

We need to rethink the taboo against working multiple jobs
Jul 24, 2025
The podcast tackles the outdated stigma of holding multiple jobs, featuring a software engineer who successfully juggles several roles. It challenges traditional views on employment and highlights the rise of fractional executives in startups. As the job landscape evolves with AI and automation, it calls for flexible work arrangements that benefit both employees and companies.
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Rethinking Single Job Taboo
- Limiting people to one job is an outdated idea that does not benefit anyone.
- Transparent over-employment could reshape talent management and employee honesty positively.
Fractional Executives Gap
- Startups embrace fractional executives for part-time senior roles.
- Large firms still rely on consulting, showing a gap in flexible talent utilization.
Work Challenges and Multi-Job Honesty
- Workers face AI replacements and outsourcing, making it harder to find stable jobs.
- Removing the taboo on multi-job holding could encourage honesty and better earnings.