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How Jack Dorsey Can Keep His Chill While Running Two Companies

The Huffington Post The Huffington Post 5/10/2015 Alexander C. Kaufman
ATHENA IMAGE © JUSTIN TALLIS via Getty Images ATHENA IMAGE

Jack Dorsey has his plate full -- doubly full.

Twitter on Monday named him its permanent CEO, nearly four months after he took over as the interim chief executive following Dick Costolo's sudden departure.

The company he co-founded nine years ago is in flux, struggling to attract new users and make money. Shareholders clamored for Dorsey to stay in the position in large part because few other business leaders seemed qualified to meaningfully correct Twitter's course. 

But Dorsey is  also the full-time chief executive of mobile-payments firm Square, a position he will keep in addition to heading up Twitter. Square is quietly preparing for an initial public offering -- a process that, judging from Twitter's own IPO, can become quite volatile .

That's a lot for anyone to take on. As much as he's going to need the people around him, Dorsey -- who's known to meditate and jog early in the morning and take long, meandering walks during the day -- will also need to turn inward for the tools to help him succeed in both roles.

Twitter is a social media company. Square processes credit card transactions. The two firms have little in common, which helps in a certain way -- perhaps there are few conflicts of interest. But the arrangement will require Dorsey's mind to be nimble. He'll navigate very different realities at the helm of each company.

"It's unusual and really challenging," Sydney Finkelstein , management professor at Dartmouth College’s Tuck Center for Leadership, told The Huffington Post.

Finkelstein said the people in Dorsey's professional inner circle will be crucial to him, perhaps more than they've ever been. 

" To make something like this work, you have to have a world-class team around you," Finkelstein explained. "Effective leaders delegate. In this case, you probably have to delegate more than normal. … You have to be able to process in your brain two different worlds."

Dorsey must also remain mindful of his own emotions to prevent himself from succumbing to stress and becoming reactionary.

“Oftentimes what we do is we withdraw and we tighten and we become reactive,” Janice Marturano, executive director of the nonprofit Institute for Mindful Leadership, told HuffPost. “That’s exactly the opposite of what we need to do during stressful times in our lives.”

Simple activities like napping, taking a walk and finding a quiet room to meditate for 10 minutes can be helpful. Some of this is undoubtedly part of Dorsey's routine already, but not everyone has time for that. Training the brain to take what Marturano calls “purposeful pauses” -- receding into the mind during a brief moment of free time -- can help keep a leader grounded, even when she or he is stretched thin.

“In times of real craziness, you have to be able to find your training that allows you to meditate with a cup of coffee, or with the two minutes you walk from this office to this meeting,” said Marturano, whose book Finding The Time To Lead was released recently in paperback. “Rather than texting along the way, you say, ‘I’m going to use that time for meditation.’”

To be sure, not everyone enjoys the perks of a chief executive whose net worth Forbes estimates at $2.2 billion. Many workers struggle as wages remain low. Nearly two million people in the United States work multiple part-time jobs, and nearly 1.6 million of those do not have a primary full-time job. That means many are likely disqualified from receiving health insurance coverage or other benefits as part of their compensation. The perks and privileges enjoyed by Dorsey and others in the executive set certainly make their struggle a bit less difficult.

Still, Marturano said the principles of mindfulness apply as much to workers stocking shelves for minimum wage as they do to someone running two large technology companies.

"We influence the people around us every day, so we're all leaders," she said. "It's about making the time to reflect." 

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