I started my freelance career in 1988. Ronald Reagan was still president, the Berlin Wall was still standing, and if you wanted to pitch an editor, you typed a query letter on actual paper and mailed it with a self-addressed stamped envelope.

Thirty-seven years later, I'm still here. Still freelancing. Still adapting. I've survived five major economic downturns as a gig worker, watched entire industries disappear and new ones emerge, and navigated the complete transformation of how freelance work gets done more than twice.

If you're feeling anxious about the current economic climate, or wondering whether freelance work can provide real long-term security, let me share what I've learned from nearly four decades of riding the economic waves.

The recessions that shaped my career

Early 1990s Recession (1990-1991) I was barely launched as a freelance writer when this hit. The savings and loan crisis, the Gulf War, rising oil prices—suddenly, publications I'd been pitching were cutting freelance budgets. I learned my first hard lesson: Verbal agreements mean nothing when companies are hemorrhaging money. This recession taught me to always get contracts in writing and to never count on any single income source.

Dot-Com Crash (2001) By 2001, I'd built a decent business writing about technology. Then the bottom fell out of the tech sector. The NASDAQ lost 78% of its value from peak to trough, and tech companies that had been throwing money at content suddenly couldn't pay their rent.

I watched colleagues who'd specialized entirely in tech writing struggle to find work for years. That's when I learned about industry diversification—not just having multiple clients, but multiple sectors.

The Great Recession (2007-2009) This was the big test. The unemployment rate hit 10%, housing markets collapsed, and even established media companies were laying off staff writers. But I was ready this time. I had clients across real estate, finance, health care, and education. When real estate coverage dried up, financial literacy content surged as people tried to understand what was happening to their money. I joined CBS MoneyWatch and my blogging about how people were losing their homes hit more than 1 million views per month.

COVID-19 Pandemic (2020) After three decades of practice, this bit of economic insanity should have been routine. It wasn't. Initial unemployment spiked to 14.8%, but the recovery pattern was completely different from previous recessions. Some industries never recovered; others boomed beyond anyone's expectations.

What saved me wasn't just having diverse clients and business interests—it was having developed the ability to pivot quickly. Within weeks, I was doing virtual speaking engagements and had shifted my content focus to address the new economic reality. I was hired by a former client to build a website specifically to showcase their pandemic response.

The Pattern I Didn't See Coming Each recession taught me something new, but there was a meta-lesson that took decades to recognize: The intervals between economic disruptions have been getting shorter, and the nature of each crisis has been fundamentally different.

In 1988, I thought I was preparing for cyclical downturns. I didn't realize I was actually training for permanent adaptability.

(And, as an aside, let’s talk about how these major, earth-shaking economic events are now happening roughly every 10 years…)

How the freelance landscape transformed

When I started in 1988, the freelance economy barely existed as we know it today. According to recent data, more than 36% of U.S. workers now participate in the gig economy, but in the late 1980s, freelancing was mostly writers, photographers, editors, and consultants working with traditional businesses.

The Pre-Internet Era (1988-1995) Everything happened by mail or phone. Research meant libraries and phone interviews. Payment meant checks that took weeks to arrive and days (or weeks) to clear. There were no freelance platforms, no online portfolios, no digital payments.

The barriers to entry were higher, but so was the barrier to competition. If you could navigate the system—get your queries to the right editors, build relationships with art directors, establish credibility with sources—you had a sustainable business.

The Internet Revolution (1995-2005) Email changed everything first. Suddenly, I could pitch editors instantly and deliver articles as attachments. Research became faster and broader. But the real transformation was the democratization of publishing.

Websites needed content. Lots of content. Companies that had never hired writers before suddenly needed web copy, newsletters, blog posts. The freelance market exploded, but so did the competition.

The Platform Era (2005-2015) Upwork launched in 2003 (as Elance). Suddenly, anyone could bid on freelance projects from anywhere in the world. The number of freelancers in the U.S. grew from about 10% of the workforce in 2005 to 15.8% by 2015.

This was terrifying and liberating simultaneously. I could compete for projects I never would have heard about before, but I was also competing against writers who would work for $5 an hour. It was scary and thrilling all at the same time.

Influencing started to become a businesses -- and something you had to do to get noticed. While it felt like you were giving away the “milk for free,” social media allowed everyone to be an expert, to showcase their wares, to demonstrate that they, too, had something to share.

The Creator Economy Era (2015-Present) Social media platforms became publishing platforms pushing empires. Substack, Medium, LinkedIn, Twitter—suddenly everyone could build an audience directly. The relationship between freelancers and traditional media shifted fundamentally.

Now I'm not just competing with other freelancers for assignments. I'm building my own media properties while also serving traditional clients. The skills I developed over decades — building relationships, understanding audiences, adapting to new formats — became more valuable than ever.

The evolution of economic threats

Each recession taught me that the next crisis wouldn't look like the last one.

1990s: Traditional cyclical recession Too much debt, overheated economy, predictable boom-bust cycle. The solutions were familiar: cut costs, wait it out, rebuild when credit loosened.

2001: Technology bubble burst This was my first experience with a sector-specific collapse that had economy-wide implications. It taught me that being too concentrated in any single industry — even a "safe" one — was dangerous.

2008: Financial system collapse This wasn't just a recession; it was a fundamental breakdown of trust in financial institutions. Home prices fell 33% nationally, and traditional safe havens like real estate became toxic.

The lesson: Diversification isn't just about having different clients. It's about understanding systemic risks and building buffers that can withstand not just individual failures, but systemwide breakdowns.

2020: Global pandemic A health crisis that became an economic crisis, but with completely unprecedented government intervention. The federal government spent over $4 trillion in pandemic relief, fundamentally altering labor markets and business models.

Some freelancers thrived as companies shifted to remote work and needed help navigating digital transformation. Others saw their industries disappear overnight. The lesson: Adaptability isn't just about surviving downturns—it's about recognizing and capitalizing on the opportunities that emerge from chaos.

2025 - and beyond Although it hasn’t been 10 years, it feels as though another recession is just around the corner. This year has been full of ups and downs as businesses try to plan and cope with the unknowable: What will happen next? Tariffs have complicated the business world. In this next downturn, which I’m already planning for, the game will be all about leveraging relationships.

What I wish I'd known in 1988

Start building your emergency fund immediately. I spent the first decade living project to project. Every recession taught me the same lesson: You need a bigger cash buffer than you think. Not 3-6 months of expenses, but 12-18 months. When you're freelancing, that cushion is your business insurance.

Focus on the math: Relationships compound over decades. That editor who rejected your pitch in 1995 might become your best client in 2010. The colleague who seemed like competition in 2002 might send you your biggest project referral in 2020. I have clients today I first met 25 years ago. Business partners I met 14 and 10 years ago. Reputation and relationships compound more powerfully than any investment.

Technology skills are your minimum viable product. In 1988, being able to use a computer was a competitive advantage. By 2000, it was table stakes. Every technological shift creates new opportunities for those who adapt quickly and new risks for those who don't. Today, it’s fluency with AI, and the systems that depend on LLMs.

I've had to learn: email, web browsers, content management systems, social media platforms, video conferencing, podcasting equipment, digital payment systems, project management tools, and AI writing assistants. The learning never stops.

Economic cycles are getting shorter and more unpredictable. The old model of 7-10 year economic cycles is dead. Recent analysis suggests business cycles are becoming more frequent and more volatile. You can't build a freelance career assuming long periods of stability punctuated by occasional disruptions. You need to build for continuous adaptation.

Industry expertise is both your greatest asset and your biggest risk. Deep expertise in any field makes you incredibly valuable to clients in that space. But industries can disappear faster than ever. I've watched colleagues who were experts in newspaper layout, magazine photography and travel writing struggle as their entire sectors contracted.

The solution isn't to avoid specialization—it's to continuously expand your expertise into adjacent areas and to stay alert to early warning signs of industry shifts.

The skills that transcend economic cycles

After 37 years, I've identified the capabilities that matter regardless of what the economy throws at you:

Pattern recognition: The ability to spot trends before they become obvious. This comes from paying attention to weak signals and connecting dots across different industries and data sources.

Rapid learning: Not just being able to learn new things, but being able to learn them quickly enough to capitalize on emerging opportunities.

Relationship building: The ability to build trust and maintain connections across long time horizons. Your network becomes your net worth, but only if you nurture it consistently.

Financial discipline: The ability to save during good times and spend strategically during bad times. This sounds simple but requires genuine discipline when everyone around you is either panicking or celebrating.

Emotional regulation: The ability to make rational decisions when markets are irrational and to maintain professional relationships when everyone is stressed.

What the next recession will look like

I don't know when the next major economic disruption will hit, but I can make some educated guesses about what it might look like based on current vulnerabilities:

Technological displacement: AI and automation are eliminating entire categories of work faster than new categories are being created. Recent studies suggest up to 47% of U.S. jobs could be automated within the next two decades.

Climate-related disruptions: Physical climate changes are creating new categories of economic risk that don't follow traditional recession patterns. Supply chain disruptions, infrastructure failures and insurance market collapses could trigger economic downturns that look nothing like previous recessions.

Geopolitical instability: Global supply chains and digital connectivity create new systemic risks. Trade and tariff wars, cyber attacks, and currency instability could create economic disruptions that cross traditional industry boundaries.

Demographic shifts: Aging populations in developed countries and labor shortages in key sectors are creating economic pressures that don't fit traditional recession models.

The freelancers who thrive through the next crisis will be those who've built capabilities that work across multiple scenarios, not those who've optimized for any single economic environment.

Finally, The Long View

Here's what 37 years as a gig worker has taught me: Every economic crisis feels existential when you're living through it, but each one also creates opportunities that didn't exist before.

The 1990s recession forced me to professionalize my business practices. The dot-com crash taught me industry diversification. The 2008 financial crisis pushed me to build deeper financial buffers. The pandemic accelerated my digital transformation and opened entirely new revenue streams.

None of these lessons were pleasant, but each one made me more resilient for the next crisis.

If you're just starting your freelance career, or if you're a traditional employee thinking about making the jump, understand this: Economic uncertainty isn't a bug in the freelance lifestyle—it's a feature. It forces you to build capabilities that make you anti-fragile.

It’s never been easier to start a business. And, the goal isn't to avoid economic downturns. That’s inevitable. Instead, focus on building a career that gets stronger with each one.

Your Turn

What economic disruption taught you the most about resilience? If you're new to freelancing, what scares you most about economic uncertainty? Share your thoughts with me—I'd love to hear how different generations are thinking about economic risk and opportunity.

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