Heather
Mojelski
Founder & Principal at RetroDev Studio
"The Messy Middle: Career Longevity in Tech"
"The Messy Middle: Career Longevity in Tech"
Thu May 14 - 12:20 PM EDT/New York (See in local time)
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05/14/2026 12:20 PM
05/14/2026 12:40 PM
America/New_York
#WTGC2026
"The Messy Middle: Career Longevity in Tech"
#WTGC2026
"The Messy Middle: Career Longevity in Tech"
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"The Messy Middle: Career Longevity in Tech"
"The Messy Middle: Career Longevity in Tech"
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Session: The Messy Middle: Career Longevity in Tech
Tech careers are rarely linear, especially over decades. This talk explores the "messy middle" of long tech careers, the stretch marked by setbacks, pivots, economic downturns, health changes, and shifting identities that many professionals experience but few openly discuss. Drawing on 25+ years across software development, SaaS, education, nonprofit leadership, and consulting, Heather shares practical insights on staying engaged, credible, and grounded in tech when progress stalls or reverses. Rather than offering simple success formulas, this session focuses on navigating uncertainty, maintaining self-trust, and building careers meant to last.Key Takeaways
- Why long tech careers are rarely linear, and how to recognize when you are in the "messy middle" rather than failing.
- How economic downturns, ageism, health changes, and role shifts intersect, and why setbacks are often systemic, not personal.
- Practical ways to stay engaged and credible in tech when progress stalls, including shifting focus from titles to influence and impact.
- How to maintain self-trust and career momentum during periods of uncertainty, without burning out or forcing artificial narratives of success.
Bio
Heather Mojelski is Founder & Principal of RetroDev Studio, with over 25 years of experience across software development, SaaS platforms, technical education, nonprofit leadership, and consulting. She has led teams, taught future technologists, and supported organizations through periods of change and uncertainty. Heather focuses on career longevity, human-centered technology, and practical leadership in complex systems.