From Risk-Averse to Self-Deployed | Wes Wheless
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Wes was laid off three times. After the third, he started questioning whether he wanted another corporate job at all.
What if the expertise he'd spent years building could create a career that didn't depend on a single employer?
In this episode of Pink Slip Pavilion, host Ashley Waddington sits down with Wes Wheless, independent consultant and author of The Expert's Privilege, to talk about navigating multiple layoffs, leaving corporate America, and turning years of professional experience into an independent consulting business.
Wes's first layoff came during the 2008 financial crisis. At just 24, he was devastated. With bills to pay and little savings, he immediately started looking for another corporate job.
His second layoff came in 2020, after six years at a tech company. This time, his reaction surprised him.
He felt relieved.
After years of corporate pressure, the layoff gave him an opportunity to disconnect, decompress, and reconsider what he wanted.
He eventually joined a startup, only to be laid off again during the 2022 tech downturn.
After getting laid off twice in two years, Wes started questioning whether he wanted to spend the next decade jumping between employers, hoping each new job would last.
That's when he began exploring independent consulting.
That journey eventually inspired his book, The Expert's Privilege: A Self-Deployment Guide to Leaving Corporate and Going Solo.
In this conversation, we explore:
- Getting laid off three times throughout a career
- Why losing your job can sometimes feel like relief
- Navigating unemployment and a difficult job search
- Questioning the security of corporate employment
- Leaving corporate after a layoff
- Starting an independent consulting business
- Turning your professional experience into marketable expertise
- Overcoming imposter syndrome when going solo
- Recognizing your value beyond your job title
One of Wes's biggest messages is that you've spent years developing expertise that has value beyond the organization employing you.
You don't necessarily have to abandon your career to leave corporate. You may simply need to rethink how you use the experience, knowledge, and relationships you've already built.
His advice to anyone navigating a layoff?
"Use it as an opportunity to think bigger."
Your next chapter doesn't have to look like your last one.
CONNECT WITH WES
LinkedIn: Wes Wheless
Website: myparachuteplan.com
Book: The Expert's Privilege wesbook.com
Pink Slip Pavilion shares real stories about layoffs, career transitions, reinvention, and what comes next.
New episodes every Wednesday.