Category Archives: Personal Development

When Your Dream Job Disappoints, How to Find Plan B

Especially for all of the young adults I know and love.
After years of planning, preparing and perhaps paying for an extra degree, you finally land your dream job—and discover you don’t like it.

It’s a surprisingly common dilemma. The idea of a “dream job” is drilled into job seekers these days. Increasingly, people expect to find jobs that provide not only a living but also stimulation, emotional fulfillment and a sense of purpose. The image of a career as a source of passion is promoted by career advisers, self-help books and even the glamorous characters in TV dramas. But fantasies about a job can blind job-seekers to workaday realities and to consideration of the best fit.

Dream vs. Reality
Name: Caroline Kelso Winegeart
Dream Job: Advertising executive
Reality: Working in the hip, creative office of a big ad agency wasn’t enough to compensate for the stress of having to manage budgets while fielding phone calls from media reps, all under intense time pressure.
Comeback: Focused on building her social-media skills and worked in the field at a smaller agency until leaving for a marketing business. Now runs her own branding and Web-design business,

Told she had creative talent, Caroline Kelso Winegeart targeted advertising in college, heading the advertising club at her university and landing an internship at a big New York ad agency. “This was going to be my foot in the door, to get this glamorous ad-executive job I thought I wanted,” she says.

Her first job after college in 2010, as an assistant media planner at McKinney in Durham, N.C., “felt like my dream job,” she says. She liked the people and was thrilled to join an agency with national brands and a hip, creative image.

But she hadn’t anticipated the complexity of managing a large budget for two accounts, while being bombarded by phone calls from media reps with ad space to sell. A heavier work load and more time pressure than she had expected left her feeling “stressed and so overwhelmed all the time.” She had been naïve, she says, to think that “the place I was working was more important than my actual role.”

Turning a dashed dream job into a win requires overcoming disappointment, looking hard at where you went wrong and making the most of the skills you have picked up. A good strategy is to ask yourself, “Where can I go from here, to avoid making a complete U-turn?” says Helene Lollis, president of Pathbuilders, an Atlanta leadership-development consultant. That may mean using your current job to develop skills and contacts that might serve as stepping stones to something else.

Ms. Winegeart liked using social media, so she made building skills in that area a focal point of her work. That helped her land a new job building a social-media department at a smaller agency. The skills she gained equipped her in 2011 to leave advertising and take a position for two years as operations manager for, a marketing business run by her boyfriend Jason Surfrapp. Ms. Winegeart, 25, has since started her own branding and Web-design business,

Unexpected failures can be beneficial if they jolt people into new ways of thinking, according to a 2011 study in the journal Social Psychology. People who stop and think deeply about what they might have done differently tend to be more creative about reaching goals in the future, the study says.

Some people enter a field for the wrong reasons. Others become enamored with the seeming glamour of a profession, only to find the workplace culture impossible. Sue Shellenbarger and guest Ashley Stahl discuss common missteps and turnaround strategies. Photo: Obi Onyekwere.
All the plans Ashley Stahl made through adolescence, college and grad school were to prepare for her fantasy career in national security, she says. She got a master’s degree in international relations, learned Arabic and networked intensively for six weeks in Washington, D.C., attending 90 different events. At age 23, she landed a job with a defense contractor to run a program for the Pentagon. “I was excited and anxious about this huge opportunity,” she says. “I was living my dream.”

The work, however—preparing senior officials for deployment to Afghanistan—had drawbacks that she hadn’t foreseen. She felt isolated in the male-dominated, intensely competitive culture of military bases and the Pentagon. The hours were so long that “my job took over my life,” she says. She also realized she had underestimated her aversion to violence. When her employer asked her to consider traveling to war-torn areas overseas, she quit after eight months on the job. “By that time, I’d seen too much raw footage of the worst-case scenarios in the world,” she says.

Change of Heart
Name: Ashley Stahl
Dream job: National-security expert
Reality: She felt her job was taking over her life and decided she didn’t want to work in the male-dominated culture of military bases or to travel to war-torn places overseas.
Comeback: Listening to feedback from friends, she learned her real strengths lay in helping people plan and achieve their career goals. She is now a speaker and career coach.
Working with a career coach, Ms. Stahl realized she had been ignoring feedback about her real skills from friends and acquaintances, who told her she was good at helping them open up, talk about their careers and learn to network, find jobs and win promotions. She worked briefly at two other jobs, in crisis-communication and political-risk consulting, Then Ms. Stahl, who is now 26, quit to work full-time as a Beverly Hills, Calif.- based speaker and career coach to teens and young adults.

How long should you stay in a dream job gone bad? Quick departures are more common in some industries, such as high-tech work, than in others. It can be fine for skilled employees who find a new job quickly to leave within a few weeks, says Kathryn Minshew, founder and chief executive of, a career-planning website.

But don’t flee unexpected challenges too fast. It is usually better to stay 12 to 18 months to show stability. Also, some people need time to recover emotionally after a career dream goes up in smoke, says Adele Scheele, Los Angeles, author of “Skills for Success.” She adds, “If Job A isn’t satisfying to you and that’s your dream job, you can’t just flee to Job B. You may carry your depression with you.”

It’s important to be aware of why you are drawn to certain jobs. A common mistake is to pick a career without weighing related factors, “such as culture, management style or the work-life arrangement,” says Pamela Slim, a Mesa, Ariz., author of “Body of Work,” a book about managing changing career paths. “You can be passionate about being a trial attorney without realizing you have to work 20 hours a day,” she says.

Some people target dream jobs for unconscious reasons. People who enter sports psychology training programs are sometimes former athletes who failed to achieve their goals. They may dream of basking in reflected glory, according to a study last year in the Journal of Applied Sport Psychology. This makes the work—listening to athletes’ problems and helping them figure out strategies to improve—harder, because the psychologists can’t keep a healthy distance from clients’ negative emotions and problems, says the six-month study of diaries and in-depth interviews with seven students.

Cheryl Heisler, president of Lawternatives, a career consulting service in Chicago for lawyers and professionals, recommends making a pro-and-con list of all the job characteristics that will affect your happiness. It may be important to you to have the latest job tools, or to avoid offices with a party culture, for example, she says. “Any jobs get held up against that pro-and-con list, and that keeps you honest,” she says. Talking with people who are already working in the job you want can uncover potential surprises or red flags.

Ms. Heisler advises recasting your broken dream as an asset in job interviews. Stress what you gained, such as new skills or insight into another industry, sending the message: “I got to learn something new. I’m a different person than I was before.”

Write to Sue Shellenbarger at
When Your Dream Job Disappoints, How to Find Plan B –