Fail Forward: One Success Is All It Takes

You could fail once, ten times, or even twenty times in a row. But if you find success on the twenty-first try—then you’ve won, and those "failures" only add to your story of success.

The problem arises when you fear failure, see it as something to avoid at all costs, and have a negative reaction to setbacks as they occur.

When you try to avoid failure at all costs, you move at a snail’s pace toward your goals, stressing over every decision and task, constantly worrying about whether your efforts will work. This fear of failure can cause you to give up once failure inevitably happens. By quitting or failing to learn from your mistakes, you ensure failure. Don’t manifest failure by fearing it.

There’s a way to use failure to your advantage, and it all starts with a mindset shift.

Reframe How You View Failure

You only need to succeed once to change your life.

It doesn’t matter how many times you’ve tried. If your goal is to become an entrepreneur and achieve financial freedom, and you find life-changing success on your twenty-first attempt, then you’ve succeeded.

It’s not that you succeeded despite all your failures—you succeeded because of them.

Personally, I haven’t reached the point of life-changing success yet. I’ve failed a lot, but my failures have improved over time, and I can feel myself getting closer. Each failure isn’t a step back; it’s a step forward. I’m discovering what does and doesn’t work while building skills and knowledge along the way.

Seek Failure to Make Progress

Strategically seek failure. Try things with calculated risk and without expectations. Structure your attempts so that failure won’t be detrimental to your entire operation. Think of failure as an investment, much like paying for a college course.

For example, if you want to try a business model, decide how much money and time you’re willing to lose, and then take the risk. You’re investing in the lessons and skills you’ll gain during the process. Who knows? You might even succeed.

I did this when I listed my first product on Amazon. I allocated about $4,000 to the attempt and gave myself a year to see if I could make it work. I assumed I might lose the money, and I was okay with that. I knew the process of researching a niche, finding a product, creating a listing, and launching an e-commerce product would teach me a lot—and it did.

In the end, I didn’t lose money. I actually made some. It wasn’t life-changing, but because I accepted failure as a possible outcome before I began, I believe I set myself up for a small success. Most importantly, I learned valuable e-commerce and internet business skills. The money was just a bonus.

Reflect on Failure to Build Skills and Knowledge

With each failure, there are lessons and skills to take away. Stack those lessons as tools for your next attempt and eventual success.

When something doesn’t work, don’t dwell on it or feel sorry for yourself. Don’t get mad that you couldn’t make it happen. Instead, analyze what went wrong and why. Identify where you fell short and focus on filling those gaps in knowledge and skill.

Failure is data. It shows you what works and what doesn’t, allowing you to adjust with new knowledge and new skills.

My List of Failures

I’ve failed at many businesses throughout my life, and I still haven’t found the success I’m looking for. Here’s a quick rundown:

• A t-shirt brand in high school (sold a handful of shirts, then quit)

• Re-skinning iOS apps in high school (made about $500–$800, hit a roadblock, then quit)

• A car detailing business before I had my license (made $0, then quit)

• Selling no-nicotine vapes at 16 (a terrible idea—maybe sold three)

• Selling beats and music in college (made about $1,000 total but eventually moved on)

• Swing and options trading (made some money, lost even more)

• Selling a private-label product on Amazon (most recent—about $3,000 in profit so far, and I haven’t quit)

Looking back, I can see why each of these ventures failed. That’s a good sign because it means I’ve grown.

Just realize the only way to truly fail is to give up entirely.

Remember this quote from Samuel Beckett:

“Ever tried. Ever failed. No matter. Try again. Fail again. Fail better.”

One success is all it takes to change your life. Keep failing forward. That's what I'll be doing.

If you've read this far, I appreciate you and would love to connect over social media.

Send me a DM at @onejacksonriley on X!