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Eyes on the Prize: Managing Late Career moves for Boomers

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Members of the Baby Boom generation have set cultural precedents for decades as they age through the population. Now that Boomers are at or near retirement age, their workplace situation and the kinds of jobs they hold are changing again. Younger Boomers are experiencing the pinnacle of their careers, while older Boomers explore ways to transition to less demanding jobs that will help sustain them mentally and financially in their later years. 

Many career Boomers are now at the peak of their professions, with expertise, authority and status earned over a lifetime in their field. For the last few decades, these workers have successfully relied on personal networks and impressive resumes to remain in place or to change jobs. However, as more and more of their Boomer peers retire, their professional networks are increasingly made up of Gen X and Millennial workers. When a Boomer in a senior position is laid off or leaves a job for personal reasons, it’s getting more challenging for them to get back into the workplace at the same level, especially in a difficult job market.  Some Boomers find themselves already retired, only to experience a change in their financial situation that leads them out of retirement to top off their reserves. Other factors create challenges to re-entry, too, such as new technology, workplace culture, physical limitations, supporting a familiar lifestyle, age discrimination, and the need to maintain a certain level of benefits.  

Job seeking requires you to be on your toes with a strong awareness of changing expectations and demands in the workplace. Here are few tips for Boomers who are trying to re-enter the job market, change positions, or come out of retirement: 

Leverage your best assets. 
Who’s got more experience than you? Leverage your experience subtly, best perhaps by highlighting the number of people across the industry that you personally know or have worked with. Name dropping of current contacts in high places is a much better play than spinning “back in the day” yarns that may educate your interviewer but will quickly date you out of his or her comfort zone. Make sure to offer interviewers a balance of specific skills they’ll hear about from younger workers, too, even if you realize that social media awareness is not nearly as important as having gone to college with the most important guy in their supply chain. 

Put Humble Pie on the menu.
Some of the skills you’ve always relied upon to impress peers and potential employers may now subtly work against you. The best recipe now includes confidence tempered with humility, somewhat like Don Draper eating crow in the last season of Mad Men. Put potential managers at ease and try to subtly let them know you won’t make them obsolete, or try to run the show. You’re not an up and comer. You’re impressive, so no need to try to impress anyone. You want to own it, but without any hint of entitlement. This is especially tricky when you may not know your interviewer until you see them. Be prepared for anything.  

Technology retraining. 
Technology changes so frequently that even if you consider yourself tech savvy, there’s no harm in putting yourself at the bleeding edge. You’ll compare more favorably to Millennial workers who live and breathe the newest gadgets and apps, plus you’ll feel more confident to slip in references to the latest productivity and in-house marketing tools when you interview.  

New management styles. 
Maybe you’ve managed thousands of people in your career. The truth is, the core skills required to work well with people don’t change that much, but the jargon and the structures that are used to organize those efforts tend to be trendy. An awareness of the ideas emerging from within business schools will not diminish your amazing people skills.  Decades of interpersonal rapport deserve an update in the way you describe your tried and true skill set. Plus, you could probably use a better understanding of how to manage the Millennials who have recently come to outnumber Boomers in the workplace, maybe for the very reason that you did raise one or two of those Millennials yourself. 

Work on gen-next relationships.  
Make a point of finding peers you identify with who are younger than you. Spend time working with them, listening to them, hanging out with them after work and thinking about how they differentiate themselves from your Boomer peers. Forge personal and professional bonds that reflect the best synergy between your respective attributes. You’ll be better able to spot the key personality traits and communications styles that become more and more important as younger workers move into positions of authority around you. Plus, you’ll increase the number of allies in your field who are less likely to retire to Belize 18 months hence.  

Plan for what’s next.
Strategize about your next job in a way that will provide a parachute. Without asking in the interview, do your research to find a situation that might be open to having you consult back to your employer with more flexibility in a few years, or that might offer a part time schedule when the time comes. Be thinking ahead to your retirement transition. Who knows. Maybe you’ll find the last job you’ll ever need.  

The whole package. 
Make sure the benefits offered satisfy all your immediate and future needs. If you don’t qualify for Medicare yet, either because you’re under 65 or you have not yet worked at least 10 years in a Medicare-qualifying job, then your benefits should definitely include something to cover you until you become eligible, and should contribute to your eligibility.  Also, ask about family leave, if you are caring for an elderly parent. 

Coasting to the finish. 
If you’re an older Boomer looking for modest part-time work, emphasize your work ethic, your flexibility and your willingness to take instruction from managers half your age. Make sure the job easily matches your physical capabilities.

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