Failing for the first time in your 40s

Posted by Arjun Moorthy

Nov 20, 2018 3:19:25 PM

When I was in my first startup in 2002, I was trying to convince my boss Milan, the VP of engineering, to let me go to India and set up our offshore development team. I was 25 and had never worked outside the North America. Milan asked me if I’d ever failed at anything before. I said “sure, I’ve failed at exams, at getting some promotions, at getting into grad school etc” but he didn’t react and I felt like I didn’t answer his question correctly.


A few years later, in 2009, I happened to be in Las Vegas with some colleagues watching the finals of the US open. The Argentinian Juan Martin del Potro beat Roger Federer to win his first and only grand slam. Unable to control his emotions he burst into tears. I turned to my boss, Dave, and said “why is the dude crying” to which Dave said “Arjun, have you ever won anything in your life?” We all laughed but I had a feeling that I had never really won anything big, and that maybe I hadn’t really ever failed big either. 

I’m 41 now and have been running my start-up, The Factual, for about two and a half years. I’ve failed at several things but distinctly on the first 3 ideas I’ve had for the company. I’ve also failed to hire the right talent, to motivate them the right way, to invest money wisely, to build compelling products, and to get press - all of which I thought I was good at. I’ve learned along the way and am better at most of these now but the grind has broken me physically and the failures have almost broken me mentally.

Things are starting to look better now but I don't know if I'll find success. But I do know what it means to give it your all and still fail. And regardless of the outcome I suspect I will weep simply for having survived this self-inflicted ordeal.



After publishing this post I heard from a few founders with words of support. I'm very grateful. When I talk to other founders I realize that so many posts about Silicon Valley paint an awfully skewed picture.

This tweet on how much of a scam startups are, or that famous post from Techcrunch's Michael Arrington on how many founders just want to raise and flip a company... these belittle the vast majority of folks in the startup ecosystem - founders, employees, investors - who are working insanely hard to build something valuable. I salute everyone that tries and am in awe of everyone that achieves any modicum of success.

Topics: career advice

Career Advice I Wish I Knew Earlier 

Hello.  I started this blog to distribute some of the best career advice I have been given over the many jobs I've had.  I've been fortunate to work for and with some great bosses like Brian Halligan, Francis DeSouzaNancy Kamei, and Rick Roberge, and some unique companies, like The Boston Consulting Group, that invest heavily in making each employee a success even after leaving the firm.

The advice and training I received here stands in contrast to my experiences with some not-so-great bosses and companies I've also worked for.  I'm continualy amazed at how valuable good advice has been in my career so I hope to pass on the good advice, and insights from mistakes I've made, via this blog. 

Thanks in advance for your comments, particularly when you can improve upon the ideas posted.

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