Every dream you’ve ever had—whether it’s starting a business, becoming a speaker, or selling your art—has more potential than you realize. But there’s a key to turning that passion into something that actually pays the bills… and most people miss it.
Recently, my friend Justin and I had a powerful conversation about this very topic: When should you turn a hobby into a business? And how do you know if it’s even the right move for you?
We’ve both been down this road in different ways. I turned my lifelong passion for art into my first business as a graphic designer. We both transformed our love of public speaking into a brand and career that’s taking off. And in doing so, we both learned some hard truths about what it really takes to turn your passion into your paycheck.
If you’re thinking about making the leap, here are 5 things you absolutely must know first:
1️⃣ Your Relationship With Your Passion Will Change
One of the biggest surprises? The thing you love will feel different once you start charging money for it.
When I first started my graphic design business, there was a honeymoon phase—doing what I loved every day and getting paid for it felt like a dream. But soon enough, the “business” side of things crept in: demanding clients, employees who didn’t deliver like I would, payroll, taxes… you name it.
Justin shared a similar experience from when he ran a national golf handicapping system in South Africa. Golf had always been one of his favorite sports—until running that business made it feel like a chore. He didn’t even want to play on the weekends anymore!
Key takeaway: You need to make peace with the fact that turning pro will shift your relationship with your passion. And that’s okay—as long as you’re prepared for it.
2️⃣ You Need Specific Ambition, Not Just General Ambition
Justin brought up a brilliant quote:
“General ambition creates anxiety. Specific ambition creates direction.”
It’s easy to say “I want to turn my hobby into a business.” But vague goals won’t get you there—and they’ll leave you stuck in your head. The moment you get clear (e.g. “I want to earn $5,000/month from speaking engagements within 12 months”), you give yourself a target.
Specific ambition fuels action. Without it, you’ll stay spinning in “what if.”
3️⃣ Test the Market Before You Go All In
One of my personal “King Moves”: Launch in 24 hours.
Why? Because real validation comes when strangers—not friends, not family—actually pay for your product or service.
I shared a story about a woman who printed 1,000 postcards for her dream beauty salon… before she even signed the lease. Don’t put the cart before the horse! You need feedback from the marketplace early. Offer your product for sale. Speak for free (at first) to build experience. Sell your art or services to people you don’t know.
Until people are paying for what you offer, you haven’t really tested your idea.
4️⃣ Stay in the Side Hustle Phase Longer Than You Think
There’s no rush to quit your day job—sometimes, keeping your passion as a side hustle is the smartest move.
In my early days, I had a 3-day-a-week job at a newspaper. That gave me time and money to grow my freelance design work. It was actually a “sweet spot”—paychecks from the job, income from the side hustle. I only jumped to full-time entrepreneur after building a strong foundation.
Not everyone needs to go full-time. For some, keeping your hobby as a side hustle preserves the joy while still making extra income. And that’s perfectly fine.
5️⃣ Build Feedback Loops to Get Better
Another truth: Passion isn’t enough. You need skills—and those only grow through feedback.
I compared it to learning golf: if you practice the wrong swing over and over without coaching, you’ll get worse, not better. Same goes for your business. You need honest feedback from the market (via paying customers), mentors, or coaches to level up your craft.
Don’t wait until you feel “ready.” Launch small, get feedback fast, and iterate.
Final Thoughts
In the end, here’s what I always tell aspiring entrepreneurs:
Start fast. Learn fast. Adjust fast.
If you’re considering turning your passion into your paycheck, don’t overthink it. Test the idea quickly. See how it feels. And remember—success comes from clarity, action, and a willingness to grow.
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