@valerie-light oh boy ... this question is multifaceted, really. And a comprehensive answer would be really LONG.
So I'll try for a short answer!
I've been freelance illustrating for about 12 years now. When I started out, I was desperate to find work -- not the best situation and one I wouldn't recommend if you can at all help it! -- so I signed up on Elance and that's where I got my first illustration jobs. (Elance has since become Upwork.) On a site like that, you're probably not going to get paid anywhere near industry-standard prices (I certainly wasn't) and most of the clients aren't industry professionals so both freelancers and clients are usually in the same boat -- learning as they go. If you're looking for experience, though, that's one place to get started. It did give me experience in communicating with clients, managing my time, and delivering projects by the deadline.
That being said, I no longer work on Upwork. Now, jobs come to me through SCBWI, my website, social media, and referrals. I'm also trying to transition to working with bigger publishers so my next step is finding an agent -- I'm doing my homework and have a list of agents to submit to, but since I don't currently have an agent, I'm not the one to ask about finding an agent.
If you have a game plan and know exactly what kind of illustration jobs you want to pursue, you would be further ahead focusing on that industry, rather than scrambling to find just any illustration job, like I did when I started out. For example, if your goal is to become a children's book illustrator, learn all you can about how the children's book industry works and try to network and make some contacts with editors, agents, art directors, and publishers. Yes, that's a broad net and a slow process. Start by joining SCBWI (the Society of Children's Book Writers and Illustrators) and take advantage of the resources they provide, including conferences and webinars that will put you in touch with those editors, agents, and art directors. (There are similar organizations in just about every illustration path.)
If you're looking for advice and tips about being a working illustrator and the business side of things, a great resource is Will Terry's book What They Don't Teach in Art School: An Illustrator's Guide to Making Money in the Real World.
Other quick tips:
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Check out YouTube. Watching artist channels has broadened my understanding and knowledge of the art business, as other working artists are sharing their unique experiences and what has worked (and not worked) for them. A few that I've really enjoyed: Kendyll Hillegas (who works primarily in editorial and food illustration), Art Business With Ness (by this forum's very own @NessIllustration), Anoosha Syed (who is a children's book illustrator), Bobby Chiu (really love his artist interviews), and Illo Chat (which is also a podcast hosted by two professional children's book illustrators).
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Listen to podcasts. There are some really informative ones out there, and they're fun to listen to while you're illustrating. There's Three Point Perspective, Illo Chat (mentioned above), and The Illustration Department Podcast, to name a few.
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Take a few SVS Learn classes. A lot of your questions are answered there, especially the ones about work flow. I've personally enjoyed the Jump into the Studio interviews with different working illustrators.
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Mine the resource you have! You know a creative director -- if they're willing and have time, they will be able to give you practical advice and answer many of those questions.
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"Hire" yourself. If you want to know what the work flow is like, you need to have the actual experience. If no one is hiring you yet, give yourself a small illustration job. That will help you figure out a work flow that works for you and it will also give you an idea of how long it takes you to do an illustration ... and areas where you are struggling and could use some help. If you need the accountability, ask someone to be that accountability buddy, or approach an illustrator to see if they would be willing to mentor you. (They might ask to be paid for that, as their time is limited and valuable.)
Okay ... it happened as I feared it would ... this answer got really LONG even though I tried to keep it short! There is SO MUCH to your question and I honestly haven't even scratched the surface. Will Terry wrote a whole book about it! Hope this can get you started. If you have any questions, feel free to ask. And have fun jumping into the illustration pond!
