It’s almost an understatement to call Kara Cutruzzula a go-getter. Cutruzzula is a widely published freelance writer and editor, a playwright, lyricist, and librettist who pens musicals, the author of the creative productivity newsletter Brass Ring Daily, and the voice behind the podcast Do It Today.

How does she keep herself inspired, productive, and bold enough to delve into new creative projects? And what lessons does she have for strivers of all kinds who need a jump start to get ambitious projects off the ground? Cutruzzula captured her infectious energy in two motivational journals: Do It for Yourself, released by Abrams publishers in 2020, and Do It Today, released this fall.  

Do It for Yourself is a beautifully illustrated, easily digestible journal with creative prompts to stay motivated and make things happen. Do It Today was crafted in light of the pandemic, in which so many people struggled to find motivation. It’s an empathetic, gentle guide with short essays, prompts and open-ended questions to give readers space to dream and plan–even if it just means accomplishing a small goal today. 

From Day One spoke with Cutruzzula about the wisdom inside both journals, what will resonate with business professionals, and what to expect from a third journal now in the works.

From Day One: I’d love to hear about you and what led you to this first motivational journal, Do It For Yourself.

Kara Cutruzzula: I had been writing the daily newsletter Brass Ring Daily about work life and creativity for three or so years. I chronicle my creative output–highs, lows, in-betweens, talked about rejections, failures, and how I kept trying–and got a readership from that. Through there, I was connected with an editor at Abrams, and they were looking to do a motivational journal and said that the themes were basically what they wanted to cover in a journal.

It’s sort of a roundabout way to publish a book, but I liked that it happened this way. It’s a perfect example of just doing work that you care about, that you are naturally drawn to, and then being recognized for that and having something else grow out of it. 

The journals take you on a journey and build off themselves. How did you structure them, were you pulling from your own motivations and habits? 

I feel like every creative or professional work project has all of these different stages. And sometimes we forget that there are stages, and we just think, OK, this is taking forever, or, I have a new hurdle and don’t know how to handle this one. 

Breaking down projects into different stages was really helpful for me as I moved through my own work. I wanted to share that and outline that for readers and mimic the experience of going through something like this. 

There’s always this stage of internal motivation: How do you get going? How do you beat back the fear that might prevent you from thinking about your mission statement, thinking about the things you might even want to be doing? Eventually you do move out of that to doing the daily work, like building momentum in the small tasks, the big tasks, creating micro and macro goals.

Once you continue to build your project, whether that’s a business or a creative project, you will come across setbacks. You’re looking at that point at your routines, anything you’re procrastinating doing, all of the things that feel really complex and like roadblocks that come up, thinking about how to push past those. 

Even in talking about these different stages, you could see there’s so many different ways to get stuck. And the whole point of both of the journals is to keep you moving forward. And once you’re finished, it’s about finding a finish line, or creating a finish line for yourself, and then figuring out how to move onto the next one. And then you start the loop all over. 

The message of the first journal resonated with readers enough to lead to the second journal, Do It Today. What were you trying to communicate through the second journal? 

I think that people have soured a little bit on the idea of motivation. Five years ago for me, it was much more about “Rah rah, let’s hustle and get motivated.” After going through the pandemic, that message personally doesn’t resonate for me as much. 

I think if you can make progress on one small thing relating to meaningful work, I think that feels really satisfying. So it’s not looking at a strict, hard, punishing motivation, but more this gentle encouragement with yourself and admitting you might be tired, you might have a setback, you might put a project aside. It’s about not beating yourself up about it. I think that message relates to people a lot more these days.

Both journals are beautifully illustrated and very creative. Tell me about working with the illustrators and why that was an important component.

We had two wonderful illustrators: Tessa Forrest illustrated the first journal. And Tyler Spangler illustrated the second one. 

I think there’s been a hole in the market in what’s available to readers that are both nice to look at and can and can provide really tangible, concrete advice about how to move forward. A lot of business, productivity and time-management books feel a little clinical. I just found myself not really drawn to pick that up all the time. 

I was thinking about what feels good to open, read, and would feel encouraging even if you just have 10 seconds. The idea was to marry concrete advice with something with high aesthetic value that is encouraging that would speak to a wide, universal audience. 

Much of From Day One’s readership are HR and other business professionals. How do you think they can best utilize the journals? 

I’ve heard from software engineers, entrepreneurs, lots of professionals who relate to the ideas inside. I don’t think you have to be “creative” to want to move more towards the things that are important to you, and to spend time on the work that is meaningful to you. One of the principles in the book is to start before you’re ready. I feel like that is a mantra that definitely relates to people in business, where sometimes you need to embrace this idea that you’ll never have everything you need to begin, you might not feel ready, but you’ll figure it out anyway. 

What are other mantras or tips from the journals that have really resonated with readers or that you yourself turn back to again?

Two things come to mind. In the first journal, one of the prompts is writing your future Wikipedia entry. It sounds kind of silly, but I think it really forces you to look at what you actually want to leave behind and what will be the main bullet points. I’ve seen a lot of people write their Wikipedia entries and they end up finding that the things that they actually want to do or that they want included in that entry are not the things that they’re working on every day. So where is that disconnect, and why are they not able to do the work that is most meaningful to them? It’s a macro overview of what you want to do, where you want to spend your time, and what you might want people to say about your career 30 years from now.

In Do It Today, I have a chapter on rejection and failure, which is a popular topic. One technique I’ve used with my own projects is writing a thank you note to whatever rejection comes your way. Thinking about the risk you took to even approach the thing that led you to failure is incredibly helpful, because you’re reminded again that you’re trying to do something, you actually put it out there, you applied for the thing. Closing that chapter is always so satisfying to me and it allows you to move on. 

What is your latest project? What are you working on now?

I write musicals, books and lyrics for musicals. And that was a very challenging thing to do during the pandemic, when we were all on Zoom. But now that I’m back in person, I started writing a new musical with a collaborator, a composer named Kristoffer Bjarke, about people running a marathon. It takes place physically in the heads of people who are running in a small-town race and the places you mind goes when you’re stuck out there for 26.2 miles. 

I also have a podcast called Do It Today, which is an interview series where I talk to notable figures and friends in creative industries and non-creative industries about what they’re doing that day and how they’re doing it. 

I noticed a lot of people coming out of the pandemic with these incredible projects, writing books, musicals, career pivots, all sorts of things. I wanted to know about the micro, day-to-day behind that, so I call people up and talk about challenges they’re facing that day, what’s their biggest goal, and finding advice and habits and things that hopefully listeners can adopt in their own lives. It’s been a very instructive experience to see a lot of these techniques play out in real life.

Will there be a third journal? 

You know, three is a nice number. So we are doing a third coming out in fall of 2023. It’s going to be Do It–Or Don’t: a Boundary Creating Journal. This one is about how to say no to all the things you don”t want to do, and how to create helpful constraints and containers for the work that’s most important to you. Because all the encouragement in the world cannot get you to a finish line if you don’t have the time and space to do the work.

I can’t wait to read it and feel inspired in a different way. Thanks so much for this work.

Thanks, it helps me. I do it to help me with my own creative work too. I hope people can find things to relate to there, because we’re all just working through it. Just bringing people in and having conversations about these things is always really helpful. 

Emily Nonko is a freelance journalist based in Brooklyn, New York. In addition to writing for From Day One, her work has been published in Next City, The Wall Street Journal, The Guardian and other publications.