What is the easiest job to pursue in the creative/graphic/web design field for someone that did not major in said fields but has put together a decent portfolio through freelancing?

You're in luck, because the country is full of low barrier-to-entry schools that will grant degrees to people who shouldn't have them - so its easy to blend in and appear impressive even amongst trained designers. I will tell you that there are very clear signals that I get from candidate portfolios that show their level of training. Some people have innate talent and can put together a great looking portfolio. Here are some of the things I look for, so perhaps you can focus your efforts here to help improve your portfolio and compete with the trained recruits: Typography - this is biggest thing missed. Most people who are innately skilled but lack training rarely think to manipulate the text itself, preferring to stay in the realms of shape and color. There are a lot of fundamentals of typography: do you pay attention to the rag, have you adjusted your leading, have you attempted to use the text as a compositional element rather than just words, have you selected an appropriate mixture of fonts. Process - I ask candidates about how they arrived at their design. Designers that lack training will not have gone through a process, they will have just sat down and started. Trained designers iterate on their compositions and will demonstrate this by talking about the steps and decisions that led up to what I'm being shown. So, when you talk about your work - make sure you can discuss your design decisions deliberately. Show that you can think first, then design - because design is not just pushing pixels; creative directors need people that understand this. Regardless, there are a lot of jobs in and around Creative teams for individuals like yourself. Internships or Associate Design Positions - entry level positions are designed for people coming out of school or with little experience. The work will be more grunt-like until you prove yourself, but the grunt-work is a training vehicle. Just show you have talent for composition and can work with other creatives and this job can be yours. Art Director - At larger agencies you can find entry level Art Director positions. These are perfect for people with Communications degrees because the role is all about communication on a campaign and conceptual level. Design and an eye for design are important - but not as important as your ability to generate ideas. You will need to show an understanding of design; however, since you'll be directing designers. You will obviously need concept and campaign type work in your portfolio to pursue this kind of position. Resource Management / Traffic / Project Management - creatives need help staying organized. It is one of the skills few of us have. What's worse is that project managers who haven't worked around creatives are clueless when it comes to how things get done. It seems to take a creatively minded person to be able to organize and help creative teams execute. Traditional PM's fall into linear thinking while a creative person tends to be more comfortable outside traditional boundaries. These positions require very little education and training and are a great way to get your foot in the door. Good luck in your pursuit.

The fact that you have a communications degree, with a business minor, should give you an advantage over 'proper' designers. I don't know you, your portfolio or your design skills, but I'd say that you would make a good webmaster or any other role that requires all-round web skills, presumably in a smaller company or start-up. Of course, if you've managed to build up a solid portfolio and have a list of happy clients, there is absolutely no reason why you shouldn't go after 'pure' design jobs. Most employers will want to see your portfolio and will be happy to hear that you have a few years of freelance experience. Your degree is secondary.

Pardon me but I'm going to refactor your answer just a bit... The fact that you have a communications degree, with a business minor, WILL give you an advantage over 'proper' designers. Ultimately design (or any sort) is about architecting a solution to some problem. So instead of being limited to just pretty colours and eye-catching (but useless) interfaces, you bring a broader set of tools to the table. Tools that increase your value as a communications solutions architect. There's certainly no shortage of great designers. On the other hand, how many websites actually feel great? Yes, you are correct, having a degree is a plus. But over-using it, if you will, is a bigger minus. IMHO of course ;) Photoshop is just a tool. A tool that is only as good as the understanding of solutions of the person using it. If you feel your weakness is design and using PS then buy a book, take a class, do more tutorials, etc. Some people will be interested in seeing a design degree. That does help at times. Most other people want to see quality work and a desire to perform and excel. Moi? I would suggest you keep freelancing. If you're looking for full-time proper employment then freelancing is a good way to "date". And even if you don't get married right a way - so to speak - you'll be in the game while you're dreaming and executing your own self-made career. I hope this help.

You'll find a very large percentage of design professionals are self-taught or came from a different line of work originally. I fall under that category. I went to school for Journalism and Communications and have been a design professional for nearly 20 years. I assume that by "easiest", you mean "path for best possible success". Almost nothing that is worth it is "easy". The best designers practice their craft because it IS a challenge. Here's some guidance to create a path for best possible success: Design as much as possible. Keep freelancing. Interview everywhere. Get feedback from your interviews especially from places that DON'T hire you. Shore up your weaknesses and propel your strengths. Discover what makes you exceptional and market that difference. (Read "Purple Cow'.) If you find a place you'd LOVE to work at and they don't have any openings, offer to work at a discounted rate. I spoke on a panel at FIT with fellow advertising and design CDs and one of the biggest pieces of advice was to work for dirt cheap so you can not only get exposed to more work, but so you can also NETWORK. As I said on that FIIT panel, sometimes the best ability is availability. That means being flexible and communicating your availability to people who are hiring: Art Directors, Senior Designers, Creative Directors, Design Directors, Creative Recruiters. So you see, there is no "easy" way. You need to work for your success. Yes, there's an element of luck but you need to work to make your own luck.

Design led careers, are often portfolio led rather than qualification led. Essentially traditional qualification fall short, due to the fact you can get a pass or high qualification, but still not have a good eye for design. This is were portfolio comes into play, at the end of the day who would you rather employ some one whos got all the qualifications saying they can design, but has a rubbish portfolio of work. Or some one with no direct design degree, but a great body of work. Its a no brainier. Coming back to your question about getting into a job, the bottom rung of the ladder / door way into a design led career is interning, while doing that concentrate on building a great portfolio.