Fail Fast, Fail Forward: Turning Setbacks Into Stepping Stones for Success

Building an organization from the ground up is a journey that’s rarely linear. It’s messy, unpredictable, and humbling. But if there’s one thing I’ve learned along the way, it’s this: failure is not the enemy – it’s one of our most powerful tools for progress.?

When I began building JustFund, I was determined to redefine the way we moved money to communities. Our common application became a category-defining product:? the nation’s only grantmaking platform that integrates multiple equitable technologies to radically change the way we give.

Category-defining solutions are nearly always the result of continuous testing, learning, and adapting. Apple’s first computer was a far cry from the sleek, intuitive devices we know today. The early days of Amazon were marked by failures in everything from product selection to website functionality. The initial version of the iPhone was riddled with design and usability issues before it became the game-changer it is today.

We’ve all heard the adage, “Fail fast, fail often,” but let’s be honest – failing is uncomfortable and sometimes disheartening. I’ve learned many times over, in both my personal and professional lives, the magic is in how we respond. We need to fail in a way that accelerates learning, pushes boundaries, and brings us closer to a breakthrough.

4 Key Benefits of Failing Forward and Failing Fast

"Failing forward" is a concept popularized by author and leadership expert John C. Maxwell. It’s the idea that failure isn’t the end of the road, but rather a stepping stone that propels you closer to success. When you fail forward, you extract valuable lessons from each failure and use those lessons to adjust your course and refine your approach.

It’s a lesson I learned early in life. Growing up as a competitive gymnast, I was taught to face my mistakes rather than shy away from them. By confronting my errors head-on, I could analyze what went wrong, make corrections, and strive for a better outcome. This practice helped me ultimately win the Missouri State Championship as a teenager.?

Now, as? a parent to three teenagers, I’m learning and pivoting on a regular basis. One of my children has multiple disabilities and his complex set of challenges are so unique that we carve our own path as we figure out solutions. There have been a lot of lessons and unviable solutions along the way, but I never considered quitting. Instead of feeling defeated, I’ve felt encouraged and relieved to check off one option and narrow down other solutions for my son.?

Professionally, I’ve spent more than two decades building national organizations. Through this experience, I’ve learned that it’s not only important to “fail forward” but do the work of failing, quickly. I love the practice of intentionally and thoughtfully failing fast for nonprofits because it allows us to remain agile and responsive in addressing complex social challenges. Now, as the founder of a tech-first nonprofit, I drive our team to fail fast. Here’s why I think this practice is so important:

1. Minimizing wasted resources: Every decision you make as a founder requires time, energy, and capital. Failing fast allows you to quickly identify which ideas or approaches aren’t working, so you can cut your losses and focus your resources on what will drive the organization forward.
2. Accelerating innovation: New ideas are born from trial and error. Failing fast encourages rapid experimentation and innovation, which is essential when you’re trying to define a new category or create a game-changing solution for communities.
3. Creating a culture of continuous improvement: In an organization that embraces the "fail fast" mentality, failure is viewed as an essential part of the creative process. This creates a culture where experimentation is valued over perfection, and where learning from mistakes is prioritized over avoiding them. This approach encourages employees to take risks, challenge the status quo, and constantly iterate to improve the product.
4. Fostering customer-centricity: When you’re building something new, the product you envision might not always align with what the market wants or needs. Failing fast means testing ideas with real users as early as possible to ensure you’re on the right track. Their feedback will guide your development, helping you avoid building something that misses the mark.

How to Lean Into Failure and Use It to Your Advantage

If failure is such an essential part of building effective solutions, how do we make sure we’re leaning into it in a productive way? Here are a few tips I’ve learned for making failure work for my team and me at JustFund:

1. Create a safe space for experimentation: Encourage your team to try new ideas, take risks, and test assumptions. Reward creativity and experimentation, even if the results don’t always pan out.
2. Be data-driven: Make sure you’re collecting data at every stage. Whether it’s feedback from users, product performance metrics, or market trends, having data will help you make informed decisions and course-correct quickly when something doesn’t work.
3. Stay flexible: Failure often presents new opportunities that you may not have considered. Be open to pivoting your approach, your solutions, or your model based on the lessons you’ve learned. Flexibility is essential for adapting to the unexpected.
4. Reflect and iterate: After each failure, take the time to reflect on what went wrong and why. Use this reflection to iterate and refine your approach. Don’t just move on to the next thing—understand the root causes of your failure and use that knowledge to inform your next steps.
5. Celebrate failures as learning milestones: Change the narrative around failure. Instead of seeing it as something to be ashamed of, celebrate the learnings that come from it. Recognize the courage it takes to fail and encourage others to view failure as a stepping stone to success.

By failing fast, failing often, and failing forward, you can turn every setback into a valuable opportunity to refine your approach and move closer to achieving your vision. When you embrace failure as a key part of the building process, you give yourself permission to innovate, take risks, and ultimately create something extraordinary.