Mom Quits 17-Year Job, Now Earns Up to $2,000 a Month From Six Side Hustles While Working Half the Hours
Kennedy values the time and flexibility her six ventures provide, even when they don't guarantee financial stability

After 17 years in the same job, Anissa Kennedy quit when childcare costs began consuming much of her wages following the birth of her second child. The American mother launched six small businesses instead, creating a more flexible way to earn money and spend time with her children.
Kennedy now reports earning between $1,400 and $2,000 monthly while working approximately 35 hours, compared with 70 hours previously. Kennedy told Business Insider in an essay published on 7 November 2026 that six ventures provide additional income, although earnings fluctuate and not every business is profitable.
Toyota Tacoma Rental Earns Around $400
Kennedy rents out her paid-off Toyota Tacoma through Turo. After no longer needing it for commuting, she decided to let others use the vehicle. During nine months on the platform that year, it generated approximately $400 monthly in earned and projected income. She considers it relatively easy to manage despite coordinating collections and returns.
Photo Booth Business Starts With Less Than $5,000
After a decade working as a photo booth attendant, Kennedy launched True Reflections Photo Booth Co. in Phoenix with her husband. They invested less than $5,000 in a mirror photo booth, purchasing much of the equipment second-hand.
Kennedy previously earned $200 for a three-hour event working for another company. Her business now charges approximately $600 per booking. The couple estimate recovering their investment in fewer than 10 bookings. At the time of her account, they had completed one event and secured two more.
Freelance Writing Pays Up to $250 Per Article
With an English degree and lifestyle blogging experience, Kennedy also works as a freelance writer. Although securing assignments is difficult, successful pitches can earn between $125 and $250 for articles of 800 to 1,000 words. She has also accepted projects paying as little as $10 to build her portfolio.
Housekeeping Pays $25 an Hour
Through Care.com, Kennedy secured a weekly housekeeping arrangement paying $25 an hour and approximately $300 monthly. She occasionally cleans a friend's Airbnb property for $150, usually completing the work in three hours. Relatives provide free childcare while she works, helping preserve her earnings.
Homemade Coffee Syrups Generate 70% Profit
Kennedy started making coffee syrups to save money on takeaway drinks before turning the hobby into a business through Arizona's Cottage Food programme. She sells 8.5-ounce bottles for $12, reporting a profit margin of approximately 70%. Orders come through her Hotplate storefront, and she occasionally operates a coffee stand outside her home.
Print-on-Demand Store Remains Unprofitable
Her sixth venture is an online merchandise store run with her husband, a designer. Using Shopify and Printify, they sell T-shirts, mugs, and hats. However, the store has yet to make a profit and is currently on hold because of the time required for product design, advertising, and marketing.
More Time With Her Children Matters Most
Kennedy acknowledges that managing six businesses does not guarantee financial stability. Some ventures generate better returns than others, and she may eventually abandon those that demand too much time. Nevertheless, she has halved her working hours and gained more time with her two boys. For Kennedy, the biggest reward is having greater control over her schedule rather than simply earning up to $2,000 monthly.
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