15 Surprising Second Careers That Boomers Can Get Into
Most of us have experience with jobs coming to an end. Fewer of us have seen the sunset on an entire career. If you have seen a career come and go, try to remain optimistic and remember that, as Semisonic said, “every new beginning comes from some other beginning’s end.”
A second career can be the new beginning of a lucrative, fulfilling passion that puts your prior career to shame. Even if career number two doesn’t quite reach these lofty heights, if you shoot for the moon, you’re less likely to land on a McDonald’s cashier job.
1. Writing

The young people are barely literate. Seriously. In 2009, the American Institute for Research wrote that “nearly half of young adults ages 16-18 had Below Basic or Basic literacy.” That statistic is downright shocking, and it has come to a head.
Young people can’t spell, don’t particularly care to read (even if they can), and writing at even a seventh-grade level is out of the question for most. As time passes and artificial intelligence (hopefully) continues to make errors and fall short of human writing, older adults may find steady earnings in the writing field.
2. Chauffeurs, Ridesharing Drivers, and Delivery Drivers

Conventional wisdom says that once someone crosses a certain age barrier, their ability and desire to drive begins to decline. However, if you’re thinking solely of making money, being in the business of driving may not be a bad idea.
Of course, there are issues with Uber drivers making less money, so perhaps you’d be best served steering toward the town car clientele. Demographically, young people are in no rush to get their licenses. This means that third-party drivers will continue to be relevant until self-driving vehicles take over, which should be a good way away.
3. Social Media Influencing

Before you roll your eyes and close the laptop, bear with me. Have you ever heard the term “oversaturation?”
TikTok, Instagram, and other social platforms are oversaturated with young people. Plus, as AARP notes, there are many successful proofs of concept for social media influencers over 50. These seasoned voices have various verticals, from cooking to telling dirty jokes. Simply sharing your wisdom and tales from the good ole’ days could prove more lucrative than you suspect.
4. Teacher

What good is wisdom if it dies with you? Considering that many states face teacher shortages, why not embrace the benefits of being a public employee?
Sure, you practically need to wear Kevlar in some school districts, and you better be more steely than Dan if you’re going to survive the TikTok generation’s heckling. But, if you can get through to the youth, you might find yourself in a profoundly rewarding second career.
5. Pet Sitter

Pet sitting is one of those pinch-yourself careers. As you sit on a client’s couch binging Netflix with a mut cozied up against your thigh, occasionally getting up to walk that dog, you must ask: Am I really getting paid for this?
The question is whether your hourly rate and volume of work will be worth the effort. If you have enough money and only need a part-time career, consider listing your services on an app like Rover or contacting your pet-owning friends and family network.
6. Local Politician

If you haven’t noticed, pretty much anyone can run for office in the United States. Running at the local level may be most practical if you have an itch to serve.
Be warned: Developers, business owners, and other powerful lobbies may have sway in who gets elected. If you meet residency and registration requirements, your next step is to decide whether you want to be in the pocket of powerfulpolitical players or take the idealist route instead.
7. Crossing Guard

You’re not going to get rich being a crossing guard. In Florida, crossing guards’ pay averages around $11 an hour, and the hours are typically limited to the morning and afternoon. That said, a gig that allows you to be outdoors and interact with fresh faces isn’t necessarily bad.
You might also consider other school-centric jobs like lunch lady and hall monitor. These jobs are not especially taxing and may come with benefits provided to many public employees.
8. General Assistant

People need help. Businesspeople are perpetually busy, and wealthy parents need help arranging their schedules and kids’ lives. If you know your way around a calendar, can schedule appointments, and are generally willing to serve as a helping hand, you may be well-suited to be someone’s assistant.
You might have a specific title, such as administrative assistant, personal assistant, or office administrator. You’ll need to do your homework on the duties associated with such specific roles.
9. Fundraising

Many non-profit organizations would not survive without fundraisers’ hard work. Many Boomers derive immense joy from attending cocktail parties, so why not get paid to attend those cocktail parties while tastefully asking others for money?
You may be a particularly effective fundraiser if you can work for an organization you’re passionate about. Theaters, mentorship programs, and animal-focused charities are just a few ideas for jogging your mind.
10. Greeter/Usher

Are you the friendly type? Are you not easily overwhelmed by large crowds? Being a greeter, usher, or combination of the two may be a logical second career.
Hospitals, Walmarts, chain restaurants, and event venues are among the types of businesses that often use greeters, ushers, or both. These gigs typically range in annual pay from around $25,000 to $45,000, depending on where you work and the organization that hires you. A relatively low-effort job, greeter may be especially suited to those with firm financial footing (like those seeking a second career).
11. Museum Guide

If you are willing to learn new subject matter and have solid people skills, consider seeking work at one or more museums in your area. These working environments tend to be relatively relaxed, intellectually stimulating and well-air-conditioned.
If you try to get a job at a prominent or art-focused museum, you might find yourself in a fight with candidates who recently graduated with a Master’s of Fine Arts—and they can be vicious. However, there may be many other venues (history and engineering are common subject matter for museums) looking for help with clean criminal records and wanting to educate the clientele.
12. Real Estate Agent

Real estate agents are in the trust business. You can probably believe that homeowners and buyers, who are often of older age, don’t necessarily trust the Instagram-obsessed “hustle culture”-embracing the new wave of real estate agents. A few gray hairs may be exactly what the older generation of buyers and sellers are looking for in an agent.
Getting a real estate license is a relatively low-risk venture, and overhead costs are also low in this career. Why not give dealmaking a shot?
13. Secretary

The cliche of the smoking-hot secretary is overplayed. A smiling, comforting face at the front desk is just as welcome a sight as an attractive one. Plus, competence should win out when a boss is choosing a front-desk attendant, and you may have decades of relevant experience that translates well into a secretary position.
Can you answer phones? Show arriving customers’ attention? Master a complex calendar and multi-task with the best of them. Good help is hard to find, and open secretarial positions may be more abundant than you realize.
14. Financial Advisor

Becoming a Certified Financial Advisor requires education and licensing, so you’ll need to invest to be a CFA. If you’re willing to pay the cost, though, plenty of people are looking for a trustworthy money manager.
Many customers are hesitant to take financial advice from someone younger than they are. This understandable wariness may work in your favor if you become a CFA as a second career.
15. Babysitter

Experience matters when talking about children’s lives. While the stereotypical nanny is a young woman, many parents would prefer a more seasoned, emotionally steady individual to care for (and, ideally, impart wisdom to) their kids.
Whether or not you’ve raised kids or have grandkids, babysitting can be a viable career, though it may not offer full-time hours. Few career paths can be more rewarding than caring for malleable young people, so consider this high-impact means of earning income.
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