What Creative Business Can I Start for Under $100

Imagine starting a side hustle with your creative skills that generates cash every single month.

Even better, imagine building a side hustle that costs you $100 a less to start.

The reality is that there are tons of side hustles that you can start today, and honestly, they won’t cost even close to $100. Many of them can be started for free!

In this article, I’m going to share with you seven side hustles you can start for next to nothing that can make you money every month.

Sell Products on a Marketplace

Designers, illustrators, and business owners are regularly on the lookout for creative resources that will save them time and money.

For example, my friend Lisa Glanz sells hand drawn fonts and portrait and character creators.

By purchasing one of Lisa’s fonts and a character creator and Etsy seller can create a line of products quickly that are unlike anyone else’s. Lisa sells fonts for around $19 and her character creator for $29-$49.

That means for less than $100 a new Etsy seller can be up and running with some great looking art on their products.

Lisa makes some fast money with minimal effort (after the product she’s selling has been created) and her customers get a solution to their problem at a great price.

Here’s some marketplaces you can get started selling your products:

Creative Market


The Hungry JPEG

Price to Start Business

Only time and a copy of Adobe Illustrator which can be purchased via subscription which can currently be purchased for as little as $20.99.

Teach a Course

Creating a course can be extremely profitable and costs little money to do.

Good Enough Donut Shop
CreativityPassive IncomePhilosophy

Make Garbage

“The safest way of not being very miserable is not to expect to be very happy.”

Arthur Shopenhauer – German philosopher

We’re all familiar with beginner’s luck.

You play Backgammon for the first time and beat the pants off your opponent – even though you have no clue what you’re doing.

You play Street Fighter II for the first time and demolish your brother despite the fact he’s been working on his special moves for weeks.

You paint your first landscape in a Oil Painting 101 and it’s a masterpiece. Then you paint like a six year old for the rest of the semester.

The Secret Behind Beginner’s Luck

What’s going on here? How can we excel at a skilled activity on our first attempt and then fail right after?

I choose to believe it has something to do with Arthur Shopenhauer’s quote.

When we make a first attempt at something we often expect to fail. Or at least are relatively indifferent to the outcome.

When you play that first game of Backgammon you don’t understand it, you could care less if you win, and you probably expect to lose.

You’re probably starting to imagine how liberating that can be.

Whether you’re starting a business, a 100 day challenge, or writing a novel – one of the most empowering ways to approach the task is to assume you’re about to make garbage.

Of course, when you make garbage the pressure is off.

Tell your friend you’re finally writing an album of original acoustic folk ballads and it’s going to be serious garbage.

You’re free to write, experiment, fail, push boundaries, sing horribly, and not play in steady time.

The funny thing is you’ll probably create something pretty good.

At the least, it will be better than the garbage you thought you were going to make.

Retro counterfeit diamond

Counterfeit Diamond

This diamond isn’t real.

I mean. Yeah, it’s an illustration.

But it’s also not a real illustration.

I got lazy and made a Frankenstein diamond.

Let me explain, I interviewed my friend Dina Rodriguez (AKA Letter Shoppe) for an episode of Passive Income for Designers. She made a really solid point about getting good at stuff. Read More


The Importance of Wasting Time

I was listening to Brené Brown’s Audible book The Power of Vulnerability today on a trip to IKEA.

Through qualitative research (I’m recollecting the audio, so I’m probably not wording this correctly), she discovered that people who unconditionally love themselves shared similar qualities.

Here are two of the qualities people who unconditionally loved themselves shared:

  1. They spent a greater amount of time playing. I’m not talking creative play at work or anything like that. We’re talking actual play. For example, jumping on a trampoline or playing a board game.
  2. They spent a greater amount of time sleeping. We’re talking 8-9 hours of true sleep every 24 hours.

I haven’t gotten far enough in the book to know exactly why this characteristic pops up. But I have a theory.

Individuals who truly love themselves put taking care of themselves at the top of the priority list.

Even when I consciously make an effort to take care of myself, I don’t treat myself this good.

Here’s the warped way I can sometimes view taking care of myself:

  • Exercising on the elliptical in my garage.
  • Forcing myself to eat some vegetables.
  • Tracking eight glasses of water in an app.
  • Writing down my goals for the day.
  • Going for a 10-minute walk outside.

Is there anything wrong with any of these things?

No, not really.

But if a good friend asked me to prescribe them tasks to take care of themselves it would look more like this:

  • Take an hour walk in nature and contemplate a passage of spiritual writing. No phone.
  • Slowly savor a delicious meal made with fresh ingredients.
  • Meditate for at least 20 minutes in the morning and evening.
  • Write a letter to let someone know how thankful I am for them.
  • Spend an hour playing a game of Backgammon with a friend with some delicious coffee.

Notice the difference here?

The former list crams self-care down my throat. It’s an unproductive way to try to take care of myself.

The latter list takes heaping portions of time. It forces us to give up some of our productivity.

How Can You Waste Some Time This Week?

What can you do for yourself this week to give back to yourself?

What can you do that is a waste of time regarding productivity (but a valuable investment for you as a person)?

Take 60 seconds and leave a comment below letting me know what you plan to do. I’d love to hear your ideas. Plus it will act as a living list of ideas for other readers. 




Why Knowing Nothing is a Good Thing

Why It’s Awesome to Be a Beginner

A few days ago I purchased Shunrye Suzuki’s book Zen Mind, Beginner’s Mind.

One of the first things Suzuki emphasizes in the book is this quote:

“In the beginner’s mind there are many possibilities; in the expert’s mind there are few.”

One way of looking at this is the expert tends to become blind to opportunities and stubborn in his ways. The beginner sees opportunity and novel solutions everywhere.

For example, I’ve run RetroSupply for five years now. The business has generated a healthy six-figure income year in and year out.

If I’m honest with myself, this has made me rigid. I tend to believe I know how to make something succeed. I follow worn paths that have worked in the past.

So when I started my daily drawing ritual 30 days ago, I was immediately humbled by my lack of knowledge. I’m a designer and not much of an illustrator.

I quickly realized I was not good. And each day as I drew and posted an illustration I felt humility, saw the entire world from new angles and saw many possibilities for myself.

But what made this almost magical was how having a beginner’s mind changed the rest of my life.

Here are some things that have happened since I started drawing:

  • I see new ways to bring more value to RetroSupply.
  • Everday experiences are richer. Drawing has helped me see the beauty in everyday objects.
  • I find myself going into a flow state when I draw. Something that wasn’t happening nearly as much over the past few years.

How You Can Reignite Your Beginner’s Mind

Do you want to instantly have a fresh view of your business, art, personal life, and the world in general?

Choose a daily practice you can start today. Start developing a new skill that can be done in 30 minutes or less each day. Ideally, the skill should put you in a flow state.

Here are some examples of skills you might try:

  • Gardening
  • Cooking
  • Painting
  • Learn an instrument
  • Play a sport

Once you’ve chosen your activity practice it 5-7 days a week for at least 30 minutes.

Document your process publicly. You could use Instagram if it’s a visual practice or even Twitter (for example, Day 1 | Practiced the transition between the D and G chord in open position for 30 minutes).


I didn’t think this drawing practice would have such an impact on my life. But just a little time each day doing something with a beginner’s mind can rewire the way you see the world (and yourself).

If you have 20 seconds respond to this post. I’d love to know about your experience with beginner’s mind, activities that put you in a flow state, or a new practice you’re committed to starting.