Britney Spears' Team Is Preparing Her for Post-Conservatorship Life: 'It's Going to Be Difficult,' Says Source

After 13 years of living under a conservatorship, Britney Spears might soon have full control of her life again.

Following months of court battles, the pop star, 39, won a huge victory on Sept. 29 when a Los Angeles judge suspended her father, Jamie, from his role overseeing her $60 million fortune as the conservator of her estate.

With her attorney Mathew Rosengart now focused on "terminating the entire conservatorship" at the next court hearing Nov. 12, her team is preparing her for a life without the legal arrangement in the meantime — and expressing some concern.

Since she's had every decision made for her since 2008, "no one knows if she will be able to care for if the conservatorship is eliminated," a source close to Britney tells PEOPLE in this week's cover story, on newsstands Friday. "It's going to be difficult for her to create a whole new life after so many years of restrictions."

Britney was placed under the conservatorship in 2008 after her erratic behavior culminated in two 72-hour psychiatric holds. In the decade that followed her life and career seemed to chug along smoothly, at least from the outside, with Jamie, 69, at the helm as she performed on tours and in residencies and recorded four albums.

But cracks began to show in January 2019 when the star suddenly canceled a new Las Vegas show, Domination, and announced a career break as Jamie recovered from his own health crisis, a ruptured colon.

That April Britney checked into treatment at a wellness facility — a decision she claimed in court in June was forced on her by her dad. Then, in August 2019, Jamie was involved in an alleged altercation with Britney's now 16-year-old son Sean Preston and was put under a restraining order preventing him from seeing both of Britney's sons, Sean Preston and Jayden James, 15, whom she shares with her ex-husband Kevin Federline.

RELATED VIDEO: Britney Spears and Fiancé Sam Asghari Joke About Having a Baby Together

Weeks after the alleged altercation, court documents revealed that Jamie was stepping down as his daughter's personal conservator. (Jodi Montgomery, Britney's longtime care manager, replaced Jamie as the conservator of her person, responsible for medical decisions, while Jamie remained on as the conservator of her estate.)

In the months that followed, Britney fought in court to have her father removed from her conservatorship. Since getting her wish last week (accountant John Zabel is now temporarily in Jamie's role), "she is very hopeful," the source says. "Britney thinks everything will be totally different with Jamie out of her life."

A significant hurdle ahead is a potential mental health evaluation, which is typically required by the court before a conservatorship is terminated.

"She feels whatever she does, they'll find a reason to fail her," an insider says of Britney. "She has zero trust in the process." (Britney has referenced her medication and therapy sessions in previous court hearings, but her medical records, including any mental health diagnoses, remain private.)

According to forensic psychiatrist Dr. Rebecca Crandall, who's not involved with the case, Britney's request to skip the evaluation isn't "impossible," but she likely will have to "show up in front of the judge and be able to document and prove she's been clothing, feeding and sheltering herself for a while."

Her legal team and conservators are also working on a plan for her finances should the conservatorship end.

"The goal is to have the conservatorship terminated but continue protecting Britney and her finances," says a source close to the situation, who adds that the star's fortune will likely be put into a trust with professional managers.

As she navigates new challenges, the closest person in her life now is her new fiancé, Iranian-born actor and model Sam Asghari, 27, who popped the question at their L.A. home in mid-September.

"He is a great influence on Britney. When Sam is around, Britney's days are very focused," says the source close to Britney. "When she is alone, it's hard for her to motivate herself. He's encouraged her to think about performing again, but it seems she's just not ready."

Now back home in L.A. from her vacation with Asghari to French Polynesia, Britney — who shocked fans hours after the most recent court decision when she shared a series of nude vacation snaps on Instagram — is envisioning her new future.

She's planning for a "small wedding as soon as possible and wants to have more kids," says the source close to her.

At the end of the day, the star dreams of a "simple" life that includes working out, spending time with her children, creating art and gardening, says the source. "She wants the conservatorship to end, but she doesn't seem to have a plan beyond this."

Adds the insider: "She just wants to start fresh."

For all the details on what's next for Britney Spears, pick up the latest issue of PEOPLE, on newsstands everywhere Friday.