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Dear Retirement Coach;

I’m a 69-year old, happily married man who retired from a very busy career in the healthcare information technology sector about 2.5 years ago. I was unprepared as to how to fill my time after full time work and it’s “getting to me” now ;)

Even though my wife and I were blessed with our first grandson four months ago and participate fully in his life, I’ve reached the point where I’ve decided that I’d like get back to some type of paying work that will help me engage with others, get my brain firing and earn a few dollars to help out on our strained retirement budget. I do not, however, wish to step back into the very busy and stressful digital health implementation work which requires extensive overtime and a steady stream of headaches.

I am wondering if you could point me in the direction to help me find job opportunities for people in my situation? Are there are any job web sites that cater to folks in our age bracket?

Best regards

Looking For More in Retirement

Dear Looking For More in Retirement;

Thank you for reaching out and sharing your story. Congratulations on becoming a grandfather!

First, I want to acknowledge that it’s completely natural to feel the need for more stimulation and purpose, especially after a rewarding career like yours. Retirement is an exciting time, but it can also bring uncertainty as you transition from a full professional life to a new phase.

As a certified retirement coach, I often hear from people in similar situations—enjoying the freedom of retirement but missing the engagement and challenges their careers offer. It’s common to want meaningful work that suits your lifestyle without the stress, long hours, and deadlines you may have had before. You’re not alone in seeking new ways to contribute and stay mentally engaged.

Reimagining Work in Retirement

One idea is to consider work that taps into your expertise while giving you control over your schedule. With your background in healthcare IT, part-time or freelance consulting might be an ideal fit. Many organizations value the skills and experience of seasoned professionals and look for experts to help on a project or advisory basis. This could allow you to stay connected to your field and gain intellectual stimulation without the full-time commitment.

Several platforms can help you find part-time or project-based work tailored for professionals in or nearing retirement. FlexJobs and Work At Home Vintage Experts (WAHVE) are excellent options. WAHVE, in particular, connects older professionals with remote roles in fields like insurance and HR, and while it’s U.S.-based, many roles are available to Canadians. These options can allow you to maintain flexibility while staying connected to your field.

Closer to home, NextWork is a Canadian platform that matches experienced professionals with part-time and project-based roles, helping you leverage your years of experience without committing to full-time hours. Workhoppers is another option, offering freelance and contract work for those seeking flexibility and engagement in their fields.

Expanding Your Horizons

While healthcare IT might feel like a natural path, retirement also provides an opportunity to explore other fulfilling options. Consider how you could channel your passions, hobbies, or interests into meaningful work.

This could mean shifting toward teaching or volunteering. CharityVillage is a Canadian resource that lists part-time and volunteer positions in the nonprofit sector. These roles often offer flexible hours and can align with causes you care about, enabling you to make a difference while maintaining a work-life balance. If giving back resonates with you, Encore.org might be a valuable resource. This organization helps retirees transition into second careers that emphasize purpose and social impact.

Many retirees find these roles mentally stimulating and deeply fulfilling as they enter this new phase of life.

Aligning Work with Personal Interests

Retirement is also an opportunity to reflect on your personal passions. Consider hobbies or activities you’ve always loved but didn’t have the time to pursue fully. Now you can explore whether a passion could become a part-time role, a side business, or even a new career.

Turning a personal interest into something more can be unexpectedly rewarding. Whether it’s teaching a course, writing, blogging, or exploring artistic pursuits, these activities can bring joy and satisfaction. Often, our most meaningful work stems from our passions rather than our professions.

Striking the Right Balance

As you explore these opportunities, it’s important to consider what balance looks like for you now. One of the joys of retirement is the freedom to structure your time. Maybe it’s a few days of work each week or flexible hours that allow you to enjoy time with your grandson while engaging in meaningful work.

Finding the right balance between your newfound freedom and a sense of purpose is key. Take your time to decide what this balance means for you—there’s no need to rush, and there’s no single “right” way to approach it. You’ve built a successful career; now is the time to create a fulfilling, joyful life on your own terms

Final Thoughts

The goal in this new chapter isn’t to replicate the stress of your working years but to discover ways to stay engaged, contribute, and feel energized. You’ve earned the freedom to explore what this next phase looks like for you. Whether you choose part-time consulting, volunteering, or pursuing a personal interest, the possibilities are endless.

As you move forward, remember that retirement is about choice. You decide how to spend your time and what brings you joy and purpose. With your experience and skills, you are perfectly positioned to make this phase of life both fulfilling and rewarding.

Warm regards,

Toni

Certified Retirement Coach

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Susan Williams is the visionary founder of Booming Encore. With over 28 years of experience in corporate senior leadership and executive roles, she realized there was a significant gap in resources for those seeking a purposeful and healthy later life. Driven by her passion to make a difference, she decided that if she couldn't find it, she would create it and launched Booming Encore in 2013.

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Founder, Booming Encore

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Mary Eileen Williams, M.A., NCCC, is a job search expert, author, blogger, speaker and radio host. As a Nationally Board Certified Career Counselor with a Master's Degree in Career Development, she has over twenty years’ experience working as a career strategist for jobseekers and career changers. Her book, Land the Job You Love: 10 Surefire Strategies for Jobseekers Over 50 provides mature applicants with the critical information they need to successfully navigate today’s competitive job market. Eileen is an active contributor to the Huffington Post and also makes frequent appearances on both radio and TV and has been interviewed for Market Watch, Money Magazine, Kiplinger and several other national and international publications. Eileen is the host/founder of the popular boomer blog and radio show called Feisty Side of Fifty.

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Antoinette Petrillo is a former financial executive with over 25 years of experience leading teams. Upon retiring, she noticed a lack of support for professionals transitioning to retirement. Motivated by her passion for coaching and helping others lead confidently, Toni founded her own practice focusing on assisting professionals in navigating this significant life transition. You can reach Toni through her website, Retire with Intention.

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