What Bob Ross And Painting Taught Me About Tools

This week I want to keep things simple and share with you the tools I use on a regular basis to complete my projects and manage my business.

My Experience:

As far back as when I was learning how to paint as a child by watching Bob Ross create “happy little trees,” I’ve been fascinated by a creator’s workspace and tool set. For some reason I would always associate the tools with the quality of the creator’s work. I even purchased Bob Ross branded paints and brushes with the hopes that it would help me paint just like Bob himself.

Maybe some of this fascination was because marketing and advertising companies created it (by pairing up spokespersons with some brand products), but perhaps more likely this fascination was because I was trying to find an easy solution for the underlining problem. I believed that the right tools made a difference. Whatever the reason was, I spent tons of hours and money watching Bob Ross and buying Bob Ross name brand products with really few positive results in my quest to learn how to paint.

Now let me fast forward 10 years to high school. High school is where I first learned the craft of design, drawing and painting. Beyond learning about the benefits of hard work and putting in an extra ten percent into my projects, I learned color theory, figuring drawing, painting, as well as conceptualization. This class was specifically designed to help me create a portfolio that would not only get me accepted to a college, but also help me earn a scholarship to help cover the costs. The Commercial Art program taught by Mr. Krol had a huge reputation for getting students full ride art scholarships to a variety of colleges in the midwest. However, he did so without teaching us how to use a fancy computer (in fact we had only one and I never learned Photoshop until college), expensive art canvases or paints. We simply used watercolor paper, cheap tempera paint and ebony drawing pencils. These supplies could be found at pretty much any arts and crafts store, nothing like the Bob Ross Oil Paints that I used early on in my life.

The paint came in large bottles with the consistency of water. I didn’t know how to paint with anything else. Every time a college recruiter came into our class to talk about their college or review our portfolios they were amazed at the quality and sophistication of our work compared to other students. They always asked what paints we used. We’d always show them the bottles of tempera paint lined up across the sink. Their mouths would always drop because it’s the same craft paint any four year old would use. The difference was we knew the fundamentals of painting and color and how to manipulate the chalky paint to our benefits. For over a decade students would create award-winning art, and win hundreds of thousands of dollars in scholarships to the schools of their choice, all with just cheap gallons of paint and Mr. Krol’s teaching.

The moral of this story is that I invested a ton of money on name brand tools early on in my career as I was trying to learn how to paint, but the real problem was not with my tools, but that I didn’t know how to paint. No amount of money could change the fact that I didn’t understand the fundamentals of color and how to manipulate paint to create a desired effect.

The same is true today. Sometimes I find myself spending money on software and other things that I soon realize didn’t solve the core problem, but instead just wasted my time and money. Yes, I do believe that you need to make some core investments into  hardware so that things are reliable and efficient. I also feel like some tools are just the expense of running a successful business. However, your tools should never be viewed as the ultimate solution to a larger more underlining problem.

So what tools should you use and what tools should you just forget about? Well because I love sharing things with you, I’m going to share my entire tool set and workspace with you. From my desk, down to my software.


  • Multi-Table Stand Up Desk*
  • Multi-Adjustable Desk Chair*
  • Apple Keyboard*
  • Apple Magic Mouse*
  • 27” Apple Thunderbolt Display*
  • Apple Headphones*
  • Apple 13” 8G Macbook Air*
  • Apple iPad Pro
  • Moleskine Notebook*
  • Plants & Natural Light*

Design & Development:

Business & Management Software:

Workflow Software:


*Represents my most used tools and a good place for you to start.

By sharing my list with you, my hope is that you can compare it to your own list and realize the things that I use are not super fancy and in fact you too may be using them already. One of the secrets to becoming a successful designer or freelancer is knowing the core fundamentals and how to manipulate your toolbox to your advantage.

You can find my entire toolkit and get special offers on some of my most favorite tools when you visit my tools & resources page.

What I’ve Learned about Software and Services.  

  • The tool means nothing: Perhaps one of the most important things I’ve learned in my career is that the exact tools you use to create your designs contribute very little the final product. Before you can worry about investing in tools you need to learn the core skill. A tool is just a tool. Just like an expensive hammer doesn’t make a great carpenter the same is true with design software.
  • Changing too often affects productivity: I’ve found that by changing too often, I’m not only losing money, but I’m also losing a ton of time and time is money. This time spent on migrating to new platforms and learning new software can greatly reduce your productivity and that’s time you won’t get back. If you scale that time across your entire team, you’ll soon see the effects of that lost time.
  • Those tiny monthly investments do add up: I do love that a variety of tools are available to help me run my business. These tools can sometimes save me a ton of time, keep me organized and looking professional to my clients. However, this benefit does come with a minor cost. I sometimes get too carried away with investing in products and wind up having to reevaluate every few months because those tools do add up and affect the bottom line. Perhaps the most interesting thing about when I reevaluate, is that in most cases, I always wind up right back to this core list that I have outlined above.
  • Keep your tool set simple: Sure this list looks pretty large at first glance, but if you evaluate each tool you’ll discover that it’s a pretty simple set of tools. Each tool serves its own purpose with very little overlap with one another. This simple tool set helps me fill in gaps within my business to make it easier for me to focus on design and growing my business vs. trying to keep a handle on the day to day.
  • One tool doesn’t fit all: This took me awhile to realize, but as you consider using tools to improve your workflow etc. know that no two tools are equal. What works for one person may not work for another. Each tool is set out to solve a different problem. The best thing to consider is finding a tool that fits the closest to the main pain you are trying to solve. Is it team collaboration? Maybe it’s prototyping? Whatever the problem is, you may need to make small adjustments every now and then. However, if the tool solves your biggest challenges you’ll be able to use that tool for a pretty long time and most likely you’ll evolve processes around it.
  • The tool won’t fix the core problem: I’ve noted this above, but what I’ve learned so far in my career is that the tool won’t fix the core problem. No matter how feature rich your project management tool is, it won’t solve a possible project management issue you may be having with your clients. These tools just become a layer that sits on top of your business. Until the core issues are solved, you’ll actually end up creating more problems for yourself with this additional layer on top.

My Takeaway:

Finding the right setup can take some time. Be patient. The right tool for you really depends on your needs. What works for some won’t always work for you. The tools I’ve outlined above are tools I find myself always using. Some of these tools I’ve been using since day one of Greenline Creative, so at the very least I hope it serves as a starting point for you. Keep in mind that I may not use all of these tools every single day, but I use them enough that the benefits outweigh the investment.

If you’re unsure whether you should be investing in tools, consider looking at your day-to-day productivity. If you find that some of these tools could actually improve your workflow and business processes, give them a test drive for 30 days or so. You don’t have much to lose on a free trial. However, if you feel like things are running smooth as they are, don’t add a wrinkle into things until you find that you may really need to do so. Listen to yourself, your goals and your business. It will tell you when and where to invest.

When it comes down to just investing in software for yourself as a designer, think about your design workflow. Is there a way you can improve productivity in your day? When you can improve productivity you’ll generally save time, and time is money.

Whichever way you want to look at it, just be sure you’re not trying to mask a larger problem. Remember, your tools should never be viewed as the ultimate solution to a larger more underlining problem.

I’d love to continue the conversation with you. What tools do you use that I didn’t list above? Also, if you have any specific questions about any of the tools I’ve listed above, I’d be happy to try my best to answer them.

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