UPWORK:

I've been playing with 99designs here, and there for the past 3 months, and have pretty much made a 5 figure income from winning contests, and having a few one-to-one projects. 

• Focus your time on "Guarenteed" labeled contests as the contest holders here are usually more serious, and aren't likely to scam you with a refund. Doing this has boosted my winning chances by over 70% and I did not have to deal with a "locked contest" that is due for a refund in the next few weeks. 

• Before entering a 99Designs contest pay attention to how active the contest holder is at giving feedback. Little to no feedback = stay far away from this soon to be locked contest. A nonresponsive contest holder is one of the worst. When I enter a contest I always make sure that a contest holder is at least 70% responsive. 

• Always, always, always stay away from copyrighted images. If you have to use images in your designs please make sure that you use stock images, and properly label them. Imagine that you created a design, worked very hard on it, and the contest holder loves it. Now imagine having your design being reported, and taken down right when the contest holder lets you know that they chose your design for their contest. Now the contest holder is irritated, chooses another designer, and you ultimately lose just because you used a copyrighted image (using copyrighted images can also get you sued as well as the contest holder so please keep that in mind). 

• Make sure you sell your ideas to the contest holder when submitting a design. A crucial mistake that most designers at 99Designs make when submitting a design is leaving the comment area blank. Never do that. Communicate your ideas clearly, and efficiently so that they can understand the thought behind the process. When I broke down why I did certain things to the contest holder they asked questions, and gave compliments which ended up to winning the contest. 

• Don't stick to one area of design. If you like designing logos that's fine but do not limit yourself to just logos. There are so many categories to choose from at 99Designs that many designers do not pay attention to. When you limit your potential you also limit the amount of money you can earn at 99Designs. 

• Report other designs that violate the rules. So you're in a contest where the contest holder has to pretty much choose between you and another designer's design. You notice that they used a copyrighted image from deviant art (not the deviant art stock section, but the general ones that clearly state it is not a stock image), and they did not even link to it in their design (they are concealing the crime). It also happens that the image they are using is the main subject the contest holder likes. What should you do? Report it. An easy win. 

The best way to promote yourself or gain a huge amount of exposure in a short amount of time is by gaining the attention of a huge audience. 

• Offer posts that are relevant to the brand and helpful for their audience--especially if it is in your blog's niche. For example, if the massive blogger is all about giving tips on photography don't try to pitch, and promote your post about cooking grits to them. Pitch a related topic such as tips and tricks about camera lens or something. 
• Don't be a desperate spammer. Don't go on twitter and "@" the brand 100 times telling them to check out your post (huge red flag)
• Choose enticing or controversial titles for your blog posts, Facebook posts, tweets, etc. If you blog about very controversial topics you need to find a bigger creator who also blogs similarly, and pitch yourself to them. Targeting the audience of someone who is within the same niche works better. 
• Always use an image when linking to your post on social media before showing them to bigger brands  as well as your own audience (social media posts with images get twice as much engagement) 

• Poor website design. If the text is hard to see or read, and the site is clunky then there's problem.
• A super slow website. If it takes too long to load people will leave in search of the next best thing. 
• Too many pop-up advertisements (especially the ones that open new scam webpages). Everyone hates them and will think you're a spam site. 
• Extremely poor grammar---this goes without saying.  An app like grammarly can help. 
• Extremely complex grammar (readers need to understand what you're saying without having to look at a dictionary every 2 seconds--unless that's the audience you are going after. Since most people are average readers I don't recommend this writing style)