This is for anyone who’s trying to make money from what they love—and it’s not working.
You’re watching your credit card balance climb. Your Kickstarter sits at 26% funded with just 17 days left. People keep telling you “the money will follow” and “just believe in yourself,” but those words start to feel like accusations. Like if you can’t make this work, it’s because you didn’t want it badly enough.
My grandfather used to say, “Love what you do and you’ll never work a day in your life.” Beautiful sentiment. But when you’re multiple years in and still breaking even, it starts to sound like a setup.
Here’s what I’ve been thinking about: What if you’ve been approaching this with blinders on? Not because you’re stubborn, but because that’s what we’re told to do: “Stay focused. Don’t get distracted. Keep your eyes on the prize.”
Maybe you don’t need blinders. You need guardrails.
Blinders keep you locked on one narrow path: “This passion must become my income, exactly as I imagined it.” Guardrails keep you safe while you explore: “This passion matters to me—let me find all the ways it can exist in my life.”
But here’s the thing: most of us don’t actually know what we’re guarding. We think we do, but we’re often protecting the form (the novel, the gallery show, the album) instead of the essence underneath it.
👉 Ask yourself: “why does this matter to me?” Then ask it again. And again.
Four or five times until you get past the surface answers (“I love photography”) to the core truth underneath (“I need to capture moments that would otherwise be forgotten” or “I crave the solitude of observation”).
Once you find that core, you might discover it can be expressed in ways you hadn’t considered. The love of storytelling doesn’t have to mean publishing a novel—maybe it’s leading workshops, or consulting for brands, or something you haven’t imagined yet.
Here’s the uncomfortable question: What would it look like if you didn’t try to monetize this thing you love? What if you protected it, kept it pure, and found another way to pay your bills?
I’m not saying give up. I’m saying there’s a difference between patience and striving, between faith and financial negligence. You can hold both: the dream and the reality check.
Your passion matters. But it doesn’t owe you a paycheck. And you don’t owe it your financial stability.
What if finding “another way in” meant being open to your passion showing up differently than you planned—maybe as your livelihood, maybe as your sanctuary, maybe as something in between?
The only real failure is abandoning what matters to you because you couldn’t force it into the shape you thought it had to take.
Three things to try this week:
1. Map your “why” to different vehicles
Take 20 minutes with a piece of paper. Write your core “why” at the top (the answer you got after asking yourself “why does this matter?” 4-5 times).
Below it, create three columns:
- Keep as passion: Ways this stays non-monetized and protected
- Adjacent income: Skills from this passion that solve problems people pay for
- Different expression: How this could show up in your life in unexpected ways
Example: If your why is “I help people feel less alone through stories”—that could be a podcast (current plan), corporate communication consulting (adjacent), or volunteering at a hospice (different expression). All honor the core. Not all need to pay you.
2. Run a 30-day experiment
Pick ONE small, defined way to test an adjacent income stream. Not a full pivot—an experiment with clear boundaries.
- If you’re a painter: Offer a 2-hour “creative unsticking” session for $150
- If you’re a musician: Teach one beginner how to write their first song for $200
- If you’re a writer: Ghost-write three LinkedIn posts for a small business owner
Set a deadline. See what happens. Learn from real market feedback, not just theory.
3. Give yourself a financial guardrail
Decide on your number: “I’ll invest X more dollars and Y more months into monetizing this passion in its current form. If it’s not generating Z by then, I’ll try a different approach.”
This isn’t quitting. It’s honoring both your passion AND your wellbeing. Write it down. Tell someone you trust. Treat yourself like you’d treat a friend you care about.
Reply and tell me: What’s one way your passion could exist in your life if money wasn’t the measuring stick? Just hit reply. I read everything.
We got this – together 💪
x Claire
Struggle with negative self-talk?
The Practice is a set of 30 cards that systemically rewires your brain away from self-doubt to self-trust.
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