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The Key to a Successful Career Shift: Asking for Help

Many people switching fields are loath to reach out to someone who already knows how to get the job done. Here's how to ask with confidence.

By Marc Miller

My colleague was in her 20s. I was old enough to be her father. But I had switched careers in midlife to be a math teacher in an inner city school, where I could tell that she knew what she was doing. I, on the other hand, was ready to jump out the window.

So I asked her for help. Begged might be a better word. If she would give me her lesson plans, I figured, I would follow her every move, like a little puppy dog — a 6-foot-4-inch puppy with hair loss and wrinkles — until I got the hang of teaching. Voila!

Advice From a Career-Design Coach

I’ve made seven career changes, currently work as a career-design coach for other boomers and just wrote Repurpose Your Career: A Practical Guide for Baby Boomers. My experience and research has shown me that asking for help is the biggest hurdle people in midlife face when shifting careers. But it’s also the essential first step.

(MORE: How to Start a New, More Meaningful Career)

We really struggle, however, before asking others for assistance. It’s hard to swallow your pride, forgo speeches to new, young co-workers that begin “I was doing such and such before you were born” and instead say, “I need help.”

Men Are Often the Most Reluctant

Asking for help changing careers is especially tough for men. (Kind of like asking for directions.) I know that’s a blanket generalization, but research backs me up.

Women tend to work cooperatively; men tend to compete for the alpha position. And requesting guidance is a definite concession of the alpha spot.
5 Strategies to Ask for Help Shifting Careers
But if you’re considering a career shift — whether you’re a man or a woman — and want to increase your chances of success, I suggest you adopt these five strategies to ask for help:

1. Craft a sharp elevator pitch. To get answers to your questions about entering a field, you need to be able to clearly state the type of work you want to do. A 30-second elevator pitch is the best way to get your message across. (Next Avenue’s work and volunteering blogger, Nancy Collamer, has tips on how to create one in her post, “The Perfect Elevator Pitch to Land a Job.”)

Once you’ve perfected your elevator pitch, share it not just with others who already have a job like the one you want, but with everyone you meet. You never know who’ll have the keys to unlock the door. Gratefully accept any advice or offers of introductions.

(MORE: 9 Lessons From an Accidental Entrepreneur)

2. Ask for AIR. When you seek out someone in your prospective next career, offer to buy him or her a cup of coffee or lunch. But don’t request an informational interview; that says you want a job and can scare people off. Instead, ask for AIR: advice, insights and recommendations.

Advice Tips on what it takes to break in and succeed.

Insights The kinds of things someone usually learns after years in the field: the skinny about its culture, politics, pitfalls and key players. You want to learn who is on top and why. Then you’ll have a better sense of how to make your own way.


Recommendations Find out who you should talk to next and ask, if appropriate, for an introduction. Request names of good books to read and classes to take, as well as industry groups that can help you start networking effectively.

3. Cultivate your tribe. A tribe is the group of your friends and relatives who are pulling for you. They’re the ones who’ll hold your hand through the career shift and support you when you’re discouraged.

Asking for help isn’t just about getting questions answered; sometimes, it’s about assisting you emotionally when things aren’t going well. Your tribe will be there for you when you make mistakes — and when you triumph.

Make a habit of connecting with members of your tribe individually, meeting for coffee or a walk. Share the latest steps of your journey. They’ll help you stay sane and likely draw inspiration from your story.

4. Admit your weaknesses to people who could assist you. One of the hardest parts about asking for help when changing careers is telling others what you don’t know.

Say you’ve been a curmudgeon about social media, proudly (if privately) never joining Facebook, Twitter or LinkedIn. Since social media can introduce you to people in your new field and help you stay up on its latest news, now’s the time to confess your ignorance to someone you know who’s an ace at social media and ask for an informal 101 course.
(MORE: Career Shift: Ignoring Naysayers to Become a Nurse)

5. Say thank you. Every time someone is useful in your career transition, show your appreciation and spread the word. If his introduction led to a job interview, tell him and express your gratitude. People like knowing they have helped.  
The Bottom Line

I’m firmly convinced that nobody makes a successful career change without the help of others.

You may start off feeling like a panhandler. But you’ll quickly see that, in addition to a free cup of coffee, your questions give people the chance to show off as experts. And that makes everyone feel good.

Just be sure to be as willing to give as good as you get. While you’re asking for help, someone might ask you to share insights. Do so with gusto. Karma works!

Marc Miller Marc Miller’s career journey has included 22 years at IBM; several tech startups; a painful stint as a high school teacher; raising funds for the Jewish Community Association of Austin, Texas; training employees in 35 countries and a near fatal bicycle accident that changed his perspective forever. Miller now works as a career design expert for boomers and is the author of the new book, Repurpose Your Career: A Practical Guide for Baby Boomers. Read More
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