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024: Preparing for the Ultimate Career Move - Retirement

Posted By Digital Enterprise Society, Wednesday, October 30, 2019
Updated: Monday, October 28, 2019

024: Preparing for the Ultimate Career Move - Retirement


On this episode, Thom and Craig welcome Donna Kastner, founder of Retirepreneur to take a look at the steps professionals in their 50s and 60s can take to wind down a full-throttle career intentionally and productively.  Donna shares a snapshot of what today’s workforce and retirement really look like and how those realities impact people who aren’t quite ready to fully retire. She shares several tips to help safeguard careers against ageism, keep up with technology, and avoid becoming obsolete in their industry.  This conversation is not just for those nearing retirement age as Donna also shares advice for Millennials and Gen-Zers to capitalize on their interactions with the older generation. Today’s podcast is for anyone that has ever thought about what they want their final chapters of their professional career to look like. 


On today’s podcast, you will learn:

How today’s longevity economy affects retirement

  • Does it make sense to complete your life’s work in your 60s if you plan on living into your 90s? 

  • The options that are available when you’re ready to dial back from your full-time career but are not quite ready for retirement. 

  • The health benefits associated with staying engaged in a field you love after retirement.

The factors that affect professionals in their 50’s and 60’s

  • Ageism is still a reality for too many companies.

  • Economic downturns factor into advanced employee layoffs, so more experienced professionals need to be prepared for forced early retirement.

  • Full-time positions are often not offered to older professionals despite their qualifications. 

Preparatory career steps that older professionals need to take

  • Identify your strengths and take time to further develop them.

  • Start thinking about this transition in your 50s so you are prepared for it in your 60s. 

  • Embrace the current technology that employers use to get your next job or side hustle, including LinkedIn and Zoom. 

  • Leverage your experience and wisdom in ways that will make you valuable to any company.

  • Recognize that your weaknesses will never be your strengths, and still work to shore up those weaknesses. 

Advice for optimizing interactions between Millenials, Boomers, and Gen-Z-ers

  • Be cautious of stereotyping — don’t make assumptions about the capabilities of any individual based on their generation. 

  • Recognize and prioritize the importance and value of face-to-face interactions.

  • Cross-generational networking is a critically important factor to enhancing your career. 

  • Take risks, learn from them and keep trying no matter what stage of your career you’re currently in. 


Donna Kastner is the founder of Retirepreneur, a collaborative community for professionals in their 50s and 60s.  Having spent a good portion of her career as an event experience design consultant, Donna’s now building a dynamic collaboration community for executives age 55+ who are striving to make a smooth segue from a full-time job to part-time consulting gig. With, Donna's championing a movement to help others design flexible and fulfilling encore careers. Through articles, videos, podcasts and workshops, Donna’s ushering in new conversations about blending work and retirement. You can visit her website here or find her on Facebook and Twitter.

Tags:  Career  Mentorship  Podcast  Retirement 

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