The CEO’s guide to success in retirement

Picture your retirement. Do you envision long holidays in France? Sunny afternoons at the golf course? Leisurely dinners at your neighborhood café?

Retiring as a CEO isn’t always this idyllic — at least in the beginning. Some have described the move from work to retirement as jarring and upsetting, akin to falling into a black hole. Others say they felt grief, fear or aimlessness after losing their identity, schedule and sense of normalcy.

“Being a CEO makes you feel like you are needed, wanted and have a meaningful part to play,” explains Vistage Chair Simon Holt. “For many people, walking away from this is hugely mentally challenging.”

There are ways to ease this transition, however. In this CEO retirement guide, we outline seven ways to plan for retirement so you can stay happy, active and productive after the C-suite.

1. Plan your exit strategy ahead of time.

Think you want to retire in the next year or so? Start planning your exit with your senior leadership team now. A longer runway will ensure a smoother transition, giving you and your team sufficient time to find your successor, communicate your news, keep your staff calm and get your clients on board. Not only will your business benefit from a slow transition, but you will too. When your last day in the office comes, you’ll want to experience the satisfaction of leaving your business in a good place. If you have unfinished business, you might feel guilty or regret retiring.

On a personal level, talk to a financial advisor about your plans as early as possible. “Many people do the financial aspects of retirement planning, but they don’t actually work out what they are likely to need to fund their future lifestyle,” says Holt. “You need to work with your financial planner to ‘know your number,’ based on a forward-facing cashflow analysis.”

2. Sketch out a list of things that are important to you.

Make a list of the people, places and things that you care about most. These could include family members, hobbies, charitable causes, business areas, special interests and other activities. Don’t worry about specifics; the goal is to get a general idea of how you’d like to spend your time in retirement.

If you want to continue working in some capacity — as many retired CEOs do — this exercise will also help you find the sweet spot between what you care about and where you can contribute. For instance, if you’d like to serve on a board or be part of an executive mastermind group, start imagining theoretical opportunities that would energize or excite you. Knowing this in advance will make it easier to say yes or no to opportunities as they arise. Being selective is important, as many retired CEOs say they’re offered far more opportunities than they have time for.

3. Discuss a plan with your partner.

Your partner supported your leadership journey, and now it’s time to show your appreciation. Work to understand their priorities for retirement and discuss how you can achieve them together, whether that means traveling, volunteering or spending more time with your grandchildren. Open communication with your partner will ensure that you both are on the same page about what each of you would like to do individually during retirement and what you both want to do together.

4. Keep using the intellect you have cultivated.

When you leave the C-suite, you have a deep well of experience that can be used to help others. Consider mentoring budding entrepreneurs or advising young companies. At the same time, find ways to keep your brain active. For instance, consider writing a book that captures lessons learned or wisdom you’ve gained as a CEO.

5. Earn a recurring income.

In retirement, the last thing you want to worry about is money. For that reason, you might want to supplement your retirement assets with some sort of recurring income. Many retired CEOs opt for executive coaching, as it offers a flexible way to continue working, learning and giving back. It’s also work that former CEOs find personally and professionally fulfilling.

“I became a Vistage Chair because I love to play a part in other people’s success,” explains Holt. “You coach to make a real difference in someone’s life and career. That’s far more exciting than going to work to make a living.”

6. Network.

Stay active on social media — especially LinkedIn — and keep attending conferences or professional meetings on a routine basis. Make people aware of who you are and where your expertise lies. You never know when a connection will generate a referral or introduction that leads to new opportunities.

7. Keep learning.

Use your newfound free time to learn about the subjects you’re passionate about, whether that’s the stock market, Mediterranean cooking or antique coin collecting. Perhaps you can join a book club, sign up for conferences or audit classes at your local community college. Continuous learning offers so many benefits: It increases your cognitive function, broadens your social circle, helps you discover new interests and makes you feel more well-rounded.

Your second career

Retirement isn’t the end of the road for the chief executive, or the end of a career. It’s your opportunity to switch gears and start a second career — completely on your terms.

“Everybody’s different,” says Holt. “Some people will do charity work. Some people will mow the lawn. Some people will invest in companies. I wouldn’t recommend a specific course of action. I would recommend being clear about where you will get your passion and self-worth from, whatever that may be.”

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