The Creative Generalist

The Creative Generalist

Are 30-Day Challenges Worth the Effort?

Creative people love purpose and intention, but sometimes it's the thing holding them back.

Dave Conrey's avatar
Dave Conrey
Jul 31, 2026
∙ Paid

It’s the last day of July, which means the last day of my sketching challenge for the month, and honestly, not soon enough. I struggled, found peace, had some fun, and at the end, I tried to find some powerful meaning to it all. I wanted to justify the effort by figuring out how sketching would find its way into my work.

It won’t!

I’m not an illustrator. I can kinda draw people and things, but there’s no clear solution, and the sketching process doesn’t really help me with the work I’m making… or does it? What if the result is extrinsic instead of intrinsic? What if every monthly project so far has been the same; little to no direct value to my current work, but loads of value in another way?

So far, I’ve done three monthly challenges: journaling (undocumented publicly), photography, and sketching. Before I started any of those, I had not made a single piece of physical art in several months. The last piece I made was in September out of a personal obligation to a friend, but it was such a struggle, when I handed over the piece, I closed the studio doors and didn’t go back in unless I needed. I didn’t even ask for the art piece back, I was so ready to be done.

But here we are in July, and I’ve made nearly twenty different collages; more than the amount of sketches I did in that same time, but what does that mean?

When I put my head to the question, it took me all of about 47 seconds to realize the result of the monthly projects was the creative impulse. The making of benign things helped me get to the making of the meaningful work. That’s all the clarity I needed, and made every failed experiment worthwhile.

But there’s more.

Want to Go Deeper?

I work to bring quality content to all subscribers, and becoming a paid gets you some serious bennies. Free subscribers get twice a month updates, but members get:

A weekly dispatch, every Friday - The raw thinking behind whatever I’m working through that week, and behind-the-scenes work done in the shop as I rebuild my online sales.

The monthly creative challenge - Each month I try a creative impulse I haven’t mastered to see how it adds (or takes away) from my work. Free readers get the takeaway, but members get the process while it’s happening: the resistance, the almost-quitting, and the heroes journey (yeah, it’s like that).

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First look at LostMixtape.com - The sales side of things, which is ever-evolving. I share my e-commerce experiences, new product drops, decisions before anyone outside this list sees them, and real-life strategies for selling creative goods.

Member-exclusive chat - Where the conversation happens away from the public comments. Also, direct line to me, always.

Finally, I’m a bit of a wild stallion, going off script (and apparently mixing my metaphors), and handing out goodies randomly whenever I get the impulse. No guarantees on that, but I feel a generous streak coming on… just saying.

The realization that the challenges I gave myself weren’t giving the desired effect has be second-guessing the choices for the next challenge. First, because I have a big project I’m working on this month and a challenge will only make the other things, well, challenging. Second, I a questioning my original choice for a challenge this month, but I don’t know if the alternative choice is the right answer either. So I’m putting it to a vote, but you’ve got to hurry up with your choice.

Option 1 is to create a month of handmade ACEO/ATC sized original art pieces and test selling them on Etsy. I’ve been seeing more videos about this lately, and I thought it would be a fun experiment so I could report back on whether it worked or not.

Sabrina Ward Harrison – @nathanunger on Tumblr
Art: Sabrina Ward Harrison

Option 2 is to practice my hand lettering style more because I can directly apply it to the work I’m doing now. I’m taking my cues from one of my favorite artists, Sabrina Ward Harrison, because she has such a unique approach to the typographical poetry within her work. I would like to be as confident in my own typographic exploration, and this might be a good way to get there.

So which do you think I should explore this month (with the other moving to September)?

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You have three days from Friday to vote, but I’ll go whichever way the majority vote goes, and I won’t taint the well with my own vote, either.

Want to go on a Side Quest with me?

Ok, the cat is out of the bag; I’m starting a snail mail club, and it’s called Side Quest, a zine concept where club members get the option to participate. Since embracing the idea that my randomness is actually my superpower, and where the Creative Generalist was born, I made a decision to create a project celebrating creative experimentation and providing an opportunity for others to participate.

I’ll have more detail this coming Tuesday, but the gist is every month, members will get a package in the mail that includes a zine, an art print, sticker(s), and exclusive paper materials to help you create your own work. Also, as you move through the editions, the challenges will get a little more exploratory. The goal is to encourage play, but even if the work isn’t typical of what you normally create, as I’ve shared above; the hope is that all of it lends to free creative expression.

The first copy is going out to members around the third week of September, and for this inaugural edition, one lucky member will win the original featured art, which I started working on yesterday, but I already messed up.

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