Career Moves Leaders Regret Rarely Look Dramatic in the Moment
This quiet stretch as the new year starts to ramp up is when many people start thinking differently about their careers.
Not in a goal-setting way.
More in a looking back way.
It’s when questions surface gently:
- Should I have handled that differently?
- Why did I wait so long to act?
- What might have changed if I’d trusted myself sooner?
When leaders reflect honestly, the career moves they regret aren’t usually bold risks they didn’t take. They’re quieter choices—moments they let pass because it felt easier to stay put.
Key Takeaways: What people most often regret about their career decisions
- Career moves leaders regret are usually about confidence, not effort
- Waiting too long to ask for feedback can quietly stall growth
- Avoiding support often leads to isolation, not independence
- Strong careers are built through trust in leadership, not solo performance
The Career Decisions Leaders Most Often Regret Waiting On
Waiting Too Long to Speak Up
Many leaders look back and realize they had good instincts long before they trusted themselves.
They stayed quiet in meetings. Deferred when they had a point of view. Waited until they felt “ready.”
What they often regret isn’t caution — it’s how long they stayed on the sidelines.
Confidence at work doesn’t appear all at once. It’s built by using your voice imperfectly and learning from what happens next. The best ideas and decisions rarely arrive fully formed. They emerge through feedback, discussion, and iteration.
Waiting too long to speak up can quietly delay visibility and influence. Speaking earlier doesn’t lock you into a position — it brings you into the process.
Guessing Instead of Asking for Feedback
One of the most common career growth decisions leaders regret is trying to figure everything out alone.
Guessing what others think.
Guessing how you’re perceived.
Guessing what “good” looks like.
Over time, this creates distance. To others, your guesses may look like assumptions, and too often, your assumptions won’t match what others see. Eventually, it can weaken trust in leadership and limit learning.
Leaders who reflect on this regret often see it clearly: asking for feedback earlier would have helped them course-correct faster, build stronger relationships, and avoid unnecessary missteps.
Pushing Through Instead of Getting Support
Many high performers pride themselves on resilience.
They push through stress. Figure things out on their own. Handle more than they should — quietly.
What they regret later usually isn’t the effort. It’s the isolation. Keeping their head down and doing a lot of work can feel honorable, but it can also lead to a lack of visibility. People see you as more of an individual contributor than a leader.
Getting support earlier — through mentors, peers, or coaching — creates perspective, alignment, and momentum. Pushing through alone often slows career growth decisions more than leaders realize.
Managing Tasks Instead of Learning to Manage Relationships
Early success often comes from execution.
Later success depends on relationships.
Leaders frequently say they wish they had learned sooner how to:
- Build trust across teams
- Navigate difficult conversations
- Collaborate instead of carrying everything themselves
Strong results rarely come from individual effort alone. They come from shared ownership and trusted relationships.
Not Volunteering for the Difficult Assignment
Many leaders can point to one project they avoided because it felt risky, visible, or uncomfortable.
In hindsight, they see it clearly: that project would have stretched their confidence and skills, expanded their judgment and network, and changed how others saw them.
Career moves leaders regret often involve underestimating themselves—and waiting for certainty that never arrives.
What These Regrets Have in Common
Most people don’t regret a lack of effort.
They regret:
- Not building confidence earlier
- Ignoring the perspectives of others
- Failing to invest in trust and real collaboration
- Trying to do everything alone
Career growth decisions are shaped less by hustle and more by the clarity that comes from self-reflection in leadership.
Clarity changes trajectories faster than hustle.
Keep Learning
Career growth is closely tied to confidence and managing yourself and trust and building teams. Leaders who invest in these skills tend to move forward with greater ease, visibility, and impact over time.
- Explore Confidence at Work: How to Build It and Why It Matters
- Explore Why Trust in Leadership is The Fastest Way to Improve Team Performance
FAQs
What career moves do leaders regret most?
Career moves leaders regret most often involve waiting too long—hesitating to speak up, delaying feedback, avoiding support, or underestimating their readiness for bigger challenges.
Why do confident leaders make different career growth decisions?
Confidence at work allows leaders to act earlier, seek input, and take thoughtful risks. This leads to better career growth decisions over time.
How does trust in leadership affect career growth?
Trust in leadership enables stronger relationships, better collaboration, and increased visibility—factors that significantly influence long-term career progression.
