Yesterday, I was talking to a friend who works for a Fortune 500 company. She'd just learned about layoffs coming to her division and was genuinely panicked. "How do you handle not knowing where your next paycheck is coming from?" she asked.

I had to laugh — not at her situation, which is genuinely stressful — but at the assumption that traditional employment offers more security than gig work. The truth is, gig workers have been building resilience muscles for years that the rest of the workforce is just now realizing they need.

According to recent data, 57% of contracting workers work more than 40 hours per week, and just 1% of gig workers felt dissatisfied with their job. We're not just surviving uncertainty — we're thriving in it. Here's what we've learned about building resilience that applies whether you're freelancing or sitting in a corporate cubicle.

The Long Road to Resilience

When I started freelancing in 1988, the internet didn't exist. There was no email, no online banking, no digital payments. Getting work meant cold calling, sending query letters by mail and waiting weeks for responses. Getting paid meant watching the mail for checks that then took days to clear—if they didn't bounce.

I've lived through multiple recessions as a gig worker: the early 1990s downturn, the dot-com crash, 2008-09, and the pandemic. Each one taught me something different about survival and adaptation.

The early '90s recession hit when I was still figuring out the basics. I learned the hard way that you can't rely on verbal agreements and handshake deals. Contracts matter. Payment terms matter. Having backup plans matters.

The 2001 downturn taught me about industry diversification. I was too heavily concentrated in work for one client when the bottom fell out. That's when I started diversifying, branching into consulting and marketing.

2008 was brutal—but by then, I had systems in place. Multiple income streams, deeper emergency funds, stronger relationships. There was about a six month period where I lost half my income. But I used the downturn to build new skills and capture market share from competitors who couldn't adapt.

The pandemic? After three decades, I leaned into what I could count on and then pivoted faster than most traditional businesses. Within weeks, I was doing virtual speaking engagements and had shifted my content focus to address the new economic reality. I landed a big gig with a long-time client, who felt my approach would be unique and garner lots of attention. They were right.

Each crisis built on the lessons from the previous ones. That's the compound effect of decades of gig economy work.

Let me be clear about something: I wasn't born resilient. I've been a gig worker since 1988 — that's years of building this muscle, year in and year out. Some years, it really hurt. I wondered whether I'd make it through the next month, let alone build a sustainable career.

In the early years, a single project cancellation would send me into a spiral that lasted weeks. I'd question everything: my abilities, my career choice, my financial judgment. Now? I let it go and just move on, keeping my eyes on where I want to go.

The difference isn't that I've become a different person. It's that I've systematically built resiliency skills over a lifetime that help me bounce back faster each time.

Resilience has three specific components: (1) emotional regulation (not panicking when things go wrong); (2) cognitive flexibility (finding alternative solutions quickly); and, (3) practical systems (having backup plans ready to deploy). You can develop all of these, regardless of your starting point.

Resilience Isn't a Personality Trait—It's a Skill Set Built Over Time

Wall Street has a saying: "Don't put all your eggs in one basket." I learned this principle the expensive way during my first decade as a freelancer.

In the early days, I made the classic mistake: I had one major client that represented 60% of my income. When they lost a key contract and had to cut freelance budgets, I lost most of my income overnight. That was 1993, and I never forgot the lesson.

Here's how I think about diversification:

Client diversity: I work with magazines, radio stations, individual coaching clients, and corporate consulting gigs. If one sector hits a rough patch, others keep me afloat. And, I do what I can to maintain relationships, across space and time. Even if we haven’t worked together recently doesn’t mean we won’t in the future - if I stay in touch.

Skill diversity: Writing, speaking, media appearances, financial analysis, trendspotting. Each skill reinforces the others and opens different opportunities.

Timeline diversity: Some projects pay immediately, others take 60 days. Some are one-time gigs, others are ongoing relationships. This smooths out cash flow bumps.

Industry diversity: Real estate, personal finance, media, technology. When one industry struggles, others might be booming.

My corporate friend? She had one job, one boss, one paycheck, one industry. When trouble hit, she had no alternatives ready. That's not security—that's income concentration risk.

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