Should You Take The Leadership Leap?

Leadership is a craft, it takes decades of practice


Calvin Bushor

3 years ago | 6 min read

Are you thinking about becoming a leader of a team? Are you asking yourself if you should take the leap but don’t know if it’s right for you? Are you a newer leader and are struggling to figure out how to transition into your new role? Are you asking yourself if this is the right path for you, and are considering bailing on your decision to lead a team?

I too struggled with all of these questions. I didn’t know if I should stop my career as an engineer and start a new one as a leader. I didn’t know if I was making a mistake or if I would be any good at leadership. I had massive impostor syndrome and often contemplated going back to being an engineer.

This is that story. From taking the leadership leap to almost quitting, I will share what I went through in becoming a new leader and help you navigate this muddy water as you wade through it yourself.

Chapter 1: The Leadership Leap

It was 2012 and I was a senior software engineer responsible for building some industry-leading fin-tech products and services. Prior to this opportunity, I experienced rapid growth in my career, starting as an intern and turning into a senior engineer within four years.

Our company was growing at a tremendous rate and there was an incredible demand for new software team leaders. My leader approached me and pitched the idea for me to lead one of our development teams focused on building our new showcase product.

I was ambitious and even a tad arrogant, thinking it would be easy and good for my career, so I said yes!

My leadership leap was a mixture of timing, need, and being pushed into it by my leader. It wasn’t necessarily something I pursued. I was curious about leadership, mostly because I looked up to my leader and envisioned myself following in his career footsteps. I never interviewed for my first leadership gig but rather, I was tapped on the shoulder.

This is the biggest regret I have on my path to leadership. I didn’t have to sit in front of anyone and answer hard questions like, “why do I want to be a leader?” I never had to be introspective to understand why I felt I was a good fit for leadership and I didn’t have to come to the conclusion that it was something I wanted to do.

Lesson #1: Figure out why you want to be a leader first!

If I knew why I wanted to be a leader and if I interviewed for the role, I would have had a much better understanding of what leadership really was. Instead, I thought of leadership as the next step in my career but I soon realized that leadership isn’t something you can just achieve. It’s much much more than that, and I was not ready.

Leadership is a commitment and a craft in and of itself.

Everyone’s path is different. Some of us pursue leadership and some of us stumble into it. While I encourage others to pursue leadership through training and interviewing for it, I am grateful for the path I took because it forced me to learn some hard lessons about myself and to grow into the leader and person I am today.

If you don’t know why you are a leader or why you would want to be one, read my article about finding your Why

Chapter 2: Drowning, failure, and fortitude

The next two years were some of the most difficult in my early career. I quickly found myself in way over my head. I didn’t have a ton of leadership training, mostly just raw leadership skills and a lot of energy and charisma.

I didn’t know how to lead a product development team, yet I found myself in meetings with senior leadership, representing all of Technology, answering questions I had no business answering.

Several engineers on my team quit, our project was behind schedule, and to top it off, my leader and mentor, the one who pushed me into leadership, left the company.

I felt lost and very alone at the time and I didn’t know what to do. Just when I was about to quit and go back to engineering, two significant things happened.

  1. My “accountabili-buddy” called my BS! I was in all sorts of agony over my recent perceived failure. My accountabili-buddy* and I went out for some adult beverages and had a solid heart to heart. We had some real talk and he was blunt and direct with me, stating I wasn’t all-in as a leader, I was split, playing half engineer and half leader. He said, by being half good in two places meant I was actually not good in either. I needed to be all-in on either leadership or engineering, and I needed to make a decision! He was right, so I had some thinking to do and a decision to make. (*Accountabili-buddy: Someone to partner with throughout your career, holding each other accountable to becoming the best version of yourselves.)
  2. The CIO called me into her office and we had a “chat.” She reflected on the situation; my mentor leaving, the state of the project, and the recent turnover of the team. I thought I was cooked, this was it. She didn’t let me off the hook at all but she surprised me by not firing me and instead, challenged me to learn from the moment and to push through. She wanted me to find a way to lead the team to succeed and she told me it was time to grow up and to become a real leader. She believed in me when I didn’t believe in myself.

Lesson #2: Leaders need leaders

Leadership can be very lonely at times because you don’t always have someone to go to. Your team has you to go to as their leader, but who do you have to go to? When my leader left the company this feeling was amplified for me, and it took time to realize that I needed a new leader.

The funny thing I’ve learned on my leadership journey is, your leader isn’t always the person you report to, it’s someone that helps you when you need support and real talk.

In the example above, I lucked out and found two new leaders. One of them happened to be my friend, who could relate because he’s experienced it prior, and the other was the leader of a 2,000 person organization, neither of whom I reported to.

These two people gave me leadership by being direct and helped me see reality. Most importantly, they supported me and believed in me when I needed it more than ever. One of the most inspirational things a person can do is, to give the gift of belief in another person.

Their support and their leadership allowed me to develop the fortitude to commit to leadership, and I use this lesson often to help me through the hard parts of leadership, the ones you don’t understand until you experience it for yourself.

Chapter 3: All-in on leadership!

It’s been almost a decade since this career-defining moment for me, where I chose to commit to leadership instead of going back to engineering.

Upon reflecting, it was a scary moment because I was officially letting go of my past career and moved towards a new one. It was also freeing because I was able to give leadership the focus it deserved so that I could truly begin to master it.

I started to focus on the people and how to help them grow in their careers. I started to focus on the team, learning what a healthy, happy, high-impact teams is all about. Our team started shipping on schedule, people experienced promotions, and we got our product MVP live!

Lesson #3: Leadership is a craft, it takes decades of practice

To this day, I continue to practice All-In leadership. It’s been the most challenging role I’ve ever experienced but it’s also been the most rewarding because I get to help people and teams become unstoppable. As a leader, I get to give that gift of belief and support others need to push through and realize beyond their potential.

I’ve been able to develop stronger empathy, vulnerability, and humility to become a more approachable leader, one who is more human and able to connect with all types of people. I’ve committed myself to the leadership-life and I will continue to practice my craft for years to come.

Are you ready to take the leadership leap?

Do you know your Why? Do you have accountabili-buddies and other leaders you can go to for support and real-talk? Are you willing to commit to an entirely new career that requires decades of practice? Okay, then, jump!

Thank you for taking the time to read this article about Leadership Life! Leadership is not easy, let’s practice together!


Created by

Calvin Bushor

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







Related Articles