Ep 118: Are you feeling stuck in your career but not ready to retire — and definitely not ready to start from scratch? In this episode of The Retirement Success in Maine Podcast, Ben and Curtis sit down with career strategist Mike Dwyer, founder of Emplana Career, to reveal how professionals in their 50s, 60s, and beyond can pivot into their next chapter without losing all the progress they’ve already built.

Mike brings decades of experience from the private and public sectors and he shares how to outsmart today’s job-market challenges, beat the bots and AI that screen résumés, and use his proven five-day Emplana Career Framework to uncover new opportunities fast. From networking that actually works, to building a personal “career board,” to breaking into leadership roles or mission-driven organizations later in life, Mike gives listeners a playbook for creating meaningful, energizing work in the second half of life.

If you’ve ever wondered, “What’s next for me?”, this episode delivers the clarity, confidence, and inspiration to take your next step — without starting over.

Chapters:

Intro & Guest Background – Setting the stage and meeting Mike Dwyer of Emplana Career. [00:01–02:50]

Why Career Pivots Feel Hard – Mike’s journey, the résumé story, and why professionals feel stuck. [02:50–09:05]

Today’s Job Market Realities – AI, bots, applications disappearing, and how to fight back. [09:05–14:47]

Networking & Connection – Getting in the right rooms, networking for introverts, and building real relationships. [14:47–24:59]

The Emplana Career Framework – Mike’s 5-day workbook and how to explore roles without starting over. [19:16–28:32]

Leadership, Culture & Mentorship – Moving into management, evaluating culture, and finding helpful mentors. [28:32–45:18]

Energy from Innovation Ecosystems – How startups and mission-driven orgs unlock opportunities later in life. [49:51–53:10]

Retirement Success – Mike’s vision for easing into retirement with curiosity and purpose. [53:10–54:23]

Ep 117: In this episode of The Retirement Success in Maine Podcast, Ben and Curtis explore how the principles of improv can help retirees strengthen relationships and find new ways to connect. Their guest, Chip Brewer, has performed and taught improv for more than 20 years, working with Fortune 100 executives, educators, and students, as well as authoring his debut thriller novel.

Chip shares how core improv lessons like “yes, and,” active listening, and making others look good can bridge generational gaps, spark joy in everyday family interactions, and turn awkward moments into opportunities for deeper trust. From navigating conversations with teenagers, to building shared stories with grandkids, to keeping family gatherings fun and inclusive, this episode offers retirees a playful yet practical toolkit for enhancing connection and meaning in retirement.

Chapters:

Meet Chip Brewer, improv performer, teacher, and author. [00:01–02:44]

From Amsterdam stages to teaching Fortune 100 companies. [03:06–07:19]

“Yes, and,” active listening, and making others look good. [07:47–13:12]

Using improv to bridge gaps with kids and grandkids. [13:12–27:25]

Why embracing flaws leads to deeper trust. [36:05–39:48]

Simple improv games retirees can try at home. [44:23–48:25]

Chip’s personal vision for a fulfilling retirement. [49:12–50:43]

Ep 116: In this episode of The Retirement Success in Maine Podcast, Ben and Curtis welcome Jenna Biehn, Senior Sales Director at Dirigo Pines, to dive into the challenges and opportunities shaping the future of senior living. Jenna shares her path into the industry and the powerful lessons she’s learned helping families make decisions about retirement living. From the growing shortage of units and caregivers to the risks of waiting until a crisis strikes, she explains why early planning and open family conversations are essential to preserving independence and choice.

Jenna offers a candid look at the innovations and advocacy needed to prepare for the baby boomer wave, while sharing her own vision for retirement success. This episode delivers both practical guidance and a broader view of where senior living is headed in the years ahead.

Chapters:

Jenna’s transition into senior living and what makes the work meaningful [03:07–04:32]

The lack of planning and why families often make decisions in crisis [04:45–05:59]

The looming supply-demand gap in senior living and workforce shortages [09:18–12:44]

How lifestyle expectations are reshaping communities (socialization, enrichment, fitness) [22:21–26:26]

Why planning early preserves choice and independence [27:17–32:10]

Innovative models and advocacy needed to meet future demand [34:35–45:38]

Jenna’s personal vision of retirement success [51:23–54:27]