The Power of the Thankless Job

Why the roles others avoid often create the greatest opportunity

At several critical points in my career, I accepted roles that others actively avoided.

They were seen as low-prestige, high-stress, and offering little upside. In some cases, even touching the problem felt like grabbing a live wire. Most people advised me to stay away.

In retrospect, those decisions were among the most valuable I ever made.

A Role No One Wanted

When I was offered the HR leadership role at Pitney Bowes by CEO George Harvey, nearly every senior leader I consulted urged me to decline. They saw it as a thankless job, highly visible when things went wrong, but unlikely to create a path to broader leadership. They advised me to wait for a more traditional operating role.

Two people saw it differently.

My father-in-law, an experienced outside counsel to a public company, viewed the role as a developmental opportunity. My father, who had left school at age 14 during the Great Depression, gave even more pragmatic advice: the CEO would be grateful to someone willing to take on a difficult problem, and the job would likely be secure and well-compensated precisely because others did not want it.

I accepted.

What I Learned

That decision revealed a counterintuitive truth that shaped the rest of my career and life: When a role is viewed as unattractive or risky, it often comes with fewer competitors, less interference, and far greater freedom to act.

In other words, the very factors that make a job “thankless” can make it uniquely powerful.

I was not viewed as a contender for the CEO role, and I was not behaving like one. As a result, no one was working hard to stop me. That gave me room to focus on doing the job exceptionally well.

Over time, we redefined key aspects of the HR function, particularly in how we approached employee health, benefits, and engagement. The company had been investing heavily in benefits, but those investments were increasingly viewed as entitlements rather than drivers of performance or commitment. That disconnect created both a challenge and an opportunity.

Because the issues had reached a level of urgency, my freedom of action was far greater than it would have been in a more stable or prestigious role.

Three Principles of “Thankless” Opportunity

Looking back, I have come to recognize three patterns that distinguish thankless jobs worth embracing from those best avoided.

High-Impact Problems Create Asymmetric Opportunity

The best thankless roles sit at the center of problems that matter.

At Pitney Bowes, rising healthcare costs and declining employee engagement were not peripheral issues. They were fundamental to the company’s long-term performance. Addressing them required rethinking the implicit contract between the company and its employees.

When a role gives you the chance to influence outcomes at that level, the potential upside far outweighs the perceived downside.

Neglected Roles Offer Freedom

Prestigious roles attract attention, competition, and second-guessing. Thankless roles often do not.

That lack of attention creates space to experiment, to act, and to lead without constant interference. When expectations are low or unclear, performance that might be considered incremental elsewhere can be transformative.

One of the most important advantages I had in that HR role was simple: no one was working hard to stop me.

Proximity to Reality Beats Prestige

As General Counsel, I had a broad view of the company but was often brought into decisions after key directions had already been set. In HR, I was embedded much closer to the flow of the business.

To do the job well, I had to understand the economics of each business unit, the challenges faced by front-line employees, and the informal networks that shaped how work actually got done. Our employee and labor relations teams were particularly valuable in surfacing the cultural dynamics that formal reporting often missed.

This proximity to reality provided insights that no executive committee presentation could replicate.

A Pattern That Repeats

Decades later, I have seen the same pattern play out in very different contexts.

In Naples, Florida, I joined my condominium association board at my wife’s urging, ,a role many people describe as the ultimate thankless job. I was elected president by my fellow board members.

During my tenure, we faced challenges unlike anything in the property’s 50-plus-year history: transitioning to professional management, navigating new structural and financial regulations, rebuilding after multiple hurricanes, upgrading infrastructure, and addressing rising insurance and tax pressures.

None of these issues were easy. All of them were necessary. The role demanded time, persistence, and difficult decisions. But it also offered something else: the opportunity to make a meaningful difference in a community that mattered to me.

At the end of that period, a group of owners funded and installed a plaque in our lobby expressing their gratitude.It was not something I expected. But it reinforced the lessons I had learned decades earlier.

Where the Real Opportunities Are

The roles that look least attractive on the surface often offer the greatest opportunity to learn, to lead, and to create lasting impact.

They are the places where problems are unsolved, expectations are unclear, and competition is limited. They are also the places where initiative, judgment, and persistence can matter most.

In a crowded field, most people compete for the same visible opportunities. But great careers are often shaped elsewhere: in the roles others choose not to take.