El Paso, Texas (CNN) Beto O'Rourke is on the road -- but he doesn't seem to know where it's leading.

Two weeks after leaving Congress, O'Rourke drove north this week on Route 54. He researched his family's history in northern New Mexico, visited colleges there and in Oklahoma's Panhandle, and stopped at a motel in Kansas. Then he described what he'd seen in a travel diary-style post on Medium . Aides wouldn't say where O'Rourke, who is deciding whether to seek the Democratic presidential nomination in 2020, will visit next or what he's doing.

The road trip follows weeks of O'Rourke selling his authenticity by filming scenes at the border, across El Paso and beyond. But the Medium posts and viral videos have done little to answer one of the biggest questions looming over him: Is he ready to be president?

Steve Ortega, who served alongside him on the El Paso City Council and is among his closest friends, said he believes O'Rourke has yet to resolve the question in his own mind.

Over coffee on Wednesday in El Paso, when asked that question directly, Ortega replied, "I'm not sure he is. That's why he is still deciding what he wants to do."

"If he puts himself forward, he's going to have to justify to himself that he thinks he is the best person for the job, and that's a very deliberate process that he's going through right now," Ortega told CNN. "He's not going to run if he thinks there's someone else that can do a better job than he."

Several friends say that one of O'Rourke's biggest concerns is the toll a presidential run would take on his wife and three children.

In a private conversation late last year, O'Rourke and former President Barack Obama talked about the strains a bid for the presidency takes on a young family. And they discussed the need for authenticity as Democrats choose a nominee to take on Trump, according to two people familiar with the exchange.

O'Rourke is answering questions about a 2020 bid during his road trip by citing worries about time away from his family, too.

Jasmine Estrada, a student at Oklahoma Panhandle State University -- where O'Rourke stopped Tuesday to speak to students, professors and staff -- said she asked him whether he will run for president.

"He said that he is still thinking about it," she said. "His biggest concern is his family, so I guess he's just -- that's what he's thinking, how it's going to affect his family and all of that."

O'Rourke is also trying to determine how he would fit into a crowded Democratic field, where his experience falls short of the resumes put forth by some potential rivals.

"He needs to mentally, emotionally, physically be 100% into a run or it will reflect on his campaign," Ortega said. "He's flattered by the 'Run Beto Run' and all the groups that want him to run for office, but ultimately he himself needs to be all in."

It seems as though O'Rourke is more than happy to have this conversation out loud and in the open, a rarity for a politician considering a bid for the presidency. His unannounced road trip, which took even friends in El Paso by surprise, came with a very public airing of his uncertainties.

"Have been stuck lately. In and out of a funk," O'Rourke wrote in a Medium post. He added, "Maybe if I get moving, on the road, meet people, learn about what's going on where they live, have some adventure, go where I don't know and I'm not known, it'll clear my head, reset, I'll think new thoughts, break out of the loops I've been stuck in."

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O'Rourke shattered fundraising records and built a national following through his social media livestreams of his campaign last year to unseat Republican Sen. Ted Cruz. Along the way he became a darling of the left: A documentary about his Senate bid co-produced by Crooked Media, founded by former top Obama staffers, is set to premiere in March at the annual South by Southwest Film Festival.

A closer-than-expected loss to Cruz left O'Rourke without political office -- but it didn't eliminate interest in an O'Rourke presidential bid. After insisting during his Senate run that he would not run for president, he acknowledged in a mid-December town hall that he had begun considering it.

Weighing on O'Rourke is pressure from friends and political allies -- especially those in El Paso who see him as a strong voice to combat President Donald Trump's fear-mongering about the southern border.

"He is a generational political figure. I've been around for many years and have never seen anything like him," said former El Paso Mayor Ray Caballero, whose tenure inspired O'Rourke's first foray into elected office -- a 2005 city council bid. "Beto's in a class by himself historically. None of the current aspirants are in the same league."

A quixotic road trip could certainly be soul cleansing at this early stage of exploring a presidential run, but if he ultimately decides to join the race, his path will be far more restrained by conventional rules of the primary contest.

What O'Rourke has not said is what he would do as president or why he wants to run. He's blasted Trump's border wall, through a video seen more than 5 million times, but when asked by The Washington Post what should be done to solve the problem of people overstaying visas, he said, "I don't know."

It's an answer that could come back to haunt him, if potential rivals seize on his lack of specifics to a question asked of a former congressman from a border state.

But Ortega and other friends described it as classic O'Rourke -- an authentic answer that may not easily fit into the routine political mold.

"If he doesn't know the answer to a question, he's not going to go on the fly and say, let me make up an answer that sounds good that the folks in Iowa will like," Ortega said. "He's going to tell you, 'Look, I don't know the answer to that question. Let me research it and I'll get back to you.' "

Howard Campbell, an O'Rourke friend who's a professor of cultural anthropology at the University of Texas El Paso, said O'Rourke holds broad appeal that spans typical boundaries.

"He's kind of a chameleon, someone who appeals to multiple identities and multiple styles of life," Campbell told CNN. "Beto, of course, is a four-letter word. It resonates very nicely."

To admirers of O'Rourke, there are few apologies for his blank slate. Should he run, questions about his experience will be front and center in a campaign, just as they were 12 years ago for a freshman senator from Illinois named Barack Obama, who at the time of his presidential announcement was a year younger than O'Rourke.

O'Rourke is expected to make a decision by February, people close to him say, adding that they have no idea what his final answer will be.

"I would not be surprised if he announced in the next several weeks. I would not be surprised if he called me up tomorrow and said, 'I'm not doing this,' " Ortega said. "It could go one way or another."