
The Unspoken Shift from a Side Hustle to a Full Time Business
Let me be unabashedly nerdy for a second: I love SEO.

Let me be unabashedly nerdy for a second: I love SEO.

When you're starting a side hustle while working full time, tax season can feel like a whole new level of complicated. Suddenly, you’re not just dealing with a W-2; you’re navigating business expenses, quarterly estimates, and a maze of forms. It’s no wonder so many people consider hiring a professional. A good tax advisor can do more than just file your return; they can help with Financial Planning for Business Owners and pinpoint deductions you might miss, often saving you more than their fee costs.

If you're one of the millions of Americans pursuing home based business opportunities or starting a side hustle while working full time, your home is likely your headquarters. That spare room or corner of the den isn't just a place to escape—it's your office. And that means you might be eligible for a home office tax deduction, a powerful tool in your small business tax management toolkit.

It’s a common belief that starting a business requires a mountain of cash. But what if that’s not true? The reality is, many successful ventures start with surprisingly little. Michael Trainer kicked off his media production company with just $2,500 for a camera—an investment he later recouped in full. He went on to work with Nobel Prize winners. Tara Gentile launched her publishing business with $80, and a year later, she was earning $75,000. For Chris Dunphy and Cherie Ve Ard, it was $125 that started a software consultancy that now pulls in over $75,000 a year while they travel the world.

Hollywood has a formula for making you desperately want to see a movie months before it ever hits theaters. They spend hundreds of millions on a blockbuster and know they have a tiny window to make it all back. So, they don't just release a film; they orchestrate a launch. It starts with a teaser trailer a year out, then a full trailer, then a media blitz that builds anticipation to a fever pitch. By the time opening weekend arrives, people are lining up, eager to see what all the buzz is about.

It all started in an office in Anchorage, Alaska. Scott McMurren was working in media sales for a local TV station, a job that gave him a great view of Mount McKinley and a list of contacts all over the state. He also hosted a travel show on the side, but he never thought it would amount to much. For two years, his friend Gary Blakely had been nagging him about a business idea, but Scott kept brushing it off. Finally, worn down by the daily grind and his friend’s persistence, he caved. “OK,” he said, “let’s give it a try.”

It was 2008, and Jen Adrion and Omar Noory were just one year out of design school. They were doing what they were supposed to be doing—Jen was teaching at their alma mater while freelancing, and Omar had landed a job at a local design studio. From their tiny apartment in Columbus, Ohio, they were making ends meet with a side business with job structure. But the reality of commercial design work was setting in, and it felt a lot like burnout. Jen found herself wondering if she’d made a huge mistake, questioning if she should have pursued a completely different career.

John le Carré once wrote, "A desk is a dangerous place from which to view the world." I’ve taken that to heart. My office is often a seat on a Cathay Pacific flight, a guest house in Asia, or a hotel room with a view of the Hong Kong skyline at 2 a.m.

Gary Leff is a lot like many of us. He starts his day with email, managing his responsibilities as a CFO for two university research centers. It’s a good job that he enjoys, but the emails that come in during the “early early” morning are from a different venture entirely: his part-time consulting business. This is the reality of starting a side hustle while working full time.