The "Un" Generation

This week’s Finance Friday is about the new retirement reality: the calendar says one thing, the market says another, and your bank account has its own opinion. Governments are nudging people to work longer. “Unretirement” gigs are quietly becoming normal. Insurance companies are rushing out new longevity annuities. Real-estate platforms want you to be a fraction-owner instead of a landlord. Weight-loss drugs are forcing planners to rethink health spending. And finally, a wave of money apps is actually being built for people who remember life before the internet. Bigger picture: your next 30 years of money may look very different from your parents’—and that’s not all bad.

✅ Today’s Money Moves (Pick One)

Once upon a time, retirement had a clear finish line: 65, gold watch, cake in the break room, golf brochure. That script is falling apart. Surveys in both the U.S. and Canada show a growing share of people 55+ now expect to work past 65—some out of necessity, others because they actually like the idea of a “soft landing” instead of a hard stop. One Canadian report even framed it as a “tough financial decision” as older workers weigh higher costs against earlier retirement dreams.

A few big forces collided at once. Inflation made everyday life more expensive. Markets bounced around just enough to make people nervous about drawing down savings. And lifespans stretched, turning a 30-year retirement from rare to reasonable. When you do the math, many people realize: if your retirement could last as long as your career, the money has to last longer too.

The upside: “working longer” doesn’t have to mean grinding at the same job forever. Many older adults are negotiating 3-day workweeks, consulting gigs, or seasonal roles that keep income flowing without draining energy. Earning even a modest amount—say $15,000–$25,000 a year—can dramatically reduce how much you need to withdraw from investments. If you’re curious, a good step is to plug your numbers into a free calculator like Fidelity’s Retirement Score or Vanguard’s tools, then sanity-check your plan with a human.

And if you like reading with a highlighter, a book like Working After Retirement can be a good way to turn that “ugh, I may have to work longer” feeling into “okay, here’s how to do this on my terms.”

Vanguard just projected public markets may return only 5% annually over the next decade. In a 2024 report, Goldman Sachs forecasted the S&P 500 may return just 3% annually for the same time frame—stats that put current valuations in the 7th percentile of history.

Translation? The gains we’ve seen over the past few years might not continue for quite a while.

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Closely related to working past 65 is a phenomenon researchers now call “unretirement”: leaving full-time work, taking a breather, then returning in a new, often more flexible role. It’s part financial, part psychological. People miss structure, community, and a sense of being useful—but they don’t miss long commutes and office politics. The result: a growing wave of 60-, 70-, and even 80-somethings quietly signing on for part-time projects or second careers.

It rarely looks like going back to the exact same job. Instead, think:

The financial power of unretirement is sneaky. Even $1,000–$2,000 a month can delay Social Security or CPP withdrawals, reduce portfolio stress, and give you permission to spend on things you actually enjoy. If you’re curious, sites like FlexJobs, Upwork, or AARP’s work hub can be good starting points. And yes, there are even books like Second-Act Careers if you’d rather curl up with a plan before diving in.

Insurance companies have noticed what you already know: people are living longer, and they’re scared of running out of money. Enter longevity annuities—also called deferred income annuities—which start paying later in life (say, at 75 or 80) and keep paying as long as you’re alive. They’re not new, but they’re getting a fresh wave of attention as planners look for ways to turn “what if I live a long time?” from a fear into a feature.

You take a slice of your savings today—maybe 10–20%—and buy a contract that promises a guaranteed monthly income starting in the future. The trade-off: that money is locked up, but the payoff is that if you do live into your late 80s or 90s, you’re not solely depending on the market or your own spreadsheet.

Longevity annuities aren’t for everyone. They can be a fit if you: have decent savings but are terrified of outliving them, don’t have a generous traditional pension, and value simplicity over maximum flexibility. If you’re curious, resources like this deep dive or accessible primers from firms like Schwab can help you decide if this belongs in the “maybe” or “nope” pile. And yes, there are consumer-friendly guides like annuity guides on Amazon if you want a calmer explanation than anything a salesperson will give you.

If you love the idea of real estate but hate the idea of fixing toilets, the industry has a pitch for you: buy a tiny slice of a big building instead. A wave of platforms now lets everyday investors put a few thousand dollars into apartment complexes, warehouses, or medical offices—and then get a share of the rent and potential growth, without stepping on a ladder.

Real-estate investment trusts (REITs) have existed for decades. What’s new are “fractional” platforms and private funds designed for smaller minimums and more direct story-telling: “Here’s the building, here’s the city, here’s the plan.” Some target income-focused retirees explicitly, promising steady distributions and glossy investor dashboards.

Fees, liquidity, and risk. Unlike a simple REIT index fund, many fractional deals are harder to exit and depend heavily on management skill. Before clicking “invest,” it’s worth reading a plain-English guide like Real Estate Investing for Retirement and checking what percent of your total portfolio is already in property via your home. Real estate can be a powerful diversifier—but you don’t want your entire future riding on one market.

You’ve seen the headlines about Ozempic, Wegovy, and other GLP-1 drugs. Most coverage focuses on weight loss, drama in Hollywood, or shortages at pharmacies. But in retirement planning circles, these medications are raising a different question: how do you build a 20- or 30-year plan when one monthly prescription can cost as much as a car payment?

For some older adults, GLP-1s are covered because of diabetes or heart risk. For others, coverage is limited or non-existent. That leads to difficult tradeoffs: pay out-of-pocket now and trim spending elsewhere, or skip a drug your doctor thinks could help. Financial planners are starting to model multiple “health cost scenarios” instead of one neat line item.

If you’re on an expensive drug, it’s worth asking your doctor about alternatives, patient assistance programs, or coverage appeals. On the planning side, you can treat high-cost meds like a temporary project: “For the next 3–5 years, we’ll spend X more on health and Y less on other categories.” Budgeting tools like YNAB or Mint can help you visualize that tradeoff. And a simple health-focused notebook or medical expense logbook can keep the paper trail from getting overwhelming.

For years, financial apps seemed designed for 23-year-olds who love charts more than sleep. That’s starting to change. A new wave of tools is aimed directly at people 55+ who want clarity, large fonts, real humans to call, and fewer bells and whistles. Think: one screen that tells you what’s coming in, what’s going out, and what absolutely must not be missed.

Designers are finally listening. The best of these apps focus on:

Banks and credit unions now offer “senior accounts” with app experiences to match, and fintech startups are following. Before moving everything, you can test drive a tool with one account or card and see how it feels. And if you prefer paper, that’s fine too—apps can simply become a second pair of eyes. A solid old-school companion is something like a household budget planner you can keep in the kitchen drawer while your phone watches for anything weird behind the scenes.