Taking the Leap

How do you decide when it’s time to take the leap? regardless of what that leap might be?

It’s challenging to truly convey the intense anxiety and fear that accompanies the switch from one airline reservation system to another. After what feels like an eternity of managing spreadsheets, determining fare bases, setting baggage allowances, comparing economy to premium economy equivalents, and juggling a myriad of other variables, there comes a pivotal moment. Sales are halted, and all existing tickets are converted into new ones with new booking codes. In just a few hours, everything will either proceed smoothly, allowing customers to purchase flights, check in, and perform all the expected tasks, or the entire system will come to a standstill, leading to widespread panic.

For me, the most significant insights are these: The go/no-go decision-making process has its time and place. It’s crucial not to take that leap until you’ve done everything possible to mitigate the risks. However, there comes a moment when you simply have to take the plunge, see where you end up, and then continue pushing forward. Fortunately, when we faced this challenge, everything worked out in the end. But I’ll never forget that day and the overwhelming fear it brought!

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When Life Goes Wrong

Life is unpredictable. Somewhere in the midst of 2015, the brilliant startup company I was part of turned out to be not so brilliant, and it fell apart. I had exhausted all my savings, and when the paychecks ceased, I spent three months supporting my family solely on credit cards. A promising opportunity emerged, contracts were drafted, but it never came to fruition. Then, another exciting chance in IoT presented itself. Just after they made an offer, but before anything was finalized, the company was acquired, and all hiring was halted.

Out of sheer necessity, I found myself working at a regional airline. This unexpected turn proved to be transformative, largely due to the incredible colleagues and mentorship I received (a special shoutout to Colin Lewis!). Additionally, we embarked on an extensive digital transformation, introducing a new website, check-in systems, and a revamped ticketing system. This experience provided me with a deep understanding of how airline ticketing systems operate.

From there, my career trajectory was swift. I evolved into roles such as a technical architect, product manager, and now, a CTO for product-based software. Throughout this journey, I constantly battled the nagging feeling that I wasn’t good enough, a sentiment rooted in the memory of the failed startup. There are profound lessons to be gleaned from failures, but even more significant lessons emerge when things go unexpectedly well. It’s crucial to resist doubting your worth and to understand that you’re as valid as anyone else. The true lesson lies in humility. If you believe you’re superior to everyone else, you inadvertently position yourself to feel inferior as well. The essence, I believe, is to trust that, like everyone else, you have a valuable contribution to make!

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Rock Star Engineers

Rock-star software engineers are not necessarily the best engineers. They might be engineers who have plateaued in their growth or gatekeepers hindering the progress of your software. Truly impactful software is developed within a communityโ€”a community that thrives on innovation, standardized practices, clear code with comprehensive comments, and meticulous planning followed by execution. Such communities require effective leadersโ€”leaders who amplify the strengths of their members, address their weaknesses, and clear hurdles to enable them to contribute optimally. The ‘rock-star’ archetype doesn’t typically offer these qualities. Instead, we should be lauding the collaborators who possess a clear vision and the capability to realize itโ€”the unsung heroes who drive progress.

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