Writer regrets (and how to avoid them)

The other day I shared a 16 minute video for my paid subscribers called “Creative Success Often Feels Like Failure.” It explored how oftentimes we will reach a creative milestone or goal, only to feel a sense of emptiness and being let down. I talked about why that is, and shared specific strategies to reframe how we think about success in order to feel a sense of satisfaction, momentum, and meaning in how you create and share.

In the comments, readers shared their own stories around this, and one really jumped out at me, and I want to explore what she said today.

In 2017, Maria Maggio Fisher published her first novel, The Summoned Guest. She describes how fulfilling the process was of writing and completing this book:

“How I felt upon completion DID surprise me. It felt like I was meant to write in a way that even having a meaningful career never felt for me. When readers contacted me or local book clubs read my book and invited me – I felt a deep sense of satisfaction and alignment with not only the readers (which was great) but my life’s work or purpose.”

That’s such a huge moment in life! She underscores how important our creative work is to who we are.

In my video, I talked about “lottery ticket thinking,” which is the concept of hoping that a small action on our part will lead to outsized results. With a lottery ticket, we spend a buck or two, choose random numbers, and hope for the chance of receiving millions of dollars in return.

Maria then described the other side of her experience of how she shared her book with the world:

“In writing my novel, which I found very fulfilling, I put in lots of hard work No lottery thinking. But I didn’t allow the final product and launch the respect of this same hard work. Here I had lottery thinking. This came about partly by having followed stories, like you mentioned, of the “overnight” big successes of some self-published authors. Partly I had limited energy leftover from working in my career and was impatient to turn the page on my first novel, which had been a 3 year passion project.”

“You can guess how little traction my novel got by the way I went about publishing it. I felt very disappointed in how quickly things quieted. I felt regret that I didn’t get any pro help (team) for editing or launching. At the time I thought this could never be undone. I was surprised how disappointed I was in myself and the self doubt that followed..Had to get honest with myself about the mistakes I made that contributed to the results. But also be proud of what I did accomplish, all I learned, there was much good.”

“Eventually I admitted to what failed, let go of the first novel success dreams and moved forward. Knowing I was a writer. Not just someone who wanted to write, which I had been for years.”

Of course, I love the wisdom she shares, celebrating what she accomplished here. But she touches upon other concepts I want to explore today about how we share our work, and the possible regrets that a writer may feel in the process.

The Pressure of Sharing

There is risk in writing. And there is risk in sharing. I encourage you to embrace these both.

It is so difficult to share what you write, whether that is in a book launch, or publishing a newsletter. For many writers, they did the brave act of giving themselves permission to create, but when confronted with the idea of sharing, they demure.

They may hesitate to take action, playing narratives over and over in their mind, which prevent them from sharing:

  • “I wrote it, isn’t it someone else’s job to promote it?”
  • “I mean, who’s to say if what I wrote is even any good. If it’s good, people will find it. Great work rises to the top.”
  • “Besides, it will look desperate if people see me promoting my own work.”

But I have found that something magical can happen when we share our work. We learn how to find that connective tissue between why we write, and how to talk about it. We find unexpected connections in how people receive it, and how it inspires them.

For a book launch, it is often accompanied by massive expectations because most writers spend years on the journey to create a book. They want to feel it was “worth it” in some way that is apparent in the world.

So many people tell me they work with me because they want to feel they gave their book their best possible chance. They want to be intentional and strategic, and make the process fun and meaningful. However you choose to share wha you create, I want you to honor the actions you take, and let go of the potential guilt of what you can’t do. This should be a process infused with joy and fulfillment.

Time and time again I have heard people express regret that they didn’t try. In some cases, they offloaded their expectations to others, and hoped that somehow “the marketplace” would work some kind of magic to connect the book with readers.

I believe that each of us has a unique creative voice. I grew up as an artist, and can think of thousands of conversations I have been a part of with those who create — where they talk about their work not out of some self-promotion, but because they love talking about what inspires them.

I encourage you to be intentional about what you create, and to celebrate these actions. This isn’t something you are obligated to do. Instead, it is something you have the opportunity to do. To have a life filled with conversations and connections around the themes and craft that inspire you.

One way to solve for this? Normalize the idea of talking about what you create. There are two ways of doing that:

  • Practice talking about what inspires you and why you create, in the context of your everyday life. I help writers do this all the time, finding the exact language. This process creates a gateway into your creative world, a “way in” for those around you. What is a simple example? Maybe I see a neighbor at a local cafe on a Monday morning and they ask, “Hey Dan, how was your weekend?” And I reply, “Good! Went to New York City with my oldest, and spent a few hours on Sunday working on an essay about how writers can navigate creative expectations — and regrets.”
  • I encourage you to develop connections with colleagues. Creative work often starts alone, but as it develops I find it always benefits from having others in your creative circle. Those who create as you do, who you can hear about their experience sharing their work, who you can ask questions to, and who makes you feel less alone as a writer. Having colleagues normalizes the idea that we are allowed to talk bout what we create, the creative process, and what inspires us.

I don’t want you to regret that your work didn’t reach readers simply because you never made a strong effort to share it. The good news is that you get to define what that looks like, where you dive in, where you set clear boundaries, and how it connects to why you write.

Overwhelmed by Too Much Information

The internet has given writers access to so much information about things they could possibly be doing to share their writing. In many ways, this is amazing, the gift of knowledge.

However, there is a downside to it, where a writer can find themselves drowning in information. They compile lists of hundreds of potential ways to share their work, and end up feeling that they can’t get to it all, and that no matter what they choose, they will regret having not tried a different tactic.

Likewise, information gathering, research and analysis can be a great way to prevent action. I see this all the time, the person who refuses to talk about their writing because they want to wait for their website to be ready… six months from now. Or because they feel there is one perfect way to launch a book, and they are still figuring out what that is, so they delay talking about their writing until book launch is upon them.

How to solve for this? Take small simple actions. Experiment! Then, repeat.

This sounds scary, right? When I work with a writer, we find this balance between a clear and concise plan, but also ensuring that the process feels infused with authenticity, meaning, and joy. No one can predict success, so we embark on a discovery process to identify what feels right, and we adjust along the way.

What I find is that this removes the pressure and regret people often feel. Having a plan can make you feel prepared, and it can also give you clear direction. The consistency of taking small meaningful actions teaches you so much not only about what works, but what feels right to you.

This isn’t always about identifying the “best practices and maximizing ROI.” Instead, it is about identifying a process that makes you feel great about being a writer, and how you connect with readers.

I have this quote hanging on the wall of my studio next to a photo of Fred Rogers (from the TV show, Mister Rogers):

“I am very concerned that our society is much more interested in information than wonder. In noise rather than silence… How do we encourage reflection?… Oh my this is a noisy world.”

Fred Rogers

While we can’t always control the world at large, I feel we can control how we approach our own craft in writing and sharing. We can get clarity on specific actions to take, and encourage an ethos that fills you up, instead of overwhelms you.

No One Knows What Works

I read this post the other day from Kate McKean and it resonated:

“When writers ask about the market, especially writers newer to the scene, they think editors and agents have some kind of specialized knowledge to analyze and synthesize what we see in market trends to avoid the dips, to stay afloat, to come out the other end unscathed. And we do not! I mean, we have experience. We know what happened last time and what maybe worked or didn’t work. But very little of that can be extrapolated to predict future trends or outcomes. We can try! We can look back at the cycle paranormal romance took in the 2010s and see how long it’s taken to come back as romantacy and that might help you figure out if you should write that romance about weregophers this year or next. But that doesn’t mean I can definitely sell a romance, or your romance about weregophers. The market is going to do what the market is going to do, and we only know anything in hindsight.”

I have shared a few posts in the past using the phrase: “No one knows what works, but doing stuff works.” This is wisdom that Jennie Nash and I repeat to each other often:

I tried to fill those posts with useful examples that embrace this idea. To me, this concept is meant to be freeing. That if no one can promise success, then it should encourage you to make the best effort you can, to have fun in the process, and to be satisfied with what you learn along the way.

It is meant to prevent the regret people feel of “doing the wrong thing,” or the disappointment they feel in things outside of their control, such as “the market.”

I spend so much time researching people’s experiences in how they create and share, and I look across creative fields. I want to end with two stories that I have been thinking a lot about in the past month:

  • Actor Kumail Nanjiani was reflecting on the trauma he felt when the movie he had high hopes for (Eternals) ended up not performing as expected. He concluded: “I realized, I can’t be so results based in my work anymore, because I can’t really control it. I can control my experience, I can control how I am with the people around me, I can control what I learn from it, I can control how I work. But I can’t control what people will think of it.”
  • Dee Snider of the band Twisted Sister, talked about his life after his success waned. He had huge success in the mid-1980s, and says, “By the early 1990s, I was broke… I remember in 1991, riding a bicycle to a desk job answering phones in an office for a couple hundred dollars a week… No one would believe that the guy from MTV would be sitting here at a desk answering the phone. But it was the best thing that ever happened to me… It made me start over. This time around I was more appreciative and respectful of people around me and what it takes. [To appreciate] the delicacy of success… I went into radio, movies, acting, and voice over work. I did well in these things.” Why did this resonate with me? Because again, it makes this point that there are always things outside of your control. But you get to focus on the craft of how you create, how you share, and how you connect with others.

Let me know in the comments: do you have regrets in how you have shared what you create? Or, to ask the opposite way: what are the regrets you desperately want to avoid!

Thank you for being here with me.
-Dan