Since 2008, I’ve been joining or crafting my own creative challenges. Here’s a list with links to view:

~50 Songs in 50 States: a place-based songwriting challenge (2020-current). Began as ‘Solitoury’ (writing songs in Midwest places to convert childhood memory & trauma) & ‘JiTR’s Great Adventure’ (writing songs in every state on a road trip to/from Colorado & New Mexico – where my sister had recently moved, and where I was considering moving – to explore how different places feel as a songwriter). In 2022, I took a ‘songwriting tour’ (no shows, just songwriting) to the Pacific Northwest. After those three trips, this idea of ’50 Songs in 50 States’ was born – and I continued writing songs while on tour as a performing singer-songwriter, amidst playing shows (writing ‘at least 3 songs per state’ and on the ‘Southeast U.S. Friendship Tour 2023,’ and many more on the ‘West Coast Tour 2025’), along with crafting some intentional ‘songwriting adventures’ (Pittsburgh/Buffalo, Gulf Coast/Austin TX & New England) – most of these trips surrounding other necessary travel – from the Buffalo Gay Men’s Choirs singing my work, to performing at my friend’s memorial at Joe’s Pub in NYC. The songwriting is now completed through 48 continental U.S. States (as of November 2025). Some of the songs are currently shared in lo-fi / demo form (like this one). The final project will be a studio album called ‘States of Being (& Believing): 50 Songs in 50 States’ – with 50 songs, 1 song per state.

~444 Hearts: a ‘heart songs’ challenge (2019, 2024-current). A project for connecting with other songwriters, and the people I love. Mostly cover songs, but some heart-centered originals.

~52 Dreams: a ‘creative life’ tasks challenge (2019, 2026-current). A project to give structure to a wild & free creative life. Assigning self one to-do per week, related to the business side of creative life.

~12 Albums in 12 Months: writing &/or recording an album a month for a year (2018-19). This was the 1st album and 12th album.

~365 Songs in 365 Days: writing a song a day for a year (2017-18). Shared daily on YouTube and sometimes Instagram. This began as ‘creativity activism’ – as a way to inspire fellow creatives to share their voice, and create structure for myself in a changing world.

~FAWM (February Album Writing Month) – wrote my 11th album in Chicago (2011) as part of this global challenge – here’s a link to one of the songs.

~50/90 Challenge (50 songs in 90 days, an international challenge): my first songwriting challenge, here’s my archived 2008 page.