Day 1: Let's begin

with Jennifer Wilkin Penick

Hello, friends! Day 1 of The 100 Day Project is here. How are you feeling?

It’s normal to be excited, to not feel ready, to wonder if you’re doing it right. It’s all normal! The main thing is to show up. If you’re like me and you can’t help but put a lot of weight on the “official” beginnings of things—the first of the year, the opening page of a notebook—try not to judge your early efforts, especially if this is new to you or you’re feeling rusty. There will be plenty of opportunities ahead. There’s nothing you need to perfect today—the only thing to do is to begin.

To get us started today, I’m excited to share a short conversation with Jennifer Wilkin Penick on what it’s like to begin and return again (and again).

It’s Day 1! You’ve done the project four times now. What’s going through your head as you start a new round?

I’m thinking that I feel both eager to get started and then I also wonder if I have set up good parameters for myself for this year’s project. I think that I have. For me it’s important to have some structure, but I also need to leave myself room for exploration and discovery.

You’ve mentioned that you choose topics that are “repetitive meditative work”—what about that works for you?

I think that there are a lot of different goals with creatives doing The 100 Day Project. Personally, I absolutely love having a project that sets me up for some regular quiet time. I RELISH having a repetitive mindful aspect to what I have chosen so that I can combine relaxing with art-making. I am creating time for myself to play and not stress out about the task ahead. I want it to feel approachable, enjoyable. (But I understand that others may enjoy a more technically complex task.)

What’s the difference between choosing something you genuinely enjoy doing versus something you think you “should” be doing?

I guess that for me doing what I “should be doing” implies thinking about some sort of external judgement. Although I love sharing what I make as part of The 100 Day Project, I work hard for this to be something that I genuinely enjoy making... and to not focus on what others may like. Doing something that I sincerely enjoy makes me eager to come back, while doing something that I “should” be doing risks shifting the focus from a pleasure to perhaps more of a duty.

You talked about how your projects become a resource you return to—how seeing all 100 pieces together reveals something you couldn’t see day by day. What’s valuable about that accumulated work?

Working with the same creative prompt for 100 days produced, for me, unexpected patterns, ideas, shapes, and approaches. It has been great for me to return to the finished 100 pages that I made as part of the project in 2025 and revisit those new ideas that cropped up. Doing this allows me, even at a distance of time, to think about incorporating these elements into my creative practice.

For someone who is new to the project or feeling anxious about whether or not they can really do this, what would you tell them?

I would suggest what I think that you also recommend: choosing something that feels manageable time-wise. It’s easy to feel optimistic at the start, and it is also easy to feel defeated when you PLAN to set aside time and then, well... life gets in the way and after 3 busy days you end up feeling disappointed with yourself. Once you’ve DONE The 100 Day Project once, you will have a better sense of what project scope will work for you. But to start with, I would either choose something that doesn’t take too much time, or maybe something that is in a small format. This will allow you to easily “catch up” when you have busy days that keep you from art-making, without making you feel like giving up. I also take advantage of the occasional day when I have MORE time than usual and I will do a couple of days’ work on the project at once. In the end it’s your project; you make the rules.

Anything else you’d like to share?

Last year I took my 100 Day Project traveling with me. Since I had started in February, and I led a mixed media program in Italy in March, I worked on my 100 Day Project while leading my program in Umbria. I’m running the same program again this year, and my 100 Day Project will come with me this year, too. In the meantime there are free (and not-free) classes and workshops (online and in person) that I offer throughout the year. See what classes are coming up HERE.

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Thank you to Jennifer for sharing. Her reminder to choose something manageable that you enjoy will serve you well over the next 100 days!

Let’s take Jennifer’s advice. Before you think too far ahead, set up the simplest version of this project that you can realistically return to for the next 100 days.

CREATE THE CONTAINER

Choose the smallest version of your project that still counts. Write a clear commitment:

“For the next 100 days, I will…”

Make it something that will still be doable on an off day. If you can do it in just a few minutes, you’re on the right track.

FIND YOUR ANCHORS

Decide when and where this project will take place in your life. For example,

• a time of day

• a physical spot

• or another habit you’ll connect it to

FOR YOUR PROJECT TODAY

Treat today like a warm-up, especially if you’re starting something new or returning after a break from making. Start to notice what feels good and what doesn’t. Let your observations guide your next step—don’t judge this one.

FOR INSPIRATION

Jennifer began with a simple idea and followed it. Day by day, project by project, it grew. What unexpected place might your project take you if you keep showing up?

Art by Jennifer Wilkin Penick

→ Follow Jennifer to see more of her work.

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A couple of logistical notes:

If you’re unsure where to find people or how (and where) to share your project, this post walks you through it:

How and where to share your #The100DayProject 🎨

The most important thing is to do your project. Sharing is part of the practice, but you can work towards it. Keep it simple to start.

Here’s what to expect over the next 100 days:

• Paid subscribers receive a daily creative prompt throughout the project (it’s not too late to join if that sounds like something you’d like to receive) and a dedicated community space in Substack Chat.
  

• We’ll also be sharing posts from the community in our Instagram stories. Tag your images or videos with @dothe100dayproject.

• To find people participating, search #The100DayProject on Instagram or browse tagged photos from @dothe100dayproject.

If you want a creative village, be a villager—go say hi to someone!

SHARE IN THE CHAT

Come introduce yourself in the chat here and tell us about your project. What are your anchors?

Rooting for you, always!

XO,
L