Project Management Happy Hour How to quit your job and completely fail as a PM contractor
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Jan 15, 2026 Thinking of becoming a contractor? Discover two compelling stories of transitioning from corporate jobs, highlighting the critical role of relationships and reputation. Learn how sales skills are essential for contractors and the importance of avoiding commodity pricing. Hear about the challenges faced during the 2008 financial crisis and how strong client connections can sustain a contracting career. Plus, tips for starting small with side gigs and leveraging networks for a smoother transition into independent work.
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Quitting Into The 2008 Crisis
- Kim Essendrup quit her job in 2008 to subcontract directly to a favorite client but the project collapsed due to budget cuts.
- She almost had zero income but was rehired as a subcontractor and sent overseas for a year-long contract.
Relationships Trump Job Boards
- Independent work depends heavily on relationships, reputation, and perceived value.
- Commodity marketplaces like Upwork risk a race to the bottom on rates.
Be Your Own Salesperson
- Always treat selling your services as a full-time job when you go independent.
- Continuously ask clients what comes next and position yourself to solve future problems.