Running a Shop How to Lead Leadership

Lead Fearlessly

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“Where in your life do you need to fail to make it better?”

That’s the question that business consultant and communications expert Josh Dye, who has worked with shops to improve leadership skills through his company, Convene LLC, says every business owner should ask themselves.

“I think one of the reasons it’s important is because often times, things that used to be productive routines that we set up in our businesses grow stale,” he says. “You have this opportunity to get out of the routine that’s become a rut and implement new processes.”

The reasons a routine goes stale vary—people, technology or the industry itself can change—but to remain happy, healthy, productive and profitable, making changes is critical, Dye says. That doesn’t, however, mean it’s easy. In fact, Dye says that for many shop owners, change involves a certain amount of pain.

“Making that transition can feel like failure because you have to acknowledge that something you set up is no longer working,” he says.

That’s where the idea of failing fearlessly comes into play: Dye says that to stay ahead in business, leaders need to be willing to take a risk, feel uncomfortable and, if an idea does fail, look at the valuable lessons that can be gained from it.

“The idea of failing fearlessly is really for two groups of people: For one group, it’s those people who are frustrated and unhappy and things aren’t going well. The other is where things are going well but they’re desiring greater fulfillment,” he says. “Much of failing fearlessly is looking at the patterns, the routines in your business and finding out, ‘This isn’t working anymore but it’s uncomfortable to fix it.’ That’s probably the thing you most want to fix or address.”

Dye outlines his top tips for motivating yourself as a business owner to lead fearlessly and tackle the uncomfortable aspects in your shop that prohibit you from moving forward.

1) Think critically about the changes in your business that need to take place.
To begin the process of understanding what you need to face, Dye suggests asking yourself, “What is the thing you always talk about wanting to do but never do?”

“You might be talking to your staff regularly or your significant other, telling them that this is something you’ve been saying you want to do but don’t act on and do,” he says. “If someone feels their business is stuck in a rut, they often need to listen to the ways they’re talking, the things they’re identifying to their friends and family. Really, those are the guiding light for what you need to act on.”

Look for patterns in your life or begin to pay attention to what you frequently discuss or even complain about. You’d be surprised at how quickly those patterns jump out, Dye says.

Another pertinent question to consider is, “What is something you feel like you tried once but quit too early?” That could be because the timing wasn’t right, people around you criticized the decision or you second guessed your own decision. Dye says nearly every leader has examples of times they tried to implement a good idea but didn’t see it all the way through or only attempted it half heartedly. Just because you tried it once and it didn’t work doesn’t mean it was the wrong choice, he says. Finally, make a list of the areas of your business that make you frustrated or unhappy. Dye says it’s an unusual practice but it can be helpful to see it laid out and prioritize those areas based on importance or frustration level.

2) Create an inventory of your relationships.
An important step to leading fearlessly is also understanding your relationships, Dye says. You need to understand who in your life creates stress and keeps you fearful versus those who support and encourage you. Dye calls this task a relationship inventory. First, make a list of everyone in your life, professionally and personally, that bring you energy, connect you to positive things, are good influences and who you feel energized by after spending time with them. Then, make another list of those who create setbacks and leave you feeling drained after spending time with them.

“If you don’t have people in the first list, we often need to change our social routines to meet new people and that’s where, as an adult, it can be challenging,” he says. “You need to change your networking routines to meet new people who are where you’re at now in your life.”

“You’re going to become a more resilient person even from making a wrong decision.”
—Josh Dye, owner, Convene LLC

Regarding the second list, Dye suggests taking a hard stance and making decisions around those people. If possible, consider spending less time with the person and create some distance. If distance isn’t an option, he says you may need to have a difficult conversation and address what you’ve been avoiding or simply end the relationship entirely (such as firing an employee). The point, Dye says, is having a firm understanding of the relationships in your life.

3) Make a final decision.
Now that you understand both the people and the areas that are causing you stress, Dye says the next step is to pick one of those things and make a decision to do something about it.

“Often, you need to act before you believe you’re ready. What I realized is that you end up having this battle with your emotions and feelings and you stop yourself from acting because you feel you’re not ready or you’re concerned about the consequences or if other people are going to criticize or you’re worried it might not work,” he says. “The reality is that if you’re in a place where you’re unhappy or where you’re not productive anymore or profitable, failing is remaining unhappy, unhealthy, unprofitable. Failing fearlessly is acknowledging where those areas are and doing something about them.”

Dye says that business owners need to redefine courage not to mean something drastic like rescuing someone from a burning building but actually relate it to a process or a decision.

“It takes a difficult decision and actually addresses it and makes a decision to do something about it,” he says. “What are you going to do? You’ve done enough thinking, now you’ve made your final decision.”

4) Prepare thoroughly.
Just because you’ve made a decision to act doesn’t mean the change needs to happen right away. Next, you need to prepare and consider the potential impact of the decision on employees, the business, the finances, and from a legal standpoint.

“You do all the preparation so when you make that first step, you’ve done as much preparation as you can,” he says. “Things don’t have to happen fast. What I’m getting at is that when we realize we have to make a change, we think all of a sudden, it’s just going to be this really fast-moving process that’s really overwhelming. It doesn’t have to be if you’re willing to feel uncomfortable and act within feeling uncomfortable.”

5) Take the first step.
“It really is at this point about doing something. I know that sounds a little oversimplified but we do a lot of planning and brainstorming, but often there’s very little action and that’s where the failing fearlessly part comes in,” Dye says.

Even if you feel uncomfortable, Dye says to to take the first step. In fact, he says to get comfortable making decisions that you don’t always feel good about.

“Good decisions don’t always have to feel good,” he says. “It’s something you don’t feel good about and you feel fear and a lot of uncertainty, but you’ve come to a place where you know it’s the right decision for you and you’re ready to make it.”

The reality, Dye says, is that you don’t always know if a decision is bad until after you’ve made it—but that shouldn’t stop you from making difficult decisions moving forward.

“You may choose the wrong direction, but that’s actually the point. Even if you do make a bad decision, you’re going to learn something from that. You’re going to become a more resilient person even from making a wrong decision,” he says. “I’m not advocating for unthoughtful, random decisions. But if you’re being intentional about your business and intentional about your life, you can make a decision that you might later regret but that you learn something from it and become better as a result of that difficult experience.”

6) Endure and/or embrace emotional discomfort.
Feeling uncomfortable isn’t necessarily a good feeling, but the more you’re able to endure or embrace that discomfort is crucial to failing fearlessly. Fear, anxiety and frustration aren’t signs you’ve made a bad decision; it’s actually simply a part of tackling something difficult, Dye says.

“That’s a common emotion associated with living, with change, with moving in a new direction,” he says. “It’s usually a mixture of joy and fun and anxiety and fear and frustration. You’ll get further in life and business by understanding the breadth of emotions and that you can still make good decisions throughout those unpleasant emotions.”

The key is to understand that those emotions will pass and any inconveniences are generally temporary, Dye says.

“Changing vendors or changing staff roles is really inconvenient,” he says. “But usually just for a short period of time. Because we’re so convenience oriented, sometimes we’re not willing to endure a moment of inconvenience for long-term gain.”

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