How I Quit My Job With $35 and Started a Business

Handwritten text stick note - Actively Disengaged Employee.

If you’re working a 9-to-5 job and secretly dreaming of running your own business one day, let me tell you—you’re not alone.

I’m Al Haywood, co-founder of Haywood Digital Marketing. A little over a decade ago, my wife Tona and I were both working steady jobs. I was part of the administration team at a public school district, and Tona was teaching high school biology at a local Catholic school. On the surface, life was stable. Good jobs. Decent pay. Benefits.

But under the surface, we were both dreaming of building something of our own. And while today we run our business full-time, helping entrepreneurs show up online, getting here was anything but a smooth ride. And we’re not the only ones who’ve felt this way. According to Guidant Financial, 55% of entrepreneurs start businesses to be their own boss, and nearly 39% do it because they’re dissatisfied with corporate life. So if you’re sitting at your desk wondering if there’s more out there, you’re definitely not alone.

The Decision to Leave a Steady Job

After years of working in school administration, I wish I could say I heroically quit my job to follow my entrepreneurial dreams. But let’s keep it real: I didn’t decide to leave- I got laid off. Now, in the public school system, getting laid off doesn’t always mean you’re permanently out. It just means the budget ran out where you were working. In my case, the high school I was at couldn’t afford my salary anymore. But don’t worry, there were offers. Oh yes, three other high schools wanted me. The problem?

• One offered a paycheck so low it would’ve had me auditioning for a spot on “Extreme Cheapskates”.

• Another offered the same pay—but wanted to pile on job duties like I was collecting Pokémon.

Meanwhile, deep down, I’d always felt a calling toward entrepreneurship. You can hear the whole juicy story in Episode 1: Getting To Know Al of the WE Pivot Podcast—part of our “Who is This Cute Couple” series. So instead of staying in the school system, I took the plunge. Truth is, I’d been developing websites on the side since 1999 and had built up a modest little client base.

Our very first customers after launching HAYWOOD SBS, LLC in 2014 were a small café in Noblesville, Indiana and a local Chicago automobile mechanic. The café gig was a website maintenance contract that paid a whopping $35 a month. And let me tell you—that $35 went a long way at Aldi grocery store. As for the mechanic? We built a one-page website for $300. It might not sound like much, but at the time, that felt like a million bucks—and it gave us the confidence that we could actually get paid for doing this work.

Now, don’t get me wrong—there’s nothing light about leaving a stable paycheck, benefits, and the routine of working a 9-to-5. But I wanted more freedom. More ownership of my time. And the chance to build something lasting.

Now Tona—that’s where the real bravery came in.

She stayed at her teaching job until 2016. But the day the principal told her she’d be teaching five classes in a row with no prep time, switching rooms on a rolling cart, AND setting up and breaking down science labs in random classrooms… well, that was the day Tona said: “Nope.” For three years, she held down her 9-to-5 while I worked to grow our business. Her income was our lifeline during that time.

So there we were: both officially out in the world of full-time entrepreneurship.

And here’s the thing nobody really prepares you for: we’d just gone from a combined six-figure income to… $35 a month. Now what do you do? How do you pay the bills, keep food on the table, and somehow fund a business at the same time? That’s what led us into our next chapter—and let me tell you, it wasn’t always pretty.

How We Really Funded Our Business

I wish I could tell you we’d saved diligently before I left my job. That we’d set aside a year’s worth of living expenses and planned every detail.

We didn’t.

Instead, when I resigned, I used the retirement pension I’d built up over five years in the public school system to keep us afloat. That money covered our living expenses and some of the early business costs. But eventually, that money started running low. So we turned to credit cards to help fill the gaps—both for business expenses and sometimes personal bills. And it turns out, we’re far from alone. Reports show that about 8–10% of new businesses get funded through retirement savings (Guidant Financial), while around 21% of small business owners use credit cards to launch their ventures, according to the Federal Reserve’s Small Business Credit Survey. While those numbers made me feel slightly less reckless, I still wouldn’t recommend it. Looking back, I can say this without hesitation:

It would have been a whole lot smarter if we’d started saving while we were both still employed. We made it through, but it was stressful, and there were plenty of sleepless nights.

The Reality of Using Retirement and Credit Cards

Let me be real with you:

• Tapping into my pension felt risky.

• Relying on credit cards felt even riskier.

We used those funds for things like:

• Website hosting and software

• Training courses to learn new web design technologies, and digital marketing trends

• Equipment upgrades

• Living expenses during dry months

We weren’t spending frivolously. But the costs added up fast. And while we eventually paid off our debts, I don’t recommend starting a business this way. We’re definitely not the only ones who wish we’d done things differently.

According to a QuickBooks Small Business Survey, 56% of business owners say they wish they’d saved more before leaving their jobs. If you’re dreaming of leaving your 9-to-5, I’d encourage you to start building your financial safety net now. Even small amounts add up over time. It’s never too early to learn how to start saving for a business.

What We’d Do Differently

If Tona and I could go back, here’s exactly what we’d change:

• Build a savings buffer while working. Even a few hundred dollars a month set aside would have helped tremendously.

• Test the business as a side hustle. Validate your idea and see what people will pay for before quitting your job.

• Pay off as much debt as possible first. We’d have had a lot less stress if we weren’t juggling credit card payments.

• Plan for at least 6-12 months of living expenses. It’s not always realistic, but it’s an ideal goal.

Your 9-to-5 paycheck can be your first business investor. Use it wisely so you’re not forced to drain retirement accounts or rack up credit card debt.

The Naysayers and the Fear

People had plenty of opinions when we started talking about leaving our jobs:

• “Are you sure you want to walk away from good benefits?”

• “Isn’t that risky?”

• “Businesses fail all the time.”

Some meant well. Others were simply projecting their own fears. We wrestled with fear ourselves—especially as debt piled up. But through prayer and a firm belief that we were called to do this, we kept going. You have to find ways to overcome fears of starting a business.

How We Found Our Path

After Tona joined me full-time in 2016, we divided and conquered. I took the lead on web design and creative projects. I’ve always loved working with visuals, building websites, and creating designs that help businesses stand out. Tona leaned into digital marketing, SEO, and—more recently—AI tools that support small businesses. She’s great at digging into the data, learning new strategies, and figuring out how to make marketing more effective and affordable for small businesses.

We both kept learning. We attended free workshops (sometimes just for the free breakfast!), networked like crazy, and connected with people who helped us grow.

Not every event was worth it. Some were pure sales pitches. But every experience taught us something—even if it was just how to better explain what we do.

Some of our best connections, like our good friend Tim Fitzpatrick from Rialto Marketing, turned into partnerships and friendships that still support us today.

Your Skills Aren’t Wasted

One big lesson I’ve learned: No skill you learn in your 9-to-5 is ever wasted. My years in administration gave me organizational skills, people management experience, and a knack for problem-solving. Tona’s teaching background made her exceptional at explaining complex topics simply- a skill that serves our clients every day. Whatever you’re doing now—project management, customer service, IT support—it’s all preparing you for running your own business.

The Road Ahead

Today, Tona and I run Haywood Digital Marketing (HAYWOOD SBS, LLC) full-time, helping entrepreneurs and small businesses show up online. We’re also exploring how AI can make digital marketing for small business more affordable and accessible because we know how overwhelming it can feel when you’re starting out. Do we still face challenges? Absolutely. But we’d never trade the freedom and purpose we’ve found through entrepreneurship.

How AI Is Changing the Game for Entrepreneurs

We’re living in the age of AI and it’s one of the biggest opportunities I’ve ever seen for entrepreneurs, especially for those still working a day job or running a side hustle. When we started our business, many of the tools and shortcuts available today simply didn’t exist. Back then, creating content, building a website, or figuring out marketing strategies was time-consuming and expensive.

Now, AI is making things faster and more affordable:

• You can generate blog posts or social media captions in minutes instead of hours.

• Tools can help you analyze competitors or SEO trends without hiring a big marketing agency.

• AI design tools make it easier for non-designers to create professional graphics or logos.

• Even brainstorming new business ideas or marketing angles is easier thanks to AI-powered suggestions.

For side hustlers and aspiring full-time entrepreneurs, this means you can make real progress—even in the limited time you have outside your 9-to-5. That’s why Tona and I developed our AI Digital Marketing Toolkit, designed specifically for small businesses and entrepreneurs. Our goal is to help you:

• Create content creation for creative entrepreneurs quickly and easily

• Save money by reducing the need for expensive freelancers or agencies

• Focus on running your business instead of getting bogged down by tech and marketing overwhelm

We believe AI levels the playing field, giving smaller businesses a real shot at competing with bigger brands. And we’re excited to help entrepreneurs like you take advantage of it.

My Advice for You

So if you’re working your full-time job and dreaming of starting a business, or thinking of quitting to pursue your side hustle full-time, here’s what I’d say:

• Start saving—even small amounts add up.

• Learn new skills while you’re still employed.

• Test your business ideas before quitting.

• Don’t wait for perfect timing—it doesn’t exist.

• Embrace the tools available to you—especially AI—to save time and money.

• And if faith is part of your life, lean into it. It’ll carry you through the hardest days.

You can build the business you’re dreaming of. Just try not to fund it the way we did—by draining your retirement and leaning on credit cards.

I’m cheering you on.

Want to learn more about building your business online—and how AI tools can help? Check out Haywood Digital Marketing, explore our AI Digital Marketing Toolkit, or tune in to the WE Pivot Podcast, where we talk about real-life strategies for entrepreneurs who want to make the leap.

Al Haywood, Co-Founder of HAYWOOD Digital Marketing