CEOs Who Came Out of Retirement Better than Ever

Retirement looks different for everyone. Some people retire early and never look back; some retire later in their careers, and some retire and then decide to go back to work.

No matter what your retirement looks like, there’s no right or wrong answer. Just take these CEOs as examples. They retired and then came out of retirement better than ever. Let’s look at their stories as an example of some unique retirement journeys.

Howard Schultz

Howard Schultz is the current CEO of Starbucks, but his time at the helm of the company has been anything but linear. He started working at the coffee chain as the director of retail operations and marketing in 1982 and proceeded to buy the company in 1988. He took Starbucks public in 1992 but stepped down as CEO in 2000.

After a huge international push, Schultz returned as CEO of Starbucks in 2008 to help revamp the brand. He stepped down again in 2016 and became an executive chairman. He had big dreams of working on other businesses and potentially even running for president. But in March 2022, Kevin Johnson, the former CEO of Starbucks, announced his retirement, and Schultz once again stepped into the role. We will see where this recent development takes the brand (as of now, Schultz is just stepping in as interim CEO), but one thing is sure: Schultz can’t seem to stick with retirement and keeps coming back better and more innovative than ever.1

Jack Dorsey

Jack Dorsey is a CEO that can’t help but bounce back after several retirements (plural). As the co-founder and CEO of Twitter, he has been through many ups and downs with the company. In 2008, Dorsey retired and became chairman of the board, but later, after Dick Costolo resigned as CEO, Dorsey stepped back into the role. He started as interim CEO but became the company’s permanent CEO in 2015. Between 2015 and 2021, Twitter underwent extreme scrutiny, including having to testify before the Senate Intelligence Committee. In November 2021, Dorsey announced his (final?) retirement. He will remain on the board until 2022.2

Steve Jobs

The name "Steve Jobs" is synonymous with the growth of Apple, but did you know that in 1985, Jobs actually left the company he helped found to start a new endeavor? Due to disagreements about where the company was headed, Jobs resigned (or was forced out) and started NeXT, a tech company that specialized in computer workstations intended for higher education and business use. Unfortunately, the company struggled to take off. However, this ended up being a blessing in disguise for Apple. In 1996, Apple bought NeXT, which brought Jobs back to the company. Although not a headline success, NeXT was the humble beginning of the MacOS we know today.3

After Jobs returned to Apple, he helped grow the company and its brand into what it is today. There’s no telling what might have happened if Jobs hadn’t come back and led the company to success. He retired in 2011, less than two months before his death.

Michael Dell

Michael Dell is the founder and CEO of Dell Technologies, one of the leading companies in technology infrastructure. Dell is most famous for its PCs, but it operates in many other verticals. Michael Dell spent most of his 20s building Dell from the ground up; he retired from the company in 2004. During his retirement, he spent time on various philanthropic missions.4

Dell returned to the company in 2007 and regained his role as CEO. He helped lead the company to success by introducing new, innovative products. He also got Dell computers into major retailers, such as Wal-Mart, and aggressively grew the company overseas. His retirement was short-lived and for good reasons. His success is one of the best examples of returning better than ever.

Myron Ullman

Myron Ullman is the former CEO of JCPenney. In fact, he served in the role of CEO twice, once from 2004 to 2011 and again from 2013 to 2015. Today, Ullman serves as chairman of the board at Starbucks (after Schultz regained his position as CEO).

As you can see, retirement looks different for everyone, even super-successful CEOs. There’s no one-size-fits-all approach to this important time in everyone’s lives.

Do you have a written summary of your entire plan that includes a status of your current financial position, what you are trying to achieve, and the step-by-step process of your plan that is required for success?  Maybe you’ve had an advisor for years but are unsure if your current plan is congruent with achieving your financial goals and aspirations. Or maybe you’ve been doing all the planning yourself, or you have never completed any real retirement planning other than funding your 401(k) when you were working. 

No matter what situation you are currently in, you can benefit from getting a second opinion. Take your first step towards achieving holistic financial wealth by scheduling your no obligation, second opinion appointment.