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Success and Failures

How 'Failing Up' Actually Helps Your Reputation

It takes more than success to build a memorable personal brand.
How 'Failing Up' Actually Helps Your Reputation
Image credit: Klaus Vedfelt | Getty Images
Guest Writer
Reputation management and personal branding expert
8 min read
Opinions expressed by Entrepreneur contributors are their own.

I sat with my new client to begin what would be an intense three-hour personal branding “intake” session, the first step in my reputation management coaching. I asked him what makes him great. What makes him memorable?

“Failure,” he said. “I’m an expert at failing.”

I’ve heard many responses to my question, but none that took me back like this one did. Failure? Isn’t that what we’re taught to run from, hide from and never admit in the light of day?

Failure, as he described it, was his specialty. He’d been a serial entrepreneur before landing his current role as president of a fast-growing technology company. He’d started more companies than he could realistically list. And most of them failed.

They failed for a lack of planning, market timing, funding, liquidity, wrong talent, wrong leadership, wrong marketing or any one of the many reasons he listed. And as each one failed, he took note. While he failed many times, he didn’t fail at the same thing twice. Each time, he learned from the failure, right-sized what needed tweaking and moved forward with new information and bold confidence.

Much has been written about the keys to driving success and accomplishments. Few books are written about the power of failure. Those that are written are either inspiring (Keep going! You got this! Don’t give up!) or academic (analysis of the many failed inventions Nikola Tesla tried to bring to life ) or cliché (leading with Edison’s quote, “I have not failed. I’ve just found 10,000 ways that won’t work.”)

Can failure ever be a key to success?

Failing-Up

If the definition of “fail” is to be unsuccessful in achieving one’s goal, then how can we “fail-up?” Failure implies down, as in moving down in success, not up like achievement.

Failing up refers to taking risks, shooting higher and learning from events where we missed our goals. In his work on the topic, actor-turned-author, Leslie Odom Jr., encourages us to give ourselves permission to fail, to come up short, in order to pursue our dreams. If we don’t try, we’ll never succeed. If we fail, we can learn from it. But if we don’t try, we’ll never move forward.

Similarly, in her powerful work around embracing vulnerability and risk, Brené Brown, the research professor at the University of Houston who spent years studying courage, vulnerability, shame and empathy reminds us, “Embracing our vulnerabilities is risky but not nearly as dangerous as giving up on love and belonging and joy -- the experiences that make us the most vulnerable. Only when we are brave enough to explore the darkness will we discover the infinite power of our light.” As she shares, it is in realizing our frailty and humanness that we connect with others who are also realizing their humanity.

Failing up is not about putting spin on your mistakes or “reinventing yourself” as new-and-improved. It’s not about blanching your reputation to be seen as having “learned from your mistakes.” Failing up is about realizing that we can learn as much from what didn’t work as what did.

It’s also about not stopping when confronted with failure. If it’s that easy to stop you from building that company, taking the company public, hiring that innovative team, creating that new category, then you were likely not meant to do it. If Steve Jobs stopped innovating each time he launched a product at Apple that flopped, we wouldn’t have today’s technology. As was noted when he died, “he’ll also be remembered fondly as the poster child for how making mistakes -- and even failing -- can sometimes end up being the best thing that ever happens to you.” His reputation for innovation, perseverance and courage in technology continues even today.

Related: 9 Quotes on Success and Failure from J.K. Rowling

Failure and Business

Years ago, I spoke to a group of graduate communications students about the risks and rewards of being an entrepreneur, the process of building an international brand and the many lessons I’ve learned coaching senior executives. We talked about failure.

Entrepreneurs know failure. Whether it’s pursuing the wrong business strategies, hiring people we thought were as skilled at our work as they had let on, or partnering with clients or investors we knew better than to try to engage with, we know how to fail.

One of my failures came early into my business. I built a series of information-rich webinars on reputation management and personal branding. They were well-developed and informative, and I launched the platform expecting to sleep as the cash rolled in. Instead, I heard crickets. Sales were pitiful and my business brand and reputation were taking a hit. I took the site down and walked away in defeat.

At first I thought, “I’m not good at online learning… I should stick to live speaking programs only… I suck at delivering content through the internet.”

Upon reflection, the platform didn’t work for many reasons: 1. I was too new to the game. I didn’t have a following or tribe who knew my work and was interested in paying for it online. 2. While I’d researched pricing of similar offers, mine was too high. Combined with #1, this made the sale too steep. And 3. I didn’t invest enough into creative marketing targeting my specific audience. This last one was hard to swallow, since I spent many years as a chief marketing officer.

Had I closed my mind to the idea of online learning, and not taken away these gems, I might have rejected the opportunity to join with Lynda.com (now LinkedIn Learning) to produce several incredible courses on reputation management, personal branding and military transition. I found out that I am great with online learning, with the right partners, timing, and followership.

Related: The 3 Stages of Failure in Life and Work (And How to Fix Them)

Failure and Resilience

Now, more than ever, we need to lean into (and promote) our learnings -- good and bad -- to build thicker skin, greater resilience and bolder followers (tribes). I’ve learned this from my work with the military.

In the military, failure is not an option. Failure of a mission or strategy is not viewed as a “learning opportunity” because lives are at stake -- lots of lives! Service members are taught to push through adversity, overcome challenge and discomfort and to get up after falling down. Yes, there is analysis after the fact (an After Action Report or AAR, as it’s called) to learn what worked/didn’t, but the presumption isn’t that failure is to be embraced as soldiers storm the battlefield.

It’s their resiliency to get up each time they are knocked down that I’ve learned from: their ability to continue to want to improve, learn, suffer, learn again. Resilience is the greatest skill I’ve learned from failure, and I’ve learned it first hand from coaching thousands of veterans who live with the need to adapt and overcome on an hourly basis.

Related: 10 Blessings That Come Hidden in Rejection, Losing and Failure

Reputational Management and Failure

Many of my clients have failed. Not all have proudly displayed their track record of unsuccessful ventures as the client I opened this article with, but they have experienced the “agony of defeat,” as the broadcast staple goes. Failure in managing their reputation. Failure in protecting their promises and keeping them sacred. Failing to put others’ needs before their own yet professing to practice servant leadership.

Reputation risk management leverages failure. In helping a client overcome negative perception, I look at what they learned, what they did differently afterwards, and how they used their “prison sentence to find God,” so to speak. Then we make a choice whether that failure becomes part of their personal and professional narrative or not. There is an option.

While people want to hear repentance and regret, more importantly they want to see proof. Audiences want to see more than lip-service. In my experience, customers, clients, peers and other stakeholders will forgive if they see evidence of change for the better.

Going forward, accept that failure happens. To all of us. Consider a new framing around failure: If we learn from mistakes, we find magic in that learning, and can build a reputation that is memorable and positive.

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