Thanks to a good friend – Aldrin D’souza – I was transported back in time when he sent me a link to the inimitable Frank Sinatra singing “I did it my way” a few days ago. And ever since I hit play and listened to the mesmerizing vocals, the song and the lyrics have been haunting me.

Why? Because it is full of life lessons. Simple yet profound.

Here are the five that I think we can all learn a thing or two from

I did it my way – The song title itself caused me to dig deeper. For the longest time I was doing it somebody else’s way. A colleague (actually more than just one) who got rich by way of Silicon Valley IPO or an acquisition. And I followed his way. Or a friend much younger who became a VP. And I had to change course to follow her. Until a couple of years ago when I finally decided to try it my way. Leaving a stable job and branching into the unknown. Actively seeking to help friends and colleagues with whatever mentoring I can offer. Connecting people that I think can benefit from mutual association. I can look myself in the mirror today and say “I am doing it my way”.

Regrets I had a few, but then again too few to mention – We all look in the rearview mirror and contemplate what could have been. I am no exception. What if I had taken the chance that I took by getting into podcasting, writing, speaking a decade ago. Would I have led a more purpose filled life earlier in life? But, the trick is not to look backward but rather learn quickly from the hard lessons and surge forward. We all have regrets, but having too few to mention like Mr. Sinatra means we have our life script on the right note. Not regretting taking chances.

I bit off more than I could chew, but through it all when there was doubt, I ate it up and spit it out – We all are faced with choices all the time. We can take the conservative, tried and trusted, safe route. Or chance it, experiment with something new, take a leap of faith. But one will never grow, or learn from failures and become a better version of oneself until one is able to bite off more than one can chew. And then spitting out the undigested part. A mentor of mine passed on these words of wisdom to me once – “Ashwin, when you come to a fork, take it”. That means sometimes biting off more than I can chew rather than eschewing eating.

I’ve had my fill, my share of losing, and now as tears subside, I find it all so amusing – Isn’t it so true that failure is always the best teacher. And for those for whom failure is a foreign word, chances are that you did not experiment relentlessly and take enough chances. If you were to ask me, the three layoffs in my career, were the best teachers ever. Each time I thought I had failed myself, my family, my friends. And when the tears subsided, each time I learnt something new and yes, in hindsight it is a tad amusing.

And finally

And now, the end is near, and so I face the final curtain – True, we never know when the end is near, when the curtain will finally fall. As I am writing this, the news just hit that the basketball legend Kobe Bryant and his daughter were killed in an unfortunate helicopter crash. #RIP Kobe and Gianna. Even as we pretend that tomorrow will always be there, we must act with urgency that today maybe the day the curtain falls. And if it did, would you have lived a life worth living?

Ask yourself the question

Did you do it your way?



    Empathy, Education, Empowerment

    Mine is a typical Indian immigrant story: an Engineer who became an Engineering Manager, who grew antsy and segued into Product Management then rose to VP and SVP. During those years I fancied I was innovating and experimenting, but in reality I was wearing a corporate straitjacket. Constrained by my industry’s insular mindset, I became a slave to the definition of my job. Inevitably, I ended up dissatisfied. So, I did something unusual for a man in my position: I stopped to reflect. I searched my life and talents for what was fulfilling and had purpose. I discovered I enjoyed storytelling to promote understanding. I loved mentoring and helping people become the best version of themselves. Importantly, I realized I was still passionate about the tech industry, particularly the issues surrounding privacy and ethics. Today, I’m pursuing my passions. I like to think of myself as an accelerator of technology and positivity. I’m the COO of UberKnowledge, bringing cybersecurity awareness and training to demographics that are underrepresented in the industry. I speak at conferences highlighting the need for a sharper focus on the ethics surrounding the technology industry.  I write articles and blog posts using analogy to simplify technology trends and complex topics like AI and IoT. I host podcasts with CISOs and other industry experts. The purpose of these is not to sell snake oil or products but to bridge the chasm between security vendors and customers so that the real problems can be solved to make the world a safer place. Underpinning all of these efforts is my belief that life’s purpose for us all is simply to connect. And the best way to do that is through generous and positive gestures.