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Path to dream job rarely a straight line

DEAR J.T. & DALE: I’m looking for a career change, from sales management to training and development. I’m now in banking, but my passion is traveling, and I would love to land a training position in the travel industry. That is my dream job. Any advice on how to start the process? – Darlene

J.T.: Start by seeking out anyone who has successfully transitioned from sales management to training. Those are the people who will be able to suggest the best way to network and to present yourself as you pursue your ideal job. They even might be able to open some doors for you.

DALE: Let me turn J.T.’s suggestion into a specific assignment: Find five people who are currently in your dream job, and speak to them about how they got there. You can use social media and networking to find the people, then email them and ask to speak with them, explaining that you are doing a research project assigned by two career columnists. We will expect you to report back. However, there’s more to the assignment: I also want you to get those five dream jobbers to describe how they spend their workdays. That’s because I’ve seen so many people spend years getting their “dream job” only to discover that it’s nothing like they’d envisioned, whereupon they feel cheated and doubly lost.

J.T.: That assignment will help in another way, as well. There is an expectation in job searching today that you be very clear in who you are and what your strengths are as they apply to the role. Only by truly understanding the job can you begin to develop a personal brand to sell to the new industry.

DALE: Meanwhile, you should be open to the possibility that a single jump from your current position to your dream job is not feasible. That’s likely, and that’s OK. What you’ll do instead is evolve toward the new career – for instance, move into sales management with a travel company, or into training with a banking institution. Your goal is to evolve from one career into another without starting over. The shortest distance between two careers rarely is a straight line.

DEAR J.T. & DALE: I have not been employed since graduation from medical school in December 2008. At that time, I was dealing with a very odd legal situation, and I also began experiencing strange immune problems. I’m doing fine now, though my doctor never did nail down a diagnosis. I realize that this employment gap makes me an unattractive job candidate. How do I get employers to look past my résumé and give me a shot? – Erin

J.T.: How do you get employers to look past your résumé? Don’t show it to them. Hear me out …

You will continue to get shot down if your résumé is their first impression of you. Sending a document that shows a large employment gap is all they need to write you off. Now, imagine meeting the same people at an event. Picture yourself chatting with them about the industry and having meaningful conversations about the work they do. Then, when they say, “What do you do?” imagine saying you are looking for work in the field. Don’t you think they’d be interested in learning more about you? The answer is yes, because their first impression of you will be of a smart, engaging professional, not someone who hasn’t worked since medical school.

DALE: I know what you’re thinking, Erin, and yes, even if you become a star at networking, eventually they will find out about your years of non-employment and wonder. Normally, I urge job searchers not to talk about medical problems, because it scares away most employers. However, in your case, your doctor’s inability to “pin down a diagnosis” probably is a blessing. You can single out a medical explanation that won’t raise concerns about your future health, and as you do, the gap disappears as an issue.

J.T.: Yes – tell your story in an upbeat way, showing them what you’ve learned from your life experience and how it’s made you resolute and eager, and you’ll be an attractive job candidate.

Jeanine “J.T.” Tanner O’Donnell is a professional development specialist and the founder of the consulting firm jtodonnell. Dale Dauten resolves employment and other business disputes as a mediator with Please visit them at, where you can send questions via email, or write to them in care of King Features Syndicate, 300 W. 57th St., 15th Floor, New York, NY 10019.