What’s Stopping You from Reinventing Your Career?

By Heather Cairns-Lee and Bill Fischer

A recent Microsoft study of 30,000 people revealed that 46% of workers are considering a major career pivot or transition after the Covid years. For many, this search goes beyond just a change of role and into the realm of personal renewal or reinvention. In our experience, many of the professionals who such express an interest in reinvention ultimately fail to follow through.

The hardest part, we’ve found, and where many professionals get stuck, is simply getting started on leaving the status quo. This is particularly true for senior executives. Personal reinvention requires reappraising life choices and imagining alternate paths — but this becomes more difficult when the path a leader is on is seen, at least outwardly, as successful. Because leaders’ identities are so dependent on their work, it can also be hard for them to consider different possibilities. And while these executives have been educated in strategic planning and change at the organizational level, reinvention at a personal level is not part of the curriculum at most business schools.

More ironically, there are also habits that are core to executives’ success that stand squarely in the way of personal reinvention. In our work teaching and coaching thousands of managers, we have identified four traps – self-sufficiency, overthinking, procrastination, and searching for the answer – that prevent leaders from taking the first steps necessary for considering and exploring possible new versions of themselves for the future.

In our work, we have found ways to help leaders recognize which traps they are falling into and start imagining a way out — largely inspired by design thinking principles such as rapid prototyping, making ideas visual, and getting quick feedback. Understanding what these traps are can help you take those first steps — and succeed in your quest for reinvention.


Leaders often talk of their self-sufficiency with pride. These leaders rely on their own contributions, work well independently and seldom require motivation or management from others – behaviors that have earned them their senior roles. However, self-sufficiency has a flip side: It can limit connections with others, resulting in restricted access to new ideas, feedback and encouragement. It can also hide a leader’s doubts and insecurities from others. Individuals who are highly self-sufficient need others to help them overcome this trap of self-sufficiency and asking for help may seem obvious, but it also takes courage, especially when admitting to career vulnerability.

Fritz, a finance executive in the pharmaceutical industry whom we met on one of our workshops, is a classic example of an executive trapped by self-sufficiency. His considerable self-reliance meant he took the lead on most work projects and presentations and believed that working with others and delegating slowed him down when he could do things himself. His self-reliance had initially helped him succeed in his career, as he developed a reputation as a “go-to person.”

However, his habit of self-reliance was particularly unhelpful when the company he worked for began restructuring, as he felt adrift and out-of-touch with the changes taking place. He got the sense that he was being pushed out, yet had no one with whom to discuss the situation. His self-reliance nearly got in the way when a colleague asked whether he wanted to have lunch and a chat.

About to respond with his usual “No, I’m fine thanks,” he realized that he was not fine and that a conversation might just be helpful to hear some other perspectives on what was happening in the company. Saying yes to that conversation was the start of him getting out of his own way and a longer exploration of reinvention.

If you tend to be reluctant to ask for help, or to accept it when offered, it may be a sign of the self-sufficiency trap. If so, find someone you trust and let them know that you would like to talk things through. Jack Welch, former GE CEO, stretched this remedy to “reverse mentoring” where senior executives turn to younger digital natives in order to master digital convergence.


Sharp analytical skills are critical to good problem solving and leadership through complex situations. However, when reinventing themselves executives can get stuck claiming they simply need “a little more time to think things through” before actually taking any steps to make a change. The overthinking trap is born from a dependence on analysis and logic as the way to solve problems that overlooks other ways of knowing — emotional, intuitive, visual or embodied. This overthinking leads executives to miss signals from these neglected sources of data and prevents learning from experimentation. Yet personal reinvention is an embodied, experimental experience and executives cannot simply think their way into the future.

Take Em, for example — another executive we have worked with. A veteran of a 15-year career and responsible for the strategic direction of a philanthropic organization, she found that her workload was wearing her down and limiting the time she could spend with her young family. She was surprised to find that she felt disconnected from a job she had once loved. Every time she started to imagine doing something else, she reasoned that the job had once been engaging and that there were others lining up for her role. Her rationalizations prevented her from paying attention to her felt sense of disquiet and of imagining a new future.

We asked Em to literally draw a prototype of a possible next step for her. She sketched a journey with diverging paths and herself with an inner compass that was fueled by intuition. She considered each of the possible future paths, asking herself: How energizing it would be? How much it fit her own skill sets? And, how it would affect the rate and direction of her career progress? She realized it was time to leave the organization she had loved. Em followed her inner compass of intuition, resigned from her executive role to pursue an advanced degree in psychology to prepare for the next step in life and have more time with her family. She tells us that stopping her overthinking about her past role created space for her to dare to imagine a possible future that she finds exciting and energizing.

If you catch yourself frequently saying “let me think that through,” you are likely overthinking. Instead, notice other often-overlooked sources of data — emotional and  intuitive — and take an experimental approach. Personal reinvention is best served by doing, rather than thinking: Trying things out and learning from the outcome. Attention to physical cues, your intuition about how the experiment worked, as well as others’ reactions can provide sources of data that can help you get out of the overthinking trap.

The Right Answer

Our society teaches that there are “right” and “wrong” answers from our schooldays right through to the workplace. But, often, there are no discernible right answers when looking out over the unknown of a reinvented life or career. Executives who have confident replies at the ready in the context of their current roles become suddenly silent when they’re asked about their personal futures.

As a scientist, Sam had been educated to find the right answer to the problems in front of him. After 20 years as a chemist in a large German firm, he started to feel ready for a change of direction and yet he found himself searching for the elusive right answer to what that direction should be. As a result, he remained in his role despite the feeling within him that something needed to shift.

When we began to work with Sam, it was clear that as a scientist he understood the language of experiments very well. So, our work with him emphasized the need to conduct experiments in order to make progress on the work of reinvention. We asked Sam to bring the same level of curiosity to examining his life that he brought to his experiments. We encouraged him to conduct experiments to identify sources of fulfillment in life and at work. Within time, he realized that there was no “formula” nor right answer, but many exciting options, and the choice was his to make. He decided to stay in his role for the next two years and to deliberately make time for some experiments to explore options. He set one professional experiment in place by offering support to a local start-up and one personal experiment to rekindle his love of music by joining a choir.

If you tend to search for the “right” answer when evaluating choices, this may be a sign that you might shy away from embarking on experimentation or accepting mistakes as a pathway to learning and growth. It can be useful to ask what alternate paths are there?


The easiest excuse to avoid starting a reinvention process as an executive is all the other urgent work you have to do. Successful leaders are rewarded with ever-greater responsibilities, which means that they have less and less time to focus on their own longer-term aspirations. That limited bandwidth can also fuel anxiety: It can be hard to imagine a nebulous future when weighed down with the very real demands of today. More than this, personal reinvention can be scary. Who among us hasn’t hesitated in the face of a big decision, not for more insight, but simply in the hope of deferring choices to avoid the associated anxiety and self-doubt? We also know from psychology that people procrastinate to avoid ambiguous, difficult and unstructured situations or decisions — and personal reinvention checks all of these boxes.

Barbara had become disillusioned with her career in marketing. She didn’t have much time for nurturing her aspirations, however, because of the demands of the job and attention to her young children. Introduced to one of our workshops by a friend, she realized that the real problem wasn’t a lack of time; it was that she didn’t know where to start. At the workshop, we encouraged Barbara to more precisely articulate and then visualize several possible future paths, much as we had done with Em, and then appraise them analytically, in order to be able to compare and contrast their attractiveness, suitability and fit. Doing this allowed Barbara to test these possible career journeys, and select the path she felt was best suited to her goals and capabilities. Barbara carved out some time to test some of the ideas she had drawn and eventually found her new path as a graphic recorder.

If you tend to procrastinate, ask yourself why you are putting off important decisions about your life? And, why you are choosing to prioritize other tasks? The adage “just do it” can help take a first step and act as a reminder that reinvention is an iterative process, so taking that first step no matter how small is better than a perfect idea that remains untested.

The common denominator in these traps is that they aren’t bad habits in and of themselves — quite the opposite. Executives follow strategies that have worked well for them throughout their lives — self-reliance, thinking their way to an answer and throwing themselves into work that demonstrates their loyalty to the status quo. But it also keeps them safe from the messy, emotional work of exploring new possibilities.

Only when executives recognize the dissonance between their inner yearning and the status quo can they address existential questions about who they are and what they want from life. Confronting the traps — their legacy beliefs — that prevent them from doing so can help them finally imagine their next selves and start on their way.