My Journey of Mastering the Art of Business with an Artist's Temperament

“You cannot make money by being an artist!"?

"Go find a proper job!"

These are the things many parents often say to their kids when they were young.

Singapore and many developed countries and cities aren't kind on people with an "artist's temperament". The increasingly high cost of living breeds pragmatism, and the competitive nature result in stress from having to keep up.

While this has been changing for the better, many people still struggle to unlearn this mindset that’s build on an Asian mindset of "面子" (saving face) and “怕输” (fear of losing out).

This article is for those who are running (or who are thinking of running) businesses, and who have what I call an “artist’s temperament.” And by this, I am NOT talking about running a business, while indulging in your artistic hobbies. I am referring for those who run? your business as an extension – or more accurately – an expression of your artistry.

For example, you may run a business which directly involves art - creating and selling works of art, offering some professional services such as photography, graphics design. Or you may go into domains like UX Design or advertising.

Okay! I've thrown several big words at you here. Before we continue, let's define what I mean.

• My Definition of Art: In essence, art is the expression of human experience, imagination, and emotion through various forms. It bridges the visible and invisible and conveys truths and perspectives, connects us to our shared experiences, inviting us to explore our emotions and view the world differently, revealing life's beauty and complexity.
• Artist's Temperament: People with an artist's temperament usually experience heightened sensitivity and are able to feel emotions more profoundly and see the world through a lens that captures both its beauty and its complexity. This sensitivity allows them to ?be highly attuned to the subtleties of their environment and the nuances of human experience, and notice details others might overlook and to connect with feelings and ideas that are often unspoken.

If you don’t resonate with this, but know somebody (perhaps someone close and important to you), then read on and let me know if you resonate.

However, if you feel “what’s this mumbo jumbo?” Then I invite you to scroll away and spend your time reading something more worth your while.

Straddling Business and Art

Running a business with an artist’s temperament, you’re fighting for your artistic expression. For many, the fight for your artistic expression is a lifelong fight, often fraught with a sense of indignation and loneliness. You may sometimes struggle with wanting to disprove the archetype of a "starving artist".

As an entrepreneur with an artist’s temperament, I’ve often found it difficult to straddle these 2 apparent extremes. I hope that my own experiences can provide you with inspiration as you fight to protect your artistic inclinations.

What’s Challenging?

1) For Artists, the Work is Never Done

Firstly, let’s get to what’s challenging about being in business while having an artist’s temperament. One of the hardest things about having an artist temperament is the feeling that the work is never fully done. As I go through life, I always gain new insights and ideas that I would like to include into my work to make them more powerful.

However, this also leads to never completing the work - think the La Segrada Familia, Antoni Gaudi's unfinished Catholic Cathedral even after more than 100 years of construction.

A common saying in business and work is “Completed is better than Perfect.”

I get this on a cognitive level, but I also have a strange feeling that the idea of “perfectionism” as people understand it usually may not describe the way those with an artist temperament think. It’s a unique “brand of perfectionism” that may be more accurately described as some mixture of “artistic integrity”, “expressive authenticity” and “pursuit of transcendence.”

?However, this is not realistic or even good for business. If we’re always working on completion of a project – whether it’s publishing a book, or developing a business plan, a deadline is necessary to get things moving. Otherwise, work will take on what’s called Parkinson’s Law - the idea that work will expand to fill the time allotted for its completion.

The Antidote: Create Mini-Showcases based on Realistic Deadlines

With my workshops and keynote speeches, the delivery date is always planned in advance, so it puts a definite timeline to my “artistic indulgence.”

However, for creative endeavours, it can be easy to get carried away. In order to do that, it’s useful to break down the project into smaller milestones, and then create “mini-events” or what I call “showcases” for them. When you have a showcase, it simulates a mini-keynote speech, an exhibition or a masterclass and a deadline to focus your creative energies.

Enlist accountability partners along the way, and when they are helping us to organize these showcases, we will be motivated by not letting their energies go to waste – this is another way to create a sense of urgency.

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2) Getting Caught Up in your Own Art

For many Artists, the ability to work on one’s own art is the reward in itself. If they are totally committed in their work as a masterpiece, they are in love with their work. While that may sound very nice in work, it may become challenging in business for one reason.

They may get so caught up with their art that they suffer from what authors Dan and Chip Heath termed as “The Curse of Knowledge.” This is a phenomenon where the more you know about something, the harder it is for you to imagine what it’s like to lack that knowledge. Your knowledge has “cursed” you and you have difficulty explaining it with others because you can’t recreate the state of not knowing.

If you cannot communicate your vision to your team, confusion, uncertainty and frustration abounds. If you cannot communicate your value in a way that prospect understands, you cannot sell.

What may make it even worse is that you feel frustrated about having to “explain my art” to others, feeling like it cheapens it. Or, you may even turn to arrogance or snobbishness as a defence mechanism, "No point casting pearls on swines! Why bother explaining this to the bourgeois?"

This attitude is what’s going to drive you out of business. You’ll be left in the ivory tower of your artistic haughtiness. In business, nobody is obligated to buy from you, or to believe in your dreams unless you can communicate them well enough. This is what I teach in my leadership communications and storytelling workshops.

The Antidote: Acknowledge that Business is more than Meeting Numbers, but also an Art Form

I’ve learnt long ago from a wise mentor, “The market’s the genius, not you”. This is a great reminder that business is a great representation of the laws of human nature and life.

Remember the earlier definition that art is the expression of human experience, imagination, and emotion through various forms. You can use your artistic inclinations in your communications - be ARTiculate and ARTful in how you run and structure you business.

If you can find a problem that you’re good at solving, and that people will pay to solve, and you’re able to communicate your offer well and actually deliver on your promise, your artistry will be highly appreciated and potentially lucrative.

This leads me to the next point...

What’s Joyful?

1) Incorporating Playfulness and Exploration into your Work

2018 was a year I hit a creative roadblock in my business. I was still getting training gigs, but was quickly falling into the trap of being a “soft skills trainer.” I was struggling to stand out and be known for a special blend of skills and insights that I bring to the table.

I’d neither climbed Mount Everest nor ran a multi-million-dollar business. I’d neither written a New York Times’ best seller nor was I a celebrity. I felt I was just a typical Singaporean boy, who’s gone through the traditional educational rout, risk-adverse and quite sheltered.

Yes, I was abused and bullied as a child, and I’d suffered from a decade of depression. But I was sick and tired of telling the same old stories that actually reinforced a narrative that I’d been “hard done by.”

But a few moments served as catalysts for a journey of discovery and transformation. First, Ron Kaufman , one of the greatest speakers on customer service in the world watched a speech of mine and commented that I had "dramatic potential" and asked if I had any theatre or acting background. Back then, I didn't, so he suggested that I pursue it.

He was right, I had once harboured dreams of performing on theatre, but had my aspirations crushed by being labelled a "gu niang" (which actually means "a gentle lady" in direct Chinese Translation, but in Singapore - depending on the inflection in pronouncing the word - is actually slang for "faggot."

Then at the grand ripe age of 37, I decided to follow Ron's recommendation, and at the encouragement of another mentor, Avi Z Liran, CSP, Author, Global Leadership EX Speaker , I flew to London for a 10-day Intensive Improv Theatre Workshop by the late Keith Johnstone, the founder and OG of Improv.

It opened up my world and allowed me to bring more fun and play into my business, as I shall elaborate next...

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2) Run Your Business as a Masterpiece?

Running your business gives you the freedom in which to create the reality you want to have. You can become the leader you wanted but don’t have the opportunities to have. You get to create innovative solutions you wished you had.

Like most artists, I take great pride in everything that I do. No two speeches I’ve delivered are exactly the same. I always work closely with my clients to craft a customised speech or training to meet their specific needs.

I never just resort to simply regurgitating content and “sending the message” across. I look for ways to express the same idea more creatively, more interestingly – whether through an image, a metaphor or analogy or a unique story. Even better, I’d look for ways to curate a memorable experience through which they draw their own learnings.

As a coach, I think very deeply about my clients’ problems and always look to work with them to co-create novel solutions to those problems. My clients often tell me that they feel seen deeply for their unique individual selves – just like they’re art masterpieces.

It's been an incredible journey of self-discovery and self-acceptance as I continue to run my business and seek growth and expansion. There are days when my artist's temperament still threaten to hold me back.

I have by no means "arrived" and like a typical artist will say, my business is a work-in-progress (W-I-P), in fact, I am still a W-I-P.

If you can relate to me, I encourage you to never give up hope, and believe in the "bad-ass" that lives inside you. Do not let fear or other people's expectations hold you back from giving the world the fullest of yourself.

To further inspire you, I leave you with this passage from one of my favourite books, "The War of Art". In the book, the author Steven Pressfield shared this...

“Are you a born writer? Were you put on earth to be a painter, a scientist, an apostle of peace? In the end the question can only be answered by action.

Do it or don't do it.

It may help to think of it this way. If you were meant to cure cancer or write a symphony or crack cold fusion and you don't do it, you not only hurt yourself, even destroy yourself,. You hurt your children. You hurt me. You hurt the planet.

You shame the angels who watch over you and you spite the Almighty, who created you and only you with your unique gifts, for the sole purpose of nudging the human race one millimeter farther along its path back to God.

Creative work is not a selfish act or a bid for attention on the part of the actor. It's a gift to the world and every being in it. Don't cheat us of your contribution.

Give us what you've got.”