He Had $180,000 in His 401(k), Then One Decision Left Him Driving Uber 75 Hours a Week at 58

At 58, Bill Lewis is working seven days a week instead of preparing for retirement. He spends about 75 hours behind the wheel for Uber and Lyft. He earns roughly $75,000 a year from driving. Lewis values the freedom the work gives him. But he also knows why he needs those long hours.

He once had about $180,000 in his 401(k), built during a career that included more than two decades on Wall Street. Then he made a decision he now regrets.

Lewis used his retirement savings to open a Nestlé Toll House franchise after losing his Wall Street job. Four years later, the business had failed to deliver the return he needed. At 58, he is still working to earn the money he once hoped his retirement savings would help provide.

From Wall Street to a Bakery Franchise

Lewis began his career in 1989 as a runner at the American Stock Exchange. He eventually became a broker and spent more than two decades working on Wall Street. But technology transformed the industry. Algorithms reduced the need for people on trading floors. Lewis was laid off in 2013. He decided to try something completely different and become a business owner.

A franchise seemed appealing because it offered an established brand and a business structure. Lewis chose a Nestlé Toll House retail bakery franchise. He put his retirement savings into the venture. The first year appeared encouraging. The franchise recorded strong sales growth compared with the previous year. But strong sales did not solve the bigger problem.

Lewis said the cost of operating in the mall made it difficult to turn the business into a profitable operation. He ran the franchise for four years. By the end, he said he had made less during those four years than the $7 he earned on his first Uber ride.

The $180,000 Decision He Wishes He Could Undo

Lewis has little doubt about what he would change. He regrets using his retirement savings to fund the franchise. If he had kept the money in his 401(k), he believes he would be in a much better financial position today.

Instead, he needed another source of income. Lewis began driving for Uber in 2017. He later joined Lyft and learned how to make the work pay. The biggest attraction is flexibility.

If something happens at home, he can stop driving. If his car needs repairs, he does not have to ask an employer for time away from work. But flexibility has not meant fewer working hours. It has meant more.

Every Ride Has to Make Financial Sense

Lewis says he has become increasingly selective about the journeys he accepts. Uber gives him about eight to 10 seconds to assess a ride. He considers the payment, mileage, fuel, and potential return journey before making a decision. He cited an example of an offer of about $80 to drive 75 miles to Brooklyn.

Once he considered the return trip, fuel, and roughly $25 in tolls, Lewis said the journey could actually cost him money. He has therefore not accepted an Uber trip into New York City for about five years. Instead, he aims for rides that meet his target of $30 an hour.

He has also started taking more Lyft rides. Lewis says Lyft's estimated hourly rate makes it easier to identify journeys that fit his target. Since becoming more selective and using Lyft more often, he says his pay has increased by almost 25% since earlier this year.

At 58, He Keeps Driving

Lewis's retirement plans look very different from what he once expected. The $180,000 he had accumulated in his 401(k) is no longer there. His franchise did not provide the financial security he hoped for. His solution has been to keep working. Lewis still values the independence of gig work. But the hours show the financial consequences of his earlier decision.

Seven days a week. About 75 hours. At 58, Lewis is not slowing down. He is driving to earn the income he needs today while facing a retirement future that could have looked very different had he left his savings invested.