What If I Fail?

Photo by Eyasu Etsub on Unsplash

“What If I Fail?” is a question Mid Career Professionals Are Quietly Carrying

At some point in a mid career journey, the questions change. Early on, we tend to ask how questions. How do I get promoted? How do I get better at this? How do I prove myself? Later, the questions become heavier, quieter, and more existential. What if I fail? What if I have chosen the wrong path? What if this is as good as it gets?

For many mid career professionals, particularly those moving into senior or C suite roles, the sense of responsibility intensifies. The stakes feel higher and decisions ripple outwards. Other people’s livelihoods, wellbeing, and futures can begin to feel closely tied to your own. With that responsibility comes a different kind of pressure. Not always visible or spoken aloud, but very present.

This often shows up as a question about responsibility. Is it the level of responsibility that makes the stakes feel higher? The move into senior leadership can bring status, influence, and autonomy, but it can also bring a weight that surprises people. A sense that mistakes now cost more and that there is less room to experiment, to wobble, or to not know. The fear is rarely about competence. More often, it is about consequence, and about failing at a stage where you feel you should know better.

Another useful question is what made you become an owner, whether that ownership is literal, emotional, or psychological. Ownership often begins as a desire for freedom, impact, or integrity. Over time, it can quietly turn into obligation. Responsibility hardens and choice starts to feel like duty. Revisiting why you stepped into ownership is not about nostalgia. It is about reconnecting with agency, not just accountability.

Coaching conversations often slow down around a gentler question. What is interesting about this for you? This creates space where judgement usually lives. Instead of asking whether something is right or wrong, it invites curiosity about what is actually going on. Mid career professionals are often excellent problem solvers, but far less practiced at being curious about their own inner experience. Curiosity lightens the load because it replaces self criticism with inquiry.

One of the most powerful reframes at this stage is questioning false binaries. What if it is not either or? Not success or failure, not staying or leaving, not responsibility or wellbeing. Mid career pressure thrives on these narrow choices. When they are questioned, complexity is allowed back in and new options begin to emerge.

From there, the conversation becomes more practical. In real terms, how might you carry this responsibility in a lighter way? Not by dropping it, but by changing how it is held. This might mean clearer boundaries, shared leadership, or redefining what good enough looks like at this stage of life.

The deceptively simple question what could you do shifts the focus from rumination to agency. And asking what difference that might make brings the attention back to the human being beneath the role, not just performance or outcomes, but sustainability.

Mid career is not only about what you can carry. It is about how long you can carry it, and at what cost. Sometimes, the most responsible thing a leader can do is learn to carry their responsibility more lightly.