After a full life in the paparazzi glare that has included an Olympic gold medal, multiple marriages, paterfamilias to a famous growing brood, Bruce Jenner is undergoing a radical transformation, from celebrity athlete and Kardashian accessory to becoming a woman, according to sources at People Magazine and TMZ.

Twitter and Facebook have been afire with speculation as Jenner, a former decathlete, has ventured out sporting neat French manicured nails and long locks tied in a ponytail. Stepdaughter Kim Kardashian slipped to ET, “I think everyone goes through things in life, and I think that story and what Bruce is going through, I think he’ll share whenever the time is right.”

What Jenner, 65, may be going through, is not unique. The former Olympian is joining a visible and growing population of older people who have transitioned in later life from one gender to another after having had marriages, kids, and a career. The reasons for the transition are myriad such as the improving climate for the LGBT population and the visibility of famous transgender celebrities such as Carmen Carrera, a model and burlesque star, and actress Laverne Cox, who stars in the Netflix show, Orange is the New Black. But while the mass of non-famous transgender people don’t have to deal with TMZ, they are facing unique challenges and issues related to their age and status—whether they be psychological, medical, and financial.

“It varies a lot, income to income,” said Mara Keisling, founding Executive Director of the National Center for Transgender Equality, about issues facing older folks. “Someone who is a person of means will have a different set of challenges compared to a person who does not.”

While there is no exact number on the population of older transgender people, common obstacles abound, according to experts like Keisling. Challenges include ostracism from family, friends and the larger world. They can lose their livelihood if work colleagues turn their backs.

While there is no exact number on the population of transgender senior citizens, according to the survey, “Out & Visible,” conducted last year by Services and Advocacy for GLBT Elders or SAGE, which is based in New York City, 48 percent of transgender people who responded are worried about becoming a burden on their family and friends compared to 32 percent of non-transgender people. About 42 percent worry about where they will live when they are older, and about 44 percent are concerned that their doctors would not accept them if they knew their true gender identity. More than half are worried about access to healthcare and twice as many older transgender folks have experienced housing discrimination, compared to non-transgender people, according to the survey.

This is unlikely to happen to Jenner, who enjoys the benefits of celebrity; the high cost of drugs, surgery, electrolysis and other procedures are affordable for him. For other trans people, however, the costs of transitioning are usually not covered by health insurance yet.

The downside is Jenner will be doing all this in full public view, and will have to learn all new behavior patterns under a microscope. Younger people who take hormone blockers before puberty don’t have to deal with already-set physical appearance and have not lived many years as another gender, said Keisling.

“Testosterone is such a strong drug,” she said.

Keisling has a good friend, who was partner in a law firm, who had lost a client when she had transitioned and thus became unemployed. But because she had made partner, she was financially set, said Keisling. Other transgender folks are not nearly as lucky. They can suddenly find themselves at the age of 55 without a career and little prospects for making money. They face a toxic mix of transphobia, ageism, and bias against the unemployed, said Keisling.

Ally, who had transitioned in her late 50s, is out to her family and dresses as a woman. But when she goes into business meetings, she dresses as a man. She works in the psychology field but her sector is more conservative than most.

“I don’t think it would help me in my consulting work,” said Ally, who identifies both as a man and a woman.

Jennifer Leitham, a well known jazz musician and vocalist who was Mel Torme’s bassist for 10 years, had people turning her down for gigs after she had transitioned at the age of 48. At a smaller scale than Jenner, she had to suffer through a spate of bad articles about her transformation that forced her to stop talking to reporters for four years.

“I feel great, but negativity comes from how people perceive you,” she said.

As for why they had decided to make a change in later life, there are many reasons, according to Ellen Weirich, who runs a finishing school for transgender women. Most of her clients are between 50 and 70 years old.

“They may have dressed alone secretly. They get around 50 and the urge to dress becomes stronger and they come to me,” she said. They are not getting any younger and they are tired of repressing it.

But times have also become more accepting, said Alice Levine, a 65-year-old New Jersey resident, who had transitioned when she was 57. She and her wife Wendy Roome, a client of Weirich, were also featured in the Daily Beast article.

“It’s kind of summed up by that Bob Dylan song, ‘The Times They Are A-Changin,’” she quipped.

Like Jenner, Levine had wives and kids before she decided to take the plunge in becoming a woman. And her reasons for transforming herself and her life are common among some of the older people interviewed for this article: information and other resources on transgender issues and medical interventions were not there when they came of age in a more conservative time.

“Most of us lived on islands because of the age,” she said about the isolation.

For every person who transitions, how much they transform is unique to each individual, said Andrea Bowen, 28, executive director of Garden State Equality, a New Jersey-based LGBT advocacy group.

“People understand themselves at different ages. Everybody’s process is really different,” said Bowen, who is a transgender woman and transitioned at the age of 25.

Some people go through the full suite of medical intervention while others are content to simply take hormones or none at all.

As for Jenner, Leitham, who was the subject of a documentary about her own transition, wishes the athlete well.

“The circumstances Bruce Jenner is dealing with is off-the-charts crazy. It’s very difficult as you are dealing with the hormonal ebbs and flows. It’s an not easy task,” she said. “If I could give any advice, it is to get some time for yourself and be in a meditative state for a while.”