Episode 56: How to Create Income Without a Corporate Job: Portfolio Careers, Self Employment and Other Ways to Make $$

If you’re stuck in a slow job market or waiting for the right role to come through, how do you keep your bills paid and your career moving? In this episode of Careers at the End of the World, host Jenn Walker Wall explores practical ways to make money without a traditional 9-5 job. Whether you’re between roles or looking to diversify your income, Jenn breaks down the options from portfolio careers and freelancing to contract work and side hustles. Instead of chasing quick fixes, she offers grounded strategies for generating income, building momentum, and staying engaged while the job market recovers.

Episode Highlights

How to differentiate freelance vs. contract work and decide which path makes sense during a job search.
The role of fractional and interim leadership jobs in bridging employment gaps.
Why ecosystem building and networking for referrals is critical when starting self-employment.
Tips for launching a low-barrier side hustle or pilot project without overthinking or overspending.
Why creating income outside a corporate job can help prevent career burnout and provide more flexibility.

Episode Timestamps

02:30 – Why today’s job market is so unpredictable
07:10 – What is a portfolio career? (with examples)
13:45 – The rise of contract and fractional work
19:20 – Turning rejection into a freelance or consulting opportunity
24:15 – Easy side hustles that actually pay (including pet sitting and adjunct teaching)
28:40 – How to talk about freelance or contract work on your resume

Resources and Links

Revive Your Job Search Workshop: September 30th (tickets $47 or free for community members)
How to Job Search at the End of the World (On Demand): free with discount code “CAREERSATTHEEND” until September 25th
Work Wonders Careers Job Search Community
SCORE Mentorship Program

Credits

Podcast editing by Vienna DeGiacomo, Good Story Branding