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“Are you fearless?”

A reporter once asked me that question. How I wish I could have answered her with a bold swagger and a confident yes.

But despite 20-plus years of entrepreneurship and a penchant for motorcycling, I’ve had plenty of things that have kept me awake at night. Particularly in the early years of building my business. I feared losing clients or key employees. I feared failure – with a passion.

But after experiencing some of my greatest learnings from botched attempts — for example, launching a service no one wanted to buy or losing a pitch for a piece of business we really wanted — I’ve stared that tiger down.

The main thing I worry about now is doing or saying something that would somehow violate my values. But I think that’s a rather healthy fear to have and keep.

What are you afraid of? Regardless of what title you hold or where you are on your journey, you’re afraid of something. We all are.

Yet we long to be more fearless in our leadership. I’m inspired by “Fearless Girl” — the bronze statue of a defiant girl standing in front of Wall Street’s iconic charging-bull statue. I want to be that courageous in the face of all things menacing.

But let’s face it. Leadership can be scary at times.

And despite our best efforts to hide those things we’re afraid of, we spend a good deal of time trying to avoid them. That’s human nature, and our preservation instincts are there for a reason. But if you focus too much on your fears, you’re hurting yourself in other ways.

So what’s the secret to breaking through? Here are a few of the bigger fears leaders face and some thoughts on how to tackle those things that scare you the most.

• Anticipate but don’t fixate – Fear of “what could be” can be quite paralyzing. In motorcycling, you learn to assess potential hazards in the road ahead and make necessary adjustments in the moment, but you don’t fixate. If you stare at the pothole or oil slick you’re trying to avoid, you’ll drive straight into it. Most of the things we worry about in life are unlikely to happen. It’s good to think ahead and prepare for the worst, but when you let your thoughts dwell on worst-case stuff, you’re catastrophizing and draining energy needed to react and respond with precision. Keep looking ahead, but maintain some perspective so you can channel your efforts into dealing with what you know, not worrying unnecessarily about what could be.

• Mourn the loss, and move on – Fear of failure is a big one. But failure is inevitable. No one crosses the finish line first every time. You must learn to let go of frustration as quickly as possible and turn loss into learning sooner. It’s okay to be disappointed, but get it out of your system and move on. Set a deadline for mourning (e.g. a day or a week); then get up and get going again. The sooner you can bounce back, the sooner you can try again for the win. And the next time around, apply what you learned so you are smarter, better, faster and stronger – and the win is more within your reach.

• Go for it, take that leap of faith – Fear of looking foolish often holds us back from going for it. As a result, we miss out on a big win because we were afraid to take a chance. But how many times can any of us honestly say we are prepared for the next big challenge of our career—or our personal life, for that matter? Regardless of where we are in our leadership experience, the first thing we have to embrace if we want to lead at our best is a willingness to explore the roads—even if we feel unprepared, unqualified, and unsure. Step out and take a chance. You never know where it might lead.

• Know what matters most – Fear of disappointing others haunts many leaders throughout their lives. Often we attempt to live up to others’ expectations for us. Yet all of the nonsense and chaos – the “head trash” – consuming our thoughts serves only to divert our attention away from the things that really count. In that case, we end up trying to become the leader others want us to be, not what we want for ourselves. In the end, it’s what you think of yourself that matters most. The internal battle is the hardest one. Double down on the things that matter most to you and remember who you are and what you believe in. This will give you the power to push through this fear.

There’s a common thread here – did you pick up on it? Fears don’t go away. There is no magic wand to make them disappear. Instead, we overcome them.

You must learn to embrace your fears and understand they are just a normal part of any leadership journey. Once you accept that reality, you’re one step closer to conquering them.

And guess what? The more willing you are to face them, the less power they hold over you.

I want a share a quote that really sums up this mindset from someone who had good reason to know a lot about fear, but who refused to let it consume or define him: “I learned that courage was not the absence of fear, but the triumph over it. The brave man is not he who does not feel afraid, but he who conquers that fear.” – Nelson Mandela

Facing your fears is the key to overcoming them. But don’t just face them; run towards them. They only appear big when you shy away. They get smaller the closer you get.




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