What Retirement Might Look Like for the Characters of ‘The Office’

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Despite ending over 10 years ago, the U.S. version of “The Office” remains one of the most culturally relevant sitcoms and popular shows. Since moving to Peacock in 2021, it’s brought in nearly 900,000 new subscribers for the streaming platform, according to Parrot Analytics.

But aside from all the media lessons that can be learned from “The Office,” the relatable characters from the show can also provide a humorous yet honest reflection of the full spectrum of financial choices that employees of any company might make.

Here’s what retirement planning and the eventual golden years might look like for some of the main characters of “The Office.”

Michael Scott

He may be a lovable fool, but he’s not particularly good with money, as evidenced by the Season 4 episode “Money”, where Oscar tries to help Michael build a budget to get out of debt.

However, Michael does seem to have a way of landing on his feet, only to get caught up in more shenanigans.

“Michael Scott was on track with his retirement contributions — he was invested in a combination of traditional equity and bond index funds — until he raided his 401(k) to pay a franchise fee for ‘Pluck This,’ a hair salon specializing in eyebrows, ear and nose hair,” said Robert Johnson, Ph.D., a professor of finance at Creighton University’s Heider College of Business. “The franchise failed, and he is trying to catch up by actively trading his account. His market timing is failing to produce results, and he has suffered huge losses in his 401(k).”

He may not have much of a nest egg when he reaches retirement age, but luckily, his wife, Holly, has been a diligent saver and investor, so they’re able to get by. Michael is happy to keep working for as long as he can, and he gets a job humanizing jokes for an AI greeting card company.

Jim and Pam Halpert

Everyone’s favorite couple is doing alright money-wise. In the finale, Jim and Pam say they’re moving to Austin, as the sports marketing firm Jim and Daryl co-founded has expanded. 

Hypothetically fast-forwarding, the couple not only earns a comfortable living but also bought a home in Austin before the market exploded, giving them an additional financial cushion. They’ve also been smart about retirement planning.

“Jim watched a YouTube video featuring Warren Buffett and Charlie Munger at a Berkshire Hathaway annual meeting and fully funds his 401(k) with stock index funds,” Johnson said. “He also has a separate brokerage account in which he dollar-cost averages into Berkshire Hathaway Class B shares. Jim doesn’t concern himself with market volatility and is well on his way to a comfortable retirement.”

Similarly, Pam understands the sensible move of upping her retirement savings each year. In her early years at Dunder Mifflin, she was only saving 3% of her salary, but she then started increasing that by 1% until she got to a 15% savings rate, giving the couple an even more secure nest egg.

Ryan Howard

Ryan rocketed his way from temp to vice president of North East Sales, but his journey on “The Office” was full of ups and downs, which likely mirrors his financial life.

“Ryan is completely undiversified, as his entire retirement fund is invested in cryptocurrencies,” Johnson said. “He is contemplating early retirement but has no hobbies and no idea what he would do with his free time.”

While he could likely make early retirement work thanks to crypto’s soaring prices, his lack of a plan leaves him extremely vulnerable. If the crypto market dips, or he moves his investments into a new meme coin that crashes, he could find himself basically having to start all over again.

Toby Flenderson

Toby may be Michael’s favorite punching bag, but he’s hypothetically got his act together retirement-wise.

“Toby is better situated for retirement than any of his Dunder Mifflin colleagues,” Johnson said. “For years, he maximized his tax-deferred retirement contributions and invested in aggressive equity growth funds. He experienced sleepless nights during the COVID-19 pandemic but made no changes to his 401(k) plan and has been handsomely rewarded.”

In the finale, Toby moves to New York after getting fired from Dunder Mifflin, where he’s trying to write the great American novel. While he probably struggles in that department, his 401(k) keeps compounding, and he has enough to maintain a comfortable lifestyle in retirement.

Andy Bernard

Andy’s retirement planning is likely all over the place.

His impulsive nature translates into poor investing behavior. “He believes he can time the markets and actively trades his retirement funds,” Johnson said. “Unfortunately, he consistently buys high and sells low.”

Andy moved entirely to cash during the height of the COVID-19 pandemic and returned to stocks only after the market recovered. Still, his eventual job at Cornell’s admissions office likely helps him get back on track thanks to the school’s generous retirement benefits — and he’s happy supplementing income with crooning gigs.

Kevin Malone

Kevin is a bit of a conundrum. He’s an accountant and a skilled poker player, but he also invents his own math rules and loves to gamble, potentially to his detriment.

When it comes to retirement planning, his background doesn’t translate into an “understanding of financial markets, but he is convinced that with respect to investments that Andy Bernard has no idea what he is doing. Kevin periodically asks Andy for advice and does exactly the opposite. Kevin maxes out his 401(k) contributions and, as a result of Andy’s advice, has built a sizable nest egg,” said Johnson.

Luckily, he knows not to touch his 401(k) because of the tax advantages, but he does have some debt from making too many prop bets. So, Kevin and his band Scrantonicity pack their weekends playing weddings and bar mitzvahs until he gets out of the hole.

Stanley Hudson

Stanley is said to have retired to Florida City, Florida, in the finale, where he spends his time carving birds. 

He largely lives on Social Security and cash-like savings. According to Johnson, Stanley saved diligently but was overly risk-averse, favoring money market and government bond funds in his 401(k). While disciplined, that caution limited his long-term growth.

Phyllis Vance

Phyllis and her husband, Bob Vance of Vance Refrigeration, enjoy a comfortable retirement.

“They accumulated a small fortune through her prudent stock market investing and his sizable equity in the business,” Johnson said. “Bob is seeking a buyer for the firm, and the couple plans extensive travel in retirement.”

Creed Bratton

The mysterious Creed gets by in a way that’s comfortable for him, but perhaps no one else. His retirement planning is likely unconventional.

“Creed mistrusts financial markets to the extent that he doesn’t participate in the Dunder Mifflin 401(k) plan. He is a doomsday prepper and has significant savings in gold coins that he keeps locked up in a safe hidden in his home,” said Johnson.

While the price of gold has shot up recently, that probably doesn’t benefit Creed, as he has no intention of selling.

Oscar Martinez

Lastly, Oscar probably represents the type of person who has the financial side of retirement down pat, but he hasn’t given enough attention to what he wants his retirement to actually look like.

“Oscar has oversaved for retirement, living extremely frugally during his entire work life,” said Johnson. “He has followed a plan developed 30 years ago by a fee-only financial planner he engaged. Oscar has been a saver all his life and is having trouble transitioning into his recent retirement. He can’t break his frugal habits.”

Which One Are You?

Though hypothetical, these scenarios mirror how many people approach retirement. Some save diligently but invest too cautiously. Others undersave and work well into their later years. And some prepare financially but forget to plan for life after work.

Retirement planning and retirement itself can be challenging, so it’s important to discuss these issues with family and consider engaging a professional, such as a financial advisor.

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