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Courage Over Comfort

Rumbling With Shame, Accountability, and Failure at Work

Adapted from Rising Strong

I think the people who wade into discomfort and vulnerability and tell the truth about their stories are the real badasses in this world.

This is especially true of people who rumble with failure. These are people who choose courage over comfort, accountability over blame, and are able to embed key learnings from failures into their lives.

For early interviews about the rising strong process, I was able to meet with Andrew—a senior leader at a successful advertising agency and a total badass.

I recognized some of myself in his story, and I think you might, too.

Andrew is known around his office as a listener, a thinker, an expert in strategy, and the keeper of culture. He’s the guy who doesn’t say much, but when he does, everyone listens. His point of view is sought by colleagues throughout the successful advertising agency where he’s worked for twelve years, especially when it comes to estimating costs and putting together bids for pitches. One colleague said, “Andrew is the reason it all works. His word is gold and everyone trusts him.”

In most advertising agencies, teams respond to proposals from potential clients by creating pitches that include their creative concepts and the estimated cost of executing them. This is notoriously stressful work, with fierce competition among ad agencies for clients and frequent tension between a company’s creative and business teams. The creatives strive to wow the clients, while the business team has to make sure the project nets a profit. One of Andrew’s primary responsibilities is overseeing the financial estimates and approving the final budget that accompanies every bid—­basically, telling the prospective client, “We can do it for this much money.”

Because Andrew has always framed the tension between art and money as necessary and valuable to the process, he is highly respected and liked by both sides of the organization. A colleague from the creative side said, “If Andrew tells me that we need to bring down expenses to make it work, I know he’s thought about it, and I know he understands what he’s asking me to do. I do it.” One of Andrew’s direct reports said, “I’m learning from him and I trust him 100 percent. He’s one of the most thorough people I know. And he’s a straight shooter.”

People who wade into discomfort and vulnerability and tell the truth about their stories are the real badasses in this world.

The trust and influence that Andrew has earned over the years have also positioned him as the unofficial watchdog of the company culture. He accepted that there would naturally be tension between colleagues from time to time, but he had little tolerance for gossip, favoritism, and back-­channel negotiations. Even in heated arguments, which there were plenty of, he was always up-front, respectful, and appreciative. This set the tone for the entire agency.

People who wade into discomfort and vulnerability and tell the truth about their stories are the real badasses in this world.

Everyone at Andrew’s agency was ecstatic when they were asked to pitch a huge ad campaign for a well-­known and influential brand. The proposal was especially exciting because the brand’s needs intersected very well with the agency’s strengths. The creative team was grateful for the big-­budget opportunity to showcase their work and hoped to add the high-­profile company to their individual portfolios. The business team saw the tremendous revenue potential in this new strategic partnership. Within hours, the atmosphere in the office was electric. People were calling home to let their families know they’d be spending long hours in the office over the next two weeks. This pitch would require all hands on deck.

Andrew wasn’t quite as excited as the rest of the team. Everyone was already stretched thin. They had just the right number of projects in various places on the design and production timeline. Adding another—­especially one of this size—­could tip the balance. He also had mixed feelings about the client, who had a reputation in the industry for treating partners poorly. One of his good friends, a colleague who worked in a related field, had once described the client as a bully. Andrew was mulling over these concerns when Manuel, a senior member of the creative team, showed up in his office.

“We’ve got this,” Manuel said. “People are psyched about the project, and we can do it.” His enthusiasm was contagious, and Andrew didn’t want his doubts to squelch the team’s passion, so he jumped in. “I know. We can do this.” Andrew was generally measured in his responses, but he also liked a challenge and wasn’t immune to the growing energy.

For the next couple of weeks, Andrew worked long hours with the team to develop their pitch for the first round of selection. Managing internal relationships and building team cohesion during that period felt like a full-­time job. When people are stretched, their coping skills start to fray. A mere twenty-­four hours after Andrew spoke the words We can do this, the account manager and the creative director stood in front of him, having it out with each other.

Despite the fatigue and tough group dynamics, the entire agency came together to celebrate when they found out they had made it to the second round of the selection process. The win felt like a balm for the frazzled, emotionally and physically exhausted team.

But Andrew was still worried about the burden the heavy workload was placing on everyone, and he continued to have some nagging concerns about the client’s reputation. Still, he was invested now, so he pushed down his uneasiness and joined in the celebration.

The second round of the process required Andrew and the pitch team to fly to the Midwest for a face-­to-­face meeting with the company’s branding team. In Andrew’s words, “This is where things went south.”

“For almost an hour, I watched our team put heart and soul into explaining our ideas and concepts,” he said. “Meanwhile, the entire branding team sat there typing away on their laptops, rarely, if ever, looking up. We’re used to some degree of inattention during these meetings, but it was obvious that these side conversations weren’t even related to our pitch.”

Two people on the branding team then asked questions that had been addressed in the presentation, confirming that they had been too busy emailing or doing whatever it was on their laptops to even pay attention. After a third member of the branding team made an inappropriate and disrespectful comment to the presenter, Andrew told me, “I did nothing.”

He looked at me. “Within minutes of that meeting ending, I thought to myself, I am a screwup. I am a failure. I let them down and they will no longer trust me. It was absolutely a facedown moment for me. My team had worked sixty-­plus hours a week for two months only to be completely dismissed by a group of people I had known, in advance, had the capacity and propensity to do that. Why hadn’t I done something to prevent this? How would they ever trust me again?”

Nobody talked much on the car ride to the airport or on the plane ride home. The team members were deflated and angry, and absolutely exhausted. The long hours had taken a toll on their health and their relationships both inside and outside of work. Andrew said, “The only thought in my head during the entire trip back was, I’m a screwup. I didn’t protect my people. I didn’t do my job. I’m a screwup. I failed. I’ve lost their trust. The tape was on a constant loop in my head.

“When I woke up the next morning, my first thought was, I’m a failure and a screwup. My second thought was, I need to get out of this. I need to make this work. I need an easy fix. Who else is to blame? Who else was responsible for this mess? Then it hit me. I’m hustling. Not only that, I’m underneath a rock. I need to get out from underneath this rock first. I can’t make any good decisions from under here. I thought of your work and realized, Shit, I know this rock. It’s shame. I called a friend who is also familiar with your work and told him the story. I told him that I couldn’t get past the voice saying I’m a screwup. I couldn’t get past how much I had let everyone down, including myself. I couldn’t get past losing their trust.”

When I woke up the next morning, my first thought was, I’m a failure and a screwup. My second thought was, I need to get out of thisI need to make this work. I need an easy fix. Who else is to blame? Who else was responsible for this mess? Then it hit me. I’m hustling.

Andrew told me that making that call to his friend was incredibly difficult, but the rising strong talk was still fresh in his mind, and he realized he was in it. He added wryly, “I was willing to give it a shot—­desperate times call for desperate measures.” His friend’s reply was, “I get it. And I think you might have screwed up. But you make a hundred judgment calls every day. Do you think you’re going to make the right call every time? Does making a bad call make you a failure?”

He went on to ask Andrew what he would say to someone who worked for him if she had made a similar mistake. Andrew replied automatically, “That’s different. Making mistakes is a part of the process.”

After hearing himself say that, Andrew sighed. “No mistakes allowed,” he said to his friend. “This is my perfectionism talking, isn’t it?”

“Maybe so,” his friend replied. “That’s probably why you called me. This is my stuff, too.”

Andrew described the feeling that came over him during that conversation as relief. “It was so helpful to recognize that rock as shame and to make the choice to get out from underneath it. It doesn’t mean that what’s ahead is going to be easy, but it does mean that I can stop hustling. I can start making decisions that are in line with my values. At this point in my career, I need to know how to own my mistakes and set things right.”

When Andrew got to work that day, he was greeted by a team that was still emotionally spent, but also completely confused. Despite their reading of the pitch meeting as a disaster, it turned out that they, along with one other agency, had made it to the final round. No one knew how to react. That’s when Andrew called a meeting to decide their next move.

Andrew described the feeling that came over him during that conversation as relief. “It was so helpful to recognize that rock as shame and to make the choice to get out from underneath it.”

“I have to tell you,” he said, “when we decided to take on this project, I was so focused on proving that we can do this that I forgot to ask the most important question: Should we do it? We were stretched to the max before we started, and I knew this client was potentially a bad fit for us. It was my job to step back and ask questions, and I didn’t. I screwed up. I made a mistake, and I apologize. I hope I can regain your trust.”

The room was quiet until Manuel finally responded, “Thank you for saying that. I do trust you. What happens next?”

Andrew told them that given the time everyone had put in, and the money and resources invested by the agency, they needed to decide as a team if they should continue or not. His vote, he said, was to walk away. Manuel seconded Andrew’s vote and looked toward Cynthia, the account manager. The tension between Manuel and Cynthia was no secret, and everyone in the room knew that Cynthia could probably tell you, to the penny, what the aggressive pitching process had cost the agency over the past two months. Cynthia leaned forward in her chair and said, “I saw the way they treated Manuel yesterday. I vote hell no.” The rest of the team agreed, and the vote was unanimous.

In addition to the financial consequences, Andrew knew that fallout was likely in the advertising community. It’s highly unusual to get that far in a pitch process and pull out. But this was a risk that he, the team, and the agency’s owners were willing to take. During the call to the client explaining their decision, Andrew did not blame the decision on the poor behavior of the company’s branding team, but instead took responsibility for not accurately assessing the fit and timing. Several months later, he received a call from a leader in the company’s branding division asking about his team’s experience. Andrew had the sense that the brand was trying to understand its growing reputation as a difficult partner. This time he told her more directly what he thought about the culture clash and the behaviors he found to be unprofessional.

Andrew and his colleagues told me that something changed the day they decided not to pursue the pitch. Andrew attributed it to Manuel and Cynthia coming together to protect the team. His colleagues agreed about the power of that moment, but they also said that Andrew’s willingness to own his mistake and apologize shifted something in the spirit of the place. The one thing they could say emphatically was that the levels of trust, respect, and pride within the team skyrocketed after that experience. Andrew said, “We worked together. We fell together. We climbed up together. That changes people.”

I love Andrew’s story because of what it teaches us about failure, shame, and accountability.

We worked together. We fell together. We climbed up together. That changes people.

Here’s a person who didn’t have to own anything—­a leader who could have shifted the blame to his own team or to the brand’s disrespectful team. But instead, he had the courage to feel pain, to recognize that he was feeling shame, to reach out and be vulnerable with a friend, to own his part, and to stand in front of his team and be accountable.

The difference between I am a screwup and I screwed up may look small, but in fact it’s huge. Many of us will spend our entire lives trying to slog through the shame swampland to get to a place where we can give ourselves permission to both be imperfect and to believe we are enough.

Failure can become our most powerful path to learning if we’re willing to choose courage over comfort.

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