RedEye’s Job Fantasy Camp: 4 tips to landing your dream job

Originally posted 10.13.10 chicagonow.com/blogs/brokeass-blog

"I can’t think of anything worse than doing a job everyday that you hate." -Karl Sponholtz, interior designer

Landing your dream job is actually quite simple.

Really. In the past several months, I’ve gone behind the scenes of 10 different industries, chatted with dozens of wise professionals, and heard all about the hopes and dreams of an untold number of Chicagoans.

The experience was RedEye’s Job Fantasy Camp, where we found rock stars in their respective fields, ambitious peeps aspiring to follow suit, and got them together.

In the 10 weeks of job-hopping, I couldn’t help but notice some reoccurring themes, similar pieces of advice, and a general attitude that translated to any and every type of career.

And since knowledge, like chips and salsa, is best shared with a large hungry group, here are four things I learned about turning your dream into your day job.

"You know as much as anybody….My dad once said to me ‘an expert is someone who had an opportunity to do it and they just did it’." -Ed Scanlan, CEO, Total Attorneys


1.) It’s only a “dream” now

I’ll admit, as much as I truly believe in a person’s ability to surprise themselves in what they can accomplish, I couldn’t help but wonder “Could everyone actually have their dream job? Wouldn’t all the ‘dream jobs’ be filled?”


Yes, if we all had the same dream.

But we don’t. Not by a long shot. And of all the pleasant surprises I received this summer, this one by far took me the most off-guard.

"Sometimes you have to order things you don’t like. "If I only ordered what I liked it’d be all bacon and cheese…" -Kevin Pang, Food blogger, Chicago Tribune


"So, what’s your dream job?"

I now like to throw that question out to everyone I encounter, because there is no question more telling of a person than what they would dedicate their entire life to given any option in the world.

And of all the people I’ve asked that question, I can honestly say I can’t recall getting two of the same answer.

And as it was seen by these fellow dreamers, very few people are truly motivated by money or fame or the things we may, on the surface, associate with a “dream” life.

So while there will always be those stepping-stone jobs that need to be filled, they are just that: steps. The only dead-ends in life are the ones you build yourself.

So don’t build them.

"I’m obviously doing what I was born to do." -Cheryl Delio, Personal Trainer


2.) Stop asking “Can I?” Start asking “How much do I want to?”

One of my favorite pieces of advice came in on our first day of Job Fantasy Camp when we asked Total Attorneys CEO Ed Scanlan how one does “the deep dive” and start their own company.

"Quit," he said.

"The way to do the deep dive is to quit. Make it your only option and I guarantee you’ll make money," Scanlan told us.

While no one else advised us to put in our two weeks, a similar sentiment was had by all the pros we talked to.

"I was at the gym all the time. I decided to make the leap," said personal trainer and week three “camp counselor” Cheryl Delio.

The overall message: At some point, you are going to have to make a decision. And you’re going to have to commit. Maybe that means widening your job search. Maybe that means taking an unpaid internship. Maybe it means you work weekends. Maybe it means you decline some nights out and stay home with your wallet. Maybe it means you move.

And there is a good chance it may be the most petrifying thing you’ve ever done. But in the end, it’s sink or swim. And when it’s important, people usually are surprised just how well they swim.

Now this may sound harsh, but if you can’t fathom making certain sacrifices then maybe it’s not as much a priority as you thought. And that’s OK, because it’s your life and your dream and there’s no standard time-stamp you need to have approved. But you do need to be honest with yourself and figure out your priority list.  

"I play with poop all day, and I love it." -Dr. Rachel Santymire, Lincoln Park Zoo


3.) Sometimes you have to get it wrong before you get it right

"I thought that’s what I wanted to do…I could do it, but it doesn’t fulfill me as much as I thought," Lincoln Park Zoo’s PR director and week five’s Job Fantasy Camp participant Sharon Dewar said of her initial dream job.

The former aspiring primatologist is not alone in her detour-filled roadmap. In fact, she’s more the rule than the exception. Whether it’s a German teacher who became a video game producer, a lawyer who became a sports agent, or a PR major who became a news anchor, there is a very good chance you may not end on the same path you started.

But that, again, is OK. We put so much into milestones we set for ourselves long before we even know what the road looks like. And then we freak out when we realize we were off, or the path ends, or it’s not the route we wanted.

I’ve learned from these successful Chicagoans that we shouldn’t. Louis and Clark didn’t map out America before they took their first step; they figured it out as they went along and adjusted accordingly.

"Some days are great, I’m walking on air. Some days I want to crawl in a hole." -Scott Rochelle, sports agent


4.) It’s not always safety first

Sometimes we’re the ones holding ourselves back. We may not push ourselves as hard as we could to take that first step towards dream job to day job conversion, because doing so would make it real.

"But wait, isn’t that the whole point? Don’t we want our dreams to come true?"

Yes and no.

Because a dream, is safe. It can be as big and outrageous as you’d like. And it should be. Because, it’s a dream.

But as much as we may yearn to be a professional *whatever*, actually making physical, concrete steps towards it means there’s a chance we could fail.

There’s a chance we’re not as good as we thought, it’s not as fun as we thought, we’re not as passionate as we thought; there’s a chance we’ll realize, like so many of the people we spoke with, that we don’t want to continue on this path. And that’s a scary reality.

"You could interview the heroin addict who happened to be outside and then talk to the president of the bank," says Rice. "You have to be able to deal with both." -Special Agent Ross Rice, FBI


It may be terribly cliche, but there’s something to getting out of your “comfort zone.” But you shouldn’t strive to push yourself out there because there’s anything wrong with being comfortable or being in your “element,” but because getting outside your comfort zone is the only way to extend it; the further you push your own boundaries and challenge yourself, the further you can go comfortably and the bigger the challenges you can handle. Eventually, you can make the whole world is your comfort zone. And that, is something to shoot for.

But how?

Running a marathon is “simple,” right? It’s one foot in front of the other. But we can probably all agree it’s not easy. So as the campfires are put out and the last of the S’mores eaten, I leave you with homework.

Do something by the end of the day that inches you closer to your dream job. It doesn’t have to be huge. It doesn’t have to be quitting your job (so employers, please don’t send me angry e-mails). It can be something as simple as e-mailing that friend of a friend who works in the industry you want to get in to. It could be applying to grad school. It could be having your resume critiqued. Setting a budget so you can get some savings for that business you want to open someday. Start a blog. Tweet people you want to network with.

It doesn’t matter how big the step, as long as it’s forward, because it is amazing just how big a spark that little step can make.

"If you show you’re willing to take on ‘whatever,’ that goes a long way." -Chelsea Blasko, Video Game Producer


"You’re always against the clock. If my story runs at 9:01, it runs at 9:01, not 9:02 …you’re always hustling." -Lourdes Duarte, WGN News Anchor


"That I drive around in a Lamborghini and a big ‘number one’ sign….I’m not going to run over people to get ahead." -Billy Dec, Restaurateur, on the most common misconception about him

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