John Jones was working on Iran sanctions legislation five years ago, when his boss, New York Sen. Charles E. Schumer, turned to Arizona Sen. John McCain and said, “Look, I’m for it, but you have to convince Jones.”

The exchange left Jones “stunned,” he recalled, but also empowered, as the weight of his responsibilities as Schumer’s national security director dawned on him.

He soon joined Missouri Democratic Rep. Emmanuel Cleaver II’s office, where he served a chief of staff for five years. Late last month, Jones, 39, became the vice president of government relations for trade group Nareit.

“When you feel that you have done all that you can, move on,” he said.

Moving on is something that’s never far from the minds of Capitol Hill staffers, as they seek ways to parlay years of government experience into a higher-paying K Street job with more flexible work hours. But picking the right moment to leave can be tricky.

From the Archives: How To Make the Most of Your Hill Career

The right time

When people tell David Thomas they want to leave the Hill, he asks them to be sure they’ve thought the decision through.

“The first thing I always ask is, ‘Are you truly ready? Are you going to miss being in the center of the action?’” he said.

Thomas, 47, a partner at Mehlman, Castagnetti, Rosen & Thomas, left the Hill over a decade ago. He started out as an intern for Al Gore, when he served as a Tennessee senator, and he was California Democratic Rep. Zoe Lofgren’s chief of staff for four years.

“I haven’t looked back, [but] I know there are other people who make that change and very quickly realize they want to be in every floor fight, they want to be back behind the committee dais and whispering in the member’s ear and giving advice on whatever the issues may be of the day.”

Anne MacMillan, a lobbyist at Invariant, struck a similar note.

“One of the biggest mistakes I think people make on the Hill right now, and it might be the so-called millennial mind set, but people really get antsy much sooner than they had in the past,” she said.

MacMillan, 39, spent almost 10 years on the Hill, starting as a staff assistant to former California Democratic Rep. Bob Matsui and rising to senior policy adviser for Nancy Pelosi, when she was speaker.

“I know the pay is challenging. I just think that sometimes people burn out, or think they’re burnt out, but then they will burn out just as quick downtown because your longevity is just not as long as you think it’s going to be,” she said.

“I think your success will be longer and stronger if you have a really strong policy skill-set or network and I just find that really hard to develop in two or three years on the Hill,” she said. “The longer you stay in a job that fulfills you, in an issue set that you like, the stronger you’ll be when you leave to go downtown.”

Jones recommends setting goals early, which will help make the decision to leave easier: “It is time to go when you feel that you have done all that you can and play the role that you can to make people’s lives better.”

The family aspect

For many staffers, the decision to leave sometimes converges with their personal lives doing a complete 180.

“When I started with Zoe, I was a single guy,” Thomas recalled. “I got married and my wife and I had our first kid and what I found at that point in my life was, I loved my job, I loved being on the Hill, but once I had a family, it was a little tough getting home at night.”

Leaving allowed him to have more control over his schedule, despite the early mornings and late nights in the lobbying world.

“The hard thing about being on the Hill is your schedule is never your own. That goes for the members too,” Thomas said.

But the lobbying world isn’t always the most family-friendly either, said MacMillan, a mother of two.

“I just don’t think you see a lot of multi-client lobbyists who are women because of the networking that it takes to kind of continue that client pipeline, the after-work activities, fundraisers. It’s really challenging,” she said.

Pelosi’s office, she said, had female staffers in high positions — and, of course, there was Pelosi herself.

“She had five kids. I thought the world of her when I worked for her. She was absolutely tough, but she was fair,” MacMillan said. “I really enjoyed watching a very powerful woman do a very good job.”

Looking forward

MacMillan said she left the Hill when she had “reached the pinnacle” of her time there.

“There wasn’t a lot of opportunity for upward mobility within [Pelosi’s] office because she had really qualified, good people at the next level and two levels up, who weren’t going anywhere,” she said. “I really wanted to be one of those people. I wanted to be the closer confidante and the go-to staffer of the principal.”

But the experience never goes to waste when you move off the Hill.

“Anybody can learn issues,” Thomas said. “But … knowing the process and what makes certain members tick, how people feel about issues and how to present issues to members or leadership. You can only learn that by being up there. That’s a critical box to check if you want to be in a government relations firm.”

Jones, who started out on the Hill in 2004 as a fellow with the Congressional Black Caucus Foundation, pointed to three things that matter the most on Capitol Hill, in particular: “seniority, relationships and experience.”

He said he respects the so-called Capitol Hill lifers, whom he describes as congressional staffers who work for 20 or 25 years and then never really retire. But that’s not him.

“There’s a whole world outside of Capitol Hill,” Jones said.