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Kushal Chakrabarti

March 7, 2013, was a tough day for Kushal Chakrabarti.

That was the day he announced he was stepping down as CEO of Vittana, the Seattle-based nonprofit he founded and grew for five gut-busting years.

“It’s time for someone new to lead Vittana to the next level,” he wrote. “As for me, what’s next? Well, maybe I’ll sleep a bit more. ;)”

Or maybe not. On Jan. 20 I got an email from Kushal. The subject line read, “re-emerging.” The email linked to this.

Hard lessons are hard to share. They’re raw and they expose you. In the business world, startup CEOs have the most to expose. They’re not holed up in some office somewhere. They must be public evangelists not just for their companies, but for themselves. They’re supermen and women, at least to the outside world, at least in appearances.

So when someone like Kushal shares a hard lesson, it’s a good idea to listen.

After he left Vittana, Kushal weighed two choices: take a break or start his next project. The post where he shares his story is called “The Best Leadership Advice I’ve Ever Gotten.” That advice was this:

Kushal— You talk about starting a family, starting an even bigger company. Here’s the thing— you’re always on. That white-hot intensity of yours never turns off. What’ll your team do if you’re always on? If you’re always on, you’ll burn yourself out, you’ll burn your team out. But, worse: How’ll your family be if you’re always on? Those are going to be some seriously fucked-up kids. Here’s my advice— Go relax until you learn how to relax.

“He was dead right,” Kushal wrote. “I delivered results, but I drove people crazy doing it. I pushed people away— some of my closest mentors, friends and colleagues.” So he broke his lease and got one-month sublets in every country he’d ever wanted to live. Eventually, he did it: He learned to relax.

Intrigued? Check out the post, then come back. Superhuman grit is prized among startup leaders. After soaking in Kushal’s story, I wanted to ask: Did his year learning to relax change Kushal’s mind about the importance of uncompromising hard work?

From San Francisco, where the Vittana co-chair is helping startups think through issues in product development, Kushal sent in his answer. Like everything true, it’s complicated:

Kushal and his dog, Simba, relax in Laguna Beach.
Kushal and his dog, Simba, relax in Laguna Beach.

Q: Of all the places you went and all the interesting things you did in your year, it sounds like somewhere in the Sahara was the moment that had the most to do with your learning to relax. Tell me more about that moment, how it came to be and how you recognized its significance.

Kushal: I’ve never done heroin, but my first week away felt a bit like withdrawal — I was physically itchy, unconsciously reaching for my laptop or phone every chance I got, thinking “Oh, just this once, let me check my email really quickly.”

I was on a beach in Hawaii (and this is zero-th world problem, to be perfectly clear) and I felt like shit. It turns out random reward is the single-most addictive model of human behavior. It’s why we get addicted to Flappy Bird, FarmVille— every good game designer knows it. I was quite literally addicted to work, and I was quite literally detoxing.

Every trip after Hawaii was a little bit better than the one before. There were some incredible moments — I had the biggest shit-eating grin riding a scooter in Madrid. I could feel myself feeling better. But, honestly?

I still kinda just wanted to get back to my laptop and check my email. So, before heading to Africa, I left my laptop, phone and camera behind. I love photography, but even that bit of exposure (sorry, bad pun) got my brain spun up. Not even having the option was so incredibly freeing.

My favorite moment? Waking up to the desert sun, drinking tea, and writing for hours. Not on my iPad or with Evernote, but the good ol’ fashioned way, with a pen and some paper.

Honestly, I didn’t even realize I’d finally been able to relax until later. You know how when you break up with a cute girl (or boy), it sucks, keeps sucking, day after day, until one morning you wake up and realize, “Oh wow, the sun feels glorious— it doesn’t suck anymore…” It was kinda like that.

Q: You say you’ve clocked 100 weeks since you were 15, and wrote a post praising the “10 percent rule” and the idea of working crazy hard, even if it means you function in a “sleep deprived stupor” at times. How would you write this post today, after your year away? Would any part of it be different? Would you have different thoughts about the benefit of working crazy hard, or the same?

Kushal: Honestly? I wouldn’t write it much differently. The 10% rule —faster, harder, better— is why startups can beat behemoths, why David with a slingshot can beat Goliath in armor.

But, there’s a key phrase in there: “If you can survive long enough to catch up, they’re done for.” Stamina — that’s what that cuts to the core of.

And if there’s one big lesson I learned, it’s that stamina is equal parts physical and emotional. I saw a comment recently that nailed it: “Burnout is caused when you repeatedly make large amounts of sacrifice and or effort into high-risk problems that fail…You effectively condition your brain to associate work with failure.”

So, maybe what I’d do is write a couple sister posts to The 10% Rule: “Why The Little Moments Matter” and “Listen — Truly Listen,” perhaps?

Q: When you meet entrepreneurs who are ambitious, driven, very hard working but share some of the things you saw in yourself before your year away, what do you think? What do you say?

Kushal: Being a startup CEO is a crazy job — there’s nothing else like it. You have to walk a crazy line between having unshakeable faith in your idea, your team, and yourself with the brutal facts of everyday reality — runway, traffic, morale.

Ben Horowitz has an terrific series of articles about it. There are a lot of things you have to learn. Our own Marc Barros wrote a beautiful post about becoming a CEO from a founder. There’s an old Buddhist saying that I’ve come to love, “The teacher appears when the student is ready.”

It’s a poetic way of saying teachable moments are all around us — it’s a question of whether we’re ready to learn from them or not. God knows I sometimes wasn’t. And I’m sure I drove people around me crazy. And sometimes so do the folks I advise. Here’s the thing. The flip side of tenacity is not listening. You want founders who are bulldog-tenacious — the #1 predictor of success in life and work is grit — but sometimes that means they won’t listen to you.

Finding the right balance is tough, but it’s something everyone has to find for themselves. If I can tell them a war story to help them find it a tiny bit faster, then that’s great.

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