Insights from Real Professionals

Rethinking Work in the Second Half of Life

Over the past few weeks, I conducted interviews with ~30 professionals between the ages of 50-80, most of whom are considering the next step in their careers - whether transitioning out of traditional full-time roles, exploring new opportunities, or redefining their work on their own terms. Their experiences highlight ageism in hiring, the struggle to find meaningful roles, and the growing demand for flexible work options.

Key Trends from the Interviews

1. Ageism and Perception Gaps
A significant number of respondents (over half) reported encountering implicit and explicit age discrimination during their job searches. Many found that despite decades of experience, they were overlooked in favor of younger candidates or dismissed as "overqualified." Some described receiving fewer interview invitations after updating their resumes with later career roles, while others noted that recruiters often assumed they wouldn’t be adaptable to new technologies or workplace cultures.

2. Difficulty Finding the Right Opportunities
Traditional job platforms like LinkedIn and Indeed have not always been effective in connecting experienced professionals with the right roles. Roughly 40% of interviewees expressed frustration with traditional job platforms, citing automated rejections and a lack of roles that align with their experience. Many noted that while they still want to work in corporate settings, they are seeking more flexible arrangements - such as fractional, contract, or advisory roles - which are rarely highlighted or easy to find on traditional job boards. Instead, job listings tend to focus on either full-time mid-level positions or entry-level work, leaving experienced professionals with few options that truly match their skills and career goals.

3. The Emotional and Financial Toll of Job Loss Later in Life
Unexpected layoffs or career shifts can be particularly challenging for those over 50. About one-third of interviewees described the experience as disorienting, with one noting that losing a job later in life felt “more anxiety-inducing” than retirement itself. The financial uncertainty of finding new work - especially in industries that favor younger candidates - adds another layer of stress.

Redefining Career Paths: A Diverse Set of Goals

While some professionals are eager to pursue entrepreneurship (about one-third of respondents), the majority are still eager to continue their corporate careers in some capacity. The desire to continue working remains strong, with a majority of respondents seeking roles that allow them to contribute their expertise in established organizations. Many expressed interest in leadership, mentorship, and advisory roles within corporations that value their depth of experience.

One respondent, a former executive, is actively searching for leadership roles where they can drive business strategy. Another, a seasoned technology professional, hopes to transition into a flexible but impactful corporate position that allows them to mentor younger employees while still engaging in hands-on work. Others are taking a hybrid approach - testing entrepreneurial ventures while keeping the door open to returning to corporate roles.

Flexibility and Meaning Over Traditional Full-Time Work

The desire for flexible schedules was nearly universal among those interviewed. Many (over 80%) preferred project-based or part-time work, allowing them to balance personal interests, travel, or semi-retirement. One respondent outlined an ideal schedule of working intensively for part of the year while taking extended breaks. Another emphasized the importance of working “on my terms” while still contributing meaningfully to a corporate environment.

The Need for Better Platforms and Support

A major takeaway from these interviews is that job platforms and networking resources need to evolve to support the changing nature of work for older professionals.

• Recognition of Non-Traditional Career Paths: Whether through fractional roles, advisory positions, or structured mentorship programs, experienced professionals want to contribute in new ways - but traditional hiring models don’t always recognize or support these paths.

• Uncertainty in Career Fit: With the changing job market, about half of respondents were unclear on where their past experience would best fit into today’s workforce. After facing repeated rejections for roles they were overqualified for, many interviewees described feeling disoriented in the job search process, unsure of how to position their skills effectively.

• Stronger Professional Communities: Many interviewees emphasized the importance of networks for finding opportunities, yet some struggled to rebuild networks outside their previous industries.

• More Transparent Hiring Processes: Several respondents noted that job search platforms feel like “black boxes,” offering little feedback or clarity.

A Call for Smarter Solutions

The future of work must embrace the expertise of older professionals by offering smarter, more tailored job-matching systems. Businesses increasingly need experienced leadership, and yet hiring models lag behind. The future of work must adapt - valuing expertise, fostering cross-generational collaboration, and providing better pathways for seasoned professionals to contribute meaningfully. It’s time for platforms that go beyond keyword matching and recognize the broader value of experience, adaptability, and leadership.

That’s why we’re building Lamplighter—to bridge the gap between experience-rich professionals and companies that value their skills. Rather than forcing a binary choice between retirement and entrepreneurship, we’re creating a smarter way to match seasoned professionals with the meaningful, flexible work they seek.

---

If you're 50 or older and this resonates with you, I'd love to connect! Feel free to DM me or email me at taylor@joinlamplighter.com.