Ep. 84: Failing Forward: What Didn't Work & Why I'm Grateful It Didn't
- Melissa Cartwright

- Jan 7
- 5 min read
Happy New Year, dear singer!
If you’re feeling a mix of excitement, pressure, resistance, or even a little exhaustion as the year turns over—you’re not alone. This episode comes from a place of honesty, reflection, and a deep desire to normalize the non-linear reality of a performance career.
This past year reminded me—again—that growth rarely happens in a straight line. Some of my biggest wins were born from moments that initially felt disappointing, confusing, or like full-on failures. Today, I want to share three of those moments with you—not as a highlight reel, but as the whole picture.
Because when we only look at the shiny outcomes, we miss the information that actually got us there.
A Quick Pause Before We Dive In
January has a way of making us feel like we should be moving at full speed immediately. New goals. New plans. New pressure.
But here’s something I’ve been sitting with: winter itself is slow. Nature is resting. Animals are hibernating. And yet, as humans—especially as performers—we often expect ourselves to go from zero to ninety the moment the calendar flips.
If you’re feeling energized and ready to go, amazing. Follow that flow.
But if you’re feeling rushed, anxious, or behind before you’ve even begun—there’s nothing wrong with you. You might just be responding to a rhythm that doesn’t actually serve your body, your creativity, or your voice.
Everything you worked on in October, November, and December didn’t disappear. You’re building on it—not starting over.
With that in mind, let me take you behind the scenes of three moments from 2025 where things didn’t go as planned—and why I’m genuinely grateful they didn’t.
1. Creating My Cabaret: A Dream That Almost Didn’t Happen
Last year was a big one for personal performance goals—especially creating my own original cabaret, Sugar and Sazón.
This was my first time doing something like this in over 20 years. I produced it. I arranged the music. I told my own story. I became the music director, booking agent, and lead performer all at once. It was exhilarating—and a lot.
The premiere took place on my birthday, during Women’s History Month, and centered Latina artists who shaped my musical identity. It was deeply personal and incredibly meaningful.
Here’s the part you didn’t see on social media:
Between the premiere and the encore, I reached out to 12 venues.
Only 4 responded.
2 said yes.
The rest? Silence. Total ghosting.
SUPER frustrating.
So much mental energy went into emails, follow-ups, logistics, budgeting, and waiting—energy that could’ve gone toward the creative side of the work. And while no one owes us a “yes,” I do believe artists are owed basic communication.
Still, those two yeses were enough.
The encore happened during Hispanic Heritage Month at the Little Theatre of Norfolk, and the response was warm, affirming, and creatively expansive. New collaborations came out of it—not just bookings, but relationships.
The lesson: You don’t need universal approval. You need the right rooms.
2. Letting Go of a Steady Gig—and Making Space to Heal
Here’s a moment that felt like a failure at the time: a regular restaurant gig I’d had for nearly three years quietly disappeared. The communication was inconsistent. The commute was long. The creative spark was gone. And yet—it was steady income.
When it stopped, I panicked a little. A year earlier, I’d been fully booked for spring and summer. This time? Nothing.
At the same time, my health was asking for my attention in a way I couldn’t ignore anymore. I'm in the thick of perimenopause, dealing with GI issues, and realizing that pushing through “because the gig is good” is no longer sustainable. Had my calendar filled up the way I expected, I likely would’ve ignored the warning signs longer - signs that would also take a toll on my voice.
Instead, I had space. Space to work with a nutritionist. Space to change doctors. Space to reassess my energy, my workload, and my relationship with rest.
As singers, we don’t put our instrument in a case at the end of the night. Our bodies are the instrument - a LIVING instrument.
Letting those gigs go—intentionally or not—gave me the chance to care for myself in a way that ultimately protected my voice.
The lesson: Sometimes rest isn’t stopping. Sometimes rest is choosing sustainability.
3. A Missed Opportunity That Reignited My Songwriting
Toward the end of spring, I played a private house party—mostly covers, with a few originals mixed in. Afterward, the host said something simple and direct:
“Next time, I think we’d want to hear more of your original music.”
It wasn’t unkind. It wasn’t critical. But it landed. Then something interesting happened.
For two weeks straight, unprompted, people kept asking:
“Do you have more original music?”
“When are you releasing your own songs?”
I realized I’d been keeping something essential on the back burner. Instead of taking that feedback personally, I listened. I revisited my songwriting. I pulled out old material. I reflected on who I was when I wrote those songs—and who I am now. Some pieces still fit. Others didn’t. And that was okay.
Not long after, I was invited to two songwriter showcases—one I’d applied for months earlier and assumed I hadn’t gotten, and another that featured all female artists!
Those opportunities reminded me that I’m not just a performer who sings covers. I’m a songwriter.
That pivot has since led to being hired as a premiere songwriter for an upcoming nonprofit event—and making plans to invest in my own EP.
The lesson: Feedback isn’t failure. Sometimes it’s an invitation.
What I Hope You Take With You
Rejection is part of this work. So is rest. So is recalibration.
Getting the gig isn’t the job. Auditioning is the job. Practicing is the job. Writing is the job. Showing up for yourself consistently—that’s the job. Everything else is a bonus.
Before you compare your journey to someone else’s success, remember: you’re only seeing the surface. You don’t see the pauses, the no’s, the health scares, or the quiet pivots.
So as you move forward this year, I invite you to:
Rest with purpose
Sing with playfulness
Reflect without constant critique
Let “failures” be data, not verdicts
Go back and enjoy what you’ve already done. Let yourself be proud. Then, if something wants to evolve—play with it.
That’s how we "fail" forward.
And if this resonated with you, leave a comment or send me a message. I’m cheering you on as you take your next right step as a passionate performer. ✨ The Passionate Performer Program has been adjusted to better serve your needs - whether you need the flexibility or want a dedicated 1:1 coaching time. Check it out HERE.
Canta con amor,
Melissa









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