top of page

6 Retirement Lessons From Serena Williams

Updated: Jan 14, 2023

Legendary sports champion Serena Williams has joined the Great Resignation, announcing her retirement from tennis. While physical competition may no longer be viable, this 39-grand slam record-holder is unlikely to forego her tennis roots.

Having given many lessons to business leaders over the years, even her departure can teach us how to retire with class and sustain a hard-earned legacy.

As a behavioral scientist and Board advisor, I offer six tips to mentally prepare leaders for the much-procrastinated retirement decision.

1. Plan the


Nobody has it all. A role model for women, while two months pregnant, Williams won her last major at the 2017 Australian Open. She knows "something's got to give."

I suspect losing in the first round of Wimbledon this year hurt. Eight weeks later, she hangs up her racket. Shunning the idea of retirement, she tells Vogue “I have never liked the word retirement…It doesn’t feel like a modern word to me.”

She’s not wrong. Retirement is a distant concept that leaders in start-ups and Fortune 50 firms resist. Relabel it - retirement isn’t a dirty word or the act of lazy people. View it as an inevitable transition to a different place. Resist your human preference to focus on today and project to a better place.

2. Start Early.

Most athletes know they have a limited shelf life to maximize future earnings. Williams’s departure from tennis was neither premature nor unexpected. She performed longer than most. Ti

me at the top of any hierarchy is usually short-lived before the next batch of talent emerges.

Business owners have a duty of care to early- and mid-career employees to help them plan for retirement. With no options to consider, it’s never too late to promote financial, psychological, and practical activity planning. Even governments mandate automatic enrolment to help employees boost savings and avoid the intention-behaviour gap.

Employees must manage their own future. When I reached mid-career, I sought out board roles in organizations and charities. These proved a useful springboard to non-executive directorships years later.

3. Be Open To New Opportunities.

Many employees have reassessed values post-pandemic. Some are quitting, changing industries, or taking early retirement. Others are adding side-hustles and temporary gigs to their main sources of income.

Williams developed clothing interests, now striving to balance family with commercial and philanthro

pic ventures. As a leader, it’s important to build optionality before retirement. This reduces your psychological dependence on colleagues and routines. It also makes mental separation easier.

As Dorie Clark advocates, expand your network when you don’t think you need one. It’s an underestimated factor by busy executives.

4. Separate Your Role From Your Identity.

Since Williams first played in Compton, being a tennis player defined her. With the Oscar-winning film about her father, ’King Richard,’ her legacy is set to grow. Success makes it harder to escape a lifetime identity.

For many, the day job is is tied to personal and social identity. Emotional attachment to a career is inevitable, especially if you've built something from scratch. Every new revenue source, product, or employee represents another stamp of achievement.

Reluctance to cut ties i

s understandable. Yet many successfully move on. Athletes become commentators, coaches, or trainers. Presidents build academies and libraries.

We’re all a composite of roles - parent, teacher, son, supervisor. Ask yourself “What else do I value?” Don’t define yourself by job title or status. Separate these identities for your greatest well-being.

5. Don’t Be Seduced By Your Success.

Entrepreneurs and Founder CEOs tend to stay longer than non-founders before handing over the reins. High performers cling on most. Eighty-year-old Founder and CEO, billionaire Mike Bloomberg is still at the helm of his $40.9million revenue data empire. After twenty-five years, Bill Gates retired as Microsoft Founder and CEO to focus on software strategy. It took another twenty years before retiring from the Board.

Addicted to headlines, many founders struggle to make the psychological break. Yet companies must stay innovative. Take advice from admired leaders as necessary.

6. Craft Your Exit Strategy

Earning $45.9 million in 2021, Williams ranks among Forbes’s highest-paid female athletes. Regardless of bank balance, everyone needs an exit strategy. INSEAD Professor of Leadership Manfred de Vries

suggests the best time to transition is when ‘the job has become routine.. performance is slipping…at that sweet spot of being at the peak of their performan

ce, just before the decline.”

Sometimes burnout is the trigger. Williams advises always admitting it.

As resignations show no sign of abating, many will continue to switch or end careers. New chapters will be ignited.

Having mastered your career, embrace the Great Transition. Exit confidently with a realistic plan, security, and a fine-tuned network. With a lifetime of titles earned, I think the one that you may find most rewarding is ‘grandee’ rather than ‘retiree.’

That’s retiring with class. Advantage you.


bottom of page