Embarking on a creative journey often feels like a leap into the unknown, with self-doubt lurking at every corner. In this article and podcast, we explore the gritty reality of learning a new creative skill. I share my own story of starting an apparel project with my son and how I experienced the ever-present fear of failure. Through vulnerability, a growth mindset, and a “Snailed It” approach, we explore ten strategies for conquering self-doubt and nurturing creative success. If you’ve ever questioned your abilities as you embarked on a creative endeavor, my hope is that this article and podcast resonates with you.
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The Challenge of Learning a New Creative Skill
“This sucks,” I whisper as I stare at the initial mockup. I have spent eight hours on an initial design the t-shirt screams amateur. Which is right. I am an amateur. This is my first attempt. Still, I commit to my New Year’s Resolution of sharing more of my creative journey with the world. So, I share out my first design:
This is all part of a project I’m doing with my son, Micah. After weeks of sketching out ideas and brainstorming on the whiteboard, we have decided to launch Pawsitive Apparel. The tagline is: Be Bold. Be Kind. Be You. We have a logo that I drew and my friend Matt cleaned up. We have an initial idea of what we want to make. We have a goal of giving half of all money earned to pet rescue / adoption groups.
But now, we are both struggling. Although I love to draw doodles and make sketch videos, this is different. I’m not sure where to start or what style to do. But it’s deeper than uncertainty. The real barrier is fear. Every time I begin sketching out an idea, I set the paper down and find something else to work on. I undo what I created. In the back of my mind, I’m thinking, “Apparel? John, you’re not a fashion guy. You shouldn’t be making t-shirt designs. No one will wear it.”
So, I scrap that design entirely and shift to something new. I like it but it’s a giant rectangle:
I go another direction with a messy, choppy style but it doesn’t work. Again, the thing feels very amateur. But then my daughter makes a suggestion. What if we round the top? I test it out and love it. I then make two variations. In the end, it’s a long journey. I’ve spent thirty hours on two shirt designs. But then yesterday, I decided to take that concept of the shadow and make a new shirt. Here are two versions of that shirt.
Right now, we are still experimenting with styles. I did this shirt about being an introvert and another one with a cartoon sketch of a greyhound. We are still finding our style together. We’re starting out small and testing out what people like.
And, honestly, I’m still feeling insecure. I have no idea whether this project will pan out. There’s a high likelihood that we sell one or two t-shirts total. It’s the risk you take when doing creative work.
Similarly, I am about to launch a project called Cat and Doug. It’s about Cat (a dog whose name is short for Catalina) and Doug (a cat) who give awful advice to humans. Honestly, I’m nervous. I’ve always been self-conscious about my ability to draw. It’s been a slow process of adding my own visuals to the things I share with the world– first to the slideshows I created as a middle school teacher and later to the slides on some of my PD sessions and then eventually in blog posts, sketch videos, etc. But even now, the insecurity creeps in. So, here’s a preview of the two main characters.
I’ve created the first 15 and I plan to put them on Instagram and on a website. My goal is a new comic strip each week.
But I also know this. I need to try new creative projects that force me to experience this early stage of insecurity. It’s a firsthand way to empathize with my pre-service teachers who are experiencing the same self-doubt as they enter the practicum experience.
Self-Doubt Is Normal When You Start Something New
This isn’t a new experience. As a brand new teacher, I faced constant uncertainty. I often hedged my bets and played it safe. Although I dreamed of doing creative projects, I didn’t get started with project-based learning until my second year because of my own insecurity. On a more serious note, I wrestled with self-doubt as a new teacher when I yelled at my class and wondered if maybe they’d be better off with a different teacher. Maybe I wasn’t cut out for this gig.
My first ever sketch video took 16 hours to make because I second-guessed my every move. Now, sketch videos are a fun side hobby I do as a way to relieve stress. I almost didn’t send in my first book proposal because of self-doubt about my ability to write. Now, I feel confident about my ability to craft a book. It was about eight years ago when I did my first keynote and I got no sleep the night before because I was terrified of going up on stage. Now, I get excited when I get to go up on stage and share a message.
At the beginning, you have an idealistic picture of what you will create. You’re underestimate the time and the skills needed to master a craft. But as you get to work, you discover that everything is slower than you thought it would be. You make so many mistakes and experience intense frustration. The idealism is gone and suddenly you’re struggling with lower confidence. You’re not sure if you’ll be able to create what you want to create and you have no idea if anyone will like what you make. In this stage, you are insecure and what you need more than anything else is affirmation. Unfortunately, that’s not how it works. You don’t have much of an audience and so you won’t get much affirmation. You are an unknown and, honestly, your work isn’t top-notch quite yet.
Right now, I have no idea how long it will be before Pawsitive Apparel truly launches. I have no idea if it will ever take off at all or if anyone will like it. The same is true of Cat and Doug. I’m in this early uncertain stage.
In this early phase you might release a work to the public and face rejection. That publisher doesn’t want your novel. That YouTube video got 7 views (and 2 were from your spouse). That painting didn’t sell. In this phase, it’s easy to give up. It feels like the world is giving you a loud message that this creative craft isn’t your jam. The self-doubt actually hits the lowest point right after an initial work. Every part of you wants to give up.
But here’s the thing. If you can conquer the self-doubt, you can make something new. You realize that most creative work is a slow burn and that your success is going to take a long time. You write more novels and rework the older ones. You go back to the studio and record more songs. You experiment with new recipes. You design a new prototype.
You don’t realize it at the time but this early stage is a gift. Your lack of confidence might just make you more open to necessary feedback. Your slow growth process is allowing you to find your voice. There’s this long incubation period where you feel insecure but you’re gaining momentum. This is why so many bands have phenomenal first albums. They’ve been working through the material for years.
Slowly, you experience small wins. Someone loved your novel that you self-published. More people showed up to that club where you played a song. You taught a creative lesson and your students absolutely loved it. Or, in my case, that 4 minute sketch video goes from 27 hours to 4 hours to create and the quality is better. Later, you have to worry about the overconfidence and risk-aversion you experience with success. But there’s often this stage where you finally gain confidence and see tangible results.
And yet, none of that occurs if you can’t get past the self-doubt. So, in today’s article, I want to share strategies for tackling self-doubt.
Ten Ways to Tackle Self-Doubt in Creative Work
I don’t have this figured out entirely. On some level, I will always battle self-doubt. And I’ve learned that the existence of self-doubt is often a sign that I’m pushing myself to learn a new skill or try a new approach. If I experience no self-doubt, there’s a high likelihood I’ve become complacent and risk-averse. The goal then isn’t to avoid self-doubt. Rather, it’s to face the self-doubt and continue to hone your craft. Here are a few strategies that have helped me get past my self-doubt when it creeps in.
1. Don’t Compare Yourself to Others
If I am dealing with intense self-doubt, I find myself most tempted to try and compare myself to others. In these moments, I want to feel like I’m slightly above average (like a Lake Wobegon kid). It’s like I shrink back all of a sudden and I’m back in the fourth grade, standing at the back of the line, knowing that I might be picked last for dodge ball. It’s simple. I don’t want to suck at what I’m doing and it’s way too easy to find validation by comparing myself to the crowd.
But here’s the thing: in just about every case, comparing myself to others is actually the culprit and not the solution to self-doubt. When I was new to blogging, I looked at the stats of other bloggers but as I saw other bloggers win awards (remember Edublog Awards and Bammies?) and get speaking engagements, I started to doubt myself. I cringe at this now, but I went through a phase where I viewed it as a competition.
What sucks about this comparison trap is that you lose sight of the community. You forget about what matters. You start seeing others as competition rather than community. You get jealous when other people get opportunities you didn’t get. You grow risk-averse. But when you let that go, you end up taking chances, reaching out to people, and doing something you love simply because you love it.
2. Take a “Snailed It” Approach
A few years ago, my son designed a t-shirt with the words “snailed it” on it. While this started as a silly joke, it’s become a phrase I use all the time. Snailed It describes any project that took too long to finish but was worth it in the end. Daniel Kahneman and Amos Tversky discovered the “planning fallacy.” It’s a cognitive bias that leads us to overpredict how much we will accomplish in a given set of time. We fail to anticipate barriers and challenges and become too optimistic.
As a result, we tend to take longer than we initially planned in finishing projects (this is especially true when we are first learning a skill). We all fall into the planning fallacy. And that’s okay. We’re human.
But this “Snailed it” mindset reminds me that success isn’t solely about speed. It’s about momentum, which is the overlap of habits and improvement that leads to incremental growth over time.
Snailed It is a reminder that success is about faithfulness. It’s about showing up. It’s about continuing to try even when progress feels painfully slow. And sometimes it feels like you’re progressing at, well, a snail’s pace.
But that’s okay because when you’re snailing it, you’re looking past the urgent and focusing your long-term goals. Snailed It is a rejection of perfectionism. It’s a reminder that “fail-ure” is permanent but “fail-ing” is temporary. And creativity is less about inspiration than iteration. Snailed it is a reminder to focus on the process rather than the product and to enjoy the journey even if it’s a little messy and confusing.
“Snailed it” is a rejection of grind culture. It’s the recognition that slowing down is necessary for sustainability. And we actually need to stop and recharge our batteries. Rest is actually a critical component of the creative process.
“Snailed It” is a reminder that life is not a race. When this happens, we quit comparing ourselves to others and embrace collaboration. I know this sounds strange but for me, snailed it” is no longer just a t-shirt. It’s become a mindset that has helped me to slow down and enjoy teaching, learning, and creative work.
This mindset ultimately helps me with the slow pace of growth early on in this self-doubting phase. But sometimes it helps to look outward at the examples of slow growth.
3. Find Examples of Slow Growth
One of the hardest aspects of this early stage of self-doubt is the feeling of loneliness that accompanies it. Sometimes you feel like you are the only one who is slow at your craft. You experience this steep learning curve and it feels like others mastered things faster. You hear stories of people who found success faster. This is why it helps to find stories of people who experienced rejection early on.
The Beatles initially faced rejection from multiple record labels. Decca Records famously turned them down, stating that “guitar groups are on their way out.” Despite these early setbacks, the band persevered and continued to perform in clubs in Liverpool and Hamburg, honing their skills and sound. Eventually, they signed with EMI’s Parlophone label, and the rest is history. Their music transformed the landscape of popular music forever, with numerous chart-topping hits and a lasting cultural impact. On a side note, I think George was the most underrated member.
It might be JK Rowling and her rejection letters for Harry Potter. The same is true of Stephen King and Agatha Christie. If you’re a current 49ers fan (like me) it might be “Mr. Irrelevant” becoming the starting quarterback and leading is team to the NFC Championship game. It might be an artist like Van Gogh, who wasn’t really appreciated early on in his career. You get the idea. There are so many examples of this slow growth experience that you start to recognize that this phase of self-doubt and rejection might just be the norm rather than the experience.
4. Abandon Perfectionism
I’ve met authors who never attempted to publish their work because they continued to mess with the novel indefinitely. It wasn’t simply a matter of improvement. It was a fear of imperfection. It was a false belief that the world doesn’t need to see a creative work unless it’s absolutely perfect.
I’ve met teachers who work an ungodly amount hours and burn out and everyone says, “It’s because they didn’t take care of themselves” or “It’s because they worked too many hours” or even “They just couldn’t figure out balance.” But that wasn’t it. These teachers worked insane hours because of perfectionism. They never experienced the joy of teaching because they operated out of an illusion that they had to be perfect. They bought into the myth that teachers need to be superheroes. For this reason, my friend Trevor and I created a sketch video about the need to let go of the superhero story.
This perfectionism drives self-doubt. When you believe that you have to be perfect, you are never able to view yourself as measuring up. You will always feel like an imposter. In some cases, this can drive people to gossip about others or to embellish their own accomplishments.
5. Be Vulnerable to a Trusted Community
If I could hand out any non-education book to new teachers, it would be Brené Brown Brown’s The Gifts of Imperfection. If you haven’t seen Brown’s TEDx Talk on shame and vulnerability, it’s certainly worth a listen. I am convinced that there is this disarming element to vulnerability. There’s this power in being who you are, sharing how you are actually doing, and leaning on trusted friends to remind you that you will make it as a teacher. I find that whenever I am dealing with self-doubt in creative work (whether it is writing or teaching or illustrating), vulnerability is the avenue toward getting past it.
I’ve found it helpful to work with a mastermind group.
We focus mostly on our creative endeavors. It’s almost entirely unstructured, with random conversations about creativity hacking and productivity ideas. But last year, we did a “hot seat” meet-up where we each shared our goals, our struggles, and our dreams, and then invited each other to give feedback to one another. It was a powerful day and a reminder where I had several creative breakthroughs. But it was also one of the many ways my mastermind group has impacted my creative work.
6. Embrace a Growth Mindset
Carol Dweck has shared the two different mindsets that shape how we approach tasks. In a fixed mindset, people believe that talent is fixed and that failure is proof that you simply don’t have the right natural talent. In a growth mindset, people see mistakes as a natural part of the process and view talent as something malleable.
There’s a quote from Dweck in Mindset that I think fits in well with creativity, doubt and positive risk-taking. “Everyone is born with an intense drive to learn. Infants stretch their skills daily. Not just ordinary skills, but the most difficult tasks of a lifetime, like learning to walk and talk. They never decide it’s too hard or not worth the effort. Babies don’t worry about making mistakes or humiliating themselves. They walk, they fall, they get up. They just barge forward. What could put an end to this exuberant learning? The fixed mindset. As soon as children become able to evaluate themselves, some of them become afraid of challenges. They become afraid of not being smart.” I think the same thing happens with creativity. Kids start saying things like “I’m just not artistic” or “I’m just not good at programming.”
This idea relates to the last two concepts. If I have a fixed mindset, I will believe that I have to be perfect. I will hide how I am really doing. I will give up before I even start. However, if I see mistakes as a natural part of the growth process, I am more likely to get past perfectionism and embrace vulnerability.
7. Set Goals that are within your control.
There are so many things that you can’t control. Will that book make it into the top spot on Amazon? Will people love the art you created? Will your students have the highest test scores in the building? When you set goals based upon things that are outside of your control, you are more likely to get mired in self-doubt. Small “failures” that are outside of your control end up derailing your view of success. This is why self-assessment and self-reflection are so critical. When you are determining the measure of success, you are ultimately in control of the outcomes.
Jon Acuff provides some great advice in Finish. He mentions setting multiple, attainable goals that gradually build up to something bigger.
8. Focus on Momentum Rather Than Results
A little over a year ago, I wrote about why it’s better to have creative momentum than creative habits. Ever felt stuck in a creative rut? Ever had a dream of getting started with a creative endeavor but you just can’t make the habit stick? The challenge might not be one of habit-forming or inspiration but actually creative momentum. While habits focus on consistency, momentum focuses on consistent improvement.
Think of a habit like this. It’s a flat line.
That’s important. It helps you maintain consistency. But it’s not enough. To reach the next level, you also need to improve in your craft. You need to learn and grow. This is why we include skill development as the second variable in creative momentum. Skill improvement alone isn’t enough, though. Because without habit, it will be chaotic, with skills rising and then falling due to the lack of practice and consistency.
What we need is for skills to improve over time. Creative momentum is similar to a creative habit but it combines habits with improvements.
When you experience creative momentum, you take your craft to the next level by combining habits with skill development. You focus on the creative process but you’re also cognizant of the end result and the final product.
I make the distinction of habits and momentum in the following visual:
Note that consistency alone can help build habits. However, combining consistency with continual improvement can help lead to creative momentum. This is the core idea behind the Creative Momentum Journal.
9. Treat Your Work Like an Experiment
I keep a notecard on my desk that reads “This could fail.” Here’s why:
I sometimes flip this with the question, “Could this fail?” If my answer is nearly always, “Probably not,” It’s a sign that I’m not taking necessary creative risks. I’m not experimenting with new ideas.
So, instead of being mired in self-doubt, you get to treat your work as an experiment. If it didn’t work, it’s not a failure. It’s a chance to figure out what doesn’t work. In this view, the biggest risk isn’t failing. The biggest risk is doing nothing. This is admittedly difficult in the high-stakes environment of standardized testing. You are often placed in a situation where mistakes are not okay and where experimentation is frowned upon. I don’t have an easy answer. However, I think this is where courage plays a role in creativity and innovation. Being different is risky. Experimenting can be humbling when your school culture doesn’t embrace it.
10. Trust Yourself
When I first started teaching, I tried to be all these things I thought I was supposed to be: super professional, serious, etc. I wasn’t goofy. I wasn’t creative. It was awful. However, when I gave myself permission to teach out of my identity, I was able to thrive. Ultimately, this sense of self-trust is what eventually led to self-confidence. I had to be okay with myself first, though.
The same has been true of all of my creative work. Somebody referred to me as a “slow talker” and I began to wonder if I should do keynotes at a faster pace. But I eventually realized that a slower, laidback, story-based approach fit who I was. I had to be myself, which meant a slower delivery with more humor. It took me a while to get comfortable using my sketches in my books, slides, and blog posts. But that’s who I am. It’s not my brand. It’s my style.
So, give yourself the permission to be wildly and unabashedly different.
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