Latest / Executive Careers with Fexingo: VP, C-Suite, and Senior Leadership Career Strategy / How Senior Leaders Manage Career Regret Without Derailment
Transcript
- Lucas: So let me start with something I don't think we have ever talked about on this show: career regret at the senior leadership level. Luna: That is a heavy one. Most executives I know would never admit to it. Lucas: Exactly. It is almost taboo. You are supposed to project confidence, own every decision, and never look back. But the reality is, a lot of senior leaders quietly wrestle with a move that did not deliver what they hoped. Luna: And the higher you go, the more expensive the mistake feels — not just financially, but reputationally. Lucas: Right. So today I want to look at how you manage that feeling without derailing your career. I have a specific case in mind — a former Fortune 200 CFO named Rebecca. I worked with her a few years ago. Luna: What was her situation? Lucas: She had spent fifteen years climbing through operational finance roles — divisional CFO, then corporate FP&A director. She loved being close to the business, helping teams make capital allocation decisions. But when the CEO offered her the corporate CFO seat, she felt she had to take it. Luna: The classic 'next logical step.' Lucas: Exactly. And about eighteen months in, she realized she hated it. She was spending her days on board reporting, regulatory compliance, investor relations — all important, but none of it played to her strengths. She felt isolated from the operating teams she actually enjoyed working with. Luna: So she regretted taking the job. But she could not exactly go to the board and say, 'I made a mistake.' Lucas: No, she could not. And that is the dilemma. If you are a VP or a C-suite leader, expressing regret can look like indecisiveness or lack of self-awareness. So she came to me and said, 'I feel like I am failing, but I know I am not a failure. How do I untangle this?' Luna: What did you tell her? Lucas: I introduced the idea of a post-mortem reassessment. Not a formal performance review — a private, structured analysis of what she regretted and what she still valued. She realized that she did not regret the move itself — she regretted losing proximity to operational decision-making. Luna: So it was about role design, not capability. Lucas: Exactly. That distinction is crucial. Once she framed it as a misalignment between her strengths and the role's demands, rather than a personal failure, she could take action without shame. She started quietly networking with COO roles in similar-sized companies. Luna: She used her board network, I assume? Lucas: Yes. She already sat on two private company boards. She had a conversation with one board chair about how much she missed the operational side. That chair connected her with a search firm that placed her into a COO position at a mid-cap industrial company. She stepped down from CFO gracefully, citing a desire to return to operational leadership. Luna: So she did not burn bridges. She reframed the narrative. Lucas: Exactly. And that is the playbook. If you are listening and you feel that knot in your stomach about a recent promotion or lateral move, the first step is to separate regret from failure. Spend a weekend doing a 'pre-mortem journal' — imagine it is a year from now and you are still unhappy. What specifically went wrong? Write it down. Luna: I love that. Pre-mortem journal. Because what usually surfaces is not 'I am bad at this job' — it is 'I miss X aspect of my old role' or 'I did not realize how much Y would drain me.' Lucas: Right. And then you have a concrete list to work with. Maybe you can negotiate a scope change within your current organization. Maybe you start exploring lateral moves. But the key is to act before resentment sets in — because resentment leaks. People notice. Luna: And if you do decide to leave, how do you handle the conversation with your CEO or board? Lucas: You frame it as a strategic realization, not a complaint. Say something like, 'I have realized that my greatest value to the company is in operational leadership rather than corporate governance. I want to help you find a successor for my role and transition to a position where I can maximize my impact.' That signals self-awareness and commitment, not regret. Luna: That is smart. It puts the organization first while protecting your brand. Lucas: Exactly. And honestly, this is the kind of conversation that makes a good leader great — knowing yourself well enough to course-correct without drama. Luna: You know, talking about course-correction, I think a lot of our listeners have been through that themselves or are considering it now. And if this show has helped you think through a career move or decision, I just want to mention — we keep this podcast ad-free and listener-supported. A handful of people chip in monthly through Buy Me a Coffee dot com slash fexingo, and that is literally what funds making this many episodes. Lucas: Yeah. No pressure at all — just a quick honest thing. If you find value in the show and want to keep it going, that is the way. Otherwise, thank you for being here. Luna: Absolutely. Now back to Rebecca — she made the move to COO about six months after that initial conversation. How did it turn out? Lucas: She has been in the role for two years now. She told me recently it is the best career decision she ever made — not the CFO role, but the decision to admit that it was not the right fit and do something about it. Her regret became fuel for a better trajectory. Luna: I think that is the lesson: regret is only dangerous if you ignore it or beat yourself up over it. If you treat it as data, it can actually be a powerful signal. Lucas: Exactly. But it requires courage. Because the higher you are, the more people are watching. The key is to move quietly and strategically, not reactively. Luna: Are there any signals that what you are feeling is regret versus just a bad week? Lucas: Great question. I think duration is a big one. If you have felt unsettled for more than three or four months, it is probably not a transient mood. Also, ask yourself: do you dread Sunday nights? Do you feel energized by the work itself, or only by the status? If it is the latter, that is a red flag. Luna: What about the people around you? Do you think colleagues can sense it? Lucas: Absolutely. Senior leaders who are regretful often become slightly withdrawn or cynical. Their teams notice. And that can damage your ability to lead effectively. So there is a real cost to not addressing it. Luna: So the playbook is: diagnose, reframe, network quietly, then act with a positive narrative. Lucas: That is it. And one more thing — do not wait until you have another offer to start the conversation. That looks opportunistic. Start the internal dialogue early, and if you need to move, do it on your terms, not out of desperation. Luna: I think that is such a mature approach. Regret does not have to be a dirty word in the C-suite. Lucas: No. It is just data. And if you use it well, it can actually accelerate your career. Luna: Alright, that is all for this episode. Thanks for listening, and we will see you next time. Lucas: Take care.