The Creative Itch I've Been Afraid to Scratch for Years

For the month of July, I'm learning to sketch, but the sketching isn't the scary part.

Quick Note: I’m moving the schedule around a little (always experimenting). Going forward, occasional regular posts will go out on Tuesdays and members only posts on Fridays. Please adjust your alarm clocks.

Becoming a better illustrator is another one of those things that I’ve wanted to work on, but never took to it in a thoughtful way. My vigorously scribbled figures and completely out of perspective architecture sketches were enough to keep me away.

I took my fair share of drawing classes in college. I can draw glasses of water against a shadowed background, and can usually come reasonably close to drawing a human in repose, but there’s something about being able to draw funky, quirky, characters with a particular style that eludes me, which is short-hand for being too impatient to stick with it long enough to get the results.

Of course, real illustration comes from time and repetition, which as a creative who is always chasing the next butterfly, isn’t in the cards for me unless I force the issue.

So let’s force the issue.

Norwalk Square - Dave Conrey, 2026

July’s monthly challenge started a little early because I was almost too eager to begin (which typically means I’ll be ready to give it up in about 17 days), but I’m taking this entire month to focus on regular urban sketching. That means planting myself on the patio of a cafe with nothing more than a sketchbook, a 1mm gel pen (I like ‘em bold and messy, big surprise), and coffee big enough to get me through 20-30 minutes of sketching whatever is sitting directly in my line of sight.

1. Will this help build up the habit?

2. Will I be able to get to some level of style that feels like something I could improve upon?

3. How does any of this relate to whatever real work I’m trying to make?

Let’s address that last question first, because if I learned anything from June’s challenge, it’s that I have absolutely no idea where this ends up. The questions I had in the beginning only got in the way of the real lesson. The exercise wasn’t meant to become a new talent, but to add a new layer to the vision I have for my work, whatever that might be.

Of course I’m taking that lesson forward into this month’s challenge, but I might end up being completely wrong, so I refuse to limit myself with expectations.

As far as building up a habit, I’m realistic, and it will depend on how well I do with question #2. If I do start to establish some sort of style/method, or at the very least, a steadier hand, then the habit will more likely take hold. I’m a results oriented creative. I like the process, but if the process isn’t working, I’m moving on to something else, usually something that’s easy, but the point of these challenges is to keep myself out of that comfortable space.

And then there’s you.

The uncomfortable is where true art exists… I think

That old adage of someday never comes is true. There’s a someday thing on your list and you’ve avoided it for months or years, but why? Time? Money? FEAR?

Why would anyone want to make a deep investment into a new creative exploration unless they could guarantee some results? You might tell yourself it’s time or money, but the those are surface level excuses we give ourselves so we don’t admit that the core issue is fear.

I know because I can read our mind. It reads exactly like mine—scared to jump into anything new because you don’t want another plaque on the wall of other failed attempts. You don’t want to imagine the faces of family, friends, or fans as they look down at you and your pathetic attempt to try something new.

With all due respect to your family, friends, and fans, but FUCK THEM!

I know, harsh, but I’m not here to placate them. I’m here for you, and I believe that when we’re together, there isn’t a single creative project that’s safe. We can tackle them all, but only if we go in with zero expectations.

Not how I saw this playing out

When I first found my way to Substack (before the Notes app), I was recommended the art and musings of Nishant Jain, an urban sketch artist who has refined his style to a minimal approximation of his surroundings. He’s a master of his craft and the simplicity drew me in (no pun intended). Honestly, it was his work that made me want to attempt urban sketching in the first place, but my initial attempts were absolute trash—I wouldn’t dare show them. However, Nishant persists.

He shares his sketches and journeys weekly, and the constant reminder of me not being able to do it made me want to unsubscribe many times. I didn’t want to be faced with the reality that I never gave sketching an honest effort.

At the same time, there’s this lingering feeling that if I do use his lessons, find my way to sketching more often, will I risk being a copy cat? Will my work end up looking like I want nothing more from it but for people to call me out for being a wannabe? The professionals in the room know that’s a foolish notion, because Nishant’s are not the only lessons I’m taking from, but it certainly makes for another good excuse for me to not try.

And maybe that’s you too. Maybe you’re worried you’ll lose yourself in someone else’s work? Maybe you’ll move so far out of your lap of comfort that you’ll end up in the lap of another while also distancing yourself from what you once were.

And I suppose that’s the real challenge, and what I’ll be using this month to discover. Can I study from the likes of Nishant and other sketch artists to find myself. Will I be able to strip away the styles I’m borrowing from the people I admire and find something that’s mine?

What’s the thing you’ve wanted to try for years but haven’t—because you’re afraid it’ll either change you or prove you’re not who you thought you were?

That’s the question I’ll be sitting with for this month, and what I’m working out in the open with members, starting this Friday.

If you want to watch that play out in real time, upgrade today. Members are also getting an exclusive asset pack pulled from last month's challenge — grit and color to drop straight into your own work.

The next member-only post comes out this Friday. Don’t miss out.

Cheers,

Dave