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The 5 Big Mistakes Boomers Make When Switching Careers

What to avoid to make a transition more seamless

By Sam Meenasian

Many boomers want to change careers for a variety of reasons: to reduce stress; to learn something new; to follow their passion; to find a change of pace or to stay ahead financially. But it’s easy to make mistakes and overlook factors that are critical to changing careers effectively.

Career Switch
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So, when leaving the security of a steady job to transition to a new career, you’ll want to avoid the following five mistakes. That way, you’ll embark on your next voyage with grace and confidence.

Mistake No. 1: Not ‘Testing’ Your New Career First

You think you’ll love your new career path, but you won’t know for sure until you’ve immersed yourself in it. So, before interviewing for a new job in a new field, try to experience what it would be like.

You may need to move down on the totem pole, which can be challenging if you haven't set your expectations properly.

Start by figuring out what spare time you have to dedicate to your trial run. You may need to get creative if the job would be an office position and you currently have one. In that case, find lunch hour times or take half-days to shadow others in positions for which you might apply.

If possible, test the waters online. For example, if you want to move into marketing and already have some marketable skills — like design or writing — create an account on Upwork, the online platform for freelancers.

You could also apply for short-term gigs or projects that let you flex your skills, gain experience and better understand what you might be doing on a daily basis.

Mistake No. 2: Not Managing Expectations

Switching careers, especially after 50, can be a big change financially, mentally and emotionally. You may need to move down on the totem pole, which can be challenging if you haven’t set your expectations properly. Set realistic goals.

The key is to be prepared to learn. Some of the work skills you’ve acquired already, such as communications and organization, will be critical to your success in your new field. Find ways to excel with the capabilities you have, while gaining new ones.

Mistake No. 3: Not Knowing What Matters Most

When switching careers, it’s easy to take the first opportunity you find because you’re worried you won’t be qualified for anything else. That mindset can stick you in a position you don’t want.

So, before making a switch, figure out what matters most to you. Do you want full-time or part-time work, or does that not matter? Are you open to travel? Do you need consistent work hours or remote work opportunities? Know what you need, and make it clear to potential employers. That way, you’ll be more likely to be happy with your new path.

This kind of advance planning saves you from wasting time pursuing the wrong jobs and lets you focus on positions you’d most want.


One tip: Don’t blurt out your work requirements in a first job interview. Instead, focus on your skills and the job’s fit. Once you’re sure the job is one you want and the employer is interested in you, then you can start talking about your preferences for your working hours and location.

Mistake No. 4: Not Seeking Training First

It may be wise to acquire new skills before making a career switch. Otherwise, jumping in to a new field too quickly can set you back.

Instead of getting in over your head, setting yourself up for failure and stress, go slowly, carving out time for training on the side while you stay in your current position. This not only enhances your resumé but also provides you with valuable hands-on experience that will make you a better job candidate when you are ready to change careers.

Research the skills expected of candidates in the field you hope to enter. Then, seek training opportunities that will give you a leg up — and an inside look into the work required.

Search for online, self-paced courses that you can take at home. Also, consider in-person conferences, workshops and events that offer learning opportunities as well as networking.

Mistake No. 5: Not Having a Plan B

You’re enthused about your new career, but it’s important to do a reality check. A career change can be risky, and doing it without a backup plan can leave you with no paycheck or job. That’s why you need a Plan B if the new job doesn’t pan out, the interviews don’t go well or you decide your intended path is not right for you.

You don’t need another job lined up for Plan B, though. Just set yourself up for success if things fall through. Here are a few ways to do that:

  • Ensure your resumé and professional-facing social media networks are always current. Put photos from recent networking events on Instagram or add new certifications to your LinkedIn profile.
  • Build a strong network. Stay connected and be a resource to others. What goes around comes around, and you may need to ask one of your contacts for help.
  • Make a list of employers you’d like to work for, along with contacts you have at them. If your career switch doesn’t pan out, you’ll then be ready to start looking for other opportunities.
Sam Meenasian has used his leadership, marketing, sales and operations skills to build two successful companies over a nearly 25-year career. He co-founded USA Business Insurance and BISU Insurance, which have served thousands of small businesses. Meenasian has 10 years of prior experience in real estate and holds a bachelor’s degree in business. He shares his expertise through guest articles for such media as CNBC, Fox Business, AllBusiness, Business 2 Community, Small Business Bonfire, SmartBrief, Accounting Today and Insurance Journal. Read More
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