How to Find Your Dream Job

An eight-step plan for rebooting your career and finding a job that you love.

Oct 1, 2014
Outside Magazine

Yes, you can mix work and adventure—if you play it right.    Photo: Hannah McCaughey

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In a job market transformed by turmoil and rebirth, there are suddenly all kinds of opportunities for adventurous souls. But if you're going to transcend the cubicle, you need to think big and dare to start over. Presenting our no-holds-barred guide to making the boldest move of your career.

1. Admit That You Have a Problem

Crabby at the end of the day? Dreading Sunday night? Pay attention. It could be a sign that it’s time for a switch. Of course, there’s a big difference between run-of-the-mill workplace malaise and a major problem. “Ask yourself if your frustration is due to the tasks you perform or to office politics and interpersonal stuff,” says David Blustein, a professor of counseling psychology and a career-development scholar at Boston College’s Lynch School of Education. If you’re tired of the minutiae, consider a small change—between companies within your industry. If you’re dreading the fundamentals, however, it’s probably time for bolder measures.

2. Choose a New Direction

A smart career switch begins with what Blustein describes as “a serious process of self-examination.” Recognize that certain personality types thrive in certain industries. Extroverts and risk takers often do well as entrepreneurs. Introverts should consider gigs requiring less self-promotion (see: biologist, engineer, project manager). The most important question? Ask yourself which part of your current job—or your favorite hobby—fulfills you most. Now: How can you monetize that skill? “You want to identify the place where your passion meets other people’s needs,” says economist Adam Davidson, cofounder of NPR’s Planet Money, who is writing a book on how to thrive in the 21st-century economy. “This doesn’t call for cold-hearted pragmatism, but it doesn’t call for self-indulgence, either. Call it pragmatic passion.”

Adam Fetcher, who worked on Barack Obama’s two presidential campaigns and for the Department of the Interior before changing gears to become Patagonia’s director of global PR and communications, cautions against jumping at the first new opportunity that comes your way. “Spend time thinking deeply about where you want to work, what type of organization will give you the kind of life you want to have,” he says. “If that’s outdoors, with family—whatever it is that makes you happy.”

In some cases, it’s possible to make a quick lateral pivot to a new industry where your skill set has value. If you’re a sales rep who’s tired of the corporate grind but interested in the environment, you could target a big NGO like the Nature Conservancy, which filled several jobs on its corporate partnership team last year. Similarly, if you’re charismatic, well connected, and a decent writer, you’re primed for a future in public relations, which is currently booming as companies spend less on advertising and more on image. With a bit of smart research and creative thinking, it’s even possible to parlay your leisure interests into a dream job. Say you love riding mountain bikes and drinking beer. That might not seem like a career, but careful investigation could lead you to New Belgium Brewery, based in Fort Collins, Colorado, which is hiring “beer rangers” to sell its brews in adventure hubs across the country.

  Photo: Hannah McCaughey

3. Get Real

New technologies have resulted in job-market upheaval, replacing unskilled positions with computers and international labor. The upshot: hard skills and expertise are as valuable as ever. “The old-fashioned stuff like experience is what really counts,” says Brian Lam, founder of product-review website the Wirecutter, which has hired eight editors and researchers in the past two years. “If you want to get into a new field, you need to buckle down for a few years and become really good at what you do.”

Start by researching the skills and experience required to land the kind of job you have in mind. One simple method is to study up on industry trends through trade sources like Outdoor Retailer (for gigs at gearmakers) and the Adventure Travel Trade Association (for travel gigs). “Seventy percent of our applicants say they’re avid climbers or outdoors people,” says Anson Fogel, co-owner of the Salt Lake City production company Camp Four Collective. “That’s nice, but it doesn’t matter. We’re looking for talented people who have a body of work.”

Sometimes the best route is to go back to school. In 2011, Kit Hickey was a successful investment banker in Boulder, Colorado, but she was a little disillusioned and had a vision for a line of business attire that used the performance technologies found in outdoor apparel. She enrolled in an entrepreneurial program at MIT and partnered with another student who was a gear designer to launch Ministry of Supply. She uses her banking experience, focusing on the company’s thriving business model, while her partner geeks out on materials and construction methods.

Alternatively, you might seek out entry-level positions that help you develop experience and connections. For example, if you have a passion for adventure filmmaking but not the résumé to get hired as a cameraman or producer, you might apply to GoPro, which is based in San Mateo, California, and has been hiring content producers to scour the Internet for footage created with its cameras in specific categories like music, hunting, and fishing.

If your financial situation won’t allow you to go back to school or take a low-paying post, look for opportunities at your current job to broaden your skills. “When friends think about applying for jobs they assume are out of reach,” says NPR’s Davidson, “I tell them to consider what skills they want to have that they don’t have now. Often it doesn’t take much.”

4. Hunt Intelligently

Knowing where to look is half the battle. One common pitfall of job seekers is to spend all their time trolling umbrella job sites like Craigslist and CareerBuilder. These days most companies list openings on their own websites and social-media channels. “We use LinkedIn, and our recruiting team has its own Facebook page,” says Patty Pearce, VP of human resources at VF Outdoor, which owns the North Face, JanSport, and SmartWool. Many industries also post jobs using Twitter hashtags (like #pubjobs, the catchall for opportunities in public radio).

Another efficient strategy is to focus on industry-specific career websites. Gear and apparel makers list positions on the Outdoor Industry Association site, the action-sports jobs board, and, the website of the Sporting Goods Business association. Environmental nonprofits and NGOs like Conservation International and the Nature Conservancy post on the websites of the Society for Conservation Biology and the Chronicle of Philanthropy.

5. Create Your Online Persona

“One of the first things we do when we get a résumé is look at that person’s LinkedIn profile and Facebook page,” says Steve Sullivan, former CEO of mountain lifestyle brand Cloudveil and founder of Jackson, Wyoming, apparel company Stio. “With those tools, you get to know the person—their contacts, how well connected they are, how mature they are. People should be cognizant of public profiles.”

Crafting a professional online presence requires more than just deleting and untagging party shots. (Though you should do that, too.) For starters create a LinkedIn page, and put some love into it. “Over the course of your working life, thousands more people are going to see your LinkedIn résumé than your real résumé,” says Sree Sreenivasan, a former professor of social media at the Columbia Journalism School who’s now chief digital officer for the Metropolitan Museum of Art. Spend extra time on the summary section—“It should be deep,” says Sreenivasan—and update everything, especially the recommendations, even when you’re not actively pursuing a new job. “Potential employers rely on the recommendations,” notes Sreenivasan. “Get them in a smart, judicious way from people who supervise your work when you don’t need it—like right after you’ve completed a good project.”

  Photo: Hannah McCaughey

You should also have a Twitter account and include links in your bio to your home page (or your current employer’s home page) and your LinkedIn account. Follow industry leaders you hope to network with. “Before you reach out to someone for an introduction, a referral, or a request for a connection, make sure you’re already following that person,” suggests Sreenivasan. Your own tweets should contain links to stories about the fields you want to work in and comments about them.

Finally, keep photos for your social-media accounts simple—“a close-up, professional head shot,” says Sreenivasan—unless you’re angling for a gig with a production company.

6. Don’t Toss Your CV

When we asked the executives at leading brands in the outdoor and adventure-sports industries how hiring has changed in the social-media age, they all gave the same answer: it mostly hasn’t. While creative applications help—several employers cited candidates who submitted online portfolios, videos, and even product prototypes—you still need a strong cover letter, résumé, and personal references. Keep them one page each. “Six-page résumés are ridiculous,” says Sullivan. Focus on the basics before doing anything else. “Don’t go hiring a website designer,” says Sreenivasan, “when you should be cleaning up your LinkedIn profile.”

7. Stretch Your Network—in Person

The fact that it’s now so easy to connect with people digitally actually means that in-person meetings and personal referrals carry more weight than ever. “We filled 30 percent of our hires last year through referrals,” says Christina Gee, recruiting manager at Clif Bar in Emeryville, California. GoPro, meanwhile, makes 35 percent of its hires through referrals. Don’t have a personal connection to a company? Make one. “Find out who you need to know,” says Shawn Heinrichs, photographer, videographer, and founder of Blue Sphere Media. “Then work backward until you have one degree of separation with that person—someone who can get you a meeting.” For Heinrich, a former business executive, this meant sitting down with Peter Knights, founder of the nonprofit WildAid, one of the conservation groups Heinrichs now produces films for.

Megan Miller, founder of Bitty Foods, recommends cold calls. “I’m a huge advocate of taking people out to coffee,” she says. “They’re usually flattered when you say you want their advice. I’m the most digital person in the world. I have a huge LinkedIn network. But there’s no substitute for face time.”

One surefire way to gain access to personal interactions is by attending industry trade shows and other events where managers are on the lookout for new talent. “Actively recruiting at conferences is probably the best way to find the best people,” says M. Sanjayan, executive VP of Conservation International. Gear companies converge at the biannual Outdoor Retailer, while travel outfitters gather at the Adventure Travel World Summit. Conservation groups recruit at events like the Aspen Environmental Forum and the International Congress for Conservation Biology.

  Photo: Hannah McCaughey

But you don’t need to wait for the big summit. Whether you live in Austin or Anchorage, you can find gatherings of people with similar professional interests using forums like MeetUp and FindSpark. “Going to entrepreneurial and startup meetings really helped me,” says Ministry of Supply’s Kit Hickey, who went to every gathering she could after moving to Boston to attend business school. “I saw people making similar changes. It made me feel less alone.”

Finally, when networking, keep in mind that you’re working, not dating. “Don’t lay out all your woes and troubles,” says Sanjayan. “I can’t tell you how many people come to talk to me and say so much that I’m pretty sure I won’t be recommending them to anyone else. Remember: your goal is to get into the interview room.”

8. Seal the Deal

Once you secure an interview, prepare. Set up a Google news alert for the company, look into press coverage from the past five years, and reach out to people who have worked there and moved on. You want to go in knowing your stuff. “Not being prepared about a company’s history—that wouldn’t bode well here,” says Pearce of the North Face. Also, bring a bottle of water and some energy bars. Patagonia interviews last a full day. Potential GoPro media-team hires are brought in for a weeklong trial run.

After your interview, send a thank-you e-mail—fast. “I’d even recommend drafting a rough follow-up before the interview,” says Emily Miethner, founder of FindSpark. “Then quickly add in thoughts on specific things you discussed to personalize it.” Miethner also suggests creating another touchpoint outside e-mail. “This could be adding the person you interviewed with on LinkedIn—send a custom message—or retweeting a tweet from the company,” she says.

If you aren’t offered the job, focus on the fact that getting in the door was a huge step. Acquit yourself professionally and chances are you’ll get a second look down the line. “The first job I applied for out of grad school, I got an interview but didn’t land the job,” says Sanjayan. “The second job I applied for, with the Nature Conservancy, I didn’t even make the interview cut.” But he kept in touch with the organization and was eventually brought on as a lead scientist.

If you do get an offer, don’t take it right away: this is the time to negotiate things like more time off or the ability to work remotely. Once you’re hired, your leverage is gone.

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