(Bloomberg) -- Twitter Inc. Chief Executive Officer Jack Dorsey has picked a questionable time to spend as much as half a year in Africa.

Dorsey wrote in a tweet last week that he planned live on the continent for between three and six months in 2020, news that was largely buried thanks to the Thanksgiving holiday. But investors quickly noted the Twitter chief’s plans will coincide with a presidential election year in the U.S., which is likely to be marked with growing debate over election meddling, online hate speech and the role of tech companies in public discourse.

“There’s going to be a bright spotlight on Twitter, Facebook and a lot of other tech platforms,” said Dan Ives, an analyst at Wedbush Securities, adding that Dorsey’s absence from the country could provide fodder to Twitter’s critics. “If the CEO does this, any speed bump is over-magnified.”

Dorsey made the announcement about his trip after spending most of the month of November in Africa, where he visited with entrepreneurs and completed a 10-day meditation retreat in South Africa. “Sad to be leaving the continent…for now,” he tweeted. “Africa will define the future (especially the bitcoin one!). Not sure where yet, but I’ll be living here for 3-6 months mid 2020. Grateful I was able to experience a small part.”

The CEO’s trip, assuming it takes place, will happen as Twitter’s most high-profile user, President Donald Trump, runs a presidential campaign while simultaneously running the country on Dorsey’s platform. Inevitably Twitter will have to make tough, quick decisions, and it’s unclear how easy or efficient that will be with a chief executive halfway around the world for an extended period.

Twitter’s corporate structure could also compound that problem. The CEO has no obvious No. 2 inside Twitter, and the chief operating officer role, often viewed as second in command, has been vacant since January 2018.

But what’s bad news for Twitter could actually benefit the other publicly traded company that Dorsey leads, payments giant Square Inc. Dorsey, who has been CEO of both for four years, suggested that a trip to Africa would help him learn about cryptocurrencies, like Bitcoin -- a personal area of interest for the Dorsey, as well as a potentially big market for Square.

Square was one of the first public companies to wade into cryptocurrencies, allowing users to buy and sell Bitcoin on its Cash App in 2017. Dorsey has long been an outspoken proponent of Bitcoin, even hiring a small team at Square to work on cryptocurrency-related projects. The trip could also bring Dorsey closer to Africa’s fast-growing fintech industry, which has been a bright spot for the continent in recent years.

Like Twitter, however, Square also has no clear successor to the CEO. Its former CFO Sarah Friar, who had been widely considered to be the company’s No. 2, left to run the neighborhood social network Nextdoor.com Inc. in late 2018.

“The key question will be whether Jack installs an interim chief operating officer or president in his absence,” said Lisa Ellis, an analyst at MoffettNathanson. “If he does, I believe the Africa sojourns could be a good thing strategically for Square. If he does not, he is putting the day-to-day operations of Square at risk.” Ellis added that she expects Square’s board will push on this point. Representatives for Square and Twitter declined to comment.

The likeliest practical outcome to Dorsey’s globetrotting may be that he simply continues his job from the other side of the world. Inside Twitter, Dorsey and other executives have been promoting the concept of remote work, according to people at the company. Dorsey visited 27 Twitter offices around the world in 2019, and recently referred to remote work as “our future.”

Dorsey has long been viewed as a CEO who takes on more projects than most. “Even though he’s kind of been superman as CEO of two public companies, and juggling a lot of balls at the same time, going to Africa for three to six months -- I don’t think that’s something from a shareholder perspective that’s viewed as ideal,” Ives said. Even for Dorsey, the Africa trip would be unusual. Adds Ives: “[In] twenty years covering tech on the street, I’ve never seen a CEO go on a three- to six-month journey to another continent.”

To contact the reporters on this story: Kurt Wagner in San Francisco at kwagner71@bloomberg.net;Julie Verhage in New York at jverhage2@bloomberg.net

To contact the editors responsible for this story: Jillian Ward at jward56@bloomberg.net, Anne VanderMey

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