If you spend most of your day staring at your computer screen dreaming of doing, oh, anything else, it’s probably time for a career pivot. (Also, I get it.)

But actually take the plunge—be it by giving your side hustle more attention, asking for a flexible schedule, or venturing into a completely new industry—can feel like far too big a risk. The very real—and very scary—question of “What if it doesn’t work out?” haunts each decision you make.

To help give you that much-needed push off the diving board, author of the career change handbook Fearless and Free Wendy Sachs and co-founder of The Second Shift Jenny Galluzo weigh in with solid advice on how to figure out what you actually want to do next, and how to make it happen. So, consider yourself fully prepared for all dream-chasing.

Keep reading for the best way to give your career a second wind in 5 different scenarios.

If you need a new industry

Especially early in your career, the appeal of a bill-paying job can be too good to pass up. “A lot of women when they’re starting out just get on the wrong track from the beginning,” says Sachs. “They might be nervous they won’t get hired so they take the first job that comes their way because they need to pay the rent—and that’s a very practical reason to take a job!” But it doesn’t always mean you’ve found a perfect match.

If you’re feeling only ho-hum in your current field and know where you want to transition to, it’s time for some serious sleuthing. “I really believe in looking at LinkedIn to see the people that have [the jobs you want], and how your skills match up,” says Sachs. If you think you already have the necessary tools and knowledge, help hiring managers understand that by using the same language and phrasing you see in industry profiles. If not, setting up informal coffees with people in those roles can be a great way to figure out how to get the skillset you need for that second wind.

If you’ve been bitten by the entrepreneurial bug

“Having a side hustle is a great way to test the waters,” Sachs says.“Especially for women who want to give time to financial endeavors—writing or filmmaking or jewelry-making—start it on the side to see if you’re any good at it.” And start small. Want to run a bed and breakfast? Dabble in Airbnb to see if hospitality is all you think it will be. Ready to launch a craft-cute sweater line? Hang out a shingle on Etsy. If you find that you enjoy what you’re doing on the side—and you have a knack for it—it’s easier to make the leap to a full-time entrepreneurial role. (Fun fact: This is exactly what Lisa Price, the founder of the major beauty brand Carol’s Daughter, did.)

If you feel lost

Know you need a change but don’t know where to start? Embrace your inner dilettante. When you’re feeling adrift, casting that wide net means you’re more likely to stumble upon something that makes your heart sing. Have even a glimmer of interest in film production or bookkeeping or fitness instruction? Taking a class or workshop can quickly tell you if that might make for a satisfying career shift. And before you apply for a million different grad programs, know that acquiring new skills doesn’t have to mean committing to a brand-new degree (and the kajillion-dollar student loans that go along with it). “Whether you take a coding class or a digital marketing class or sign up for a course through General Assembly, there are so many ways to test out new skill sets,” says Sachs.

If you started a family and crave more flexibility

Sure, plenty of women relish working full time. But for others, the first or second or third baby comes with a yearning to ditch the corporate 9-to-5 in favor of something with more flexibility, says Jenny Galluzzo, founder of The Second Shift, an organization that connects experienced women with part-time professional work. “If you’ve had the big career as, say, the CMO of Neiman Marcus, maybe now’s the time to go part-time, consult for small local businesses, and get your schedule back,” she says.

Before you hand in your pink slip, chat with people in your network who have a non-standard gig to learn about the pros and cons. Launching your own consultancy may earn you a higher hourly rate, but you have to hustle for your own clients and cover the cost of health insurance and benefits. Going part-time may offer more stability and security, but it might mean still commuting into the office twice a week. There’s no one-size-fits-all solution to the working woman answer, says Galluzzo, and talking with others can help you get a gut check on what new role might work for you.

If you’re over the 9-to-5

There was a time not so long ago when “freelance” was code for “can’t hack a real job.” But that’s outdated thinking. “The job market has shifted so much, thanks to millennials—most of whom will have six jobs before they’re 30 years old,” says Sachs. If you want to hop from project to project and call the shots on everything from your hours to your hourly rate, you no longer have to worry about losing prestige. “Hopscotching around no longer looks like you’re not serious—it makes you look brave,” she says.

If you want to transition to freelance work, make sure you keep your network intact and maintain relationships—things that can prove to be invaluable if you ever need to return to a more stable atmosphere. “Your network is your currency,” Sachs says, because word-of-mouth is how so much work is doled up and snatched up. You also need to get the basics set up to market your skills: a portfolio site, an updated LinkedIn profile, and a public resume, depending on your field. Then grab a bullhorn and tell your network that you’re going freelance. “Don’t be shy about it,” says Sachs. “Ask people what they need, and how you can help them achieve it.”

For more career inspo, read how Ladies Get Paid founder (and Well+Good Council member) Claire Wasserman decided to become her own boss. And before you make any major job moves, you might want to consult the stars.