Working for free. Whew. These are fighting words for some. The concept of being asked to do work for nada (or on spec) has been lampooned in videos, illustrations, and even a dedicated Twitter account. But it’s one of life’s most nebulous gray areas: There’s no clear-cut correct answer to the “should you work for free?” question (sorryyy). Instead, the right-for-you answer is constantly shifting, dependent on your current needs, goals, and availability. What’s right for you might not be right for someone else, and what’s right for you now might not be right for you in five years.

With that in mind, there are some instances in which doing gratis work can actually be just the kick in the pants your burgeoning career or business needs. Below we dig into six situations where it might make sense, and share a look at how some top entrepreneurs feel about taking on a no-pay gig.

You’re just getting started. Your work is rad (RAD), and you knowww the world will love it. (They will!) But you’re a little stuck when it comes to getting the word out, creating in vain—and in a vacuum. One solution: Offering up some freebies to a legit company that can help boost you over the hurdle by letting you tap into their audience. In these situations, though, know that the promise of “exposure” is not enough. Get down and dirty with the details. Ask for attendee numbers for events, probe publications for their readership numbers. Will companies link back to your site? How and where—exactly—will this happen? Will they promote you, along with your work, on their social channels? On related marketing materials? Big companies should have budgets, but sometimes the only way to get that toe in the door (and land a gig that might otherwise go to a more established colleague), is by offering to do it for free. But if a company isn’t forthcoming about their audience or how they’ll promote you, they can take a hike.

Sometimes one.single.resume.line of you doing amaze work for a credible company can catapult you into the realm of paying jobs for life. The same goes for visual examples of beautiful work, whether you’re a graphic designer, photographer, stylist, or brand consultant. We know an incredible interior designer who decorated a pal’s pad for free (labor, of course, not materials), had it photographed by a profesh, and plastered it all over her site and social-media accounts. Then paying gigs for design work and requests for interviews by shelter magazines started rolling in. Nail one job down, lean on it hard when talking with future clients or companies, and see where it gets you (and, ahem, they don’t need to know you did it for free).

This is especially important when it comes to career pivots. You’re languishing in middle management at an accounting firm, holding tight to the same cupcake-baking dream you’ve had since you were knee high. But you have no idea how a successful baked-goods biz is run! You know that bakery around the corner? Consider offering to help out for free and you’ll pick up priceless on-the-job experience. Not saying this will be easy. It might mean crazy-early mornings. Scaling back to part-time at your paying job. Your hubs having to pick up major slack with the kiddos for months. But it’s doable. We actually know an inspiring lady who leveraged an unpaid apprenticeship at a hot-town San Francisco restaurant into a paying job there and then bagged a cookbook deal.

Sometimes passion projects with little-to-no budgets are attached to influential folks with big names and tons of connections. Getting swept up into their network—being on calls and trading emails with people of note, organizing events with a A-list guest lists or speakers—can land you job after job after paying job down the line. Tons of career breaks have been launched by a friendly “remember me? loved working with you” email after you’ve done solid work and built rapport with a killer new network of people-who-can-hire-you.

Back in our day, we trudged eight miles barefoot through the snow to intern for free. Welllll, not really, but we logged many an hour at unpaid internships, and several of us flipped them into paying jobs at the company we’d been interning for and at other great companies within the same industry. So, it’s possible, as long as the terms are clearly defined and you let it be known from the get-go that paid work is your ultimate goal. And no, you don’t have to be a 19-year-old college student to make this happen. Imagine striking a deal with a museum or library that you’ll take on grant-writing for free until you’ve secured the grants covering a potential salary for yourself and then some. An airtight contract is key here, but you’ve essentially created a job for yourself out of thin air.

Charity or volunteer work! This should really be numero uno on our list! As they say, this one is about giving rather than gaining. It could be anything from acting as treasurer for a nonprofit in need to accompanying your little one to the animal shelter to read to dogs every weekend. The point is that the more you give, the better you’ll feel—recent studies have shown that the secret to happiness is helping others. Just be clear upfront about the amount of time you’re willing to dedicate so that it doesn’t creep into something unmanageable that breeds resentment.

1) Interior designer and TV host Emily Henderson still does it on occasion.
2) It’s all about what you get from the deal according to #momboss Penelope Trunk.
3) Author, entrepreneur Seth Godin is all for it—with caveats.
4) Yes, No, Yes, Yes, No says designer Jessica Hische’s hilarious “Should I Work for Free” flowchart.
5) Bri Emery, the brains behind Designlovefest, will work for close friends (after setting boundaries, that is).