Will I Still Matter When I'm 66?

In 2003, Greg Jackson asked a question that echoed in my mind for years: "Will you still need me when I'm sixty-four?" I was thirty-five at the time, stepping into my first CIO role and unsure of my footing, but convinced that Jackson had captured something essential about the work ahead.^Footnote1 It wasn't about the technology itself but, rather, the question behind the question: What does it mean to matter as a technology leader when success makes you invisible?

Four years later, I tried to answer that question myself in the article "A Roadmap for IT Leadership and the Next Ten Years."^Footnote2 I argued then that the true challenge facing CIOs wasn't technical, it was cultural. The job was shifting from managing mechanics to delivering strategic value in an overall climate that is sometimes hostile to higher education. CIOs needed to stop thinking in terms of infrastructure and start thinking in terms of institutional impact. It felt radical at the time. Now, it feels like table stakes.

I'm fifty-six now. The world has changed again, and so has the job. Artificial intelligence has entered the stage, not as a tool but as a provocateur, challenging what we believe about authorship, learning, and trust. Economic uncertainty shadows every budget cycle. The once-steady cadence of higher education has given way to something more fragile, more contested. The CIO, once the translator between technology and mission, is now asked to do something more challenging: help the institution find its way through immense ambiguity.

Which brings me back to Jackson's question, but this time, it's mine: Will I still matter when I'm sixty-six?

I'm not asking because I'm worried about relevance. I've never believed our worth is measured by how many tools we deploy or vendors we manage. I'm asking because I believe leadership, at its core, is a moral act. And I want to spend the next ten years practicing a kind of leadership that doesn't just sustain institutions, but prepares them for disruption, reinvention, and grace under pressure.

From Jackson's Challenge to a Leadership Philosophy

When Greg Jackson asked whether the CIO would still be needed at sixty-four, he wasn't questioning our technical relevance. He was inviting us to reckon with something deeper: What happens to our profession when the infrastructure we manage fades into the background?

I took that question seriously, not as a challenge to defend the role but as a provocation to redefine it. If technology leadership would be measured not by uptime but by impact, then the real task wasn't to protect the servers, it was to align systems with the soul of the institution. That belief guided my work for decades. At Pepperdine, it meant implementing a new enterprise resource planning system not only as a technical upgrade but as a realignment of human processes, where project meetings fostered leadership development and collaboration became ingrained in the institutional culture. At the University of Georgia, it meant grounding digital transformation in teaching, research, and public service, enabling faculty, staff, and students to do their best work, not despite the new systems but because of them.

When the pandemic hit, that philosophy became our foundation. We didn't respond with panic. We responded with presence. Our teams didn't just shift operations online; they shifted posture: steady, empathetic, and agile. This shift was possible because the groundwork had already been laid through years of hiring for mindset in addition to skill set, building cross-functional trust, and leading with clarity in both good times and uncertain ones. The result wasn't just operational continuity; it was renewed institutional confidence reflected in our annual IT survey. Faculty satisfaction scores have reached their highest levels ever in the years following the pandemic.

That's the quiet throughline of my career: the belief that leadership is about preparing others to thrive, not just while they report to you but long after your tenure ends. It's the conviction that technology should never be center stage, but it should make center stage possible. And it's the understanding that the CIO is most valuable not when they are the hero but when their team becomes indispensable to the institution's most critical and strategic work.

So, when I think about the next ten years, the path from fifty-six to sixty-six, I don't wonder whether I'll still matter because of the tools I understand or the trends I can name. Now, I ask a different question: How do I prepare others to matter long after I'm gone?

That, more than any platform or project, will be the measure of my leadership.

The Real Work Ahead

If the first act of our profession was to digitize institutions and the second act was to align operations and inform them strategically, then the next act is to humanize how institutions engage with systems, data, and decisions.

For CIOs, the heavy lift is no longer wiring campuses or standing up infrastructure; it's making the complex coherent. What's ascendant now isn't the machinery, it's the meaning. The best CIOs will be those who help their institutions carry out this new work with competence, cultural intelligence, and institutional loyalty.

Here's where that leadership is needed most:

Simplifying Work

Higher education still suffers under the weight of layered processes, legacy logic, and well-meaning bureaucracy. For too long, institutions have mistaken redundancy for rigor and complexity for competence. The job of a CIO is not simply to automate that complexity; it's to question it. Simplifying work means streamlining workflows, eliminating friction, and designing systems that serve people, not just policies. The goal is clarity rather than efficiency for its own sake. But this work can't happen in isolation. It must be done with teams and in dialogue, as a form of organizational healing and shared understanding. When simplification is relational as well as technical, it becomes sustainable and transformative.

Protecting the Institution

Cybersecurity is no longer just about firewalls and risk; it's about trust. It sits at the intersection of infrastructure, compliance, and institutional confidence. The CIO must become the person institutional leadership turns to when the threats are invisible and the stakes are high. That requires technical readiness, yes, but also public credibility. Protecting the institution means more than securing systems; it means protecting reputation, continuity, and the moral obligation we have to our communities. CIOs must continue to build a strong technical posture, but they must build relationships even faster. They must be the calm, strategic voice in a crisis and the thoughtful guide when the next safeguard is needed.

Making Data Useful

Data is everywhere. Insight is not. The CIO's job is to close that gap, not only by managing infrastructure but by shaping culture. That means building systems that prioritize coherence, governance, and usability. But more than that, it means fostering a climate where data isn't hoarded but shared; where the questions are just as clear as the dashboards that follow. CIOs must lead the effort to make data trustworthy, accessible, and actionable. They must teach the institution not only how to read reports but how to ask better questions. Because when data becomes a shared language, decisions get better, and trust runs deeper.

Connecting the Ecosystem

In today's cloud-first environment, the real challenge isn't building systems. The real challenge lies in making them work together. Integration today involves more than aligning APIs; it requires aligning people, processes, and purpose. The CIO must serve as the institution's chief integrator, bringing together tools, logic, and trust. That includes navigating vendor contracts, shadow IT systems, user expectations, and institutional politics. Integration is no longer just a technical milestone: it's a leadership function, a form of institutional sensemaking that enables coherence across a fragmented landscape.

Driving Adoption That Sticks

Every institution today is a federation of software providers. The CIO must be both a buyer and a portfolio strategist. That means managing a growing constellation of tools in ways that align with the institutional mission, reduce redundancy, and foster real adoption. Most technologies don't fail because they're flawed. They fail because they're abandoned after implementation. Driving lasting adoption requires care. It requires user-centered design, intentional rollout, continuous support, and feedback loops that evolve the solution over time. CIOs don't just manage compliance and contracts; they cultivate behavior. Transformation does not happen when a tool goes live. It happens when a tool becomes part of how people work and trust the systems around them.

Beyond the Systems

Greg Jackson's question, "Will you still need me when I'm sixty-four?" wasn't just about job security. It was about relevance. Would CIOs matter once the pipes were built, the systems were stabilized, and the infrastructure was invisible? CIOs put this question to rest by leading digital transformation efforts: implementing faster, mobile, cloud-based systems that have moved institutions from paper to portals and from desktops to data centers. IT mattered, but now that chapter is closing.

The next chapter isn't about what we, as CIOs, build. It's about how we lead and whether we can build teams and relationships that others see as indispensable to the most critical missions of our institutions.

There will always be technical work to do: data warehouses to modernize, APIs to align, and applications to integrate. But with more infrastructure offloaded to the cloud, the technical footprint is shrinking while the leadership footprint is expanding. The real work now lies in helping systems speak to each other and in helping people understand what to do with the insights they gain.

The CIOs who will matter most in the next decade won't just manage technology. They will be the ones who are trusted to move their institutions forward, not alone and not through hierarchy, but through presence, partnership, and purpose. Because that's where the most meaningful work has always been.

Notes

1. Gregory A. Jackson, "A CIO's Question: Will You Still Need Me When I'm 64?"The Chronicle of Higher Education, January 30, 2004.Jump back to footnote 1 in the text.↩
2. Timothy M. Chester, "A Roadmap for IT Leadership and the Next Ten Years,"EDUCAUSE Review, April 28, 2006.;< Jump back to footnote 2 in the text.↩

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Timothy M. Chester is Vice President for Information Technology at University of Georgia and Vice Chancellor for Information Technology at University System of Georgia.