Are Wealthy People More Successful at Retirement?

Many say, “If only I had a lot of money, I’d really be successful at retirement.”

I’ve interviewed hundreds of people about their retirement plans and money. I’m surprised the number who feel money is a major key to retirement success.

The success of wealthy people in retirement is nuanced: while they have significant financial security (many wealthy investors do not feel financially secure until they have at least $5 million saved), they often face psychological and behavioural hurdles that can make “successful” retirement – defined as a transition to a satisfying post-work life – more difficult than for less wealthy people.

Yes, wealth provides a safety net, but it doesn’t guarantee a smooth transition into retirement:

• Overconfidence trap: Affluent households are more likely than lower-income earners to overestimate their retirement readiness. Research shows 32% of high-income households are “not worried” about their risk, compared to roughly 59% to 76% of Canadians—who are worried about their financial security in retirement.

• Lifestyle Creep: High-wealth individuals often feel pressure to replicate high-expenditure lifestyles (e.g. $800,000/$year) in retirement, which requires much larger nest eggs than many realize.

• Identity loss: Wealthy retirees often struggle with losing the power, prestige, and social connections tied to their professional roles.

• Working longer: Higher earners frequently work much longer than those with lower incomes, not because they must, but because they lack a purpose-driven plan for their free time.

• Boredom: Wealthy people often find “traditional” retirement activities like golf or pickle ball insufficient to replace the intellectual stimulation of business.

True retirement “success” for the wealthy is increasingly defined by behavioural outcomes rather than just bank balances.

• Purpose over pennies: Success is driven by how individuals use their time and maintain social connections. The trick to a happy retirement is not to concentrate on amassing an abnormal amount of wealth, but how much do you need to enable you to live and fulfill your realistic and affordable retirement.

Case: I coached a fellow who had saved over $24 million for his retirement. Though he was wealthy, he had no real relationship with his spouse, adult children or 7-year-old grandchild. His day consisted of reading a newspaper and watching sports on TV. He reported feeling sad and lonely. After six weeks of coaching, he began actively building relationships with his spouse and children and engaging in playtime with his grandchild. He has begun mentoring young entrepreneurs and establishing a foundation to help the homeless. He is finding meaning and purpose, and is energized about living!

So now, the choice is yours, concentrate only on the money, be sedentary and without purpose or get involved and make a difference. What will be your retirement?