This article is part of the Lily Lines newsletter. You can sign up here to get it delivered twice a week to your inbox.

Illustrations by Maria Alconada Brooks.

If I could go back, I’d tell my younger self to quit.

I would tell her to quit the high school friend who drained all her energy and the long-distance boyfriend she couldn’t give up. Most of all, I’d tell her to quit soccer.

When I was 15, I tore the anterior cruciate ligament (ACL), an essential ligament in the knee, playing the sport. ACL injuries are notorious in young, female athletes. I went through an hours-long surgery, a week-long, bed-ridden recovery, and then a six month-long stint in physical therapy. But I was determined to play again, because that’s how I defined myself in high school: as a soccer player.

And I played again — but I ended up tearing my other, healthy, ACL a year later. I went through the surgery, recovery, rehab; I was determined to play again then, too.

And I did. I made it through almost the entire season during my senior year of high school injury-free. But in one of my final games, I re-tore my right ACL. Everyone — my parents, my teammates, even my deeply stoic surgeon — wallowed with me.

I look back at that time wishing I had quit after the second injury — wishing I had saved all of us a little despair. But it’s often hard to see clearly when it’s time to let something go. That’s what makes quitting so paradoxical:

As we make resolutions to start a new hobby or deepen our relationships in the new year, we’re also reflecting on what might be difficult, but ultimately worth it, to give up: a job, a friendship, even a dream. We spoke with eight experts about how to know when it may be time to do so.

I, for one, wish I’d had this advice when I was 15, and then 16, and then when I was 18. I would tell her: It’s okay to quit. One day, you’ll be more than a soccer player; you’ll be a journalist, and a loyal friend, and a loving daughter. You’ll have learned how to be a quitter, and maybe that’s the most valuable lesson of all.

While it’s difficult for everyone to quit, it can be especially so for women, says Nancy Levin, an author and life coach. Women are often taught to be peacekeepers and people-pleasers, to put others’ needs before their own. When it comes to sticking something out, she suggests asking yourself: Are you acting out of obligation or desire?

Even when the answer is clear, it can be difficult to take action. “We’re so used to waiting for the crisis before taking action in our lives,” Levin says. “I’m really the proponent of rocking your own foundation first, before it gets rocked by something else.”

That’s what makes quitting so “revolutionary,” she says: It allows women to take responsibility for their own happiness.

Asking yourself questions, and giving yourself honest answers, is the first step, according to experts. Let’s get started.

Amy Gallo, author of Harvard Business Review’s “Guide to Dealing with Conflict” and co-host of its “Women at Work” podcast, says that when it comes to quitting your job, it all goes back to whether something is out of your control and whether that might change in the future. For example, if your boss is “absolutely awful” and doesn’t plan to look for another job any time soon, that might be a compelling reason to quit.

In less clear-cut cases, Gallo suggests setting a time frame for yourself: Tell yourself you’ll stick out the job for another three months or six months or a year, and don’t push that timeline out again. “If you keep pushing it out, that is a tell-tale sign,” she says. “The key is, what’s a reasonable time frame in which you can do some experimentation in terms of those things you can control and change — are they changing?”

It’s also important to take into consideration the “persistent sexism” that often permeates workplaces, she says. That might mean that you don’t get the credit you deserve, or you’re getting “talked over, interrupted, man-splained.” That can all make you want to quit, and “it’s unfortunate that it’s rare to be inside an organization where some of that doesn’t exist,” Gallo says. “So I think the question is — are you sure it’s going to be better somewhere else?”

Before you quit, start doing some research, says Gallo. Talk to friends who identify in the same way you do and set up informational interviews if you’ve heard of organizations where these issues might not be so pronounced.

Romantic relationships can be some of the toughest to see clearly, according to Pepper Schwartz, an author and researcher specializing in intimacy and sexuality. Even so, people generally know in their “heart of hearts” when a relationship isn’t working, she says: It’s a question of being afraid of life without the person but knowing you can’t live with them.

Schwartz recommends asking yourself if you feel “well and truly loved,” and if you can provide concrete examples of that. You should also take stock of how you speak to friends about the relationship — are you embarrassed to admit what you’ve done to keep your relationship going? Are those friends also expressing doubts seeing how you are in the relationship?

At the end of the day, it’s important to remember to have faith in yourself, Schwartz says. “It’s hard to get out of a bad relationship when you’re seduced by little pieces of it and not believing that you could get more than that,” she says.

On the flipside, if you’re single, want to be dating and aren’t having luck, remember: “You can’t do the same thing over and over and expect different results,” says Schwartz. She recommends talking through things with a therapist who might be able to point out patterns in your behavior, and asking: What am I going to do to make me happy and fulfilled if it’s not a relationship?

Blood may be thicker than water, but it’s important to realize that sometimes familial relationships don’t serve either person, says Jordan Brogan, chief executive officer of the Center for Families and Relationships. Ultimately, she says, “you need to make yourself a priority, because you’re always going to be the one to take care of yourself.”

Familial relationships can be hard, and conflict is normal, she says. Ask yourself:

If it feels like a majority — and the negative interactions begin impacting other areas of your life, such as your job or other relationships — then it may be time to step away from the relationship.

Brogan suggests first writing a letter with everything you’d want to say to that family member and trying to process those feelings on your own. If you do decide the relationship is unhealthy, then have a conversation and say you need a break. After a period of time apart, “maybe you come back to it, or maybe you realize that your life is indeed healthier without that person,” Brogan says.

The majority of friendships don’t necessarily end because of conflict, according to Miriam Kirmayer, an expert on adult friendships. More often, it’s a result of gradual distancing. In those instances, Kirmayer says, “it’s about questioning, are there parts of this friendship that I’m willing to spend time on and preserve? Or is it time to move on?”

People only have so much energy to give toward friendships, she says. So if you’re no longer connecting in “meaningful” ways — over deep conversations or shared humor, for example — then that energy might be better spent on someone else.

Kirmayer says the most important thing to ask yourself is:

If you come away feeling “generally stressed, anxious or angry,” then the friendship may not be worth your time. Of course, it’s important to recognize that people go through ups and downs in their own lives. But a lopsided friendship shouldn’t be permanent, Kirmayer says.

Ending the friendship might not even necessitate a conversation, she says: You can pull back more gradually and see if that person responds in kind. “They might let things go gracefully and pull back as well,” she says. “If not, then have a conversation and tell them why you’re no longer feeling on the same page or where your boundaries were violated.”

There is one rule of thumb when it comes to quitting school, says Suzanne Ortega, president of the Council of Graduate Schools: If your physical or emotional health is at risk, then you should always take time off to address those concerns.

According to data, most other reasons are personal: family responsibilities or financial concerns, she says. Schools are increasingly implementing leave-of-absence policies that allow students to step away for some time to sort out personal matters. Financial aid may be available for you, too, and it’s important to seek out information from those offices.

But when is it time to stop pursuing a degree altogether?

“Leaving a degree program is in some ways straightforward,” says Sally Pratt, vice provost for graduate programs at the University of Southern California. “If it’s ruining your life day by day, you probably shouldn’t do it.” That’s applicable advice to many realms of life, she says, but graduate degrees are designed to educate people who want to be professionals in that field; odds are, your subsequent job will be similar in substance to your graduate program.

Pratt would extend that advice to undergraduates, too. “This is my opinion: I don’t think everybody needs to go to college,” she says. “It just breaks my heart because for some people, it’s torture and it’s just the wrong fit. It’s really important that society provide alternatives that are fruitful and good and that people feel free to pursue those alternatives.”

Dreams are great — they can propel us to reach our highest potential. But sometimes even dreams need letting go, says Levin, the life coach. “When it’s a long-held dream, sometimes it’s a habit to keep thinking about that thing as something that we want,” she says. The first step is to identify if that aspiration still feels true to you.

After all, Levin says, “holding on to that dream could be taking up space and energy in your life. And when we hold onto it, we’re just beating ourselves up for not having done it.”

That’s when it’s time to quit it, she says, “so that something else that is alive can come into the space.”

My daughter was colicky as an infant. Here’s how I survived.

She screamed both before and after feedings, seeming to spit up double the volume of milk she’d drunk

Do you skip out on fun now because you’re worried about saving for retirement? Here’s what to consider.

One reader is 53 and is struggling to live for today, while also saving for the future