Help me outta my wump (web design slump)

I also mostly design and build bespoke Wordpress sites for clients as my fulltime job. So if I'm right, there are two things here - one is the uninspired creative malaise that you feel, and one is the general dissatisfaction of your development methods. Like you, I don't think they're unconnected. By now, you know what you can accomplish with Headway, and you're designing to fit that. As with any WYSIWYG development environment, you're probably hitting the barriers of what you can comfortably do quite quickly. Perhaps you should jettison the Headway theme and move into proper bespoke theme development? I'd also get a solid library of reliable plugins, your ACFs and Gravity Forms. Try and work with those, and any client's exotic requests are treated as such. 90% of the time, I'm either building bespoke themes with Underscores or Roots, or providing custom code tweaks on existing sites. I spend next to no time plugin hunting. There's no getting around entering content, but it should be a chargeable service. There are a tremendous amount of uninspired websites around, all choc-a-bloc with huge desaturated photos. One upside of this is that there's a much bigger focus on actual UX, and tbh I find this a pretty satisfying thing to focus on. Perhaps there is also someone in your peer group who you'd enjoy working with? Collaborative projects can be rejuvenating. If you land a big project it might be a good opportunity to try it out. Happy to natter on further if this is helpful, either on here or via MeFi Mail.

Magnakai, thanks. Can you elaborate a bit on what kind of code knowledge is required to make use something like Underscores or Roots?

Using Headway is your choice. It is totally possible to create wordpress themes completely by hand. I have many clients with wordpress sites that I've taken over the maintenance for and only 1 of them used Headway (or similar) and they ultimately decided to ditch it and have the design built the "old" way. If you don't like using Headway, why not just not use it? It would help to be familar with PHP but you don't really need more than that just for building themes. You'll still need plugins for non-standard functionality if you don't write code but you can style up the output just like normal.

missmagenta - I didn't say I don't like Headway. I think it's quite good, and flexible. I'm speaking more of the approach to designing sites required in the current tech environment. It's not about the tools so much as a how web design has changed, and trying to find my groove in the current paradigm. Thanks tho.

If you're going to create bespoke templates, you would need to use HTML, CSS, PHP, and probably JavaScript. What starter themes do is give you most of the structure. They're basically custom theme boilerplates. You would be hacking them up to create your own themes. Underscores is Automattic's own starter theme. Probably the simplest, it has just enough structure and information to give you a running start. Bones is a little more fully featured. I used it a couple of times and ended up ripping out enormous swathes of it. However, it is very well commented, so might be good for someone less confident. Just don't be afraid to use the delete key. Roots is an enormous, complicated starter theme. It changes a lot of default WP functionality. Definitely very useful if you can get your head around it, but I would recommend being very familiar with Wordpress conventions beforehand.