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A High Achiever's Guide to Failing

How to transform failure into stepping stones

Failure is tough to navigate, especially for entrepreneurs with high expectations for their businesses. When you're used to winning, a loss can feel like a slap to the face, which can quickly spiral into ruminating thoughts and regret. It can also trigger anxiety and make you question every move you make.

Although failures have ramifications, they’re a natural part of life, so it's essential to learn how to fail with compassion and not allow it to derail your journey. Instead, you can treat missteps as opportunities to gain wisdom, expand your business, and grow personally and professionally. 

Here are a few tips to navigate those difficult moments when you feel like a failure.

Transform it into a learning experience

Take time to process the mistake and reflect on what happened. If you prefer to reflect on your own, you can journal about it. Discussing the issue with people you trust can also lead to powerful revelations. Once you've gained clarity, it’s time to take action. 

Do you need to address specific factors that caused the failure? Are there plans you need to implement to prevent the same mistakes in the future? Determine if new opportunities have arisen from the setback, like a potential partnership. Some of the best lessons are the ones you only have to learn once, so let this experience help you put your best foot forward. 

While some entrepreneurs prefer to play it safe (especially after a stumble), transformative change occurs when you go beyond your comfort zone and take risks. Use your failures as a compass as you maneuver your next chapter.

Prioritize self-care

High achievers often believe self-care must be earned, like enjoying a glass of champagne after landing a high-ticket client. But, unfortunately, they usually aren’t so kind to themselves following a defeat. Pampering is the last thing on anyone's mindand yet, it's an excellent time to practice self-care and recharge from setbacks. 

The healing process is unique to each individual. If it's a big failure, it may take a few months (or even a year) to recover and work through it. But take your time and be gentle with yourself. 

Instead of being overly critical, allow yourself to feel all the emotions. Whether you're frustrated or disappointed, your feelings are valid. Acknowledging them is the first step to gaining closure and moving forward. If necessary, consider meeting with a therapist, as they may support your healing process in ways your friends cannot. 

Share your mistakes with others

Although failure is a part of everyone's journey, it's still met with stigma. As a result, there's often a sense of shame surrounding it. We’re quick to share big wins, but it’s easier to hide the losses. However, remember that failures are valuable lessons for future endeavors. It's a matter of changing your mindset and accepting your mistakes. 

One way of normalizing and reframing blunders is by sharing them with others. Transparency sets a healthy example for your peers to share their experiences comfortably. In addition, it provides fresh insight into your journey and a reminder that you're not alone.

There's no question that failing is difficult. It can damage your confidence and create mental barriers in your business and personal life. But when you treat mistakes as educational opportunities, you can rise from the ashes and take risks that will propel you to success. True transformation occurs when you use failures as stepping stones toward your goals.

So the next time you make a mistake, be kind to yourself and turn it into something that makes you an even better entrepreneur!


Gretchen Culver is the creative mind behind Minneapolis’ go-to design and planning firm, Rocket Science Events, but her business prowess doesn’t stop there. In 2020, she opened the doors to Minne Weddings, a brand that provides stylish and affordable micro-weddings, as a way to meet her clients’ evolving demands for small-but-significant celebrations. Named one of the “30 Under 40 to Watch” by Special Events and recognized as a top planner by BRIDES and Martha Stewart Weddings, Gretchen’s award-winning work has been featured in magazines, online, and on television

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