How the Unconventional Job Seeker Gets the Job

As a career coach you can expect that a pretty typical part of my day will be spent speaking with clients who are bewildered by their search for fulfilling work. 

I tell them: Your career has real value and potential, even if you didn’t start out with a fixed idea of what you wanted to end up doing, then pursue it in a series of obvious, tried and tested steps. 

Many of the problems people face can be similar; “I don’t know what I want to do”, “I don’t know how to get there”, “I can’t share myself in a way that highlights who I am,” or “I have short-term financial needs, but I want to explore broadly the best fit for me.”

There are also varying personalities and approaches often connected to career paths. For example, I love working with engineers and accountants because their career process is often very logical, and catering to that progression comes very naturally. I also enjoy supporting entrepreneurs and folks with a yearning for social change, because that is where most of my career has played out, and I tactically understand both the emotional and practical challenges.

But in truth, the people I like working with the most are often the least conventional.

The people who’ve had what I call “interesting” careers because they allowed themselves to follow their creative pull or intellectual curiosity.

This is only a little bit due to the fact that this is how I would describe myself. Rather, my experience when it comes to hiring or offering a strong opinion about someone during the recruitment process is, this is the path I am most inclined to follow, and it has served me well.

For example: The former elementary school science and math teacher turned program director. The ultra marathoner turned event manager. The guy who had an amazing website featuring the travels of a stuffed monkey turned communications guy. These were people who became fantastic long-term hires who weren’t “conventional” fits.

In our careers, we get the message over time that we’re supposed to behave a certain way, and check certain boxes to get ahead.

If you don’t follow the prescribed path, then you get beaten down in terms of your self-perception, doubt your legitimacy as a professional and you feel an overwhelming pressure to conform.

If you have chosen to read this article you have likely already missed the boat on following a linear path from Junior X to Assistant Director of X to Director of X to Vice President of X….

I’m not suggesting that you can walk directly into the operating room as head surgeon after spending ten years on a fishing boat, but you can find ways to translate who you are to people who wouldn’t otherwise understand why you could be a good fit.

The truth is that for many people, many of them with huge career potential, conforming just isn’t an option even if they were going to try to shove the round peg—them—into into the square hole—the job they want.

And if you’re notably different in some way, then pretending that you’re something else just isn’t going to work.

So, if people with hiring responsibilities look for someone with the specific career arc, you may not appear on the radar, or you may be rejected if you lodge a standard application.

There are two things you must do if you’re in this boat. 

First, you need to develop a network of contacts, people that can advocate for you in the hiring process, and before you even lodge an application.

The chances that your resume will move to the top of the pile are infinitely improved if you have connections that can speak to your strengths. Why even if they are using an automated system, you can be plucked from obscurity by doing this. I have written about this often, but needless to say that you need to start courting the employers that intrigue you, and getting to know the people you find compelling. 

This isn't about developing relationships with Human Resources. I’ll repeat that once more with feeling: THIS ISN'T ABOUT DEVELOPING RELATIONSHIPS WITH HUMAN RESOURCES. It’s about developing relationships with people at these organizations that can advocate for you. I’m not saying this kind of networking should be a mercenary process, and it’s important that you invest and hone your network over time. But if you have your eye on a certain kind of job in a certain market, then you’ll benefit from engaging the people you aspire to be, and have them speak up for your candidacy as a would-be employee. 

Second, and where I really want to push you, is to have you consider how you frame your self-perception in your head and how you share it with others. You are probably not a generalist. It is possible, but I have found that to be the description of those with fairly flaccid self-esteem, and the same thing with those who consider themselves scattered or unfocussed. In my experience what these people are lacking chiefly is confidence and self-worth.

If you don't own what you do well and share it with others, than nobody else is ever going to know.

Put this in words that you learn to own, and that feel authentic. 

I spend a fair amount of time with people, often simply developing a brief story or elevator pitch to help them feel like they can synthesize their work life and goals. It can be really transformative for people to own who they have been, and align it with who they hope to be next. It is one of my favorite pieces of what we do at ClearlyNext, but it can also be done with a friend you trust, who gets you. Someone who can help you try to share who you are with others. 

Ask your friend to look through your resume and tell you what they think are the connecting pieces of your work. When I work with others, it often comes up that someone might be the community builder that ensures that people feel heard or valued, or the person who develops and thinks out structures, or is the detail person who ensures that everything happens according to schedule. You may have been in very different settings but you may have shown up in similar ways. 

Let me step away from the theoretical for a moment and offer some examples of some of the people I have loved working with most, how they show up with some of the advantages of being a round peg.

Roland was very involved in making it in Hollywood. While his efforts to be the next big thing had some modest successes he had become a star in his volunteer work, spearheading and managing celebrity-laden fundraisers that raised significant funds for several charities. And on the side, he’d worked as a celebrity assistant to a certain television mom who everyone loved, but was impossible. 

He wanted to not be so dependent on the whims of an aging star, and wasn't quite sure who would see him as a fit. When we spoke I had to shift him from seeing himself as someone who could only get another job as a personal assistant. Rather, we emphasized attributes that are extremely attractive when others are hiring. 

First, his adulthood, otherwise known as competence. He gets on with stuff, he gets it done, and he doesn’t let people down when they were expecting him to deliver something. He had been an assistant with his person longer than anyone else had been able to last. Not only was he managing the staff of several houses for an extremely demanding person, he also had to make sure that the show went on, on time, starring some pretty challenging individuals. My number one compliment for someone when I am recommending them is that they are an adult and will get the work done without excuses.

Second, his heightened capacity to learn and adapt. Roland was finding ways to learn nuances and norms in three different spaces. Demonstrating his capacity to learn new things and thrive in them, and to learn new people, and thrive with them, was very important. 

Matilda was a successful radio journalist who also spent time writing a novel, shooting a documentary, launching a newsletter and shooting short films. Over time she became disenchanted with most forms of storytelling, and decided to prioritize making a much better wage. So she went into business development. Over time she came to realize that the pendulum may have swung too hard in the other direction. Now she was at a loss to figure out what to do, and how to convince someone else to take a chance on her. When we spoke I think she was a bit overwhelmed by my excitement for her. Where she saw a deficit, I saw an amazing opportunity. 

Matilda needed to own her unique value proposition. She could share stories that she could see how to monetize. With both the storytelling and the sales angles to her skill-set she was an attractive fit particularly in the non-profit sector, which helped to use these narratives to fundraise with. She was an unusual and popular candidate for many roles because she saw her specific value and where it would be relevant. She intrigued employers because when she went for communications roles, people often weren’t thinking about fundraising or sales. And when she went for sales roles, people often weren’t thinking about marketing and communications. 

Matilda was able to craft a careful narrative that shared why she was compelled to now do this work. She shared how it took her some time to figure out the fit of a role that would let her tell stories, but to have tangible goals that she could reach for each time outside the story itself and make a decent living. 

Do what you can to share an authentic and compelling reason why you are a better choice.

What have you learned, what experiences have you had that position you to be successful in ways that conventional candidates can’t?

Remember, there are probably a lot of very similar people in that pile, and your can make a compelling case.

I hope this give you confidence and helps you to not diminish yourself, or what’s possible. If you are finding that impossible to process, please reach out I'm happy to see if I can help.

Russ Finkelstein is a Co-Founder and Managing Director of ClearlyNext, a guided online program that helps people figure out what to do next in their careers. Russ is also a co-founder of idealist.org, a senior advisor at Fund the People and board member of YNPN. He is all about helping people find their way – advising and coaching for free far more than his mother would like.