Reflection of the Week
Tax Season Reflection: Failure, Progress, and the Joy of Showing Up
Another tax season is in the books—my nineteenth, to be exact. And while it’s tempting just to breathe a sigh of relief and move on, I’ve found that these moments deserve something more intentional. A pause. A reflection. A learning – the third part of the Build -> Measure -> Learn cycle.
I love recognizing how I’ve grown—professionally and personally—through the chaos, connection, and quiet lessons that only a season like this can bring.
This year, I’ve been sitting with a quote from Mark Manson that struck a deep chord:
“If you’re not failing, you’re not learning. If you’re not learning, you’re not growing. If you’re not growing, you’re not living.”
It’s a simple concept but also radical—especially for a recovering perfectionist like me. For most of my life, I’ve internalized the idea that failure means I did something wrong. That I missed a step. That I wasn’t good enough. But what if failure is just another word for living?
This tax season had its fair share of failures—or, better yet, growth opportunities. Unexpected letters from state tax agencies. Complex returns with moving targets. Moments when my systems couldn’t keep up with the curveballs. And, perhaps most importantly, moments when I couldn’t keep up—when I was overwhelmed, stretched too thin, and had to renegotiate the boundaries I thought were solid.
But here’s what I learned: I can survive a season that doesn’t go according to plan. I can navigate the frustration and still deliver great work. I can lean on my values—authenticity, alignment, connection, and freedom—and come out of the chaos feeling even more grounded in what I do.
Because, at the end of the day, I love this work. I love being a financial guide for mission-driven entrepreneurs. I love untangling the messy parts of money and business and helping clients find clarity, strategy, and empowerment. It’s not just a job; it’s an extension of how I move through the world.
I’ve always had this instinct to organize—to reorder weights at the gym so they make more sense, rearrange items in my house for better flow, and bring systems and structure to the things around me. It’s second nature. And it makes perfect sense that I’d choose a profession that allows me to bring that same sense of alignment to other people’s financial lives.
Still, even when you love what you do, a heavy season like tax time can take its toll. That’s where I’ve been reminded—again and again—of the power of the little things.
- Kevin treated me to a staycation, giving me a moment to exhale.
- Clients checked in—not just to ask about deadlines, but to see how I was doing
- And I showed up, even in small ways, for the people and causes I care about, even when I felt like I didn’t have the time.
These moments reminded me of another truth I’m holding close right now: progress, not perfection.
I didn’t do everything perfectly this season. But I kept showing up. I learned. I grew. I found new edges of my capacity and stretched into them with grace. And I let myself celebrate—not just the big wins, but the tiny ones, too.
If you’re reading this and feeling like you “should’ve done more” this season—whether in your business, finances, or personal life—please know you’re not alone. And more importantly, know this: You’re doing better than you think.
You deserve to celebrate your progress. You deserve rest. You deserve connection. And you deserve to see yourself not as someone who must always have it all together but as someone who is learning, evolving, and living with intention.
So here’s to the end of another season.
To growth through failure
To progress over perfection
And to all the little ways we keep showing up—for ourselves and each other.
Questions of the Week
1. When was the last time you experienced a failure, and what did it teach you about yourself or your work?
(Consider how that experience contributed to your growth, even if it didn’t feel like it in the moment.)
2. What small wins from the past season—personal or professional—deserve more recognition and celebration?
(Think about the quiet ways you showed up or stayed aligned with your values.)
3. How can you prioritize progress over perfection in your life or business moving forward?
(What shifts—big or small—can help you stay connected to your purpose without burning out?)
Tool of the Week
Inspired by this week’s post, the Failure Reflection Framework is a simple but powerful journaling tool to help you turn setbacks into stepping stones.
Here’s how it works—each time something doesn’t go as planned, ask yourself:
- What was the failure or challenge?
(Describe the situation without judgment.) - What did I learn from it?
(Identify the insight, lesson, or growth opportunity.) - How did I grow from it?
(Name how this experience shaped you, your mindset, or your business.)
Use this framework weekly or monthly to reframe missteps as part of your path—not detours from it. Over time, you’ll start to see failure not as a flaw, but as evidence that you’re learning, growing, and fully living.