3 Popular Jobs That Will Leave Workers Struggling To Retire

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Choosing the right career path can make it easier to build wealth and plan for retirement. Jobs in industries like healthcare, real estate and finance can be paths toward high salaries with great benefits and retirement plan options. However, many people must settle for a job with a low salary, minimal benefits or lousy retirement plans.

Here are three jobs that may make retirement difficult and what you can do to improve your options.

Ride-Share Driver

Ride-share services have taken off in popularity since the first Uber trip in 2010. As of 2024, Uber reported 161 million monthly active platform consumers, up 13% from the previous year. This increase in riders may make it seem like the job is an excellent path to earning money, but being a ride-share driver comes with its share of challenges.

On average, ride-share drivers make $21 per hour in the U.S. This comes out to a $44,000 annual salary for full-time drivers, well below the national average of roughly $67,000 in 2023. Because drivers are independent contractors, they don’t get benefits or retirement plans and must pay their own taxes. Additionally, while ride-share companies may provide auto insurance, these policies usually don’t cover when drivers are logged into the app without customers. This means they need additional ride-share insurance.

To reduce taxable income, drivers should save receipts and track expenses. Things like mileage, maintenance and cellphone usage are tax deductible. Drivers can also save money by finding insurance providers that bundle their personal auto insurance with ride-share gap coverage.

Restaurant Server

Restaurant servers take your order, bring your food and drinks, take your payment and address any questions or concerns. These positions are excellent choices for those looking for jobs with low barriers to entry and a flexible schedule. However, having a long career as a restaurant server can make saving for retirement difficult.

In the U.S., restaurant servers average a low wage of $14 per hour. However, in most cases, servers receive tips that boost their incomes. While this results in more money, it also brings uncertainty. Because of the inconsistency of tips, servers may have difficulty planning their monthly budgets and consistently contributing to retirement funds. Also, restaurants don’t usually offer benefits or retirement plans.

Restaurant servers should open Roth IRAs to maximize retirement savings. A Roth IRA allows servers to contribute and invest a set amount of after-tax dollars each year. When the server retires, they can withdraw from the Roth IRA without paying taxes. Since you don’t need to contribute to a Roth IRA every month, servers can contribute more to their retirement plans in months when they’ve made more tips to max out their contributions.

Seasonal Worker

Seasonal work is when companies hire more workers for short stints to cover increased demand due to holidays, tourism or peak business seasons. Examples include increasing hotel staff during travel seasons, hiring extra lifeguards during summer vacation, onboarding more delivery drivers for the holidays or employing event staff during sports seasons. 

While the pay for each job varies, seasonal workers face common challenges. Employers usually don’t give benefits to seasonal workers, and there isn’t much job security. These jobs may pay well for a brief period, but seasonal workers must find new roles and opportunities when their employment ends. 

The best way for seasonal workers to plan for retirement is to find other side gigs and jobs to get them through the offseason. When seasonal jobs provide an opportunity to earn a lot of money, investing that money early on can add up through compound interest. When you invest money and earn interest on the initial amount, you can reinvest that interest to make more money. This process can continually increase your gains, earning you money without doing anything. 

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