How can I leverage my 13 years of experience as a television anchor and reporter into a profitable online business that helps people?

Two key concerns are 1. Customer confusion with the 2 offerings: Imagine being in an art gallery that sells photography training and fine art or a book store that tries to sell you fine art. Even if it's the same group of people, they may be in very different mind-sets and hence may not associate both together. 2. SEO challenges with mixed messages you're sending. Which keywords would you optimize for which part of the site? Advantage would be if the customer base is the same group of people, hence offering cross-sell opportunities. For instance, if your MAIN source of leads for the training site is the art site, then this would be more important. In general, I would suggest one site for one customer group. If there is likely to be a very high overlap, then same site, with multiple sub-sites might work. In matter of fact, it'll probably be EASIER to do two sites for this than one site. Your designer will thank you :) Then tastefully add cross-links in the places where someone is likely to use them. For instance the art gallery could have a post 'How I make art' and links to your other business there. And the photog training site would have your art pics with subtle on-image links to your art biz. While I'm not a branding expert, I do find that my engineering lead approach to challenges in Marketing/Sales usually works, and provides clarity and direction.

Say "NO." It's a complete sentence.

Unless they are in some way related ie seo clients are weight loss focused you should keep two.

I do a lot of business with people on Elance (which is now being merged into Upwork and is going away, so stick with Upwork). The real challenge for US-based workers (which you may or may not be) is the price competitive nature of jobs when competing against an international workforce. There are always going to be great workers in every country and sometimes in certain areas you just can't compete on price. For example, I do a lot of business with great people in the Philippines and their work is excellent, they speak perfect English, and they are very affordable. What I usually tell people who are first getting into the space is to be honest about that in your profile and do some jobs for near-free with private pricing so you can build up your profile with good ratings. There are some disadvantages to this approach, but I find it helps to get some jobs under your belt with employers. One of the keys is going to be differentiation. You have your industry listed but skills, language, specific experience, and other niche items are really going to help here. I'm a consumer of a lot of Upwork contractors so I'm happy to do a call and discuss my experience with you. I work with people all over the world on a regular basis and I've built my business around these assets.

1. Differentiate Between Days to Produce and Days to Create I pre-schedule which days (and time blocks in those days) will be for money making activities (literally those activities that are directly linked to income generation such as being on stage and speaking, in a room with my clients, closing sales, etc) versus those where I'm creating content, generating new business ideas, networking, developing marketing materials, etc. This allows me to focus on both working in it and working on it. 2. Keep a Digital Voice Recorder With Me at All Times (with a spare battery!) Ideas seem to pop up all of the time - and I used to be a "write it down" guy who ended up with a pocket full of scrap papers and post it notes. Now I just talk the idea through and record it. At the end of the week I transfer the audio files to my pc, listen to them (using a media app that lets me play them at 2x speed) and transcribe my notes to a google document. 3. Planned Days Off - No Business Allowed Being an entrepreneur takes energy. So "charging your batteries" is critical. Do things you love outside of working (even if you LOVE to work). Personally I take the day off and go fly fishing 1-2 days per month. It does wonders for clearing my head, relaxing me, and getting me prepped and ready for the week to come! These rituals and habits are things you will benefit from starting to do TODAY. You'll not only be more productive, you'll find greater joy in what you do (and have less stress). For more tips - let's talk.