Who's Really Afraid of Taking Risks?
We keep telling people to be brave
Career advice has become almost synonymous with courage. We encourage people to apply for the stretch role, speak up in meetings, leave their comfort zone, and bet on themselves. We celebrate those who embrace uncertainty because we believe that growth lies on the other side of it.
But somewhere along the way, I’ve started wondering whether we’ve been asking the wrong side to be courageous.
What if the bigger question isn’t whether people are willing to take risks? What if organizations have quietly become the most risk-averse players in the room?
When did certainty become the goal?
Today’s hiring landscape often feels like a search for certainty. Many organizations look for the perfect CV, the exact number of years of experience, the right degree, the right industry, the ideal job title, and a career path that mirrors the role almost perfectly. Job descriptions sometimes read less like an opportunity to grow into and more like a checklist for someone who has already done the job for years.
I understand why. Hiring is expensive, promotions carry responsibility, and every decision comes with uncertainty. Choosing the “safe” candidate often feels easier to justify than choosing the person who might surprise everyone.
But I wonder whether we’ve started confusing reducing hiring risk with making better hiring decisions. Those are not necessarily the same thing.
More broadly, I wonder whether organizations have become increasingly optimized to avoid making a bad decision rather than maximizing the chance of making a great one.
Experience tells us about the past. Capability tells us about the future.
One of the biggest challenges is that experience is measurable, while potential is not. Credentials are easy to compare, easy to defend, and easy to explain. Capability is much harder to quantify.
A CV tells us where someone has been. It doesn’t necessarily tell us what they are capable of becoming.
Yet many organizations say they are looking for adaptability, curiosity, learning agility, innovation, resilience, and growth mindsets. Those qualities rarely fit neatly into a keyword search or a list of previous job titles.
Perhaps that is why experience so often wins by default. Not because it is always the strongest predictor of success, but because it is the easiest one to defend.
Are we measuring familiarity instead of capability?
Imagine two candidates.
One has spent twelve years in your industry doing almost exactly the same role. The other has spent eight years leading complex transformation initiatives in a completely different industry. They have aligned stakeholders across global teams, navigated ambiguity, influenced without formal authority, built structure where none existed, and consistently delivered results.
The products are different. The regulations are different. The customers are different.
But are the underlying capabilities really that different?
If the role depends on strategic thinking, stakeholder management, problem-solving, communication, and leading through change, perhaps the second candidate is not the riskier choice after all. Perhaps they simply don’t fit the familiar pattern.
How often do we mistake familiarity for capability?
The same question applies beyond hiring.
How often do organizations look for “leadership experience” when what they really mean is someone who has already held the title?
I’ve met professionals who have never officially managed people yet have spent years leading global projects, mentoring colleagues, coaching peers, navigating conflict, influencing senior stakeholders, facilitating workshops, building communities, and driving change across complex organizations.
Have they never led?
Or have they simply never been given the title?
Titles validate leadership. They do not create it.
Every experienced professional was once inexperienced
There is another contradiction that I find difficult to ignore.
Organizations often ask for previous experience before they are willing to create new experience.
But every leader accepted a first leadership role. Every executive presented to a board for the first time. Every project manager managed a first project. Every transformation leader led a first transformation.
None of them could demonstrate experience they did not yet have.
Someone looked beyond what was already proven and decided that potential was worth investing in.
If every opportunity requires previous experience, where is that experience supposed to come from?
Perhaps leadership requires taking risks too
This isn’t an argument for ignoring competence or lowering standards. Some roles genuinely require highly specialized expertise, and experience absolutely matters.
But not every role is won or lost because someone has two more years in a particular industry or one additional certification.
Sometimes the greatest differentiator is a person’s ability to learn, adapt, simplify complexity, build trust, and grow into challenges they haven’t faced before.
Those qualities are harder to measure. They require judgment rather than checklists. They also require courage from the people making the decision.
Perhaps that’s the uncomfortable part.
We often define courageous leadership as making difficult business decisions, navigating crises, or driving transformation. But maybe courage also looks like hiring someone because you believe in their potential, promoting someone before every box is ticked, or trusting someone with an opportunity they haven’t already had elsewhere.
After all, every remarkable career exists because, at some point, someone decided to invest in possibility rather than certainty.
So perhaps the question isn’t whether people are still willing to take risks.
Perhaps the more important question is whether leaders still are.