and thick-skinned to be a street musician. You must have a strong work ethic as well as the ability to market oneself to strangers.

The bottom line is that you must find a method to turn your previous experiences into transferrable talents that can be used in a more traditional setting.

Parkinson is now the co-founder of Post Planner, a successful San Francisco-based digital business, indicating that at least some of his abilities have transferred to the realm of entrepreneurship.

7. If at all possible, incorporate your unconventional background into the mainstream.

Finally, there’s an old adage that goes, “If you can’t beat ’em, join ’em.” I believe it was Mark Twain who stated it. What better way to succeed in our modern society than to bring your unconventional past into the present?

Like Colin, who transitioned from battling real pirates to fighting digital pirates, your best bet may be to embrace your unconventional past and blend it into the mainstream.

David Nihill, a former stand-up comedian, did just that. Nihill established FunnyBizz, a conference focused at helping business people become funnier, by combining his expertise in comedy with his work with startups and other companies in Silicon Valley.

What’s even better is that he was able to combine his unconventional comedic background with his employment in the corporate sector. That’s how you get the final laugh, my friend.

It Doesn’t Matter What You’ve Done Before

In the end, your prior experiences and background are irrelevant. What matters most is how you interpret it and if you can connect with others and have them relate to your narrative.

In today’s society, creating a smidgeon of jealousy and interest in others may be a huge plus. “Unorthodox implies fascinating,” Nihill says. You have a significantly better chance of having anything in common with someone because of your wide and unconventional background.” And that something in common may be as simple as having experienced an experience that others have always been curious about.

Meg Jay, a psychologist and author of The Defining Decade, is an example of this. When she applied for academic employment, she was startled that her interviewers preferred to chat about her experience working for Outward Bound, an outdoor leadership program, rather than asking about her university credentials (which she had plenty of). Many people have always wanted to know what it’s like to work as a wilderness guide, so rather than being a liability on her résumé, it turned out to be one of her most significant assets. Jay was notable because of her ability to communicate about being a member of Outward Bound in a relevant manner, giving the interviewers a virtual opportunity to walk a route less traveled.

“People will forget what you said, people will forget what you did, but people will never forget how you made them feel,” Maya Angelou famously stated.


“People will forget what you said, people will forget what you did, but people will never forget how you made them feel,” Maya Angelou famously stated.

John Corcoran is an attorney and former Clinton White House writer. On his blog, Smart Business Revolution, he offers networking advice and ideas. His 52-page guide, How to Increase Your Income Today by Building Relationships with Influencers, Even if You Hate Networking, is available for free download.