Episode Details

What happens when you reach the end of a successful career and realize you’re not done working?

On this week’s Keep Going, I talk with Alan Wexelblat, a longtime software engineer, UX leader, startup veteran, and MIT Media Lab alum who retired earlier this year. Instead of settling into retirement, Alan began volunteering full-time with organizations supporting immigrants and refugees.

We talk about why he made that choice, what decades of building software taught him about failure, and why he thinks the best time to get involved is when you see something broken and can no longer accept living with it.

We also get into AI and the future of work. Alan argues that AI is very good at producing output, but output isn’t the same thing as an outcome. Human judgment, experience, and an understanding of what people actually need still matter. For people starting careers right now, his advice is simple: stop worrying so much about preserving a job title and start asking where you can bring real value.

It’s a conversation about work, retirement, technology, responsibility, and what success looks like after the résumé stops mattering.