Jose Calderon played pro basketball for 20 years. Now, a daunting challenge: his first 9-to-5.

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Jose Calderon knows the pain that can be wrought by a major professional transition.

When the Spanish point guard reported to his first NBA training camp with the Toronto Raptors in 2005, he went home at night with headaches due to the language barrier. He understood what was happening around him on the court, but Calderon struggled to process the coaching staff’s instructions and to communicate with his new teammates as he mentally translated from English to Spanish, and back.

Now 38, Calderon again found himself at a crossroads this fall after a 20-year pro career that included 14 NBA seasons and stints alongside future Hall of Famers including LeBron James, Dirk Nowitzki and Carmelo Anthony. He played for five different teams over the past five seasons, in diminishing bench roles, but kept earning minimum-salary contracts thanks to his reputation as an unselfish distributor and upbeat teammate. Every career comes to an end, though, so Calderon moved his family to New York City this summer as he contemplated retirement and braced for a different type of job search.

While Calderon was staying in shape by working out at the National Basketball Players Association’s gym in Midtown Manhattan, Michele Roberts, the union’s executive director, was drafting plans to keep him in the building. After multiple conversations with Calderon and with approval from the NBPA’s executive committee, Roberts hired Calderon as her special assistant — a newly formed, season-long position that both the union and Calderon hope will become a recurring role for a former player seeking to adjust to life after basketball.

“I’ve always been sensitive to the absence of players at our New York headquarters,” Roberts told The Washington Post in a phone interview. “This is the Players Association. It’s kind of silly that it’s being run in large part by a bunch of lawyers and people with master’s degrees. I’m in regular contact with players, but it’s nice to have a body here so that I’m not calling a player who is in the middle of his game day nap or talking to someone who is so removed from the game that maybe their perspective is a little bit dated.”

Despite conquering the language barrier that once troubled him in Toronto, Calderon can’t help but feel like the new guy in a wholly unfamiliar environment. His computer and phone line are all set up in his glass-walled office, and he is grateful to have a collaborative workspace where he can wander into conversations rather than being cooped up at home. On Monday and Tuesday mornings, he joins Roberts and her senior management team in their planning meetings and departmental check-ins. Throughout his first two weeks on the job, he’s made regular lunch appearances at the cafeteria, much to the delight of his co-workers.

“I have never worked in an office,” Calderon said by telephone. “I left my home when I was 13 years old, I was a professional at 17 and I’ve been playing basketball since. There was no time for an office.”

Nevertheless, Calderon decided to take the 9-to-5 plunge with the NBPA after some soul-searching and conversations with his wife, Ana. Given that their three boys are all under the age of 10, Calderon had no interest in uprooting his family by continuing his playing career abroad, even in Spain.

This summer, he heard from multiple NBA teams about possible front office positions, but he didn’t want to rush into a major commitment without knowing whether he would be a fit. The NBA league office reached out, too, but Calderon concluded that he needed a more flexible position while he juggled his responsibilities, which include running his own charity, serving as a UNICEF ambassador and participating in Harvard Business School’s “Crossover Into Business” semesterlong program for professional athletes.

“Coming to New York this summer was about [self-exploration],” Calderon said. “I didn’t want to commit to a front office job and decide in three months that I wasn’t built for it. I didn’t have a dream job because I wasn’t sure what the best fit for me would be. That’s why this is a perfect transition role. I can touch a little bit of everything from basketball operations to finance to the international part, so that I can decide what I really like for the future.”

Since her 2014 hiring, Roberts has followed a mandate to increase player involvement in all aspects of the union’s affairs. The work done at the New York headquarters isn’t necessarily glamorous, but it includes negotiating labor deals with the NBA, addressing concerns brought by NBPA President Chris Paul and his executive committee of current players, preparing presentations for Roberts’s visits with the 30 teams, overseeing charity efforts and representing the players on disciplinary matters like fines and suspensions.

Roberts’s hope is that Calderon will follow in the footsteps of Roger Mason Jr., a former NBA player who served as the NBPA’s deputy executive director from 2014 to 2016. She credited Mason’s presence and player feedback with numerous initiatives, from expanding the union’s informational programming into areas like real estate, technology and business franchising, to adding a basketball court, weight room and locker rooms to the New York office.

From the union’s perspective, Calderon’s recent playing experience should be particularly valuable during team visits, when encouraging player involvement and soliciting honest feedback can be a challenge. Roberts, a former attorney, said she views the players like she would legal clients, aiming to “serve” and “facilitate” rather than to “run the union” and dictate decisions.

“If we’re here to serve, we have to know what we’re serving is palatable, interesting and attractive to the players,” said Roberts, who plans to hire a new special assistant every season and hopes to eventually expand the program to include as many as four recently retired players simultaneously. “Players are absolutely respectful of me and the staff, but when one of their own starts talking, that person commands a level of attention that lay people do not. Jose will generate more interest at our meetings. They listen to each other in ways that they don’t necessarily listen to us.”

Ironically, Calderon never served as an NBPA player representative during his career. He said that he was passed over for veterans with seniority during his first seven-plus seasons with the Raptors, and that he encountered incumbents during a late-career journey that included stops in Detroit (twice), Dallas, New York, Los Angeles, Atlanta and Cleveland. But Calderon’s success in forging a long career while coming from overseas was a “bonus” to Roberts and the NBPA’s international relations chief Matteo Zuretti, given that 108 foreign players were on opening day rosters and that the league’s global ambitions continue to grow.

There is, of course, one major piece of paperwork left for the new office worker to address. Calderon still hasn’t formally announced his retirement, and he sighed reluctantly when asked whether a team could pry him back onto the court.

“I know my weaknesses and I’m always honest with myself,” he said. “I wasn’t sure if I was going to be happy with the role that I had last year. I wasn’t playing, just helping and traveling the same amount. I was starting to miss my family a lot. I was watching a game the other day and I didn’t wish I was playing, which makes everything easier. When is the right time to say that this is it? [My retirement] is not official, but it’s almost. It’s about time. Maybe in the next couple of weeks I’ll make an official announcement and file the papers.”

If history is any guide, Calderon will find the words.

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