Thanks for your insight. It really resonates with me.

I think you're very right about my marketing problem :)

On the surface, my website is kinda out there. I built it from the ground up using Rake and some gems as a static site generator. I think it's very cool, and I don't expect that many people will appreciate it, but I'm hoping that one day someone comes along and says "wow, that's pretty cool, wanna help us with this Ruby thing?")

In a deeper way, this whole discussion is very helpful... it's giving me a fresh perspective on how to frame conversations with future potential employers.

And actually the other day I had an epiphany about my marketing. Sure, I chose an odd path, but I've already done so much of the work! I just need to get my random little open source tools in decent, usable shape so that people who'd find them useful might actually get a chance to use them. I need to get my half done work finished and make tutorials about it and get myself out there.

This came after I got a call from a contracting company who told me they were bidding on an interesting job that might be a good fit for me... I was so excited that I stayed up all night and finished like three old random projects at the same time, just so I could put more stuff on my portfolio. It was a wakeup call, affirming that there actually just might be some cool work out there after all... so get your shit together!

This is an interesting idea that I'll have to try.

I have the 3 primary skillset problem you describe and have a decade of "founder" experience. I thought the breadth of experience and technologies would be impressive, but I think it just confuses most employers. It seems counter-intuitive to intentionally not mention your skills on your resume, and admittedly a little ego-deflating.. but this actually makes sense.

I just thought of something else: it might be a good idea to go around and make a collection of all the different job titles that broad-knowledge people (e.g. "technical artist", "full stack") are given in different industries, and find the ones that fit you. Then study the roles. That way you'll have a language for looking for jobs and will have a better idea of where you might fit in and how to have conversations about it.

Your assertion about generalist ~= founder is pretty spot on. I've spent decades working lots of different job titles that interest me (or as the needs of the organization dictated). Putting all that down on my resume hasn't helped me much.

I was heading the direction of very focused resumes. I've also landed a low pressure founder role too, so that's nice.

A team lead position on a team that has autonomy is also a good place to be as a generalist. It's where I see myself providing the most value to my company. I've had some opportunities to move up to Director+ but blegh.

If you've worked in the different specialties at different jobs (rather than interleaving all 3), won't focused resumes have glaring temporal holes in them?

The idea is not to omit experience, but spend more real estate on the focus topic. Writing a longer description for the experience that really matches the description, and even wording less relevant experience to so that it sounds more relevant.