Heading into the Unknown: A CIO’s Personal Journey from Corporate Life to New Horizons

Early Realizations and the Tech Paradigm Shift

As I transitioned into a leadership role in IT, I observed a striking paradox: the more crucial technology became to business, the more the traditional role of a corporate IT Director was being questioned. For years, I served as an IT Director (Chief Information Officer, or CIO) in a large enterprise with a 30-person team under me. From this vantage point, I experienced first-hand the power and pitfalls of the corporate IT world.

On one hand, the CIO role promised authority, status, and a handsome salary. We commanded significant budgets and spearheaded major projects. Technology was clearly emerging as a central business driver, not just back-office support. A 2021 IBM Institute for Business Value (IBV) study even revealed that CEOs now recognize CIOs and CTOs as crucial strategists—twice as often as CMOs or CHROs (Исследование IBM: ИТ-директора укрепляют свое влияние в компаниях по мере роста значимости информационных технологий – CNews). This wasn’t the case a decade ago, indicating a newfound respect for IT leadership.

Yet, ironically, many CIOs find themselves frustrated and disillusioned. The same study highlighted that CIOs often face internal silos and a struggle to influence broader strategy. The responsibilities are huge, but the traditional corporate environment can reduce a CIO to a “professional router” or glorified office plankton, as some critics colorfully put it. Over time, I began to feel this personally—like a cog in a huge machine, dealing more with bureaucracy than innovation.

Why was this happening? Part of the answer lies in how fast technology evolves versus how slowly corporate culture adapts. We tech leaders are expected to keep operations humming 24/7 and troubleshoot crises, but also to drive digital transformation and growth. During the pandemic, for instance, IT departments became heroes overnight, deploying remote work infrastructure and AI-driven processes to maintain business continuity. Suddenly, every process from HR to sales relied on us in ways never before imagined.

However, post-pandemic, as things settled, many companies reverted to old habits. IT leaders like me saw projects stall due to bureaucracy, risk aversion, or the infamous “analysis paralysis” in decision-making. We had to push for automation and AI (37% of CIOs globally say process automation is their top opportunity) and adopt hybrid cloud architectures (CIOs reporting mature hybrid cloud usage jumped 7x in just two years). But getting a giant corporation to change course is slow and exhausting. I sometimes felt like a firefighter always on call, yet never truly shaping the fire code.

The Great Reshuffle: Why Stay When You Can Grow?

By 2019, I noticed a trend: top talent leaving even “dream companies”. At Facebook, for example, engineers like Pedram Keyani left because rapid growth made them yearn for smaller, more innovative environments. This echoed what I saw in my network—brilliant IT managers quitting stable jobs to join startups or pursue their own ventures. The media started calling it “The Great Resignation”, but it was more of a Great Reshuffle. Why were they leaving?

1. A Search for Impact and Learning: As Keyani noted, at some point “dream jobs” aren’t lifelong dreams. Talented people want to keep learning and building new things. In large corporations, roles can become so specialized or bogged down by internal politics that learning plateaus. Many of my peers felt, “If I stay here, in 5 years I’ll still be doing the same thing.” For an IT leader in a fast-moving tech landscape, that’s a frightening thought.

2. Burnout and Pandemic Priorities: The COVID-19 pandemic accelerated these reflections. People started re-evaluating life and work priorities. Some realized they wanted more family time or to start a passion project. Surveys showed that nearly 1 in 4 workers planned to change jobs in 2021, often citing the need for flexibility. In fact, Gartner research revealed that almost 40% of the recent spike in resignations was due to the rise of remote work – employees realized they could find new jobs without uprooting their lives. Why stay in a less-than-fulfilling job when a better one might be a Zoom call away?

3. Corporate Culture Clash: Classic corporate structures can stifle innovation. As a CIO, I often dealt with what I call “executive disconnect.” For instance, an IBV study found only 23% of CIOs expected pandemic-driven remote work changes to stick, whereas 65% of employees wanted remote or hybrid options. That’s a massive gap in perception. Such disconnects lead to frustration on both sides. Employees feel unheard; leadership feels unappreciated.

Many companies assumed offering remote work was enough to retain people – a mistake, as Gartner’s HR chief noted: “If everyone offers remote work, it’s no longer a differentiator”. Employees want more: career growth, purpose, a healthy culture. Ann Mukherjee, CEO of Pernod Ricard North America, put it aptly: “A paycheck is not enough – you have to earn people’s energy”. Modern workers, especially Gen Z, demand environments aligned with their values and lifestyle (in one survey, 65% of Gen Z planned to leave their job within a year in search of something better).

These realizations hit home for me. I prided myself on building a strong IT team, but I saw cracks forming. Talented engineers wanted more autonomy and purpose, not just a stable salary. Retention was becoming as big a challenge as system uptime.

Taking the Leap: My Decision to Leave the Corporate Nest

After 7 intense years as a corporate IT Director, I made the toughest decision of my career: I resigned. I didn’t have another job lined up. I wasn’t starting a new company (not immediately, at least). I simply knew I needed to step out of the corporate shadow to grow further. It felt both terrifying and exhilarating – like jumping off a moving train to catch a faster one on a parallel track.

What spurred this? It wasn’t one single event but a culmination:

• Stagnation Fears: I realized I was spending more time on budgets and hierarchy than on innovation and strategy. The job had gradually shifted from “How can IT transform the business?” to “How can IT cut costs and keep the lights on?” Meanwhile, smaller, more agile companies were racing ahead with cloud, AI, and data analytics – areas I was deeply passionate about.
• Personal Growth: At 40-ish, many professionals hit a mid-career evaluation. I asked myself: In 10 years, what will I regret more – leaving a stable job, or never trying something bold outside this comfort zone? The answer was clear. As Ryan Reynolds (yes, the actor-turned-entrepreneur) said recently, “You can’t be good at something unless you’re willing to be bad. I’ve grown more comfortable with not having all the answers”. In other words, to grow as a leader, I had to be willing to start from scratch, to possibly fail and learn in a new arena.
• Market Trends: The tech industry in 2023-2025 is starkly different from a decade ago. Cloud services, cybersecurity, and data science skills are in tremendous demand. IBM’s research highlights that 120 million workers in major economies may need retraining due to AI and automation in the next 3 years. I saw a chance to reskill and reinvent myself for these emerging areas, rather than cling to a role that might itself need reinventing. Plus, with remote work widespread, I could consult for companies globally or join a startup anywhere without relocating.

And so, I leapt. I informed my CEO of my decision, which was met with surprise and respectful understanding. In fact, by that point, several high-profile CIOs had made similar moves, validating that I wasn’t completely out of my mind. For instance, some CIOs transitioned to advisory roles or startup boards, leveraging their knowledge in more flexible ways.

Lessons Learned: From Corporate CIO to Independent Consultant

The months after leaving were a whirlwind of self-discovery, networking, and upskilling. It felt like being 25 again, but with the wisdom (and savings account) of a 40-year-old. Here’s what I learned:

1. Trust the People You Hire – Even If That’s No Longer You

One of the best pieces of leadership advice I ever got was: “If you hire someone for their expertise, give them the freedom to use it.” As an IT Director, I sometimes struggled to let go – a common pitfall known as micromanagement. Sean Brown, CEO of GO VC, rightly said that trying to involve yourself in every daily task is counterproductive.

When I left my company, I had to practice what I preached. I trained a successor and trusted my team to carry on without me. It was humbling to realize the company could survive (even thrive) when I stepped away – proof that empowering your team actually works. Micromanagement isn’t scalable, and leaving made me confront that fully. In your own ventures or teams, hire smart people and trust them; it’s the only way to truly scale any endeavor.

2. Communication is Everything – Internally and Externally

In chaotic times (like a reorg or a pandemic), I learned the critical importance of a communication strategy. As Katie Murphy of Expansion Group emphasized, you often need to repeat messages multiple times and brace for things to get worse before they improve. During the pandemic, our IT team had to assure staff over and over that remote systems were secure and reliable.

Now, on the outside advising companies, I stress this: Don’t just plan the change, plan the communication around the change. This means transparency with employees (even if they’re not all ready for it) and clear messaging to customers. For example, when shifting a service online, inform users early, often, and empathetically. If you think you’re over-communicating, you’re probably doing it just right.

Internally, I also advocate for better CIO-CTO collaboration. IBM’s study found only 40% of CIOs frequently interact with their CTOs, yet such partnerships can yield huge benefits. In my corporate role, building a bridge with engineering and R&D leaders was essential to break silos. Now, as an outsider, I sometimes act as that bridge – facilitating conversations that didn’t happen naturally within the hierarchy.

3. Embrace Flexibility – The Workforce Has Changed

One big change from my early career to now is how non-linear careers have become. It’s normal for someone to go from a big company to a startup to freelance to another big company in a decade. Skills matter more than titles. Remote work has broken down geographic barriers; a talented developer in a small town can contribute to a Silicon Valley firm without moving.

As a leader, you either adapt to this flexibility or lose talent. I counsel businesses to offer more than just money – things like career development paths, mentorship, and yes, remote or hybrid work options. The war for talent is now global and 24/7. Remember, 83% of CIOs rolled out remote work, but many employees will bolt if forced back into rigid structures. I’ve helped some clients implement “Work from Anywhere” policies, learning from companies like Airbnb and Atlassian that went all-in on distributed teams. The results? Often, happier employees and access to a wider talent pool.

4. Values and Purpose – The North Star for Future Success

When you strip away the corporate trappings, you confront your core values. Why do I do what I do? I realized I find the most joy in solving problems and helping others grow. This guided the projects I took on after leaving. I collaborated with a non-profit on a data project, joined a startup as a part-time advisor, and even mentored an aspiring CIO. In each case, I checked: Does this align with my values of innovation, learning, and integrity?

For organizations, I can’t emphasize enough how vital it is to define and live by your values. As Evelyn Webster, CEO of SoulCycle, noted, clearly defining “the company we strive to be and the behaviors required to support that” is key. Whether it’s customer-centricity, inclusivity, or agility, having that North Star guides decision-making in crises and attracts like-minded talent.

One pleasant surprise: stepping out allowed me to work with companies that matched my values. Inside a big corporation, you can sometimes feel at odds if the culture isn’t a fit. Outside, you can choose your partners. It’s like switching from an arranged marriage to dating – the freedom to seek a better match culturally was liberating!

5. Be Ready to Not Know – and Learn Fast

In my corporate life, I was expected to have answers. As a consultant and free agent, I’ve gotten comfortable saying “I don’t know, but I’ll find out.” Technology doesn’t sit still; I’ve taken courses on cloud architecture and AI to keep up (earning certifications I never had time for before). Ryan Reynolds’s leadership advice about admitting what you don’t know resonates deeply with me. It builds trust in teams and clients. No one can be an expert in everything, especially in IT where a new framework or threat appears weekly.

The key is to cultivate a learning mindset. I now block a few hours each week just for learning – whether it’s reading Gartner reports on cybersecurity or experimenting with a snippet of Python code for automation. This habit ensures that even outside a corporate ladder, I’m climbing a learning ladder.

Embracing the Future: A New Chapter with Old Wisdom

Today, I split my time between IT consulting, writing (hence this blog), and coaching new tech leaders. It’s a portfolio career I wouldn’t have imagined for myself 10 years ago. Do I miss the corporate world? Occasionally, I miss the scale and resources – it’s easier to push a big boulder when you have a big team. But I’ve found that with the right network and mindset, you can assemble “virtual teams” for almost any challenge, pulling in experts as needed. The world is far more connected now.

In fact, professional communities and networks (think International Coaching Federation for leadership coaching or ICC’s business networks for global insights) play a huge role in my work now. I regularly tap into groups like the International Chamber of Commerce (ICC) for the latest on global business trends and the ISO standards for IT governance to advise clients. It’s like I left one organization and joined a hundred others.

To my fellow CIOs or would-be CIOs reading this, a few parting thoughts:

• Your influence is growing – use it wisely. The data is clear: technology is now core to every business’s success. Leverage that to champion not just tech upgrades, but cultural upgrades in your org. Be the voice for agility, ethics in AI, or upskilling employees, not just the person who fixes Wi-Fi issues.
• Don’t fear the fork in your career path. Whether it’s an offer to join a startup, move to a different industry, or take a sabbatical to re-skill – trust your gut. Ten years from now, the IT landscape will be different again (quantum computing? hyper-automation?). The best skill you can have is the ability to adapt.
• Invest in people. Build teams that can lose together, not just win together. The support in tough times is what builds trust for the long run. And invest in yourself like a company would – training, mentorship, even therapy or coaching. A burnt-out CIO helps no one.

Writing this in 2025, I can say stepping away from corporate life was the right move for me. I rediscovered the joy of tech and leadership on my own terms. And interestingly, corporations now approach me for advice – life has come full circle! Perhaps that’s the ultimate takeaway: if you stay true to growth and values, your expertise will never go out of demand.

As we forge ahead into an uncertain but exciting future, remember that leadership is not a title but a mindset. Whether you’re a corporate CIO, a startup CTO, or an independent consultant, the real job is the same: make things better, for people and business, through technology.

Sources:

• IBM Institute for Business Value Study on CIO Influence (2021) (Исследование IBM: ИТ-директора укрепляют свое влияние в компаниях по мере роста значимости информационных технологий – CNews) – showing the rising strategic role of CIOs.
• Kathryn Guarini (IBM CIO) on post-pandemic IT leadership – emphasizing breaking down silos and driving innovation.
• Gartner Research via Business Insider – attributing ~40% of elevated turnover to remote/hybrid work enabling easier job changes.
• Entrepreneur Magazine (Nov 2021) – “Best Leadership Advice of 2021” featuring Sean Brown, Katie Murphy, Ann Mukherjee, Mita Mallick, Adrian Hallmark, Evelyn Webster, Maria Sharapova, Ryan Reynolds, Ross Franklin. These provided insights on trust, communication, purpose, humility, and action-oriented leadership.
• Business Insider (Feb 2022) – on Gen Z and Great Resignation, highlighting younger workers’ quest for meaningful work and flexibility.
• IBM SkillsBuild and Training Survey (2023) – noting massive global reskilling efforts due to tech advances, underlining the need for continuous learning.
• CNews (2018-2021) – Russian tech media coverage giving context on IT Directors’ roles and challenges in corporate settings, and local perspectives on global trends.