5 Tips to Chart Your Post-Corporate Life

As he neared the end of a rewarding corporate career that culminated in being chief marketing officer at United Airlines, Tom O’Toole resolved to design the “post-corporate” stage that followed.  

O’Toole uses the term “portfolio life” to describe the set of activities in which a senior executive decides to engage after stepping out of the C-suite. For many business leaders, that new stage commonly includes some combination of board service, teaching, and consulting.  

In O’Toole’s case, his portfolio over the last ten years has included a mix of all three: a decade of teaching and leadership at Kellogg, a combination of public and private corporate boards, and a senior advisor role at McKinsey & Company. 

Looking back, O’Toole believes strongly that the key to designing a full and successful post-corporate portfolio life is being intentional. 

“It doesn’t just happen,” he says. “The most critical questions to ask yourself are, ‘how do I want to use my time and why?’” 

Here, O’Toole offers five tips for leaders looking to their future beyond the C-suite. 

Start planning early 

Corporate executives are accustomed to planning strategically for the long term. How they intend to spend their post-corporate years requires similar forethought. Leaders should begin laying the groundwork and putting in place the building blocks for their post-corporate endeavors well in advance, O’Toole recommends. 

“People ask me, ‘When should I start this planning process?’” he says. “And my answer is always, ‘Two years ago.’” 

A mistake he sees senior executives making is retiring, taking time off, and then expecting to find their first board position or teaching gig a year or two later. 

Instead, you should think far in advance about how you want to use the years ahead and take the steps to make it happen, O’Toole says. 

“Better too early than too late,” O’Toole observes. 

Clarify your purposes 

When contemplating how to spend your post-corporate life, it’s important to identify the activities that have the greatest purpose for you, that you want to continue doing, and that you find most engaging.   

O’Toole recalls working with an advisor who told him that O’Toole seemed happiest when he was learning. He said, “If you stop learning, you’re not going to be happy.” For others, the motivation may be to stay engaged as a practitioner in your field. The key is to determine what you find fulfilling.  

“For many people, a fundamental question is, ‘how am I going to keep learning and developing new skills?’” O’Toole says. “I hear leaders approaching retirement wonder, ‘how am I going to stay involved?’ Often, what they’re really saying is, ‘how am I going to stay relevant?’” 

“Leaving the C-suite can be like looking into the abyss for people,” he says. “You need to be clear about your purposes to navigate through the transition.” 

Map your purposes onto your activities 

Once you have determined what matters most to you in retirement, then you can map those aims onto the respective elements of your post-corporate portfolio life.  

Executives often say that they want to serve on a board, or teach, or do consulting. But they need to be clear with themselves about why they want to do these things and which purpose each is intended to serve.  

Executives who want to serve on a corporate board, for instance, should be sure the actual requirements and responsibilities align with their profile and purposes. Boards can be intellectually challenging and financially rewarding and can have real-world consequences, O’Toole says.  

Teaching has a very different focus than board service.   

“Teaching is, in part, about learning the craft of teaching,” O’Toole says. “It’s about saying, ‘I want to stay intellectually challenged. I want to develop new content. I want to learn how to teach effectively.’ And, importantly, ‘I’m willing to put in the work required to do so.’”  

The third post-corporate activity commonly envisioned by executives is consulting. Consulting is a way to stay involved in actual practice and to monetize your experience, while allowing for more autonomy and flexibility over your time and workload. But “consulting” covers a wide gamut. It’s essential to be practical and specific about what you really intend and want to do.  

Go in eyes open 

Not all types of board service, teaching, or consulting are alike—and there is a lot of room to design a career that fits your interests, experience, and purpose. But it must be done intentionally.  

“It’s important to know and be clear about what you’re getting into,” O’Toole says. 

Boards, for instance, fall into three broadly defined categories: public companies, private companies, and nonprofit organizations. But even within those three categories, the requirements, expectations, and realities differ greatly. 

“When senior executives say they want to be on boards after retirement, they generally mean public or private corporate boards,” says O’Toole. But those can be quite different. “When I joined my first public board, the general counsel made my fiduciary obligations very clear to me, and that has been reiterated in multiple board situations since. The expectations and obligations of a private company director, for example, in a PE-sponsored company, are different. Similar, but with some practical differences.”  

When considering board service, ask yourself, “Do I prefer a more formal structure or more operational engagement? Do I want guaranteed compensation or will I take the risk for upside gain? How am I going to react when the going gets bumpy, with an activist or a cybersecurity incident, and the time demands go up?” 

Teaching roles, too, exist on a continuum. When people tell O’Toole they want to teach at Kellogg, he typically asks them what they mean by “teaching.” 

“What I’m really asking them is, ‘How much time and work do you want to put into this? How serious are you about developing content and learning how to teach well?’” he says. “‘Do you mean a 60-minute guest lecture a couple times a year or 30 hours of new content for high-bandwidth, fast-processor, 28-year-old MBA students?’ Because there’s a big difference between the two.” 

Consulting, likewise, spans a range from hanging out your shingle and starting an individual practice to becoming a senior advisor at a top consulting firm—and the realities of each are very different. O’Toole pushes executives to think carefully about what they want: Do they want to do business development or simply be available as an expert when needed? Do they want to build and run their own LLC or be part of a global network of top-caliber professionals? Are they doing this to generate income and stay current in their field? Or are they doing it because they genuinely enjoy working on real-world problems with companies?   

“These are all perfectly good options, but very different,” O’Toole says. “This is where it requires very intentional, critical thinking to go from these big, broad starting points to answer for yourself, ‘Okay, what does this really mean in practice?’”  

Check your ego at the door 

Once you have mapped out your combination of post-corporate activities and it’s time to get to work building them, it’s important to remember that you’re in a different position from your previous leadership role.  

“You need to check your ego at the door,” O’Toole says. That means letting go of the identity of your past roles. He notes that a year or so is the shelf life for retired business leaders to introduce themselves by leading with their former corporate job title. 

“I admire people who I know had a big job in their previous life but are humble, curious, self-effacing, down to earth, and want to keep learning, contributing, and doing a good job in their post-corporate activities,” says O’Toole.  

That ego-check also includes recognizing that you probably will need to develop some skills for which you relied on others in the past. For example, a recently retired C-level executive was surprised to learn that O’Toole, like other faculty, has personally built hundreds of PowerPoint slides for his teaching.  

It’s helpful to build an infrastructure to support your multiple endeavors—and multiple calendars. Assembling a platform that provides an office or other place to work, meeting space, support for administrative activities like billing and taxes, IT help, publishing channels, and other practical necessities is very useful for keeping your portfolio life productive and running smoothly. 

“Shortly after I left United Airlines, a colleague advised me to hire an assistant,” O’Toole says. “That was the best investment that I made at the time.”  

Once a person settles into a post-corporate portfolio life, O’Toole recommends periodically asking about each activity, “Why is this the best use of my time?”—knowing that the answers, and respective time allocations, will change over time. 

In his own post-corporate stage, the amount of time O’Toole spends on each of his commitments has evolved. At certain times, boards were a big piece. For more than five years, he served as Associate Dean of Executive Programs at Kellogg and needed to reduce his consulting and board commitments. Now, he’s concentrating on doing more teaching and learning new teaching methods, while freeing up more time for family and leisure.  

“People decide how big or small they want each slice of their time pie chart to be at different times,” O’Toole says. “But you must be intentional about it. I’m very mindful that we only have a finite amount of time to live.”