The result is a career built largely by accumulation, roles added, responsibilities expanded, titles earned, without a coherent internal logic connecting who you are to what you're building.
I've developed three questions that cut through the noise. They're not comfortable. The professionals who've worked through them honestly have found more clarity in a single conversation than in years of career management on autopilot.
What have you been doing that energizes you, and what have you been avoiding because it's uncomfortable rather than wrong?
Most people can answer the first half of this question quickly. The second half takes longer. The things we avoid because they're uncomfortable, not because they're actually bad ideas, wrong for us or misaligned with our values, are often the precise locations of our most important growth. When a professional tells me they've never applied for a stretch role, never spoken up in a meeting where they felt underprepared, never proposed an idea they weren't certain would be received well, I know exactly where their reinvention needs to begin.
If you measured your career by significance rather than success, what would you change tomorrow?
This question is borrowed from decades of coaching leaders who've reached conventional success and found it hollow. John Maxwell's distinction between success and significance is not merely philosophical. It has practical implications for every decision you make about where to spend your time, energy and attention. The answer to this question often reveals what people have been quietly waiting for permission to pursue.
Who depends on you to stay exactly as you are, and is that dependence serving them or protecting you from change?
This is the question most people have never asked themselves. The people around us, colleagues, teams, organizations, often have a vested interest in us remaining predictable. We've been typed and everyone has adjusted to that version of us. Sometimes those relationships are genuine and should be honored. But sometimes what looks like responsibility to others is actually avoidance of the discomfort of becoming someone new.
The professionals who successfully reinvent, on their own terms, in directions that matter to them, are almost always people who've asked and answered these questions honestly. Not once, in a career-planning session, but repeatedly, as a practice.
What got you here will not automatically get you there. The question is whether you're thinking clearly enough about the difference.
📌 Reinvention Summit — June 13, 2026 | Courtyard Marriott, Cary, NC — Ready to stop adapting and start leading your own reinvention? Join Glenn Llopis live. To learn more and register, visit www.reinventionchallenge.com.