What Are Leaders Scared Of?

Why is leadership so scary?


Calvin Bushor

2 years ago | 7 min read

Leadership is a scary thing. It’s riddled with monsters, ones that could eat you alive at any moment. Its terrain is extremely dangerous where one slip and you will fall to your death. Every door you open has a ghost, goblin, or ghoul behind it ready to jump at you in terror. Think of the most horrifying movie you’ve ever watched or book you’ve ever read, leadership is 10x more frightful!

Leadership is the scariest career choice I’ve ever made, but I love it.

For those considering leadership, my goal is to scare the pants off of you. Why? I want you to be eyes wide open and know what you are signing up for. I want you to understand the responsibility of leadership and respect what it means.

For those who are already in a position of leadership, I hope this piece resonates with you, enjoy. I’d love to hear what scares you!

Why is leadership so scary?

There are many answers to this question. I’ll list my top three!

1. The future of the company is in your hands.

This might sound cliche, the company’s future is in your hands, but it’s true. If you are a founder, senior executive, or first-year leader, the team you lead is looking to you for direction. Where you point, they venture. If you point, nay, WHEN you point in the wrong direction, the company suffers.

When we mess up as leaders, we always chalk it up to being a great learning opportunity. I know I’ve said it ten times this month. While it’s true, these mistakes HURT! The company loses loads of cash. It might result in downsizing or people quitting. It leads to missing out on more funding. Learning opportunities are not cheap.

Now, I know a leader is reading this right now saying, “You can’t be afraid of making the wrong move, otherwise you’ll be paralyzed.” I agree. It still scares the ever-loving pants off of me that when I mess up, what it could mean to the entire future of the company.

That’s why I take great care of my decisions. I don’t let it paralyze me but rather, I use it to help me ensure I am doing my homework and not being reckless or lazy. Business is all fun and games until you and your entire team are out of the job. Take risks. Go for the moon.

But be smart about it. Be calculated. Be intentional. If you are a little nervous or feel a tad sick to your stomach before making a big decision because you are afraid, I say, good! This means you know what making the wrong move could cost everyone involved.

2. The livelihood of the people on your team is yours to ruin.

Sounds pretty dire, right? In the first point, I touched on making the wrong call and the entire future of the company could go up in smoke. This means, everyone loses their jobs and are left competing for work in this wonderful 2020 job market. These people are parents.

They’re grandparents. They are responsible for kids and other humans. Their paycheck puts food on their table and a roof over their heads. They have bills. They have debt. They have medical situations. Cancer treatments. Injury rehab. They have a mom or dad they are caring for at home. They’re people who have lives that are depending on you and your leadership.

Too many leaders forget this. We are leading humans. Each of us has a second life outside of work but it’s the work that provides for that second life. This is where the responsibility and maturity of leadership are realized. When you can recognize the people on your team as people and connect your leadership decisions to their lives, it makes the weight of your decisions that much heavier.

I’m not scared that my company could fail. I’m terrified that should it fail, the humans on my team can’t survive. I’m also afraid of what would happen to my family, the ones depending on me. A leader understands this and considers the cause and effect of their actions.

3. When you fail, everyone feels it.

Everyone. When you make a bad pitch and you miss out on a potential investor, what happens? Best case scenario, you slow down growing the team and people don’t get bonuses this quarter. Worst case, you are shrinking the team or you’re not able to pay anyone and you’re on the verge of closing your doors.

When you chase the wrong pivot, what happens? Your competition gets an advantage, takes your clients, or worse, poaches your team. When you hire the wrong senior executive, what happens? Your business suffers and your team starts to leave.

Leadership is cause and effect. Your goal is to create the right effect. It’s like a giant game of chess where there are thousands of combinations of moves and at any moment, the wrong move results in checkmate, and you lose. The right move though, causes the game to shift in your favor. Sometimes, the right move is to just survive to the next turn in hopes your opponent slips up.

You might even sacrifice a pawn or two to influence the game. Surviving as a leader might mean making it to the end of the day, week, or month by getting to your next major milestone, figuring it out one step at a time. Sacrificing as a leader might look like passing on a cheaper client right now in hopes of a more lucrative one later. The wrong move negatively impacts everyone on your team. The right one lifts everyone up.

Let’s be real. We’re going to mess up. As leaders, we will make mistakes and those mistakes will have consequences.

For me, it’s about managing risk. I’m more willing to take some risks over others and I’ll think more than twice about moves that could cost me and the team the game. I also build redundancies and fail-safes into my team’s system so that we can handle some adversity. I’ll ensure more than one person has knowledge, access, and the skills to perform a job.

I do this because people pursue other opportunities and I don’t want my team to be in a situation where the tower of knowledge on the team, leaves. What can I say, I’m a software engineer at heart and resilient systems are my jam, especially when designing a team.

Leaders are in part architects. Not only are we leading our business and team, but we’re also designing a system that scales, thrive, and can handle a few bumps in the road. The part that scares me is when I miscalculate something and the system I’ve designed can’t handle the situation at hand. My team might be ill-prepared or I’ve made a poor assumption that has a painful side effect.

The reason I build redundancy into my team is that I once assumed someone would be on my team forever, and when they left, the team and the business suffered for months. My poor assumptions cost us time, missing our market window. It caused angst on the team, causing two others to leave the company before we launched. My team design had a massive, single point of failure and it hurt!

Did I cause you to be scared of leadership?

Being a leader means the future of the company is in your hands. Being a leader means the livelihood of the people on your team, their family, their futures, are looking to you and your leadership.

Being a leader means, your mistakes are felt by everyone under your jurisdiction. While I hope this opened your eyes to realize what leadership means and how scary it is, I don’t want you to be afraid of leadership.

Fear is a good thing. Having fear means you understand the importance and the responsibility of your actions as a leader. This fear should help you with your decision making. It should motivate you to dig deeper so that you ensure you set your team and business up for success.

Allow it to push you, to do more research, to be more present, to be all-in! Yes, we will make mistakes. Yes, look at these as learning opportunities. But really learn from them, that’s my ask.

Leadership is scary, but I love it!

Even though leadership is the scariest career role I’ve ever held, it’s the most rewarding job I’ve ever had. I love seeing the people on my team do incredible things. I love helping them overcome obstacles so that they can achieve something unbelievable.

I love coaching and developing my team into a better version of themselves. I love to acknowledge the scary things in front of us as a team and then inspire the team to go for it anyways. The good outweighs the scary all day long for me and I am grateful that I chose to be a leader all those years ago.

Many leaders I talk to say the same thing. They love leading. They love people. They love seeing their team achieve awesomely. Some days are absolutely brutal as a leader but nothing can compare to the good that comes with leadership.

What scares you about leadership?

If you are thinking about leadership, what scares you? If you are already a leader, what are the parts of leadership you’ve encountered that you’re terrified of? Acknowledge them, don’t ignore them. Instead, let them ground you. Let them motivate you. Let them inspire you to be a better leader.


Created by

Calvin Bushor

Technologist, leader, writer, and I created to help new tech leaders be better leaders and build awesome dev teams! #LeadershipLife







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