It sounds like you have plenty of skills to get started now. There's no need to keep re-training in different areas when you have experience to get started today.

My suggestion would be to pick a niche and try and become the go-to guy in that particular niche.

Let's say, for example, you are interested in men's fashion. You have experience in creating Wordpress ecommerce sites. You could call up maybe 10-15 of the local businesses in that niche in your local city/state and offer to make their website and get them in on a set-up fee and then a monthly maintenance retainer.

This approach would be lower stress (because it's something you're interested in) and also because you could create a methodical framework that you could apply to other businesses in that niche.

That's just one idea.

Second idea - create a course on WooCommerce development and put it on Udemy (or Coursera etc). Note down 10 of the biggest obstacles you've had to overcome when building sites for friends and family and then note down 10 of the most important considerations people should consider before people get started. Now you've got 20 video lessons for your course. Charge for the course on Udemy or use it as a marketing tool to get more b2b development work.

Idea 3: Go make money on freelancer.com, peopleperhour etc. Perhaps you've tried this already? Skills like yours are in demand on those platforms.

Idea 4: Take the things I noted in the second idea above, and turn it into a handbook. Sell that book via Amazon.

Idea 5: Go on Tweetdeck. Create a column that searches for people who are using keywords like "Wordpress woocommerce issue" "Wordpress woocommerce help" "WordPress woocommerce problem". Give them your clairty.fm link and tell them you'd be happy to have 5 minute discussion to see if you could help them resolve their problem.

Idea 6: Find 10 major theme development companies. Sign up to their help or support forums. Do a similar thing to what's noted above on Twitter and offer to have a quick call via clarity.fm to see if you could help.

Idea 7: Go down the route of finding existing Wordpress/Woocommerce blogs. Write posts for them about specific WooCommerce issues, problem solving or project management tips. Do this with the aim of improving your inbound consulting gigs.

Idea 8: Do the exact opposite of whatever those friends are telling you.

Idea 9: With your skills you could easily start a dropshipping company. I won't go into all the details here but just start looking at sites like Clickbank or Product Hunt to get a feel for something you're interested in. Build your site and start dropshipping products. https://www.woothemes.com/2015/06/dropshipping-beginners-guide/

Wordpress consulting alone, yeah it's probably quite competitive, but that doesn't mean there aren't plenty of opportunities for revenue. I think you will be even more motivated, successful and less stressed if you pick a niche industry, product or service to focus on.

Enjoy it!