The process of planning can be an important method of prioritization of our creative lives. It can also be a comfort—there’s something soothing about writing a list, checking off a box, making a schedule. Yet as much as planning might provide clarity and signal to others that we have it together, it can be procrastination in disguise. 

“For some people, planning can be a way to organize what might feel chaotic, but it can creep into avoidance,” says Melbourne-based clinical psychologist Dr. Jacqueline Baulch. We plan (or overplan) because we fear uncertainty. “Uncertainty is nebulous and planning is the opposite...But putting something as unwieldy as our future into a few Post-it notes doesn't really change the uncertainty itself,” says Baulch. 

Planning can also be a symptom of perfectionism. It’s easier to plan than move through the messy middle, so some may get stuck in crafting a plan rather than executing. But the creative process is inherently imperfect, explains Dr. Baulch. “Often we only want to get started if we are certain it will be polished, perfect, or successful." But the real victory comes when we're able to accept "the drivel that comes out initially and keep persevering.”

When it comes to our careers, o​ften it’s embracing fear and uncertainty that leads to the greatest opportunities​ and best work.​ Here, successful designers, artists, and writers share their strategies for moving through it and getting things done.

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The difference between constructive planning and procrastination 

Planning feels productive, but obsessing over a schedule or spreadsheet before diving into the real work fundamentally is no different than classic procrastination. The key is self-awareness to catch the tipping point where planning becomes a form of delayed action.

“You can't change something without knowing it's there,” Dr. Baluch says. “Most of what drives us is unconscious. Tuning into our bodies, thoughts, and emotions helps raise our self-awareness so we are more able to step back, shift and take charge of the process.”

Are you are planning as a way to clarify or avoid? If the answer is unclear, tune into your body, suggests Dr. Baulch. “What does it feel like in your body to be planning right now? When it’s healthy and adaptive, you might feel a sense of freedom and flow. If it’s related to avoidance, you might feel a sense of heaviness, stuckness, and fear in your body.”

Rethink your to-do list 

A flaw with over-planning and tightly scheduling our days is that more often than not, when an allocated period arrives, the set task doesn’t seem so appealing. We procrastinate instead of moving onto a task that might not be part of the plan, but nevertheless keep us moving forward.

Over-planning also doesn’t take into account the unexpected but inevitable meetings that run overtime, transit delays, impromptu phone calls, or personal responsibilities.

It can be beneficial to both our productivity and wellbeing to improvise within our days. Artist and author Adam J. Kurtz favors a long-lead to-do list over a rigid and inherently fragile daily to-do list.

Kurtz prefers to work to his own whims in order to find flow in his day. Each morning he will clear his email inbox as a way to move through smaller tasks, before referring to his "long-lead to-do list" and picking a task that fits his interest or mood for that moment.

“For the most part I'm working on self-directed projects, so I can decide I don't feel like working on the calendar, I'd rather work on this pitch-deck or shop products or something else. I let myself follow my bliss a little bit,” he says. Following the flow allows him to chip away at projects as he feels inspired.

See plans as lighthouses

Digital product designer and creator of the hugely popular Bullet Journal method Ryder Carroll thinks that planning and perfectionism often go hand in hand. “You create this perfect plan of how you're going to achieve a goal—you're going to write four hours a day for the next month, for example, and then your book will be done. But I've learned to stop setting goals that way,” he says.

Carroll now sees plans and goals as "lighthouses," or guides that help illuminate safe passages for us to follow. Rather than focusing on the plan or an end goal, Carroll has learned to pay attention to the process. “My goals are now about what I'm learning and what I'm moving towards, and course-correcting constantly.” As a result, Carroll is not as hard on himself. “As long as I'm working, as long as I'm showing up every day, I will make progress. That is enough.”

Careers are more like lily pads than ladders

Artist, art director, and creator of online store Chipper Things Becky Simpson views her career as moving across lily pads, jumping from one to the next as it appears sometimes in front of her, sometimes adjacently, sometimes behind. “It's easy to look at people who are successful or where we aspire to be and wonder how they knew which steps to take, when in reality they did one thing, and the next step or lily pad was illuminated,” says Simpson. 

This approach allows us to sit with the uncertainty of a creative career that may not have a linear growth pattern. But look deeper and we realize it’s less about having a set plan or climbing the ladder, and more about learning and growth. The lily pad theory is also a potential cure for procrastination or perfectionism-based planning: if you stay still for too long without taking a leap to a new lily pad, you will sink. "I don't have to have the answer or endpoint in mind, but I know I won't get anywhere if I just stand still," explains Simpson.

Plans might help illuminate a path, but we really don’t know what’s in store until we leap. "Looking back, I would never thought I'd be having certain experiences, but I only got there because I did these wonky side projects along the way that led to this and that," says Simpson.

Overcome over-planning:

1. Set a time limit for planning. Some might call this setting internal boundaries. Set a timer to put a container around procrastination planning.
2. Streamline your schedule. As Ryder Carroll explains, “It takes more time to rewrite things by hand, so there’s a built-in incentive to pause and consider each item. If an entry isn’t worth the few seconds of effort required to rewrite it, then it’s probably not that important. Get rid of it.” Removing unnecessary tasks allows you to focus on the real work you may be avoiding.
3. Favor progress over perfection. Pick a task and make a start. Any action is better than theoretical perfection.
4. Get comfortable with fear. Our creative lives are full of uncertainty, so find ways to accept and appreciate the opportunity to create something as of yet unknown. Consider the idea that if you’re not failing, you’re not growing.