SPECIAL REVIEW: Artistic Confidence, Bob Ross & Skillshare

Artistic confidence.  I think about this a lot.  What it means. Do I feel I have it. What story am I attaching to it- there’s always a made-up story.  Sometimes we have confidence in certain aspects or areas in our lives, but not in others.  In my experience, the way to gain artistic confidence, to overcome doubt, is to do it.  Set an intention and spend time creating art and confidence grows.  Set aside all initial doubts, push through those feelings of vulnerability, and just go for it.  Believe in yourself.  Take some instruction. Immerse yourself. 


After Ross left the Air Force, he was struggling to make it as a full-time artist. Tight on cash, he got a perm, figuring he would no longer need to pay for frequent haircuts.

Bob Ross

Can you imagine if the happy little trees icon Bob Ross never started painting because he thought- ehh, I was a first sergeant in the Air Force for 20 years, I yelled at people a lot, I have no confidence to paint and teach?  Sounds kind of silly, right?  Especially when he ended up creating over 30,000 paintings in his 52 years on earth.  He made three of the same paintings for every episode of The Joy of Painting.

I loved watching him when I was growing up.  He wanted people to believe in their ability to be able to paint too.  He took instruction from another man, Bill Alexander.  In addition to his soothing voice and alla prima painting style, weren’t we all a little mesmerized by Bob’s permed hair? Bob’s confidence helped build a $15 million-dollar business.  He helped people believe in their creative potential and that art was possible- for anyone to create. Like many, I grew up believing in that possibility.

I want people to believe in their creative abilities.


I’ve been using Skillshare to help me with my artistic confidence. I’ve got my style, and my thing that I like to do, but I’m always looking to grow and expand.  I consider it an investment in myself.  And best of all, Skillshare is offering a special trial to get 2 months for just $0.99

For those of you who are not familiar with Skillshare:

  • Skillshare is an online learning community for creators and entrepreneurially-minded individuals, with more than 19,000 classes in design, illustration, business, photography, and more.
  • Everyone can take a class, try a project, and even teach a class themselves.
  • Premium Membership begins around $8 a month for unlimited access to learning.

19,000- the variety of classes is HUGE!  One thing that stood out to me is its ad-free.  So nice to not be advertised to.  A few of the categories I selected to focus on were fine art, illustration, graphic design, and web development.

My example is from Pen & Ink Florals with Sandra Bowers- this class was only 24 minutes.  I chose it for getting to know mark making and shading better. I very much enjoy her technique.  It added depth to simple and clean line sketches.

When searching for paper to do the pen and ink drawing class, I came across a floral sketch that I did around three years ago (left).  I used the same paper for both.  Practice and keeping at it makes a huge difference.  Seeing this comparison bolstered my artistic confidence, and had me appreciating that I keep showing up to practice.

The classes I’ve looked at were anywhere from twenty-five minutes to about three hours. Classes can be saved to come back to later when you’re offline.  There was a nice feature where the classes could be narrowed down by length of time, say if you only had 15-30 minutes, it would populate the classes that fit that criteria.  Eat lunch, take a quick class, and end up with a little sketch. Classes are broken into helpful and manageable segments, so it’s easy to watch certain parts, and come back later to pick up where you left off, or skip over parts.

In the event that you are feeling speedy or slow, the play speed of the video can be adjusted. I was prone to speeding the sketching bits up, pausing, working on my piece, then restarting. Instructors share what supplies they are using, so it’s a great way to learn about those and decide if it’s worth it to you to make a supply purchase. Instructors can also be communicated with to answer questions.  One of the coolest features is that people can share their work by uploading projects, so it’s nice to browse through and see what other people have learned, and how they interpreted the learnings. You can also, of course, complete your own project and upload it to Skillshare and receive feedback from others.

A few other classes that I looked at.

Easy Doodling & Painting Fun! Create Gorgeous Botanical & Floral Illustrations in Watercolor & Ink with Yasmina Creates.  Botanical sketching always appeals to me. Sometimes I need more whimsy in my life and this class looked like good fun.

Fun and Easy Watercolors: Draw a Beautiful Coffee Illustration with Mariya Popandopulo.  Seeing all the fun coffee and tea sketches that Liz Steel does inspired me to check this class out.

Urban Sketching | Drawing What You See with Peggy Dean.  Urban sketching, all the rage these days, so of course this class was quick to save to my list.

Watercolor Gems & Jewelry with Ana Victoria.  The projects students have shared it this are amazing. It’s a longer class, about three hours and is sure to build skills. It also seemed good if you are trying to master reflective surfaces, such as glass.

There are so many options!  Skillshare is an amazing place to learn new skills, or to further develop and strengthen existing ones, and gain artistic confidence.

Try Skillshare Premium for two months for just $0.99 by clicking here.

It’s prime time to get out there and sketch- Spring!

Recommended5 recommendationsPublished in Other Cool Stuff
  1. Sharon Mann 5 years ago

    Thanks for all of the resources Jessica, I too loved to watch Bob Ross!

  2. Pamela Smith 5 years ago

    Thank you Jessica…

  3. Mary Roff 5 years ago

    Thanks, Jessica. I don’t remember watching Bob Ross but I did watch countless hours of William Alexander on PBS. Loved watching that program.

    • Author
      Jessica Seacrest 5 years ago

      I never watched Alexander, so it’s fun to hear that you did :). Supposedly there was a falling out will Bill & Bob over the show.

  4. Sharon Nolfi 5 years ago

    Thanks for the suggestions to build skills.

  5. Jill Gustavis 5 years ago

    Bob Ross’s show is on Netflix (at the moment) and I love putting it on when I’m going to bed. That or Cosmos, so soothing, lol. Skillshare is awesome too. I’m totally guilty of watching the vast majority of the videos I’ve saved and not following though with the projects, lol.

    • Author
      Jessica Seacrest 5 years ago

      Haha, it’s great to hear how other people use different things. I speed up the videos to get through to the more finished stuff. Whatever you are doing, your work is looking so good! The lilacs you just finished are amazing!

      • Jill Gustavis 5 years ago

        Thanks so much! It was definitely one of those turning point pieces where I finally PHYSICALLY understood how the negative painting technique works. I often read or see examples of stuff and say oh that’s a great technique, but it’s so different to finally have it click and implement it with some success. I hope to expand upon it even more the next time I try it which is very exciting.

        • Author
          Jessica Seacrest 5 years ago

          How long did it take you overall? To me it looked like a serious piece of work!

          • Jill Gustavis 5 years ago

            Almost a week, but I didn’t work on it everyday. Some days I’m just too tired after work to accurately assess a serious painting, lol. I’d say about 4-5 hours of sit down time. Since I have pictures from each stage, I’ve found I prefer the 3rd version the most (posted on the 18th), so it was also a lesson in learning I may not prefer to add all the detail next time.

  6. Miss Gentileschi 5 years ago

    Wonderful post, Jessica! Never heard of Skillshare before but am going to put it on my ToDo list! It sounds amazing! As to Bob Ross – I absolutely adored him! That mastership and voice were a wonderful combination, and I´m sure he was one of the reasons I got back to painting!

    • Author
      Jessica Seacrest 5 years ago

      Awesome! I hope you get so much benefit and fun from Skillshare 🙂

  7. Debra "Kate" Powell 5 years ago

    Nice review. I signed up long ago but never came to put down the $$. I’m trying it because of the $.99/month for two months special. One thing that is missing is no search feature. What if I want to search for Photoshop classes? Lettering classes? This is a big one they should fix….

    • Author
      Jessica Seacrest 5 years ago

      Hi Kate, at the top of their website page towards the upper left, there is a search box to search for “classes, skills and teachers.” I searched for lettering and it came up with 437 results and also broke them into categories and class length options. Hope this helps.

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