3 Ways to Infuse More Creativity into Your Leadership

I spend my days coaching creative entrepreneurs and professional rock stars on how to find and live their purpose. Together we co-curate their most meaningful life and career – and I’ve started to notice a concerning pattern. Most of the creative entrepreneurs I work with resist calling themselves a “leader”. Additionally, many of the professional rock stars I coach who are leaders in their companies and fields struggle to make space for their inner artist at home and at work.

Which has me wondering, what’s the hang up with being both outrageously creative and a kick-butt leader at the same time?

Long before institutions and media brainwashed us to associate the archetypal leader with images of men in wigs, army gear, and suits, the word leader was derived from the Greek word, “laitho”. Laitho means “to cause to go along one’s own way.” It’s the idea of making a new path where one currently doesn’t exist. Notably, that definition makes no mention of gender or job title. In fact, leadership from this angle looks a lot like:

  1. Identifying a breaking or broken road.
  2. Cultivating the courage to step off that road.
  3. Creating an entirely new road.
  4. Compassionately leaving road signs for those who’d like to follow.

It seems to me that leadership and creativity are actually long-time BFFs, and I’m on a mission to reunite them. Because in my opinion, the world is currently walking down a lot of broken roads, and we’ve never needed creative leaders more than we do right now. So whether you’re a creative looking to own your inner leader, or a different type of professional looking to own your inner artist, here are three things you can do to marry your creativity and leadership together.


1. Embrace vulnerability.

It’s time to put purpose back in the center of our lives and our work. That requires leadership and leaning into vulnerability. Luckily, creativity and vulnerability are close cousins.

Try This: Host a “Crappy Ideas Session”

How many times have you made something that sucked, but then the “failure” inspired your next masterpiece? If so, then you know a thing or twenty about vulnerability. Good leaders intentionally create these experiences for themselves and others. After all, how can you expect to build a better road without building a bunch of bad ones first?

So this week, hold a “Crappy Ideas Session” at home, the office, a coffee date with a fellow entrepreneur, or the next PTA meeting. Pick a problem or project you want to work on and generate as many ideas or designs as possible, free from the need to be “perfect.” Then, take a look at what you come up with and see what it inspires.


2. Flip the frame!

Innovation is the art of looking at an old problem from a new angle. The old mindsets that have created the broken roads we’re scootering down won’t be able to fix them.

Great leaders drive innovation by promoting a growth mindset and reframing the problem.

Here’s a simple way to do that.

Try This: Check Your Assumptions

Is there a problem or challenge that you currently feel stuck on? Try this out! (It’s a neat trick that I learned in engineering school.) Recruit a teammate and lay out the project or problem. Then, write down or draw out all of the assumptions that you’re making. For example, let’s say that you are planning to run a workshop and film it for marketing collateral, but you can’t seem to figure out how to make it happen.


So your assumptions currently are:

  • I have to have $2,500 to throw a kick ass event and pay a team to film it.
  • I need a professional videographer to film and edit this.
  • 50 people have to show up for this to be a successful event.
  • All locations that will be beautiful enough will be too expensive for my budget.

Then, assume the opposite. Literally flip your assumptions.

  • I don’t need any money to solve this problem.
  • I can film and edit this, or I can find someone who can do it for trade.
  • No one has to show up for this to be a successful event.
  • I can host it at a friend’s house for nothing.

Then, do a quick design session with the new assumptions. See what you come up with. (Note: this is a process I used to use as a stormwater engineer and one I use all the time with my clients. It’s very versatile.)


3. Connect the dots.

The world’s problems are massive and interconnected. They cannot be solved in isolation. We need leaders who can think outside of the silos, see invisible patterns, and show us how to connect the dots.

Try This: Mixed Media Monday

Connecting the dots is the art of combining apples and oranges to make bananas. And the simplest way to practice it is to tackle an everyday problem or challenge while doing a completely different activity.

For example:

  • Designing your next Instagram campaign while shooting hoops.
  • Creating your sales strategy while doing a sip-and-paint.
  • Brainstorming your next pop-up event while going to the dentist.

If we want to create outside of silos, we have to literally create outside of siloed environments. In other words, change our scenery. We’re conditioned to do certain activities in certain places at certain times. So give yourself permission to mix up your mediums on Monday (or really any day… I just like alliteration). Get your team together to do an activity that has nothing to do with the work that you’re doing, and see what dots and patterns appear.


The ways of thinking that have created the world’s current challenges will not be able to solve them. The world needs more creative leaders. We need people who have the courage to go their own way and to create a path for others to follow. We need people who can inspire us to flip problems upside down and connect invisible dots.

We need people who recognize vulnerability as the greatest asset they can bring to solve the world’s toughest problems.

We need artists to lead. And we need leaders to activate their inner artist. So, stop shying away from claiming your role as a leader, or stop starving your inner artist. Own both proudly and at the same time. Because what the world needs most of all is your creative leadership.

Photos by Eun Creative

Kasey Dreier

Kasey Dreier is an engineer turned life coach and entrepreneur. After almost dying twice and rebranding a Fortune 500 company by the age of 29, she quit her six-figure job and started teaching yoga for $7.50/hour. She learned a lot about starting businesses, taking care of yourself, navigating failure, and feeding her soul. Now as certified life and wellness coach she helps others discover their purpose and live a life they love.