“If you’re wrong, no one cares. But if you’re right, everyone will pay attention.”

These words from a former deputy business editor at the Daily Telegraph became my professional North Star during one of the most intense periods of career risk-taking.

It’s advice that flies in the face of conventional wisdom, which typically encourages us to follow established patterns, avoid unnecessary risks and never turn down prestigious opportunities.

But what if the most rewarding professional choices often come from thoughtful career risk-taking and ignoring the well-travelled path?

Swimming against the media current

When I launched Director of Finance Online as a challenger brand to established corporate finance media, we faced a seemingly impossible task: how could we compete with institutions like the Financial Times with their vast resources and established credibility?

The answer came in the form of radical contrarianism. While other outlets carefully reported the consensus view, I deliberately looked for opportunities to go against the grain.

This approach – a form of calculated career risk-taking – manifested most dramatically when I spotted a throwaway line in a ‘rumours’ column in the Dutch equivalent of the FT, mentioning that someone had said at a drinks party that an agreement on reconciling US and EU accounting standards would be announced within days.

This wasn’t just another corporate announcement. It represented the potential resolution of years of negotiations that had forced companies operating in both markets to maintain two separate sets of accounts at enormous expense.

Rather than waiting for official confirmation or following the cautious approach of established media, I immediately published the story. Within hours, the Wall Street Journal had picked it up, citing our publication.

We had beaten every major financial outlet to a story of international significance simply by being willing to take a calculated risk.

This became our daily approach. When a FTSE250 company announced a change of CFO, I typically had ten minutes to write and publish an article for inclusion on Google News.

Being first meant making split-second decisions about whether the markets would welcome interest rate decisions or inflation changes. The headlines needed to be bold yet crafted to work regardless of which way sentiment eventually swung.

Sometimes this meant questioning executive appointments by highlighting their troubled histories at previous companies, pushing boundaries that established media wouldn’t touch.

These controversial stories had investor discussion boards buzzing. Long before social media metrics, we were effectively “trending” through sheer editorial boldness.

I didn’t always get it right. Sometimes the FT would report that the City was furious when I’d claimed they were celebrating and vice versa. But the approach generated attention, credibility and a reputation for breaking news that matters, not just regurgitating press releases.

Saying no to prestige, saying yes to self-worth

This same contrarian instinct guided me through perhaps even more consequential career risk-taking decisions: turning down roles that conventional wisdom insisted I’d be “mad” to reject.

McKinsey & Company and the Bank of England both represent the pinnacle of professional prestige in their respective spheres. Having either on your CV opens doors throughout your career.

When both organisations offered me positions, everyone told me I’d be foolish not to accept. But something felt fundamentally wrong.

At McKinsey, after interviewing for a highly skilled operations manager role for a new division, they offered me a generic support position.

Their pitch included assurances about how they “really valued support staff”, even involving them in the recruitment process.

The reality? My “interview” with current support staff involved three young women mechanically reading questions prepared by HR and transcribing my answers without any real engagement. There was no genuine empowerment, just a performance of inclusion.

Similarly, at the Bank of England, despite being keen to hire me, the interviewers were oddly condescending about my skills and experience.

Both organisations made it abundantly clear that working for them was a great honour that would benefit me far more than I would benefit them.

The implied transaction was clear: sacrifice your sense of value for a prestigious name on your CV.

I walked away from both opportunities, despite warnings that I was making a career-limiting mistake. This form of career risk-taking – saying no to prestigious opportunities – is often more difficult than saying yes to uncertain prospects.

In retrospect, those decisions protected me from environments that were never going to value my actual contributions, only my willingness to be associated with their brand.

Leaping into the unknown when it feels right

Effective career risk-taking isn’t always about saying “no.” Sometimes it involves saying “yes” when your instincts tell you to take a leap, even as conventional wisdom urges caution.

A close friend – a futures broker in London – was offered a top position on the New York Stock Exchange in his early twenties.

Overwhelmed by doubt about whether he was ready for such responsibility, he nearly declined the opportunity.

Fortunately, my husband encouraged him to take the risk and accept the role. Years later, when we visited him in New York, he treated us to dinner at that week’s most exclusive restaurant, expensive wines flowing free. It was a thank-you for the advice that transformed his life.

Today, he enjoys an exceptional quality of life with an amazing apartment, fantastic car and substantial income. More importantly, he loves every minute of his professional life in a role he almost convinced himself he wasn’t ready for.

The contrast with my McKinsey and Bank of England experiences is striking. In his case, the prestigious opportunity actually offered genuine value, growth and recognition.

The key difference wasn’t the prestige itself, but whether the opportunity aligned with his authentic professional worth.

Developing your career risk-taking instincts

These experiences have taught me that there’s no one-size-fits-all rule for career risk-taking. Sometimes the road less travelled means boldly stating what others are afraid to say.

Sometimes it means walking away from apparent opportunities. Other times it means accepting challenges you don’t feel ready for.

The common thread is developing the critical thinking skills to evaluate opportunities based on their actual value rather than their perceived prestige or conventional attractiveness.

Here’s how I’ve learned to navigate these decisions:

• Question the consensus
  When everyone agrees on something – whether it’s how a market will react to news or whether a job opportunity is “too good to refuse” – that’s precisely when you should be most skeptical. Consensus often reflects groupthink rather than careful analysis.
• Assess value exchange honestly
  Ask yourself: “In this relationship, am I being valued for my actual contributions, or merely for my willingness to be associated with this brand?” Prestigious organisations often expect gratitude merely for allowing you to work with them, which creates fundamentally imbalanced professional relationships.
• Listen to physical reactions
  Your body often recognises a poor fit before your mind can articulate it. That feeling of unease during my interviews at McKinsey wasn’t just nervousness; it was recognition that something wasn’t aligned with my values.
• Weigh opportunity costs realistically
  Saying yes to one path means saying no to countless others. The true cost of accepting a prestigious but ill-fitting role isn’t just potential unhappiness. It’s all the better-aligned opportunities you’ll miss while there.
• Build financial resilience
  The ability to say “no” to prestigious but problematic opportunities often depends on having enough financial security to weather periods of uncertainty. Building even a small financial buffer creates the freedom to make decisions based on values rather than immediate necessity.
• Assemble trusted contrarians
  Cultivate relationships with people who think differently and aren’t impressed by conventional markers of success. My former deputy business editor colleague provided perspective that cut through industry groupthink, while my husband could see my friend’s potential when he couldn’t see it himself.
• Embrace calculated career risk-taking
  The key word is “calculated”: effective career risk-taking should be based on insight and analysis, not mere rebellion. My Director of Finance Online scoop on accounting standards was a risk, but one based on connecting dots that others hadn’t yet linked.
• The value of the divergent path
  Looking back on these experiences, I’m struck by how often the most valuable career moves involved strategic career risk-taking and taking the road less travelled, whether that meant challenging media conventions, walking away from prestigious brands or encouraging someone to leap into an opportunity they feared.

The pressure to follow established paths is immense. We’re constantly told which opportunities we’d be “mad to turn down” and which risks are “too great to take.” But these conventional wisdom frameworks often fail to account for individual contexts, values and insights.

Sometimes the greatest risk isn’t in career risk-taking itself. It’s following the well-trodden road simply because everyone else is on it.