Aaron Green’s pivot began after decades of nonstop work in the HCM technology industry. Over more than twenty years, including leadership roles at Oracle and SAP, he built a reputation as a strong sales leader. One of his biggest pivots came in 2022 when he moved from Chief Revenue Officer for SAP SuccessFactors in Asia Pacific and Japan into the global Chief Marketing Officer role.

The move stretched him professionally. Aaron came from sales leadership and suddenly found himself leading a global marketing organization while simultaneously learning the discipline itself. He embraced the challenge because he wanted growth and change.

But the pace of work had become unsustainable. By 2024, the combination of relentless travel, long workdays, and constant pressure had taken a serious toll. Aaron describes himself as severely burned out. He had already taken two months away from work earlier that year to recover, but he realized burnout was not something that could simply be fixed with a vacation. “Burnout isn’t something that you just sleep off,” he reflected. His physical and mental health were deteriorating, and he recognized that he was no longer leading at his best.

At the same time, he had trained a successor who was ready to take over. Personally and professionally, the moment felt clear. After working continuously since he was nineteen years old, he decided to step away from corporate life altogether.

What was his transition process?
Aaron approached his transition intentionally. Before leaving SAP, he created a financial plan that would allow him to step away for up to two years. He committed that during the first year he would reject every work opportunity that came his way.

He knew he needed more than rest. He needed recovery.

The first year became a deliberate period of reconnection. He focused on reconnecting with himself, his family, and his friendships. He traveled extensively, but without the frantic pace of business travel that had dominated his life for years. He stopped drinking. He focused on his health. For the first time in his adult life, he was not optimizing for productivity or career advancement.

Mental health became central to his reflection process. Aaron had long been passionate about mental health advocacy, especially for men, through nonprofit work in Australia and New Zealand. But burnout made the issue deeply personal. He began recognizing how much modern work culture, especially in tech, rewards unsustainable behavior.

He became increasingly critical of the “996” mentality spreading through parts of the technology industry, the expectation that employees work from 9 a.m. to 9 p.m., six days a week. Aaron no longer wanted a career that came at the expense of his health.

During the second year, his questions shifted. Instead of simply recovering, he began asking what kind of work and life would actually fit who he was becoming.

What is his current direction?
Aaron’s next chapter has emerged in a way he never expected. A trusted former colleague reached out unexpectedly through a WhatsApp message about a Chief Operating Officer role with a smaller healthcare technology company based in London.

Almost everything about the opportunity represents another pivot. The company is far smaller than prior employers. The industry is healthcare rather than HCM. The role is COO rather than CRO or CMO. The geography is different.

Yet the opportunity aligns closely with what Aaron discovered matters most during his time away: one country, one time zone, a more balanced culture, and work that feels more purposeful and meaningful.

Rather than chasing status or scale, Aaron is prioritizing balance, purpose, and sustainability. For someone who once measured success largely through achievement, this is a profound pivot.

What advice does he offer others?
Take the time: “Don’t wait until the end of your career to live.” Aaron credits this advice from mentor Row Henson as foundational to his decision to step away. He realized many people postpone relationships, health, travel, and self-discovery until retirement. But that later is never guaranteed.

Return to your reason: Aaron encourages people to keep returning to the reason they entered the “messy middle” in the first place. Fear inevitably appears during transitions. People worry about employability, financial responsibility, or losing momentum. But if the original reason for stepping away still feels true, then the discomfort may simply mean you are still in the process of becoming ready for what comes next.

Discomfort isn’t failure: Aaron believes many people misinterpret uncertainty as a sign they are making the wrong decision. His experience taught him that discomfort is often part of recovery, reflection, and growth.

Ignore projected fears: One of Aaron’s strongest insights is that much of the pressure people feel to return quickly to work is often other people projecting their own fears onto them.

Think beyond titles: Aaron often asks himself a deeply reflective question: What do you want your epitaph to be? For him, the answer is no longer tied to a title or industry. He wants his life to stand for more than professional achievement.

And for the first time, he seems to be building a life that might actually allow that to happen.