Navigating the Creative Labyrinth: Embracing the Messy Middle

Too often we romanticize the creative process, imagining it’s this journey of effortless inspiration and artistic epiphanies. But the reality is that it is a journey rife with unglamorous frustrations and challenges. The “messy middle” of the creative process is where uncertainty and self-doubt often reign supreme—it is a phase characterized by a sense of being lost in a labyrinth of ideas and possibilities, leaving us feeling paralyzed to find the right direction. This week, we’re going to explore the messy middle, and I’ll share some strategies on navigating through.

What is the Messy Middle?

The messy middle is a place of seeming chaos that lies between the initial spark of inspiration and the realization of the final creative product.

You’ll know you’re in the messy middle when:

  • You’ve already done a lot of work, but the end is no where in sight.

  • You feel like all you’ve done is created more of a mess than when you started.

  • You’ve been working and iterating, but your output just isn’t there yet and you don’t know why.

More specific examples:

  • As a writer, you’re struggling to distill your ideas into clear and concise topics and outlines.

  • As an artist, you’re feeling overwhelmed by the vastness of creative possibilities and stuggling to narrow down the focus.

  • As a musician, you’re struggling to find the right instrumentation and arrangement to complement the musical idea.

  • As a designer, you’re questioning the effectiveness of your design choices and your ability to create visually appealing and engaging experiences.

The Challenges of Navigating the Labyrinth

We all know that progress is never linear, it has its ups and downs. But knowing that doesn’t make the journey any less challenging.

Self-doubt and fear of failure cast shadows on our creativite spirit, and can absolutely hinder progress. The lack of visible progress can be disheartening, leading to feelings of inadequacy and questioning one's creative abilities. Decision-making becomes near impossible, as the weight of countless possibilities can paralyze the creative mind. Furthermore, feelings of being lost and uninspired can sap motivation and make it difficult to maintain focus and determination.

The most important thing to remember when navigating this phase is that it happens to all of us!

My most recent experience with this has been the amount of overwhelm I felt regularly during the process of renovating my home. I had no idea how long the project would take at the start, and I had some moments of real struggle in the midst of it—at times it was hard to strategize, I definitely made some decisions prematurely that I had to later re-think and re-do; I experienced moments of intense loneliness climbing up and down walls on nights and weekends; I felt frustrated being at the mercy of trades and their uncertain schedules.

I’ve had moments with my 500 painting project too—wondering if it’s really worth it or if the work will have the impact I hope it will have.

And I’ve witnessed people around me experience this messy middle too—like a product manager struggling to nail down scope, or designers spinning their wheels trying to find a solution that elegantly links the needs of the customer with the needs of the business.

All of these scenarios can be extrememly frustrating, leaving us feeling stuck and disheartened.

But when we’re on this journey, it’s important to continue exploring—don’t let the doubt and frustrations stop you.

Just like if you were in a real life labyrinth, you wouldn’t let yourself get stuck and stay there forever—you’d keep trying paths until you found your way out.

Embracing the Messy Middle

Remember Kelly Clarkson’s wise words, “What does’t kill you makes you stronger.” 😌

Embracing the messy middle is not about resigning oneself to chaos, but rather about reframing it as a time of profound growth and discovery. It is a period of experimentation, where the willingness to take risks and explore unconventional paths can lead to unexpected breakthroughs. It is a time to sit with your discomfort, fear, doubt, loneliness and frustrations—and share that with others, so that you can grow.

The keys to this are patience and perseverence. Remember everything is a practice, sometimes you’re simply practicing showing up. Sometimes you practice patience by taking a step back and pausing your work to reflect on the progress and calibrate your next steps. The work itself, the skills and techniques you use to accomplish the work, are a practice.

By cultivating patience and perseverance, we can navigate the uncertainties of the messy middle and emerge with a deeper understanding of ourselves, and a clear grasp on our capabilities and shortcomings.

Strategies for navigating the Messy Middle

  • Clarify your goal, define your map: You wouldn’t set off to a new destination in your car without defining that destination. So if you’re feeling lost, it can help to pause and think through the outcomes you’re trying to achieve. Depending on the type of project you’re working on, the outcome could be as simple as a feeling or mood you hope your art will invoke, or as complex as delivering a fully baked digital app to market. But remember maps can only show you the high-level detail—you can see a forest on a map, but you can’t see the individual trees—and when you are amongst the trees you might discover that the path isn’t what you expected. It’s ok to change your route along the way. But having a map in the first place will help you stay focused.

  • Create a supportive and inspiring workspace: This could mean arranging your day to give yourself the space to create, and sometimes this just means you need to take a break to tidy up your workspace! I wrote about this recently in my article about surrendering to your art, because in order to fully surrender you need to create the time and space for yourself to give in. Remember your environment shapes you as much as you shape it.

  • Seek feedback and guidance from others: Connect with others, meet up with a friend for coffee, talk about your struggles and listen to others share theirs. We are all navigating through some variation of a ‘messy middle’—keep an open mind about what you can learn from others.

  • Take breaks and allow for incubation: Stepping away from the creative process allows the subconscious mind to work and can lead to fresh ideas. When I’m painting canvases, I can only put one layer of paint on at a time, and then I have to walk away and come back to it later—doing this means I come back to each piece with a fresh perspective. And the beauty of each painting in the end is that it is layered and multi-faceted, it has resonance. The same goes for the product design work I do, I have never designed an entire user interface in one sitting—I have to leave it, to walk away, to expose it to others for feedback… the work happens in layers, in repeated attempts.

  • Celebrate small successes along the way: Acknowledging and celebrating even incremental progress can boost motivation and sustain momentum. Sometimes I quietly celebrate myself for just showing up, I’ll say to myself, “Look at you! Look at you doing your art, you gem!” (😂 OK that’s mildly embarrassing to admit, but hey we have to be our own cheerleaders sometimes!) Sometimes I celebrate a milestone by taking a day off to do something fun or comforting—like going to a museum or getting a massage. Celebrate yourself for showing up, and reward yourself for hitting milestones.

Rewards and Transformations

Embracing the messy middle is not a passive surrender to uncertainty and discomfort; it is an active engagement with the creative process. By navigating the challenges and embracing the chaos, we reap the rewards and transformations. These include:

  • Breakthroughs and unexpected discoveries: The messy middle is often the breeding ground for novel ideas and discovery—the journey is a teacher, and you learn as you work and get feedback from others. I live for aha! moments—for new insights and perspectives, unexpected mind-shifts. I often laugh out loud when they happen, giggling at myself for not having seen it before but enjoying the moment when it finally arrives.

  • Personal growth and development: Engaging with the creative process is like engaging with a higher power, I said ‘the journey is a teacher’—and it is. It’s a teacher, a coach, a sensei—however you want to imagine it. Personal growth and development are inevitable outputs of showing up and committing to the process.

  • Deeper understanding of oneself and one's creative process: The messy middle provides insights into one's creative strengths, weaknesses, and working style. Share your strengths, face your weaknesses, embrace and iterate on your working style. Let the process be a river that carries you.

  • Greater resilience and adaptability: Navigating the messy middle enhances one's ability to cope with setbacks and adapt to changing circumstances.

The messy middle is not a detour from the creative path; it is an integral part of the journey. By embracing its challenges, cultivating resilience, and employing effective strategies, you can traverse the labyrinth of uncertainty and emerge with a deeper understanding of your craft, yourself, and the transformative power of creativity.


Share your process!

What have you been up to? What projects have got you hopping in and out of those messy middle grounds these days? I’d love to hear from you, please share what you’re working on (and a link to your work if you have one) in the comments.


If you’ve read this far, thank you. I really appreciate you joining me here today.

If you enjoyed this, please subscribe and share it with your friends! I’ll write again next week with more insights on the state of the art.

This article was originally published via Substack, please go there to subscribe and comment!

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