Fail Forward: How Setbacks Become Your Superpower

Introduction – Embracing the Power of Setbacks

I’ve been rejected plenty of times.

• I didn’t make the travel soccer team.

• A bank denied me a business loan—after they asked me to apply for it.

• Last year was my lowest sales year ever.

• And perhaps the biggest failure of all: I didn’t try out for the middle school girls’ basketball team because I was afraid I wouldn’t make it.

If you told middle school Taylor that one day she’d learn to embrace failure, I would have laughed. Back then, failure meant embarrassment, risk, and rejection—things I avoided at all costs. Today, I see missed opportunities as even bigger failures than the times I actually tried and didn’t succeed.

What changed? Growing older helped, but starting a business completely rewired how I think about setbacks. Entrepreneurship—and motherhood—have taught me that success is not about avoiding failure, but about refusing to let it stop you.

The truth is, most people never go after the life they want because they’re afraid. Afraid to look foolish. Afraid of rejection. Afraid of failing in public. I know, because that used to be me.

But if you look at any successful entrepreneur—Sara Blakely, Melanie Perkins, Bobbi Brown—they didn’t succeed in spite of failure, but because of it.

I once heard a Navy SEAL instructor say that the people who survive are the ones who fail, fail again, and still refuse to give up. Entrepreneurship—and motherhood—are no different. For most of us, the greatest success is going to come after failure.

The Mindset Shift: Redefining Failure

From a young age, most of us are trained to measure success by grades, instructions followed, and safe paths. But being an entrepreneur means going against the norm, challenging the status quo, and risking failure before realizing a big win.

Sara Blakely, founder of Spanx, credits much of her success to her parents. They would ask her and her brother at dinner: “What did you fail at today?” Instead of shaming failure, they celebrated it. That small mindset shift made failure an expected and valuable part of life.

Last year, PHNX had its worst sales year ever. Personally, it was my hardest year too. Then came this year—navigating chemo while raising a one-year-old. On paper, it looked like failure stacked on failure. But here’s the truth: because of last year, I know what not to do, what I must do, and why I refuse to repeat the same mistakes.

Thomas Edison said it best: “I have not failed. I’ve just found 10,000 ways that won’t work.” Failure is data. It’s feedback. It’s a step forward.

Common Setbacks for Mompreneurs

As moms and entrepreneurs, failure takes on a unique shape.

• Rejection – from clients, investors, or even your kids at dinnertime.

• Overload – never enough time to do it all.

• Comparison traps – seeing what others have and feeling “less than.”

• Inadequacy – the voice whispering “you’re not good enough.”

The solution isn’t perfection—it’s prioritization. Here’s the framework I use to embrace failure and make the hard decisions:

1. Am I making the best decision I can with the information I have?

2. What’s my one priority this day/week/month/year that only I can do?

3. What am I willing to accept as “less than perfect” if someone else does it?

4. What should I delegate or hire out because others can do it faster/better?

When I answer these, I can rest knowing I did what matters most. The rest? Out of my control.

And when comparison hits, gratitude has been my reset button. For example, when I drove a car I didn't love, I used to feel embarrassed. But two things changed my perspective:

• I started thanking God every time I got into the car.

• I reminded myself of our financial progress and why I wasn’t driving something newer.

Gratitude + perspective turned inadequacy into fuel.

Lessons Learned From Failure

At 36, I’ve failed a lot—and each failure taught me something I couldn’t have learned otherwise.

• No one cares as much as you think. Most people aren’t judging you. Those who’ve been where you are will cheer you on. Those who criticize? Likely haven’t tried what you’re doing.

• Failure is a muscle. The more you fail, the stronger your resilience. What once derailed me for months now barely slows me down. Start small: try a new hobby, strike up conversations, or try to solve a Rubik’s Cube. By trying something new you will gain fresh perspective, practice failure, and learn something new in the process.

• Grieve, then move on. Optimism doesn’t mean avoiding hard feelings. Real growth comes when you acknowledge failure, feel the pain, and then release it. It still bothers me to this day that I didn't finish the Half-Ironman I attempted. However, most people will never even attempt a Half-Ironman. As Jesse Itzler says, "you're building your life's resume." I still want to try again to finish the race, but even in failure, my life is better because I tried.

Practical Strategies to Fail Forward in Motherhood and Business

Failure doesn’t have to be the end. It can be the foundation for your next win.

• Keep a Failure Log. Write down what happened, what you learned, and what you’ll do differently. This is your personal After Action Report.

• Seek feedback with intention. If you want to talk to someone outside your network who is an expert on your situation don’t just say, “Can I pick your brain?” Instead: “I did X, here’s where I failed, and here are 3 questions I’d love your insight on.” Be specific, be brief, and honor their time.

• Break big projects into small steps. When I manufactured the first PHNX shorts, I didn’t know where to start. So I Googled, reached out to factories, tested samples, and learned from every “no” until I got a “yes.” That one “yes” still produces our shorts today.

Failure feels overwhelming when you stare at the mountain. Focus on the next step.

Stories to Inspire

Failure is universal—even among the most successful women:

• Sara Blakely – Failed the LSAT twice, sold fax machines door-to-door, and was rejected by countless investors before bootstrapping Spanx into a billion-dollar brand.

• Oprah Winfrey – Fired from her first TV job and told she wasn’t “fit for television.” She went on to redefine media.

• Vera Wang – Failed to make the U.S. Olympic skating team, was passed over for Vogue’s editor-in-chief role, and didn’t enter fashion until 40—where she built a global empire.

Each of them failed—and each of them kept going.

Conclusion – Fail Forward, Always

If you’re still reading, congratulations—you’re already showing persistence and grit. My challenge to you:

👉 Take five minutes this week and ask yourself: “What’s one recent failure I can learn from?”
👉 Write it down. Identify the lesson. Share it with someone you trust.

For me, this looks like embracing social media for PHNX and personally. My biggest regret in business is not leaning into social media and letting my fears drive my decision. Would it have been better to start social media 5 years ago? Yes. Is it better to start today rather than tomorrow? Also yes. If you see me on social media posting cringy videos know that I'm embracing failure and learning too - and feel free to comment on the cringe! And remember:

Failure isn’t the end of the story. It’s the beginning of your next success.

 

TLDR: 

1. What does “fail forward” mean in business?
Failing forward means using mistakes, setbacks, and failures as learning opportunities instead of final defeats. Each failure gives you new information that helps you adjust, grow, and get closer to success.

2. Why is failure important for entrepreneurs?
Failure is essential for entrepreneurs because it teaches resilience, problem-solving, and adaptability. Almost every successful entrepreneur—like Sara Blakely, Oprah, or Vera Wang—failed before achieving lasting success.

3. How can mompreneurs handle failure without giving up?
Mompreneurs can handle failure by reframing it as feedback, setting clear priorities, and practicing gratitude. Building a support system—whether through mentors, family, or community—also helps balance the challenges of business and motherhood.

4. What are some practical strategies to learn from failure?

• Keep a failure log or “after action report”

• Seek honest feedback from mentors

• Break big projects into small steps

• Acknowledge the emotions, grieve, then move forward

5. Who are some famous entrepreneurs who failed before succeeding?

• Sara Blakely failed the LSAT twice and was rejected by investors before creating Spanx.

• Oprah Winfrey was fired from her first TV job and told she wasn’t fit for television.

• Vera Wang failed to make the Olympic skating team and didn’t enter fashion until age 40.

6. How can failure make you a better mom and entrepreneur?
Failure builds resilience, patience, and creativity—skills that directly transfer into both parenting and running a business. Learning to let go of perfection makes it easier to balance the demands of motherhood and entrepreneurship.