As someone who has no practical gifts that lend themselves towards a stable, lucrative career, I am a big fan of the whole “follow your dreams” thing. God gave me the ability to sing, write, talk, and telecommunicate with horses– none of which go over well in an office. Well, writing can come in handy, but it’s not fun unless I can drink wine while doing it. I did have one job that let me do that…but I still had to wear nice clothes every day, so that got old after awhile.

Pursuing dreams full-time = stress, self-doubt, and odd jobs. Here are a few things I did in my early-twenties on my quest to become Miss America and/or perform on Broadway:

  • Farm camp counselor, teaching children how to feed llamas
  • Waitress at Cheeseburger in Paradise Bar & Grill
  • “Four Loko Girl” who handed out samples in an NYC concert hall
  • Personal Assistant to the owner of a skin care company who I met on an airplane, working out of her giant condo on the Upper East Side while she wore nothing but lingerie most days (age 70, and I loved her)
  • T-Mobile Christmas Elf
  • Dancing Banana to promote Jamba Juice
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Dancing banana today, Broadway star tomorrow!

Well, I never became Miss America or starred on Broadway, but I did become Miss New York and discovered that the entertainment industry is not for me. I am way too attached to the concept of medical insurance to perform for a living. Although these dreams never fully materialized, I don’t have to look back and wonder “what if,” which feels really good.

I tried to fit myself into the “acceptable” 9-5 box these last three years, but still can’t shake my need to pursue a dream. Since singing is off the table (unless something miraculous happens), and it’s probably too late to become an Olympic horseback rider, I’m focusing on writing. Much to the pleasure of my father, I’m sure, I quit my well-paying salary job in exchange for banking on people procrastinating at work by reading my random thoughts. Keep up the good work, everyone!

If blogging for a living is not a Generation Y move, I don’t know what is. Don’t worry, I still have enough granny in me that I made sure to marry a guy with great benefits. (Kidding! Not why I married him! But I’m not, like, mad he provides our insurance…)

Since I’m pretty much a professional dream-chaser at this point, I feel like I have a little bit of insight on the matter. Trust me when I say that you need to contemplate these 5 major questions if you’re going to pursue an “impractical” passion:

1. Are you realistic about your abilities?

You know how everyone says “Someone should have told them…” when a person absolutely bombs their American Idol (RIP) audition? Yeah…don’t be that guy. Get some honest feedback about your talents before putting all of your eggs in one basket. For example, if your dream is to become a chef, make sure people actually like your food. Not your mom. And not your grandmother’s bridge club. Best case scenario, you have a gay BFF, because they’ll always be honest with you. Essentially, people who aren’t particularly attached to your feelings should be approaching you on a consistent basis with unsolicited words of affirmation.

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This isn’t to say that you shouldn’t believe in yourself or that you should get your self-worth from the praise of others, but pretty much every dream comes true because of support from other people. I’ll expand more on that point during Question #3, but I can’t stress enough– it’s important to know what you’re working with. I, for one, would never try to become a hip hop dancer despite my love for body rolls, because I have the rhythm of a drunk penguin. Passion alone isn’t enough.

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2. Are you truly dedicated?

Speaking of passion, make sure you have a lot of it (in addition to legitimate ability). If you aren’t willing to work far more than eight hours a day to make your dream happen, then you don’t care enough. I’m certainly not perfect, but when it comes to this blog, I still wake myself up early and “go to work” (i.e. Starbucks) so that I don’t find myself being lazy around the house all day. Chasing dreams requires a lot of self-motivation and sacrifice. If you don’t want to turn down a few dinner parties to make it happen, then it won’t. Good signs that you’ll reach your goal:

  • You wake up in the middle of the night thinking about it
  • You can talk about it for hours and often bore people around you
  • You would rather skip a meal to finish a related project than stop what you’re doing
  • You’re willing to be a Dancing Banana if it means progress

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3. Are you only thinking about yourself?

This one is definitely more for artistic dreamers, but keep in mind that the people actively buying in on your talent (i.e. folks reading your blog, buying tickets to your show, eating your food, purchasing your paintings, attending your yoga class, etc.) are the ones making your dreams a reality. Your hard work, aptitude, and passion matter– but a dream only becomes a career once people are willing to invest their time and/or money in whatever you have to offer. If you greatly enjoy coaching pageant girls, but don’t think about the interests and unique personalities of your clients, no one is going to hire you.

You must appeal to your audience so that people will pick up what you’re putting down. Ya feel? It’s not about gaining attention or tons of money– it’s about addressing the needs of people around you. Are you a wannabe T.V. host? Think about how you want to make your viewers feel. Challenged? Happy? Informed? All three? Then your brand and voice should be “fervent with a touch of humor,” founded on well-developed research of your chosen/assigned topic. You want to be a dancer? Take note of what people enjoy watching, and of techniques used by the best in your field to keep fans on the edge of their seats– then work on your craft accordingly. Dreams won’t take flight if they’re entirely self-indulgent. It’s about offering your talents as a way to better other people’s lives.

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4. Do you have the necessary guidance?

Your network is crucial. “Networking” is a strange concept, because [I believe] it’s insincere to befriend someone just because they have something to offer professionally. Still, be sure to develop enough relationships to build a well-equipped support system. Simply by showing interest in others, I’ve found a phenomenal web developer, an extremely talented graphic artist, and tons of bloggers and photographers willing to give their time and advice. Of course, you must be willing to financially invest in help, but you’ll also be amazed at how readily people will impart their expertise if you share a basic mutual respect. And ask nicely.

A big part of fostering these resources is offering them something in return. It can be a shout out on social media, sharing your own knowledge, proving that you notice their own personal endeavors through thoughtful compliments, or giving them a batch of homemade cookies. The point is to show that we’re all in this together, and the support is reciprocated.

No matter how great you may be, I promise that you’ll never reach success without the counsel and skills of others. This blog is an excellent example of that.

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5. Do you have a plan?

I LOVE PLANNING. Planning is my favorite. Planning is what dreams are made of. Seriously– they are. Dreams just get lost in a big sea of abstract wishes if you don’t tie them down. Capture them. You can’t expect a dream-fish to hop into your boat. You must come up with a strategy. And your strategy shouldn’t be to haphazardly stab the fish with a spear. You’ll miss and probably hurt yourself.

A plan generally has steps, or a timeline of events. Learn how to use a new camera lens on March 1st. Have coffee with someone successful in your field on February 5th. Book a gig for April 15th. Do a cartwheel by May 31st. Only drink one glass of wine on Monday. Shower on Friday. Once you have your timeline, sit down with each goal and figure out what it’ll take. Need to book a guitar gig? 1. Call bars in the area to see who is looking for live music, 2. Record videos of you playing guitar and send them to those bars, 3. Follow up on your inquiry. Want to have coffee with someone successful in your field? Find their email and send them a note. Better yet, pick up the phone and give them a ring.

“Seeing what happens” is not a plan. Sporadically following leads is not a plan. A plan is a plan, so make one.

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Not everyone has “impractical” dreams. Plenty of people find deep contentment in 9-5 careers, which can be dreams in and of themselves! No matter your dream, I hope this post helps you reach the point that you’ll have to pinch yourself…even if that means reevaluating a few things along the way.