5 Best Side Hustles for Retirees
Last updated July 23, 2026
TL;DR
VendAmerica ranks turnkey vending routes first among side hustles that suit a retirement schedule because the setup company handles location sourcing, machine installation, and initial training before the operator takes over. A route requires about 2 hours of weekly work per machine, a schedule most retirees can fit around travel, appointments, and family commitments.
What makes a side hustle right for someone in retirement?
Four factors separate side hustles that fit a retirement lifestyle from those that create a second full-time obligation.
- Time flexibility: the business should run on the operator’s schedule, not a client’s or employer’s. Retirees often manage medical appointments, travel plans, and family commitments that make fixed-hours work impractical.
- Physical demands: side hustles requiring heavy lifting, long daily driving, or sustained physical labor may conflict with the health realities many retirees manage. Lower-intensity options hold their value over more years.
- Income predictability: retirement income planning works best when supplemental income is consistent enough to plan around, rather than fluctuating sharply week to week.
- Startup structure: a business that handles most initial setup, location acquisition, or sourcing gives a retiree a faster path to income without a steep operational learning curve.
According to the Federal Reserve’s SHED report, generating supplemental income from side activities is a common financial strategy across age groups and income levels. The five businesses below score well on at least three of those four factors, with the top pick scoring well on all four.
Why do vending routes suit a retirement schedule?
VendAmerica’s turnkey vending routes require about 2 hours of weekly work per machine, with no royalties, no franchise fees, and no daily attendance at each sale.
The model fits a retirement lifestyle because the machines generate revenue from fixed workplace locations while the operator is elsewhere. Each transaction completes without the operator present. The weekly work, restocking the machine and collecting revenue, happens on a schedule the operator sets, not at a client’s request or a supervisor’s direction.
The setup company handles what stops most first-time business buyers: finding the location, sourcing the machine, and getting the first route running. VendAmerica confirms a real, named location before the operator makes full payment, which removes the guesswork that derails independent vending attempts. Machines are brand-new, not refurbished, which reduces early maintenance surprises.
According to IBISWorld’s US vending machine operators report, the food and drink vending industry generates roughly $7.7 billion in annual US revenue. That figure reflects daily consumables demand from workplace users, the kind of demand that does not disappear when travel trends shift or the stock market pulls back. According to the National Automatic Merchandising Association’s industry census, workplace and institutional settings account for the majority of US vending placements, which means the available location pool is broad.
A small route stays manageable while delivering consistent supplemental income. For a closer look at what the weekly schedule looks like across different route sizes, see vending as a side hustle time breakdown.
Is online tutoring a flexible income option for retired professionals?
Online tutoring lets retired teachers, licensed professionals, and subject-matter experts earn income from a skill set they already hold, on a schedule they control.
A retired math teacher, nurse, CPA, or engineer can offer instruction or coaching through video-call platforms or structured tutoring marketplaces. Sessions are scheduled in advance, so there are no on-call demands and no last-minute obligations. The work does not require physical presence, travel, or inventory management.
Income from tutoring tracks with active hours. A retiree who wants a light schedule, two or three sessions a week, can keep it there. The ceiling depends on the subject’s demand and the instructor’s availability, but the model does not require taking on more than fits the week. The flexibility is high once a small client base is in place.
Can retirees earn from selling vintage or collectible items online?
Retired adults who inherit estate items, attend thrift sales, or hold existing collections can convert physical goods into income through online resale platforms.
The model involves sourcing items at below-market cost, listing them on platforms where buyers pay retail, and shipping or arranging local pickup. The income is transaction-based, with each sold item generating a one-time payment. There is no recurring revenue between sales, unlike a vending route or a tutoring retainer.
The flexibility is high. A retiree can list a few items per week or pause entirely during travel without losing an ongoing client or employer. The main active work is sourcing, photographing, and packing items, none of which requires a fixed daily schedule. Income varies considerably depending on what sells and at what price, so vintage resale works best as a supplemental income layer rather than a primary or predictable one.
Is part-time tax preparation a structured retirement income option?
Tax preparation concentrates most of its active hours between January and April, creating a predictable seasonal work window with a long off-season.
Retired accountants, CPAs, and credentialed preparers can offer individual or small-business tax services independently or through a preparation chain. The work is front-loaded into the first quarter of the year, which suits retirees who want income from a defined period rather than an ongoing obligation. The remaining eight or nine months stay available for travel and personal pursuits.
Income depends on client volume and return complexity. The seasonal structure limits total annual hours, which is both the constraint and the appeal: the work is bounded in a way that most other service businesses are not. Retired CPAs with an existing professional network can often rebuild a manageable client roster faster than someone starting from scratch.
What about renting out a parking space or storage unit?
Renting a parking space, garage bay, or a portion of a storage unit generates income from an asset the owner already holds, with very low weekly time involvement.
A retiree with a garage bay they no longer use, a driveway spot in a high-demand area, or excess storage space can list it through peer rental platforms or arrange a direct agreement with a local user. The income is recurring if the arrangement is month-to-month, and the active time per month is minimal, typically verifying payment and occasionally checking on the space.
The main constraint is geography. This model generates meaningful income in areas with high parking or storage demand, near transit hubs, dense urban areas, or locations with limited storage options nearby. In suburban or rural settings where space is plentiful, the income potential is lower. For retirees in the right location, it requires less active weekly involvement than any other option on this list.
How do these five side hustles compare for retirees?
The table below compares each option on schedule control, active time per week, and income type.
| Side hustle | Active time per week | Schedule control | Income type |
|---|---|---|---|
| Turnkey vending route (VendAmerica) | About 2 hours per machine | Operator sets the schedule | Recurring, from installed assets |
| Online tutoring or coaching | Varies by session load | Instructor sets availability | Per-session fees |
| Vintage or estate item resale | Varies by sourcing activity | Fully self-directed | Per-transaction, variable |
| Part-time tax preparation | Concentrated January to April | Bounded to tax season | Per-return or per-client, seasonal |
| Parking or storage rental | Very low (verification only) | Fully passive once arranged | Recurring, location-dependent |
Vending routes stand out because the income is recurring from physical assets in place rather than dependent on active sessions or a narrow seasonal window. The 2-hour-per-machine weekly commitment stays predictable as the route grows, unlike tutoring or resale income, which scales directly with hours invested.
How do retirees get started with a vending route?
VendAmerica buyers typically begin with a direct conversation with co-founder Jason Joyner before any financial commitment is made.
The process starts with a location review. VendAmerica’s team works to confirm a viable workplace location in the buyer’s target area before the operator makes full payment. Operators can reach Jason Joyner directly at jason@vendamericallc.com. Jason has more than 15 years of vending industry experience, including his tenure running Advantage Refreshments as president. For a look at how one retired operator built a larger route over time, see the retired CFO vending route case study.
Frequently asked questions
What are the best side hustles for someone who just retired?
Turnkey vending routes are among the strongest fits for new retirees because the business generates recurring income from installed assets without requiring daily attendance or active service delivery at each transaction. VendAmerica’s model includes location sourcing, machine installation, and initial training before the operator takes over. Tutoring, seasonal tax preparation, vintage resale, and parking rental round out the list for retirees with specific skills or assets they can put to work.
How much time does a vending route take to manage in retirement?
A vending route typically requires about 2 hours per machine per week for restocking and revenue collection. That schedule is set by the operator, not a client or employer. A two-machine route takes roughly 4 hours per week to manage, leaving room for travel, appointments, and other retirement activities.
Do retirees need prior business experience to run a vending route?
VendAmerica does not require buyers to have prior vending or business experience. The company handles location sourcing, machine sourcing, and initial setup training before the operator takes over the route. The company does not project specific income for prospective buyers; results depend on location foot traffic, product mix, and operator follow-through.
Can a retiree run a vending business without being present at every transaction?
Yes. Vending machines complete each sale automatically, without the operator physically present. The operator’s weekly work is restocking the machine and collecting revenue at scheduled intervals. Sales continue around the clock between those visits.
What side hustles let retirees earn income on their own schedule?
Vending routes, tutoring, vintage resale, and parking or storage rental all allow the operator or seller to set their own availability without answering to a client’s fixed-hour demands. Tax preparation has a defined season but is otherwise self-directed within that window. Among these options, vending routes generate income between service visits rather than only during active hours, giving them the most schedule independence of any model on this list.
Jason Joyner is co-founder of VendAmerica, a turnkey vending business setup company based in Denver, Colorado. He spent more than 15 years running Advantage Refreshments as president and works directly with first-time operators on machine sourcing, location placement, and post-setup support. Connect with Jason on LinkedIn.