The Beautiful Chaos of Failure Stacking
The art of starting, pivoting, failing, and realigning
*photo from Open East.
Failure is a strange, inevitable guest in life’s journey — unwelcome but profoundly transformative. In our culture of highlight reels and success stories, it’s easy to believe that the people who “make it” are those who somehow avoided failure altogether. But the truth? Behind every major success story is a messy, winding path of missteps, setbacks, and pivots. It’s called failure stacking, and embracing it might just be the most important thing you ever do.
In this post, I want to unpack why failure stacking is essential for growth, how taking chances on yourself — even when it feels risky — leads to invaluable lessons, and why pivoting isn’t just acceptable; it’s necessary to build a life in alignment with your values and dreams.
The Myth of the Single Big Win
When we see someone crushing it in their field, it’s easy to think they had a linear path: a clear plan, executed flawlessly, leading to wild success. But that’s rarely the case. Every entrepreneur, investor and success trader I know has a graveyard of failed ideas, businesses, or trades.
In 2023, I launched a peer-to-peer fashion rental startup. It was my second attempt in the startup world after selling my first for a small profit. I poured everything I had into this p2p fashion rental concept for 1.5 years. But after navigating challenges in the business’ unit economics, operational roadblocks, market challenges, and the personal realization that scaling it wasn’t economically viable, nor did holding onto the startup world align with long-term vision (for the time being), I had to let it go. That wasn’t a failure — it was a stepping stone and I’m forever grateful to have been given the opportunity. I left with sharper instincts, a clearer sense of my strengths, and an understanding of what kind of business I truly want to build next. That wisdom came from trying and failing — not from standing o the sidelines.
Why Failure is the Best Teacher
Failure forces us to confront blind spots we can’t see when things are going smoothly. Maybe you miscalculated a trade or launched a product with the wrong product market fit. Instead of writing off those experiences as wasted time, what if you took them as lessons? Each failure ultimately give you data — about yourself, your decision-making, and the world around you.
Trade didn’t go as planned? You refine your strategy.
Business idea flopped? You discover what market demand actually looks like.
Personal goal missed? You recalibrate your timeline on your priorities.
Every “mistake” moves you closer to mastery — if you let it. The goal isn’t perfection; it’s iteration.
Pivoting is a Superpower
We often resist pivoting because it feels like admitting defeat. But staying the course out of fear of judgement or sunk costs will only lead to deeper dissatisfaction. Pivoting isn’t failure. It’s strategic evolution.
When I shifted my focus from running my startup to trading, investing, and creating content, I would be lying if I said that I didn’t care at all about what people would think, and the clout that came with being a “VC backed founder” in a “sexy industry”. But realigning with my passions for finance, education (constant learning), and financial empowerment wasn’t a step backward. It was an intentional move towards a more aligned future.
Growth is messy. People who are constantly evolving aren’t afraid to burn down old version of themselves to make space for something better.
The Mindset Shift You Need
Failure doesn’t mean you’re broken or incapable. It means you’re trying. Most people don’t take big swings because they’re afraid of looking foolish. But fear of failure keeps you stock in a loop of safe choices (that might not be alignment) — far from your true potential. Every failure moves you one step closer to success because it sharpens your understanding of what works and what doesn’t.
Failure stacking is how you build resilience, sharpen your instincts, and develop and clearer vision of what kind of life and business you’re truly meant to create.
Building a Life in Alignment Through Risk
Taking risks is scary. But what’s scarier is staying stuck in a life that doesn’t feel authentic. When you’re willing to fail — to really, spectacularly fall on your face — you gain something far more valuable than success: wisdom, clarity, and courage.
This is your sign angels —
Don’t wait for the “perfect” condition. They don’t exist.
Don’t be afraid to pivot. It’s part of growth.
Don’t fear failure. Stack it. Learn from it. Move forward.
Your future self will thank you.
ps - I’m always rooting for you.
xx,
Sunny