How Freelancing makes you a Leader - Part 1

In this series, I will be sharing 3 stories as a freelancer and how it helped me become a a leader(Head of Engineering)

Most people start freelancing because they want to make money on the side. But I did not start like that. I became a full-time freelancer to solve real problems for real companies while embracing my freedom of choice and time.

But that journey is never easy. You have to quickly skill up, not just technically but also in other dimensions. You will soon realize your tech skills matter only about 50%. Unlike a full-time job, you can never pause, there are no set goals, and in the initial days, you’re stabbing in the dark, hoping to get clients. Very soon, the reality is that I was fully running my own business, juggling different business functions.

Is it worth it? Looking back, 100% yes.

Will I do this all over again? 100% yes.

Here is why…

Leadership Story - 1

The first time I felt like a leader was when I worked for a client as their in-house Airflow expert. I helped resolve Airflow issues on their customers’ infrastructure. A forward-deployed engineer, if you may.

Before this, I had never been in a customer-facing role at that scale. As I settled into this new world, I enjoyed customer conversations and problems. This was problem-solving on steroids; you must be quick, knowledgeable, and most importantly, know when to seek help. I enjoyed the hustle and the everyday challenges of the role.

That day came, and the real test of customer-facing roles came only when things went south. Pissed wasn’t enough to describe the client's anger.

Part of their infra has been down since that morning(their night), and their Airflow pipelines aren’t running. The client woke up, realized nothing was working, and chose rage mode. Our general rule is that if the customer reports a high-priority issue, you set up a call immediately. The team was new, and our runbooks were a WIP; there was no script to follow.

I opened all the error logs and dashboards I found helpful. Thankfully, I knew where things went wrong immediately, so I jumped on the call with reinforcements…

When I landed on the call, the customer was not ready for pleasantries. They sounded curt, pissed, and unpleasant. This is justified. A business-critical pipeline that didn’t run while the customer was sleeping is a nightmare.

In a dire time like this, common advice like “Empathy matters the most,” but they don’t want an apology; they want a fix

“I’m sorry that happened.” No more pondering or feeling sorry

“Here is the problem”, I highlighted the dashboard and opened the logs. By this time, seeing that I came prepared and I already knew what the issue was, the client calmed down a teeny bit, again, they want a fix, not where the problem is

“We need to fix the config, redeploy the pipeline, and watch for another 20 minutes to ensure nothing breaks.” 

“Alright, that’s reasonable,” the client said in a super soft voice.

I will never forget the change of tone in his voice. That was the most validating moment of that role, the first time it struck me what the JD of such a role is: to enter chaos and emerge triumphant, to take ownership of problems that you didn’t create in the first place. To keep your emotions at bay and put the logical brain to use. There is no room for ego here.

A year later, I signed off on that client, saying I wanted to be one who “built things,” not just “fixed things.” I always wondered why I ever said yes to that contract in the first place. Only the answer came four years later….

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Over to you, what was that one moment in your career when you felt like a leader?

Thank you for reading this far. P.S. No AI was used to write/edit the above piece.