How to Pick a Creative Challenge that Works

Taking on a Creative Challenge is a great way to heal from a burnout but it can backfire if defined poorly.

Everything is in the name: it’s a challenge. It will prove difficult and will take you to unexpected -and sometimes dark- places. And it’s here to challenge one specific element: your creativity.

Since 2013 I’ve completed 6 creative challenges: one 365 days, two 100 days, one 60 days, one 10 days and I just finished a 30 days challenge to kickstart 2017.

The reason why I keep taking on creative challenges is because each challenge helps me make jumps in my capacity to take risks, my self-confidence, my stamina, my skills and yes, my creativity.

Over the past four years I’ve also learned from each challenge what works well, and what doesn’t.

In 2013 I picked my first creative challenge without giving it much thinking. I was lucky enough to have framed it rather precisely (one timelapse a day for 365 days), but I was lacking one major factor: the sharing component. Every day I would record a timelapse and then sit on it until the year was done, and it’s only in January 2014 that I shared the finished video. For any random project that might have been fine, but for a creative challenge, as I’ve learned with practice, sharing daily is essential.

This lesson is one of the many I’ve learned from my mistakes, and from seeing others take on creative challenges only to abandon them midcourse (or even before that). Last year, when I started my second 100 days creative challenge, I had 20 friends starting along. We were 4 to finish.

Poorly picking a creative challenge is a missed opportunity to strengthen your creative muscle. But more serious than null benefits, are negative ones.

If you feel creatively fragile when you decide to start a creative challenge to get back on the horse, failing to complete one can reinforce the voice in your head saying you can’t create.

Just like ingredients to create a dish, there are several elements you can play with to raise up your chances not only to finish your creative challenge but also to collect the maximum benefits from it.

The first thing to understand is that a creative challenge relies on three main elements: 
- Time
- Risk
- Sharing

There’s no order. One is not more important than the other. You need those three elements to obtain the maximum benefits from a creative challenge.

Actually, you also need those three elements to activate your creativity in general. Same thing.


For a creative challenge to be challenging, you need to pick something that interests you and that you want to discover, explore further, or work on.

Because no matter how passionate you are, there will be days where you will wonder why you’re putting yourself through so much pain when you could just be binge watching whatever is to be binge-watched.

The best way to help you push through those moments is to pick something that will make you grow. So every time day you’ll create something, even if it feels half-baked, you’ll have moved further on your learning curve.

If you pick a field where you’re already very skilled at, chances are you will quickly fall back into your comfort zone and yes, you might complete your creative challenge, but you won’t have a sense of accomplishment and you won’t have grown much from it.

To activate your creativity you need to feel you’re taking a risk. That you’re pushing your own envelope. There needs to be an element of unknown and an element of interest in what you do.

My last creative challenge was about my grandmother. She was an amazing woman who used to speak out her mind and could say hilarious, beautiful and outrageous things within the same sentence. She also played an important part in the resistance during the war in Lebanon and built a foundation that made a significant difference in the life of thousands of people over the years.

I’ve always wanted to make a part-animation, part-documentary about her life but my time kept being distributed in other ways. So I decided that the creative challenge would be my way of starting exploring my grandmother’s universe.

Teita: “I won’t go to her funeral.”
Ronda “Who died?”
Teita: “You don’t know her.”
Ronda: “A friend?”
Teita: “Yes, a friend.”
Ronda: “And you don’t want to attend her mass?”
Teita: “I don’t care, she won’t attend my funerals anyway.”

If the only thing I was doing with my life was this project, I could have spent hours everyday diving into the material I have about my grandmother and produce high-quality content. But it wasn’t. I actually took on this creative challenge at one of the busiest time of my life. Because if you wait to have time to create, chances are you won’t create often. So there was a risk I wouldn’t come up with feasible ideas. Which really means that I would have to find creative ways to create something. That’s what you want.

For my last challenge, that translated into creating animations, asking family members about stories, and going deeper into my own memories, finding back anecdotes I thought forgotten.

By Feasible Idea what I really talk about is having time. And that’s our second element.


We all crave for more time. Time is the highest currency in everybody’s life. And when it comes to creativity, Time is both your ally and your enemy.

You must spend time to create. But in the context of a creative challenge, you also must set a time frame, otherwise, things will quickly get out of control, especially if you’re a perfectionist.

Creating daily means that whatever happens, you need to make time to create. Sounds obvious and yet, one of the main mistakes I see people doing is taking on challenges that will ask them way too much time on a daily basis. Sure, you might be able to secure 2 hours per day the first 3 or 4 days, but 30, 60 or 365 days in a row? During holidays, sick days and crazy work days? Unless you’re Casey Neistat, you’ll probably give up, drained. (negative benefit)

When you pick your creative challenge, you need to assess what’s the minimum amount of time you can spend daily. Is it 5 minutes? 30 minutes? 2 hours?

For my creative challenge, I decided that it shouldn’t take me more than 30 minutes, everything included. And by “everything included”, I meant: creating the drawing and sharing it afterward. (More on that point shortly).

And for the most part, I managed to do so. Some days it took me much longer. I spent 4h on the last animation, and every animation took much more than 30 minutes, but on days I was pressed with time, I also managed to create and share in less than 20 minutes.

Once you know how much time you’d roughly like to spend daily on your creative challenge, the next step is to define constraints that will help you move faster.

Constraints are essentials. Without them each day you’ll have to go through hundreds of possibilities, and by the time you’ve narrowed them, chances are you’ll already be exhausted. The best way to help your creativity is to channel it within a frame:

- Pick a Medium

I picked drawing. Sometimes animated but most of the time, a simple drawing. It can be video, audio, photo, painting, sculpture etc.

- Pick a Format

This time I picked digital. My first 100 days challenge, which also was a drawing one, I always used the same square paper. I would pre-cut them and carry them everywhere, so whenever I would have time and (ideally) an idea, I was ready to create.

- Other possible constraints

For my last challenge, I decided that I would always show my grandma sitting on her couch. I have hundreds of stories about my grandmother, but the number reduced dramatically with this constraint. At the same time, it helped me focus on creative ways to tell a story each day, rather than spending a high amount of time drawing new places and getting lost in it. This resulted in me introducing new characters and situations within the same frame, and I loved it.

During Activate Creativity, one of the exercises is a daily creative challenge. At the beginning of the week, we give participants the choice between two possible challenges, with specific constraints. One of them is that they are to spend 15 minutes on it. You’ll be surprised how much you can come up with in 15 minutes as long as you have the right constraints.

Finally, there is a third element you need to evaluate before settling on a creative challenge:


If you don’t share what you create, it doesn’t exist. That’s as simple as that. But for a creative challenge, the sharing element goes even deeper than that.

Sharing reinforces both Time and Risk. If you don’t need to share, you don’t have to finish so you won’t feel obliged to spend time daily on what you do.

Sharing also redefines what taking risks really means. Sometimes you won’t be done but the day will be over, and you’ll have to share whatever you could come up with. At that moment, you’ll learn to let go and take the risk to show an unfinished work. It will teach you to be comfortable with vulnerability and imperfection.

And like everything in life, the more you’ll experience that situation, the more you’ll feel comfortable to take bigger risks. Imagine where that could lead your creativity and growth overtime…

Sharing also makes you accountable and feeds you to continue.

People get hooked on creative challenges. They like to follow and support. Those daily likes, no matter how many they are, will help you push through. It might sound vain, but we create to connect with others, expressing something we hold in our heart. If nobody sees it, what’s the point?

When you know people are waiting for your daily challenge, it makes a world of a difference.

Sharing will also increase the amount of Time you spend on your challenge. In other words, you need to think about your distribution workflow.

The more platforms you want to share on, the more time it will take. The medium that takes the most time, distribution wise, is video; because you need to export and upload it. So when you pick your challenge, ask yourself: where do I want to share it, what do I need to do to share it, and how much time will that add daily?


  • Risk: Pick a topic or a medium you’ve been wanting to explore for a while and find what’s the sweet spot between too easy and too ambitious for you. (Find the challenge)
  • Time: Define how much time you can reasonably spend on a daily basis on average. Then define constraints to give a canvas to your creativity and save time on details so you can focus on the big picture.
  • Sharing: Commit to sharing daily on at least one platform. Then define how much additional time it will take you to do so. (Redefine your time accordingly if needed).

One last thing:

Once you’ve decided what to do and how, create a unique hashtag that will allow people to find your body of work and catch up on your journey.

Any questions, comments, reactions? I would love to hear from you. Let me know below.

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Nathalie Sejean is Activate® Creativity co-founder, a company dedicated to help you reconnect, stretch and nurture your creativity. Click here for more.