What The Office Characters Can Teach Us About Money and Retirement

Despite being off the air for over a decade, “The Office” continues to captivate audiences and influence culture. Since landing on Peacock in 2021, the show has attracted roughly 900,000 new subscribers to the platform, per Parrot Analytics. But beyond entertainment value, the beloved characters in the office offer surprisingly honest lessons about how real people handle their finances—from the catastrophic to the inspiring.

The Success Stories: Getting Retirement Right

Jim and Pam: The Blueprint for Smart Planning

Jim and Pam represent what disciplined financial planning actually looks like. After co-founding a sports marketing venture with Daryl that eventually expanded, Jim moved his family to Austin and locked in a home before the market skyrocketed, securing a major wealth builder. Their retirement approach is textbook sound.

Jim educates himself through credible sources—he absorbed Warren Buffett and Charlie Munger’s investment philosophy and fully funds his 401(k) with broad stock index funds. He’s also committed to dollar-cost averaging into Berkshire Hathaway Class B shares through a separate brokerage account. The result? Minimal stress about market swings and a trajectory toward genuine financial security.

Pam matched this dedication by gradually ramping her savings rate from 3% to 15% of her salary over time. This compound effect gives the couple a formidable nest egg for their golden years.

Toby Flenderson: The Quiet Winner

While Michael Scott may have ribbed Toby endlessly, the HR department’s most despised figure is actually sitting on a retirement foundation that outpaces his colleagues. Toby maximized tax-deferred contributions year after year and stayed invested in aggressive growth equity funds. Even when COVID-19 triggered panic across markets, he held his ground and made no reactionary moves to his 401(k). His discipline paid off handsomely.

Phyllis and Bob Vance: Business Ownership as Wealth Building

Phyllis and her husband Bob (of Vance Refrigeration) demonstrate another path to retirement security: a combination of market discipline and entrepreneurial equity. Phyllis invested prudently in stocks while Bob accumulated substantial business value. With Bob exploring a sale of the firm, the couple is positioned for extensive travel and leisure in retirement.

The Cautionary Tales: How to Sabotage Your Future

Michael Scott: Raiding Retirement for Bad Bets

Michael started with a solid plan—balanced contributions across traditional equity and bond index funds. Then came the franchise opportunity. He drained his 401(k) to fund “Pluck This,” an eyebrow and ear hair salon that predictably collapsed. Desperate to recover, he shifted to active trading and market timing, approaches that have consistently deepened his losses.

His saving grace? His wife Holly proved to be a disciplined saver and investor, cushioning the impact of his financial recklessness. Michael continues working partly by necessity and has landed gigs writing jokes for an AI greeting card company—a hustle born from earlier mistakes.

Ryan Howard: All Eggs in One Very Volatile Basket

Ryan’s trajectory from temp to VP mirrors the volatility of his financial decisions. His entire retirement portfolio is concentrated in cryptocurrency—a concentration bet that leaves him exposed to catastrophic risk. While crypto’s price surges might make early retirement seem feasible, Ryan has no contingency plan, no hobbies, and no clarity on what he’d actually do with free time. One major market correction or a pivot to a failing meme coin could force him back to square one.

Andy Bernard: Active Trading’s Victim

Andy’s impulsivity extends directly to his investing behavior. He believes he can time markets and actively trades his retirement funds, but the pattern is brutal: he consistently buys peaks and sells valleys. During COVID-19’s market crash, he fled entirely to cash, only to return to stocks after the recovery was already underway—cementing losses and missing gains simultaneously.

His role at Cornell’s admissions office provides some redemption through generous institutional retirement benefits, though his supplemental income from singing gigs suggests he’s still working harder than he’d prefer.

The Middle Ground: Discipline Without Strategy

Kevin Malone: Right Answer, Wrong Reasons

Kevin presents a paradox. He’s simultaneously an accountant and a skilled poker player who invents his own math—and yet his retirement fund has grown substantially. His secret? He asks Andy for financial advice and does the exact opposite. By following this contrarian impulse, he’s maxed out his 401(k) contributions and built meaningful wealth despite not truly understanding financial markets.

The downside: heavy prop bet debts keep him and his band Scrantonicity busy playing weddings and bar mitzvahs as a side hustle.

Stanley Hudson: Security Over Growth

Stanley retired to Florida with Social Security and accumulated savings, but his ultra-conservative approach limited long-term wealth building. He gravitated toward money market funds and government bonds—safe choices that sacrificed the compounding power of equity exposure. Discipline was never his problem; vision for growth was.

Oscar Martinez: The Oversaver’s Dilemma

Oscar followed a 30-year financial plan from a fee-only advisor and executed it flawlessly through decades of frugal living. He oversaved by virtually every measure. The irony? Now in retirement, he can’t break his penny-pinching habits and struggles to actually enjoy the fruits of his labor. His financial planning was expert-level; his life design was not.

The Unconventional Path: Creed Bratton

Creed trusts neither financial markets nor institutions. He skipped the Dunder Mifflin 401(k) entirely and instead converted his savings into physical gold coins locked in a home safe. It’s a doomsday prepper’s approach to retirement—financially unconventional but emotionally consistent with his worldview. Recent gold price appreciation may look good on paper, but Creed has zero intention of selling, meaning theoretical gains remain theoretical.

The Bigger Picture

These characters in the office illustrate the spectrum of retirement realities. Some people save diligently but invest too timidly, capping their long-term returns. Others undersave and work decades longer than they need to. Many prepare financially while neglecting to imagine what retirement life actually means. The most dangerous approach? Concentrating wealth in single bets while lacking a coherent plan.

Retirement planning requires both financial competence and life design—a combination that surprisingly few people master. Discussing these tradeoffs with family and consulting a financial professional isn’t just prudent; it’s essential.