deer in headlights: where to start, overcome unknowns, and take the first steps in exploring painting

Oh dear…where to start?

Like a deer in headlights, we may find ourselves stuck wondering where to start as a new painter. Let this article guide you through some key first steps towards taking action in painting.

Where to start

Creativity takes courage. Self-esteem is a driving force within your power to examine, exercise self-compassion, and evaluate your potential. We are ultimately responsible for ourselves, and while inherently daunting a message, so too a tool for opportunities to grow our potential.

Overcome resistance and believe in your process, and explore where to start by adopting a perspective of what I’ve come to call, an artist’s playtential. As the French fauvist painter Henri Matisse said: “The worst enemy to creativity, is self-doubt. Change that mindset around and put pen to paper, ink to brush, and screw the Judge, both inside – and out.”

Resisting Resistance

So! Now we’ve amped up our carefree courage and are wide-eyed ready to explore the artist within us. Let’s get started on this painting endeavor and ask ourselves: Where to start?

“If you hear a voice within you say ‘you cannot paint,’ then by all means paint, and that voice will be silenced.”

Vincent van Gogh

The Power of Intention 

As an echo from my first article, “Welcoming Artistry into your Life,” being an artist begins with adopting the right Mindset. Adopt an open approach, courageous attitude, have faith in your true potential, boost positive self-esteem, and cultivate presence. 

Setting an intentional time for Art and creative expression brings about a bounty of benefits. You will surprise yourself, not only with the potential of one-of-a-kind paintings to boast and parade. But perhaps more spiritually, by revisiting the flow state of our childhood, the state of present Being with your true, free Self. 

As children, we concerned ourselves far less with the space we took up in a room or public, how others perceived us as we explore and express our bodies, minds, the physical world, and thoughts. How quickly we are reminded of the opportunity for self-liberty by revisiting and embracing that inner-child and creator, who really never left, only quieted.

As I grew, I noticed this carefree-ness slip away as my teachers, peers, and my own inner-judge critiqued and compared my creations to others. I can remark on a significant shift that took place within me when my sacred, private journal/sketchbook came into the hands of an untrusted family member, who mocked my vulnerabilities and employed them against me for years to come. I kept most of my Self inside, then on, and only in hindsight realize the true consequences this blockage enacted on my mental health, creative confidence, and trust in expressing myself.

In spite of my challenges, I realized through reflection that painting, writing, music, and drawing all served such purpose for me – that I needed to, not merely wanted to welcome that artistry back into my life.

Playtential Time

Ram Dass says: “Be Here, Now.” Exactly…  Dedicate some time in your week to invite and play with your creative potential. I’ve started to call this: playtential time. From this lens we invite a lightheartedness to the space that helps relieve the pressure of performing Picasso’s on first tries at a technique or project. Make art playful, explorative, and be open to the potential of its rewards. Make playtential time sacred and safe, within your own mind and heart, and also in your environment.

As exciting an experience it is to put intention to action and open ourselves to creativity, it can also feel daunting when we sit down, paintbrush in hand, anxious to produce a satisfactory piece. Remember and repeat: art is intrinsically valuable, moreover in its process, then in the final result. 

So set aside the time to try out painting. And then take action.

If you haven’t read Ram Dass’ Be Here Now, I recommend checking it out here!

Space + Supplies + Sexpression

OK – I had fun with the last in the list, there… To take action on your artistry, you must DO! Having set aside some time, now you’ll need to declare some space and gather supplies to (s)express yourself (alright… I’ll cool down now, hehe!)


The environment you work in may greatly impact your artistic playtential. There are many factors to consider to optimize your space to create, depending on your goals, comfort levels, and the materials you use.


  • Consider your comfort level with spectators. Are you confident around housemates, your spouse, friends, and family to paint in your living room? Is it important to you to feel safe to explore without the onlookers of your household, or are you confident enough to paint outdoors on a park bench or by the beach? Vulnerability may be a strength but can also render an artist shy and timid to exlore their playtential freely.
  • Paint nights and painting classes can be beneficial for beginners and practiced painters alike. Of course, you will find yourself alongside others exploring their artistry, which may act to bond and ease everyone’s self-esteem, provide ideas and opportunities for sharing and learning techniques. 


  • Painting outside is inherently beautiful and rewarding. It may also invite great distractions, with onlookers, noise, and weather affecting your setting. In a similar vein, social events and public indoor spaces can bring their own distractions affecting the artist’s capacity to focus and remain inflow. However, some artists find this exhilerating, once comfortable in their craft.

    Consider, again, your comfort level with adapting to the environment you choose. Quiet parks, campsites, forest trails, and dry summer days may render a happier, calmer painter – unless you’re a New Yorker.
  • Depending on your chosen supplies, certain temperatures and climate conditions may be favorable for your painting experience. Watercolour, for instance, is primarily made on art paper, which doesn’t favor a wet or windy day (risking over-saturation, bleeding, or drying out too quickly). Burning Man may seem an ultimate oasis of free expression and liberty. Just watch for those sandstorms… 

Portability of Supplies

  • It is helpful to consider the quantity and practicality of carrying painting supplies to and from desired creative spaces. See supplies in the next section, as well as in my next article, “Painting Modes and Methods: What to Use and Ways to Use ‘Em.”
  • For instance, many artists find themselves organizing their mediums, brushes, easels, canvases, etc., in a briefcase or perhaps in a specially-designed carrying case found at art stores. How handy it has been to carry around everything you need to allow opportunities to paint on a camping trip, at a festival, a friend’s house, or walk to the park.
  • If you’re set on playtential time at home, perhaps you needn’t shy away from large canvases and a plethora of paints, brushes, etc., for your ‘home studio.’


My next article will outline an array of options for anyone artist-to-be to explore. Abso-freakin-lutely you do not have to restrict yourself to just one! However, it may be advantageous (and more affordable) to start by specializing in a select few. To start, most painters will want a few varieties of:

  • Paints/mediums 
  • Applicators such as brushes/pallet knives/sponges
  • Surfaces to paint upon, such as canvases, art paper, wood, etc.
  • Water dish (and some water)
  • Your creative mind and courageous spirit to play with the potential creations awaiting your fingertips!

Check out my article to be posted on March 2, 2021, for my breakdown on some great options for trying out various methods, techniques, and supplies for painting!

Express Yourself!

Charles Wright (1970) and later N.W.A. (1988) sang it right. While Wright may refer to dancing and N.W.A. poetically hyping freedom of speech, the principles of Art are all-encompassing. “Oh, go on and do it, do it!”

N.W.A.’s (1988) Rendition of Charles Wright’s (1970) “Express Yourself

Love the Process, Let go of Results 

Sir Salvador Dalí proclaimed: “Have no fear of perfection, you’ll never reach it.” Once you practice something a few times, you gain experience overcoming the hurdles of quieting your inner critic and can shift into enjoying your process. Playtential time is an easygoing, explorative experience, and meaningful in and of itself – it is not about the the finished project. In fact, loving the process may yield even more profound lessons and results than the final painting, itself. Be open to this possibility, and let go.

Practice doesn’t make perfect; it makes better. Shed your attachment to perfectionism, and your mindset will steer onto a brighter, lighter path. Playtential is a way of framing this creative time as both fun and exciting, meaningful and care-free. Feel free and in the moment, and let that $#!@ go!

Remind yourself every day of the wisdoms of artists that precede us. A fan-favorite, late landscape oil painter Bob Ross reminds us:

“We don’t make mistakes, just happy little accidents.

Bob Ross, a softly spoken, nurturing and encouraging artist and teacher, whose love for animals and painting widely receives admiration around the world.

Ready, then? You’ve set your mindset clear, scheduled some time, designated a space, and gathered painting supplies. Go ahead and…

Wait… Do I need lessons?

The best response I can give may be to ask you to ask yourself: Do you!? Completely your choice, it depends on a few considerations…

Determine your Goals

I am happy to explore and produce paintings that vary in quality, style, and techniques with little formal training in my own experience. So far, my goals as an artist have been rather recreational, more expressive and therapeutic, fun-loving, and playful.

Pause for a moment and reflect on what surfaces within you when you ask yourself: Why do I want to try painting? Have you any goals or aspirations for your artistic journey? Do you crave an outlet for releasing your emotions, alleviating stress, outpouring your imagination, and recalling your dreams? Do you see yourself with paintings displayed in public galleries, festivals, or local businesses?

If you, too, are simply curious about playing around with and experimenting with materials and your inherent skills, then I repeat: Go for it. Practice loving acceptance of your work, be it a rough sketch, few strokes of paint on a canvas, or a project that you chip away at for months.

Seek Resources

If you seek more guidance at the beginning, or to refine or expand upon your skills, look around for resources. Paint Nights, as mentioned earlier, are fun, often casual settings providing a shared community feel for painters of all skill levels. Lessons may be offered by freelancers, at community centers and artist groups or schools.

I cannot praise enough the well-celebrated, modern-day platform of ‘Youtube University.’ Mostly free and endlessly fruitful, artists and teachers provide lessons and inspiration to occupy you for as long as you pay your internet bill. 

Check out a later article examining the value of Planning Your Paintings!

We are artists, we need each other and thrive, together.

I would love to hear your questions or ideas that may resonate with you as we explore art, painting, and artistry together. Leave a public comment below, or write me personally to connect!

I am passionate about making the best of life through cherishing relationships, exploring worldly experiences, and cultivating a creative lifestyle of art, music, dance, and fitness. I am a self-taught painter, inspired by the sublimity of nature, consciousness, love and universal transcendence that binds all of humanity and nature, together.


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