Redirecting.work
Steve Blechman:
From Role Pivots to Retirement
“I’d keep working as long as it was fun.” For nearly four decades, that simple rule guided Steve across HR technology’s big waves—first as a practitioner, then a consultant, and later at a vendor and also at enterprise levels. At 65, with energy and curiosity still high, Steve made one more intentional turn: a retirement pivot designed for health, family, learning, and the music that has always balanced his life. He gave six months’ notice, tidied up a complex HRTech portfolio at Comcast, and stepped into a new chapter with the same discipline that shaped his career—especially the early advice to “pay yourself first.” Early in, he’s finding his footing, keeping his mind active, and leaving the door cracked for the occasional call to help.
What Did He Pivot From?
Steve’s career began in the early 1990s at Macy's, where he recognized a simple truth: almost no one was using technology to run HR. Seeing an opportunity, he developed a simple database program that automated the critical weekly jobs report. The task of producing that report went from four hours to a press of a button. At Lawrence Berkeley Laboratory, seeing another untapped need, he helped put PCs on desks, introduced email, and helped the department move from green screens to more advanced systems like Resumix and PeopleSoft. These systems became the playground where he learned that technology adoption is as much about buy-in as it is about features.
To deepen his craft, he joined The Hunter Group—immersed in implementations and the “how” of change—with standout customer partners like Mary Ruiz. Leadership roles followed at Towers Perrin and then Princeton University, where he led HRIS for a decade and collaborated with the Ivy Plus cohort just as many were leaping to Workday. Sensing the platform’s significance, Steve made a deliberate role pivot at 56, leaving Princeton to join Workday as a senior consultant—completing a rare 360° vantage point across user, consulting, and vendor. When nonstop travel reminded him why consulting is hard, he moved to Comcast as Director to help drive Workday at enterprise scale. He loved the work—including international M&A—yet learned a big-company reality: late-career advancement can be limited if you didn’t grow up in the organization.
The Retirement Pivot: Why Now
Retirement wasn’t an escape; it was a choice. Steve wanted to focus on his health, travel, be present for an elderly parent, and dive deeper into life outside work—reading, puzzles, music, and continuing to learn new things. His 65th milestone birthday aligned with both personal and professional signals. He staged a thoughtful transition, giving six months’ notice, and stepped away confident in the team he’d developed. Long-standing financial discipline of “pay yourself first,” practiced from age 26, gave him freedom to choose timing and pace, without chasing one more promotion.
Current Direction
This phase is about vitality and connection. Mornings often start in the gym or taking a long walk; afternoons might be books, crosswords, or a matinee. He plays piano weekly with two bands and keeps an active social and family life. He’s also the household’s “chief of staff” while his wife continues working another two to three years. He’s glad to support her passion and mindful not to “have too much fun” while she’s at the office.
Having a learner’s mindset remains central. Steve follows technology and culture through Wired, Axios, and Deep View and is exploring AI’s impact on life and HR. He’s already added The Neuron from my recommendation. He isn’t missing work. But if a former colleague calls about a thorny Workday question or needs a few hours of strategic guidance, he’s open. As he puts it: “I’m done for now, but I’m open to what may evolve.”
Advice to Others Considering Retirement (or Any Big Pivot)
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Plan the pivot—early. Give yourself (and your team) a runway. A six-month notice enabled Steve to transition cleanly and leave on strong terms.
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Buy freedom with discipline. “Pay yourself first.” Consistent saving over decades powers real choice at 60-plus.
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Balance your identity throughout your career. Keep interests alive—music, sports, volunteering so you’re more than your job when you step away.
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Invest in relationships. Nurture professional ties that can mature into true friendships. Be intentional about rekindling dormant ones.
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Keep learning. Pick a frontier (AI, a language, an instrument) and work the muscle daily.
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Honor the couple dynamic. If your partner still works, be mindful. Share the load at home, match their reality, and avoid “solo victory laps.”
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Let the next chapter emerge. It’s okay to be “done for now.” Stay open to light consulting or projects that genuinely energize you.
Looking Ahead
Steve isn’t scripting the next ten years so much as curating them: more health, more music, more travel, and learning for its own sake—plus the occasional Workday-flavored cameo when it’s useful. It’s the same throughline that shaped his career—hands-on curiosity paired with thoughtful leadership—now redirected toward a life built as intentionally as any implementation.