Retirement isn’t looking the way previous generations expected it to, and millions of boomers are supplementing fixed incomes with part-time work that fits around health limitations, family obligations, and the genuine desire to stay engaged. The jobs they’re choosing reveal a lot about what this generation values—flexibility, independence, and work that draws on decades of accumulated expertise rather than physical labor. Some are working out of financial necessity, others for social connection or purpose, but most are redefining what retirement actually looks like in practice.
1. Tax Preparation Specialists
Boomers with backgrounds in finance, accounting, or business administration are finding seasonal tax preparation work that pays well without year-round commitment. Companies like H&R Block and Jackson Hewitt hire experienced preparers each season, and the work runs roughly January through April—leaving the rest of the year completely free. The knowledge required draws heavily on experience that boomers have spent decades accumulating, making the learning curve minimal for those with relevant backgrounds.
The pay runs $18-$35 per hour, depending on complexity and certification level, and experienced preparers who develop client relationships often earn at the higher end. Many boomers in this role describe it as the ideal arrangement—mentally stimulating, socially engaging, financially meaningful, and completely contained to one season. The IRS also offers volunteer tax preparation programs that attract boomers who want the engagement without the employment formality.
2. School Substitute Teaching
Chronic substitute teacher shortages across the country have created consistent demand for reliable, experienced adults willing to step into classrooms on flexible schedules. Boomers bring classroom presence, life experience, and patience that school administrators actively value over younger candidates who treat substituting as a temporary inconvenience. Many states have relaxed substitute certification requirements specifically to address shortages, making entry easier than it’s been in decades.
Pay ranges from $100-$200 per day, though this is variable based on district and location, with long-term assignments paying more. The flexibility is genuinely exceptional—most substitute systems allow teachers to accept or decline assignments the morning they’re offered, creating true schedule control. Boomers who substitute regularly describe unexpected emotional rewards from working with young people, along with the practical benefit of school holidays automatically providing built-in time off.
3. Tour Guide and Museum Docent
Historical sites, museums, botanical gardens, and cultural institutions have discovered that boomer volunteers and paid guides bring genuine depth of knowledge that younger guides struggle to replicate. A retired teacher explaining Revolutionary War history at a historical site, or a former scientist guiding visitors through a natural history museum, delivers an authenticity that institutions specifically seek out. Many positions begin as volunteer roles that transition into paid part-time work as guides demonstrate their value.
Paid docent and guide positions run $15-$25 hourly and typically involve weekend or seasonal scheduling that works well for retirement lifestyles. The social engagement is a primary draw—guides interact with diverse groups of people daily in environments built around topics they’re genuinely passionate about. Boomers in these roles consistently report high job satisfaction driven by the combination of sharing expertise, social interaction, and working in spaces they’d visit anyway.
4. Bookkeeper for Small Businesses
Small businesses desperately need reliable bookkeeping but rarely generate enough volume to justify a full-time hire. Boomers with financial backgrounds are stepping into fractional bookkeeping arrangements—working 10-20 hours monthly for multiple small business clients simultaneously. The work is largely remote, the hours are flexible, and the pay reflects the genuine value of financial expertise rather than entry-level wages.
Rates run $25-$60 per hour, varying based on complexity and local market rates, making this one of the better-compensated part-time options available to financially experienced boomers. QuickBooks certification, which takes only a few weeks to obtain, significantly expands the client pool available. Many boomers in this arrangement describe the satisfaction of being genuinely useful to small business owners who lack financial expertise while maintaining complete control over their own schedules.
5. Airbnb and Short-Term Rental Management
Boomers who own property—or whose adult children or neighbors own property—are finding consistent part-time income managing short-term rentals. The role involves coordinating cleaners, communicating with guests, managing listings, and handling minor maintenance issues—tasks that suit organized, detail-oriented people with flexible daytime schedules. Property management companies also hire part-time coordinators specifically for boomer-aged candidates who are reliably available during business hours.
Income varies significantly based on property volume and management arrangements, but managing two to four properties typically generates $1,000-$2,500 monthly. The work is genuinely irregular rather than scheduled, which suits retirees who want income without fixed weekly commitments. Many boomers fell into this role by managing their own rental property and discovered they could monetize the same skills for other property owners.
6. Funeral Home Support Staff
Funeral homes consistently seek part-time support staff for roles that don’t require mortuary licenses—driving, administrative support, event coordination, and family liaison work. The demographic reality of an aging population means funeral homes in most markets have a steady workflow that requires reliable, emotionally mature staff. Boomers bring exactly the temperament and life experience that make this work manageable rather than overwhelming.
Pay runs $15-$22 hourly for support roles, and the work is genuinely meaningful in ways that resonate with many older adults. Boomers who have personally navigated the deaths of parents, spouses, or friends bring an empathy that families notice and appreciate. The work isn’t for everyone, but those who do it consistently describe a sense of purpose that comes from supporting families through one of life’s most difficult transitions.
7. Golf Course and Country Club Staff
Golf courses and country clubs actively prefer hiring retirees for starter, marshal, pro shop, and beverage cart roles because reliability and golf knowledge matter more than youth. A boomer who has played golf for 40 years working as a starter or marshal, brings authentic credibility that younger staff can’t replicate. The environment is appealing, the physical demands are minimal, and many positions include playing privileges that make the compensation effectively higher than the hourly rate suggests.
Pay runs $14-$20 hourly plus tips in some roles, and the course benefits—free or discounted rounds, range access, merchandise discounts—hold genuine value for golfers. The scheduling typically involves early morning starts with afternoon finishes, a pattern that suits early-rising retirees far better than younger workers. Boomers in these roles describe the combination of outdoor time, social engagement, and golf access as making the position feel less like work than almost anything else they could do for comparable pay.
8. Real Estate Transaction Coordinator
Real estate agents need substantial administrative support handling contracts, deadlines, disclosures, and communication—but don’t always have enough volume to justify a full-time assistant. Retired administrative professionals, paralegals, and business managers are entering transaction coordination as part-time contractors, working with multiple agents simultaneously from home. The role requires organization, attention to detail, and comfort with document management—skills that boomers with office careers have in abundance.
Rates run $300-$600 per transaction, and a coordinator managing four to six transactions monthly earns meaningful supplemental income without leaving home. The work is deadline-driven rather than schedule-driven, allowing flexibility around personal commitments. Real estate agents who find reliable transaction coordinators tend to retain them loyally, creating stable ongoing income rather than constant client acquisition.
9. Driver for Medical Transportation Services
Non-emergency medical transportation—driving elderly or disabled patients to dialysis, chemotherapy, specialist appointments, and therapies—has significant workforce shortages that boomer drivers are filling. The work requires patience, reliability, and comfort navigating medical environments, qualities that many boomers possess naturally and that younger workers in the gig economy often don’t prioritize. Companies like Veyo and MTM specifically recruit older drivers for their reliability and empathy.
Pay runs $16-$24 hourly, depending on the company and region, with flexible scheduling that allows drivers to choose their hours. Many boomers choose this work specifically because it feels purposeful—they’re providing transportation that genuinely affects patients’ access to necessary care. The passengers are often older adults themselves, and the generational connection between drivers and passengers creates interactions that boomers in these roles describe as among the most meaningful work they’ve ever done.
10. Library Associate
Public libraries have become one of the most popular landing spots for retired teachers, researchers, administrators, and academics seeking part-time community engagement. The environment is intellectually stimulating, the physical demands are minimal, and the work involves genuine service to community members across all ages. Libraries consistently struggle to staff positions adequately with younger workers who find the pay and pace unappealing but are perfect for retirees who value environment over compensation.
Pay runs $14-$20 hourly for associate-level positions, with scheduling flexibility that most libraries accommodate readily. Benefits in some municipal library systems extend part-time to include health coverage, which holds significant value for early retirees bridging to Medicare. Boomers in library roles describe the satisfaction of working in spaces they’ve always loved, among books and ideas, with a mission—community access to information—that resonates with their values.
11. Handyperson and Home Repair
Boomers who spent decades maintaining their own homes have discovered that basic repair skills command real market rates in communities where contractors are expensive, overbooked, or unwilling to take small jobs. Hanging doors, fixing leaky faucets, assembling furniture, painting rooms, and handling the dozens of small repairs that homeowners need done represent a consistent demand that a reliable, reasonably priced handyperson can fill. The work is entirely self-directed—boomers set their own schedules, choose their clients, and establish their own rates.
Rates run $40-$80 hourly in most markets, and referral-based practices build quickly among satisfied clients who value reliability over speed. The physical demands require honest self-assessment, as this work suits some boomers and genuinely doesn’t suit others, depending on health and mobility. Those who find the physical work manageable describe the satisfaction of solving tangible problems and seeing immediate results as deeply rewarding after careers spent in abstract or administrative work.
12. Corporate Trainer and Workshop Facilitator
Companies increasingly recognize that in-house training on compliance, management skills, communication, and professional development is more effective when delivered by experienced practitioners than by younger trainers reciting frameworks they haven’t lived. Retired managers, executives, HR professionals, and industry specialists are finding consistent contract training work with companies that value their decades of real-world experience. The work is project-based rather than ongoing, creating natural gaps between engagements that suit retirement lifestyles.
Day rates for experienced corporate trainers run $500-$2,000 depending on expertise and reputation, making even occasional engagements financially meaningful. Platforms like Clarity.fm and direct LinkedIn outreach have made connecting with corporate clients more accessible than it was a decade ago. Boomers in this space describe the work as uniquely satisfying—they’re sharing what they spent careers learning with people who are starting where they once were.
13. Online Tutor and Test Prep Coach
The demand for experienced academic tutors has grown alongside rising educational stakes, and boomers with teaching backgrounds or deep subject expertise are finding steady online tutoring work through platforms like Wyzant, Tutor.com, and direct client referrals. Retired teachers, professors, and professionals with strong academic backgrounds are particularly well-positioned for SAT, ACT, and AP exam preparation, where the content knowledge and teaching patience of an experienced adult matters significantly. The entirely remote format requires only a reliable internet connection and basic video conferencing comfort.
Rates run $30-$80 hourly depending on subject and demand, with test prep specialists commanding the higher end. Scheduling is completely self-directed, with sessions booked around the tutor’s availability rather than fixed shifts. Many boomers in this space maintain a roster of six to ten regular students, generating consistent monthly income from work that reinforces their own intellectual engagement with subjects they spent careers mastering.
14. Event Staffing and Hospitality Support
Catering companies, event venues, conference centers, and hotels consistently need reliable part-time staff for events that happen on irregular schedules—exactly the kind of unpredictable work that retirees can accommodate where younger workers cannot. Boomers bring professionalism, customer service experience, and a work ethic that event managers specifically seek out for high-visibility corporate and social events. The gig-based nature of event work means periods of intense activity alternate with quiet stretches that feel like natural extensions of retirement life.
Pay runs $18-$28 hourly for most event roles, with gratuity-eligible positions earning more. Physical requirements vary by role—working a registration desk differs significantly from catering server work—and most experienced event staffing companies match workers to roles that suit their capabilities. Boomers who enjoy social environments, can present professionally, and don’t need income to be perfectly predictable describe event staffing as one of the most enjoyable ways they’ve found to stay active and engaged.
15. Pet Care and Dog Walking
Pet care has emerged as one of the most popular part-time choices for boomer retirees, combining regular outdoor exercise, animal companionship, and genuine community connection into paid work. Apps like Rover and Wag connect pet sitters and dog walkers with clients, and boomers with established neighborhood reputations often build practices through direct referrals rather than platforms. The work accommodates any schedule—daily walks, overnight sitting, or drop-in visits—and scales up or down based on how much income and activity the retiree wants.
Rates run $20-$35 per walk and $50-$100 per night for sitting, with reliable sitters building client bases that generate $800-$2,000 monthly from genuinely enjoyable work. The health benefits of regular dog walking are meaningful for boomers whose mobility and activity levels benefit from daily structured movement. Many boomers describe pet care work as among the least stressful income they’ve ever earned—clients are appreciative, dogs are uncomplicated, and the combination of fresh air, movement, and animal interaction supports exactly the active retirement lifestyle they were hoping for.
This article is for informational purposes only and should not be construed as financial advice. Consult a financial professional before making investment or other financial decisions. The author and publisher make no warranties of any kind.
