What Happens When We’re Not Done Working?
age/proof Digest: February 10, 2026
The only weekly digest for forward-thinking people curious about the cultural and demographic shift reshaping the future of aging.
Written by a 40-something living inside the world’s largest retirement community. Here’s my round up of actionable insights this week to help us rethink what older age can be.
The Experience Premium Employers Keep Ignoring
A recent ResumeBuilder.com survey found that 1 in 4 hiring managers view applicants over 50 as a poor investment. Many cite salary expectations or concerns about adaptability. These views ignore real data.
Why it matters: Older workers bring deep expertise, lower turnover, and the ability to mentor others. Still, hiring systems filter them out before they get a chance to contribute. These are not isolated opinions. They shape team composition, leadership pipelines, and organizational knowledge transfer.
Real-world signal: Some managers in the survey said older workers are “too set in their ways” or ask for “too much money.”
Stacie Haller, career advisor at ResumeBuilder, said, “These hiring practices will ultimately hurt businesses that are already struggling to find qualified workers.”
Yes, but: Legal protections exist, but age-based bias is often implicit and unmeasured. It shows up in how job descriptions are written, how résumés are screened, and which candidates are considered a “culture fit.”
Hidden insight: Adding “age” to DEI frameworks isn’t just a gesture. It’s a move toward building teams that reflect the full working lifespan.
Takeaway: Experience doesn’t speak for itself. In today’s hiring systems, it has to be reframed and reintroduced.
Source: Inc.
The Cognitive Load Crisis
More people want to stay in the workforce longer (or have to keep working), but the cognitive environment hasn’t kept up. A recent Wall Street Journal piece documents how professionals in their 50s and beyond are adapting to memory strain using personal hacks — sticky notes, lists, routines — because workplace systems don’t offer support.
Why it matters: Memory challenges are not just clinical. They emerge gradually, especially in high-pressure roles that demand constant switching and digital multitasking. Without shared tools or norms for managing this, people are left to struggle privately.
Real-world signal: One woman described quietly adjusting her work habits to stay on track as her recall faltered.
Joanna Hellmuth, neurologist at UCSF, told The Wall Street Journal, “It is often people who are higher-functioning or have demanding jobs who notice these symptoms earlier.”
Yes, but: Disclosure is risky. Many fear that if they mention cognitive strain, they’ll be seen as unfit or obsolete.
Hidden insight: Workplaces aren’t ready for cognitive aging because they’re not even ready for cognitive load. Designing better environments now could benefit every generation.
Takeaway: You can’t outwork memory issues with more lists. Long careers need better cognitive infrastructure.
Source: Wall Street Journal
Designing for a Life That Doesn’t “End” at 65
Shawn Engel and his wife sold their home, moved into an RV, and started working remotely while traveling the country. Their decision wasn’t about retirement. It was about designing a life with more control over time and place.
Why it matters: Later life is being reorganized. For many, traditional retirement — stop working, stay put — no longer fits. Portable work and housing models create new ways to combine income, mobility, and purpose.
Real-world signal: The Engels adjusted their travel routes to match seasons and job needs.
“I don’t think we’ll ever own a house again,” Shawn told Business Insider.
Yes, but: This lifestyle depends on remote job access, health, and digital infrastructure. It’s not viable for everyone. Policy, zoning, and benefits systems haven’t adapted.
Hidden insight: Retirement isn’t being delayed. It’s being redesigned. The structure of later life is shifting from exit to experimentation.
Takeaway: The next chapter doesn’t begin at 65. For some, that’s when the map gets redrawn.
Source: Business Insider
Gen X Women Are Rewriting the Midlife Mirror
A Gen X woman posted a simple question online: “If you’re in your 50s, show us what you look like.” Thousands responded with selfies. Many said it was the first time they’d seen women their age reflected honestly, without being filtered through anti-aging ads or fear-based messaging.
Why it matters: Midlife visibility remains limited. Women in their 50s and 60s are underrepresented in media, marketing, and leadership. At the same time, they have growing cultural and financial influence. Visibility changes what feels possible.
Real-world signal: The original post said, “I’m tired of being erased.”
Mia Freedman, co-founder of Mamamia, said in Mediaweek, “No one’s talking to us. No one’s selling to us.”
Yes, but: Even in moments of empowerment, many women still feel pressure to look younger. The tension between visibility and expectation continues.
Hidden insight: Representation isn’t just about faces on screens. It’s about rewriting beliefs about middle age and who gets to define it.
Takeaway: The midlife audience isn’t waiting for permission. They’re already showing up.
A $10 Trillion Succession Nobody’s Ready For
Thousands of small businesses owned by older adults are nearing a decision point: transition or close. More than $10 trillion in business assets could change hands in the next decade, according to NerdWallet. Many owners haven’t prepared for that moment.
Why it matters: These businesses support jobs, supply chains, and neighborhood economies. When succession plans don’t exist, communities lose more than revenue. Handing off a company takes time, legal guidance, and interested buyers. Most owners haven’t lined any of that up.
Real-world signal: Fewer than 30% of small businesses have formal exit strategies.
Ruth King, a small business advisor, told NerdWallet, “Most owners don’t plan to exit. They just… stop.”
Yes, but: High interest rates make financing difficult. Younger entrepreneurs often lack the capital or mentorship to navigate a handoff. Some businesses don’t have clean records, which further complicates a sale.
Hidden insight: Local economies don’t need more startups. They need more successful transitions. Supporting buyers with capital, coaching, and infrastructure could preserve jobs and create a new generation of community-based owners.
Takeaway: The business you want to run might already exist. It may be closer to closing than you think.
Source: Daily Gazette / NerdWallet
Until next time,
Rethink Aging With Us
This is for you and you’re in the right place:
If you’re in your 30s, 40s, 50s, or beyond and not ready to fade out.
If you’re a builder, strategist, or decision-maker trying to understand what aging really means for your product, team, city, or community.
If you’re tired of “decline narratives” about age and are ready for something more honest, more useful, and more human.
Join other curious and forward-thinking people who are reconsidering what older age can be — and how to live it with intention.
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I am so so happy that I've always worked for myself (I'm 62 so that's a LOT of years) because I am NOT ready to retire and probably never will. I love my work. My dad is 87 and he still works. He's a lexicographer and writes every day, he has a blog he posts on daily, manages his own Twitter account, Instagram and teaches languages in person. My grandfather did the same, and so did my father in law. I feel bad for those who depend on a system that does not support older people in the workforce.
Bryan, the concept of adding age to DEI at firms is an interesting concept. Many firms have abandoned such initiatives overall. My company has a "young professionals" group and they keep sending out invites to everyone for meetings.
Also designing for life that doesn't end at 65 resonated strongly with me as that's what I'm planning for down the line. I highly value my flexible life even around a day job now and am unlikely to put down permanent roots anywhere. I haven't before why now? :)