You’ve probably heard some version of this advice on having a side hustle. The first person I remember saying it was in 1993, back when I was maybe 25. It was Edd Pelsmaeker, my Scuba Instructor at Appalachian State University said, “Everyone should own a business”. To me, just like that.
Now as a CPA, I’ve had the privilege to see behind the scene details of hundreds of tax returns—and I’m here to say: owning a business, even a small one, can change your life. Not just financially, but mentally, emotionally, and even socially (supposing that you’ll become 37% more interesting at parties).
This isn’t financial advice. Just educational insight from someone who knows where all the best deductions are.
So let’s get into it: here are 10 reasons you should start a business (or at least a small side hustle)—peppered with personality, CPA smarts, and a few clever affiliate suggestions to help you get going.
1. You’re the Boss.
Want to skip pointless meetings and work in your PJs? Done. When you run your own business—even a micro one—you decide when and how you work.
Whether you’re selling digital downloads on Etsy or offering freelance gigs through Fiverr, you get to call the shots.
Sure, the boss can also be the janitor and customer service rep… but at least you won’t have to circle back by EOD (you know… End Of Day).
2. Multiple Income Streams = More Financial Security
Your 9-to-5 is not the financial fortress you think it is. Layoffs, recessions, and corporate “restructuring” happen. A side hustle is like a financial seatbelt—if one stream dries up, you’re not freefalling.
It could be whatever you want:
- Selling printables via Canva + Gumroad
- Running a monetized YouTube channel
- Coaching, consulting, or affiliate marketing with Skillshare or Teachable
And your second stream of income could someday become your first.
3. You Can Monetize Your Weirdest Passion
Love painting haunted Victorian pet portraits? Making candles that smell like “freshly opened tennis balls”? There’s a niche for that. Try it.
Because you no longer need a storefront. A basic site via Squarespace or Shopify gets you rolling. And if your weird thing makes money? Suddenly it’s not so weird. It’s brilliant.
4. You Get Tax Benefits
Let’s get real: every dollar you make needs to be reported. Even if it came from Venmo. Even if it was just “a little thing on the side.”
But here’s the good part—running a legit business means you may be eligible for legitimate tax deductions. Think:
- Home office space
- Your monthly QuickBooks subscription
- A percentage of your internet bill
- That ring light you bought for Zoom
As a CPA, I’ll say it again: this isn’t personal tax advice. But when you track income and expenses well, business ownership can make April a little less painful.
5. You Become an Accidental Genius
Want an MBA-level crash course in marketing, customer service, SEO, and time management? Start a business.
You’ll learn:
- How to invoice clients with FreshBooks
- How to schedule content with Buffer or Later
- How to survive tech meltdowns with only Google and caffeine
Starting a business is one of the quickest ways to build real-world skills—because you’re the one in charge of figuring things out
6. You Set Your Own Schedule
Want to take a Tuesday morning off to sit in a coffee shop and do nothing? Owning your time is one of the most valuable benefits of entrepreneurship.
Whether you’re a night owl or an early riser, business ownership lets you work when you’re most productive—not just when someone else says it’s time to clock in.
7. You’re Building Something That’s Actually Yours
That course you created? That digital product you designed? That side hustle you scaled? It’s your intellectual property.
Even if it doesn’t go viral, it’s an asset—one that can grow in value, be sold, or passed on. You’re not just earning money. You’re building equity in yourself.
8. You Gain Confidence + Thick Skin
Spoiler alert: entrepreneurship is humbling. You’ll get rejected. You’ll mess up. You’ll Google “how to deal with negative reviews” at 2 AM.
But you’ll also:
- Learn to negotiate
- Speak about your value with confidence
- Bounce back faster than you thought possible
It’s personal growth disguised as a side business.
9. You Can Start Tiny
No investors. No warehouse. No business suit required.
You can:
- Offer services on Upwork
- Sell templates through Creative Market
- Launch a digital course from your kitchen
The barrier to entry is lower than ever. You can literally start a business during your lunch break.
10. It Might Just Set You Free
Some side hustles stay side hustles—and that’s perfect. But others? They scale. They grow. They explode.
And suddenly, you’re no longer stuck in a job you hate. You’ve got income, flexibility, and choices. And those choices? They’re the real payoff.
Final Thoughts: Who Should Start a Business?
- The creative who wants to earn from their art
- The employee who wants a backup plan
- The parent looking for flexible income
- The financially curious who want more control
If you see yourself in any of those, now’s a good time to dip your toe in. Not with a risky leap, but a smart, educated baby step.
Bonus: Tools That Make Business Easier (a.k.a. Affiliate Goldmines)
| Category | Tool | What It Helps With |
|---|---|---|
| Accounting | QuickBooks, FreshBooks | Track income & expenses |
| Website | Squarespace, Shopify, WordPress | Launching a storefront |
| Productivity | ClickUp, Calendly | Managing your biz |
| Courses | Skillshare, Teachable | Learn & earn |
| Side Hustle | Etsy, Fiverr | Sell products or services |
So, should you start a business?
If you’ve read this far, you probably already know the answer. Even a small side hustle can:
- Improve your finances
- Boost your confidence
- Expand your skills
- And give you a way up (or out)
And if you’re ready to go for it? I’m here, cheering you on—CPA-approved, tax-code-compliant, and coffee in hand.
R. A. Goldston, CPA at Large
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