Once upon a time, when you reached 65 or so, your colleagues threw a party for you, you ate a slice of store-bought cake, and then you retired and never worked another day.
When the average life expectancy was 65, that might have made sense. But if you live until 95, do you really want to sit around twiddling your thumbs for 30 years? Consider too that it costs more money to live longer. It’s a lot easier to afford a 10-year retirement than a 30-year retirement.
Then there’s the troubling trend of older workers being pushed out of their jobs before they’re ready to retire. Just because you intend to work at your current job until reaching “retirement age,” that doesn’t mean your employer shares that vision.
As you take a fresh look at your retirement and career plans, here are a few ideas to rethink retirement as you know it.
Why You Should Consider a “Rolling Retirement”
To begin with, baby boomers are woefully underprepared for retirement. A 2018 study from the Stanford Center on Longevity found that nearly a third of baby boomers have nothing saved in a retirement account. Nor are they making up for lost time — only 40% are presently contributing to employer-sponsored retirement plans.
Even among boomers with retirement savings, the median savings for those born between 1954 and 1959 was only $209,246. Following a 4% withdrawal rate, that only generates $8,369.84 per year in income — roughly $697 per month.
Earning a salary is a good reason to work longer in life. But it’s not the only reason. With health insurance premiums skyrocketing, it’s impossible to overstate the value of employer-sponsored health care plans. In fact, many people work part-time jobs specifically for the health benefits.
Also, remember that the later you start taking Social Security benefits, the more money you receive. Working for longer — even at a lower-paying job — can allow you to postpone taking benefits for a few crucial years.
Working also provides less-tangible benefits, such as a feeling of purpose, structure, intellectual stimulation, and social interaction. Without a job, many retirees spend their days watching TV alone. That’s hardly a reason to get out of bed in the morning.
For all of these reasons, Americans are generally working later in their lives. Even among senior citizens 85 and over, employment is at a record high, The Washington Post reports. But that doesn’t mean you have to keep grinding away at your high-stress job.
Instead of just flipping the switch on your working life when you turn 65, consider a post-retirement career — a fun, low-stress job that leaves you energized and excited rather than exhausted at the end of your workday.
Post-Retirement Jobs to Ditch the Stress
For many 25-year-olds, a high-octane, high-paying career sounds like just the ticket. But caffeine-fueled 12-hour workdays have a way of catching up with you.
It’s why so many people suffer from workplace burnout and turn to whatever they can find to ease the stress. While some opt for positive lifestyle changes such as slow living, others turn to alcohol, drugs, affairs, and other self-destructive coping mechanisms.
By the time you start getting letters from AARP, you’ll likely be ready to leave the high-intensity work to youngsters who don’t know any better. Here are 18 post-retirement jobs to keep the income tap running — without the stress.
1. Negotiate a Pullback With Your Current Employer
Who says you need to change careers entirely? One option is to negotiate a new arrangement with your employer. That could mean switching to part-time work hours, telecommuting to work from home (or from your beach house), or simply reducing your responsibilities.
Throw out the rulebook and decide what you really want in your job. After all, you’re already familiar with it, so you’re in a good position to pick and choose the parts you like and the parts you’d rather delegate to someone else.
After decades of constantly striving for more responsibility and more pay, pulling back feels alien for most of us. Start with these tips to negotiate your benefits and salary, and be prepared to take a lower salary if you do reduce your responsibilities.
2. Become a Consultant
You know your industry inside and out by now, along with many of the movers and shakers in it. One way to capitalize on your expertise and network is to sell your services as a consultant. You get to charge what you like, work for who you like, and work when you like.
Don’t quit your job cold turkey and launch a consulting firm. Instead, consider starting your consulting business on the side of your full-time job to test the waters, sign your first few clients, and see how you like it. You may decide it’s not for you. Or you may decide cashing in on your expertise and writing your own paycheck is the best move you ever made.
3. Become a Personal Coach or Mentor
Younger adults need the knowledge and wisdom you’ve accrued over the last few decades. Give them a helping hand and pay forward the help you’ve received over the years.
You can do this on a volunteer basis and give away your time, or you can charge for it and earn some extra money. Once you’re confident in your abilities and client base, you can opt to quit your day job and set your own hours.
If you’re interested in becoming a career coach, consider getting your Certified Professional Career Coach (CPCC) certification. Alternatively, you could work more broadly as a personal coach. Start your exploration into the field at the International Coach Federation.
4. Become a Sports Coach
Sick of the business world and want to get as far away as possible? You could go in the opposite direction and become a coach in the original sense: for a sports team.
The pay isn’t fantastic at the amateur sports level. But you get to work outside, shaping young people’s values and skills and getting exercise into the bargain. You might even have experience as a parent coach and know the drill (pun intended) already.
Start with this guide from Leisure Jobs.
5. Write
I worked for many years managing an online business, earning six figures and constantly dealing with the stress of working for a temperamental founder-owner. Now I work as a freelance writer.
Sure, the pay is lower, and the benefits are nonexistent. But I also don’t get 10pm calls from my boss, I set my own hours, and I get to spend most of the year traveling internationally.
If you’re interested in becoming a freelancer, start with this guide to finding freelance gigs and earning more money.
6. Drive
Driving is one of the most popular side gigs in America today. You could drive for Uber or Lyft, drive a truck, deliver for companies like DoorDash or Instacart, or deliver parcels for UPS or the postal service.
This is one job that’s at risk of extinction over the next 15 years as self-driving cars gain popularity and legal standing. But that’s the thing about a post-retirement job: You probably won’t be doing it in 15 years, anyway.
7. Pour Wine at a Local Winery or Wine Bar
This is my fantasy post-retirement job. It’s a quiet, easygoing gig where you get to talk to people about wine all day. What’s not to like?
You don’t have to be a sommelier or wine connoisseur, although it won’t hurt. You just need a passion for wine and the willingness to work for a small paycheck.
As a perk of the job, you normally get steep discounts on the wine sold at the establishment. It’s a far cry from matching 401(k) contributions, but it’s a fun benefit nonetheless.
8. Work for a Nonprofit
Nonprofit organizations tend not to pay well, but working for them can be incredibly rewarding.
Start getting more involved with your favorite local charities and nonprofits. Volunteer at their events. Get to know the staff, managers, and other volunteers. Offer to sit on their board. Then ask how you can work even more closely with them.
Tell them about your career history, your skill set, your network, and explain that you’re looking to change careers to find more meaningful — and less stressful — work.
The worst they can say is, “We can’t bring on any additional personnel right now, but we’ll let you know if we hear of anything or a position opens up.” Or they could say, “We’re interested; tell us more.”
9. Work as a Hotel Concierge
As a concierge, it’s your job to know the local area’s restaurants, tours, and other tourist attractions. You make recommendations and reservations for guests and then get to bask in the glow of their gratitude as they describe how delicious their steak dinner was or how much fun they had on their tour.
You probably know your city well already, and if you don’t, it’s a good excuse to get to know it better.
Don’t expect a high paycheck, but you can look forward to other perks, such as free or deeply discounted stays at the hotel’s partners, free meals at the restaurants you recommend, and potentially strong employee benefits if you work for a large corporate hotel chain.
10. Work as Resort Staff
You know those ski bums who work at the resort and spend most of their free time skiing or otherwise relaxing and having fun? It doesn’t sound like such a bad life, as long as you’ve already set aside a nest egg and don’t need a high savings rate.
And you’re not limited to ski resorts. Beach resorts, spa retreats, wine country getaways — you name it, and you could live a leisurely lifestyle working there as part- or full-time resort staff.
You don’t necessarily need to work a low-skill job alongside 20-somethings. You could work as a manager, either on the hotel side or with a restaurant, bar, diving center, spa, or any other nested business within the resort.
Working at a resort, particularly for a corporate chain, often comes with strong benefits, such as free hotel stays at partner resorts.
Check out some of the jobs available on CoolWorks, although the higher-end positions often appear on more traditional job listing websites.
11. Start Your Own Bed-and-Breakfast
You probably don’t have enough money to open a massive five-star resort. But that doesn’t mean you can’t open your own hospitality business.
Many older people have fun hosting a bed-and-breakfast as a retirement gig to bring in some extra income. They get to meet people from all over the world, talk about the local sights and attractions, and cook great meals for guests.
If it means a little extra laundry and housekeeping, so what? If you hate doing it that much, you can hire a maid part-time.
12. Tutor
My mother tutors as a side gig and earns excellent money, at least on an hourly basis. After she retires from her full-time job next year, she plans to pick up more tutoring work, giving her a flexible 15 to 20 hours of work each week.
Tutoring doesn’t come with any benefits, but you can set your own schedule, choose your own clients, and set your own hourly rate.
It helps that my mother has worked in education her entire adult life, so she has a strong network and built-in client base. But word of mouth is an effective marketing strategy for tutors as you build a client base.
If you prefer, you can tutor online. Just don’t expect to earn as much if you leave your marketing to an online service.
Like many other ideas on this list, tutoring is best started as a side gig, then expanded after leaving your old career behind.
13. Be a Substitute or Part-Time Teacher
Substitute teaching doesn’t pay particularly well, and you’re at the mercy of when schools need you. But it’s one way to keep your foot in the door of education. And, of course, you have the flexibility to turn down any assignment requests you don’t want.
Bear in mind that substitute teaching is not always a day-by-day gig. Often, schools need long-term subs, particularly to cover teachers out on maternity leave. Substitute teaching can even pave the path for a second career as a teacher, which you might find you enjoy, even if you never considered it.
Finally, one growing trend among schools is to allow part-time teachers to share classroom responsibilities. While this originated as a way to accommodate teachers who wanted to work part-time while caring for infants and toddlers, it remains an option for older teachers as well. Most commonly, it involves two teachers rotating two- and three-day weeks — not a bad post-retirement schedule.
If you’d like to see more of the world, you consider teaching English as a second language overseas. Some job opportunities even let you travel the world for free. My wife is an international educator, and we enjoy free housing from her employer.
14. Become a Real Estate Agent
Real estate agents enjoy autonomy, flexibility, and a job largely spent out of the office. If they’re good at what they do, they can also pull in a strong living.
Earning a real estate license isn’t too difficult. You take a brief course, take a state and local laws exam, and then get a position working under a broker. The challenge lies not in the licensing, but in learning the actual skills needed to succeed as a real estate agent.
You see, the course and tests don’t cover practical skills. They cover laws, such as Fair Housing regulations. So as a freshly minted real estate agent, your challenge will be developing those practical skills, from marketing and networking to negotiating and charm.
If you’ve ever sold your house without a real estate agent, you already have a little experience. The rest you can learn by working with a high-quality brokerage that emphasizes training.
15. Invest in Real Estate
If you don’t want to sell real estate, you can buy it. As a real estate investor, you’re effectively self-employed. It’s your show, and you get to call the shots. Whether those shots create profits or losses is also up to you.
You can choose among many strategies for investing in real estate, from flipping houses to rental investing to commercial investing. You can even invest in real estate indirectly without ever holding a title through companies like Fundrise, Streitwise, or Groundfloor.
Investment properties come with a slew of tax benefits to sweeten the deal. And rental properties make for great retirement income. They generate ongoing income with no need to sell the underlying asset, rents rise with inflation, and you can accurately predict the average monthly cash flow.
Rental properties make up a large portion of my own retirement planning and help balance out the equities in my asset allocation. If you’re interested in purchasing Turnkey properties that will allow you to start earning an income quickly, check out Roofstock.
16. Rent Out Your Car
I live overseas, and I come home to the U.S. twice a year for a month at a time. The first time I searched a rental car website for an entire month’s car rental, my jaw dropped at the four-digit price quote for the cheapest “economy” car.
So I’ve taken to renting cars from private individuals through services like Turo, Getaround, and Hyrecar. On my last visit home, I chatted up my rental car’s owner for a few minutes as we made the key exchange. He was retired and owned a fleet of 16 Toyota Priuses he rented short-term on Turo. They were all older, in the 7- to 12-year age range. He cleaned up on the rental fees, affording him an earlier and more comfortable retirement than he’d originally planned.
Think of it as Airbnb for cars. You own an asset, you rent out short-term use of it, and you laugh all the way to the bank.
Granted, the business model still requires some labor. You have to clean and maintain the vehicle, just as you would a short-term rental property. It’s also far harder to automate the rental process for a car. You often need to drop the car off at the local airport and pick it up again.
Plus, cars depreciate in value, while real estate tends to appreciate. But rental services price that into the margins, which tend to be high.
17. Offer Handyman Services
Are you handy around the house? Do you know how to patch drywall, paint a room, or fix a leaking pipe?
Your services are in demand.
Landlords and homeowners alike need handymen and -women who can perform basic repairs at a reasonable price. You don’t need a contractor’s license in most cases. As a landlord myself, I don’t want to spend an arm and a leg hiring a licensed contractor to tighten a leaky pipe or replace an appliance.
Therein lies the niche opportunity: affordable basic repairs. You don’t need many clients. If you meet a few larger landlords or real estate investors at the local real estate investing association, they can often throw you more business than you can handle in a post-retirement gig.
Best of all, this is a business with almost no expenses. You get paid for your labor, with no startup expenses beyond your tools, which you probably own already. That makes it a low-risk, high-reward, flexible business allowing you to earn as much or as little as you like.
18. Start a Business
Many of the ideas above are self-employment, solopreneur-style small businesses. But your choices are endless and range far beyond the bounds of this list.
In fact, a 2020 study of American small-business owners by Guidant Financial and LendingClub found a shocking 57% of respondents were baby boomers born between 1946 and 1964. If the majority of small-business owners are older adults, then you can forget about the excuse “I’m too old to start a business.”
From service businesses like accounting to food-and-beverage businesses like coffee shops, your only constraints are your imagination and expertise — and money, of course.
Get very clear with your financial advisor about how much you can afford to invest in a business and leave the rest of your nest egg in place. Service businesses with no inventory — particularly virtual businesses with no overhead — often require little or no money to launch. After all, it takes almost no money to work a side gig as a bookkeeper or tax preparer, assuming you already have the skills from your full-time career.
Final Word
Most of the jobs and gigs above don’t pay particularly well. But many also come with benefits, from health insurance and 401(k) plans to flexibility and free travel opportunities.
So forget the outdated cake-and-gold-watch retirement model. Instead, start brainstorming ideas for a second career — one that shuns high stress and long hours and instead delivers passion, flexibility, and fun.
You chased higher paychecks and greater responsibilities in your last career. This time around, just enjoy the ride.
