The Creative Process in a Series of Choices (Also: Giveaway Winners!)

J&O Kicking It In the Studio (what! what!)

Hey everyone! Winners from last week’s big giveaway are Michelle S., Andy C., and Tonya L. Congratulations to them, and thanks to everyone else who entered.

I always enjoy reading your comments. A few of my favorites included various creative entries:

This comment is designed to win. –Chris Moseir

I have goldfish crackers. I happen to know that biased judges, cats, and random number generators all get hot for goldfish crackers. –Lauren Vanessa Zink

Please, oh please, pick me fine folks,
I sure hope this competition is no hoax.
Your guide sounds like it would be fantastic,
so I thought I would go above and beyond to do something drastic.

I promise if I win to share it with everyone I know
Raving about the creations of Jen, Omar & Chris Guillebeau.

Winning this guide would sure make my day,
It would take all my troubles away.
So I ask again, once more my friend,
please pick me in the end. -A poem by Jake Jorgovan

Come higher water or hell
I’m destined to read
…Designed to Sell –PD

…haiku alert…
dear random number
generator or feline,
i hope i get picked. –Jen

Tomorrow morning at 9am PST we’re going to release Designed to Sell to the world. By this point you’re either really excited about it or are really tired of hearing about it. Either way, we’ll be underway soon. 🙂


Today I wanted to take a step back and explain a few things about the process of making things—which tends to apply no matter what “thing” you’re making.

Whenever you begin a new project, you should take the time to understand your motivations. Why choose this one? Why choose it now?

Every decision in this process comes with pros and cons. If you work on one project, you have to say no to others. (At any given time you can probably do “anything” but not “everything.”)

Next comes the matter of quality and timeliness. This one is always tough, because there are two competing messages:

1. Make this thing really awesome!
2. Get it done!

I do want things to be awesome, and we invest a ton of work in making them great. But if perfection is the standard, nothing will ever get shipped.

I don’t think it’s possible to get everything right all the time. I’ve never launched something without making at least one big mistake, and usually several. Even on the projects I feel especially proud of, I can look back and identity flaws and areas that could be improved.

Yet at a certain point you have to come to a point of completion, secure in the knowledge that you’ve made something good and it’s time to move on.

Then there is the matter of getting the word out. If you believe in the thing you’ve made, you want people to know about it (right?). You’re proud of it and you want it to have an impact (right?).

If you talk about too much, however, people will become annoyed or just stop paying attention. (But you do want people to know about it, so thus the need for balance.)

In a commercial product, the process of creative tension continues throughout every stage of production:


If you price it too high or too low, bad things will happen. Pricing is tricky: choosing to price too low can be just as bad as pricing too high.


Why is this project relevant now? What’s special about it—why will people care enough to stop what they’re doing and take action on it?

Next steps.

After preparing for a long time, hopefully the launch goes well. And then… what’s coming next? Do you continue to invest time, effort, and other resources in the project—or do you move on to something else?

Sometimes the answer depends on how much you believe in the project, other times it depends on how much other people believe in it, and perhaps sometimes it’s a combination of the two.


The Goal

There’s no single, perfect solution to these considerations. What you try to do is get as much of it right as possible.

In the case of Designed to Sell, it’s been a lot of fun to work on. I’ve learned through the process and it’s been a team effort: in addition to Jen & Omar, the primary authors, I’ve been working with Stephanie, Sean, the design crew from Jolby and friends, an independent developer, and of course the 21 artists featured in the guide.

It’s been a big project for us. We’ve invested a lot in production and tried to make something that will serve a lot of people for a long period of time.

After working on it for more than six months, Designed to Sell will finally go out to the world starting tomorrow morning. When it’s live, I’ll post the details here, along with the special bonus we’re offering the first group of buyers. Whether you’re excited about it or tired of hearing about product launches, we’ll be back to regular business soon.

Thanks for all your support either way! I’m thrilled to write for an amazing group of remarkable people.

See you tomorrow…

Question: Have you ever struggled in the creative process? How do you try to get the balance right?


Previously in the Designed to Sell saga…

A Tale of Two Designers
Mistakes on the Road to Creative Freedom
Lessons from Six Creative Pros
Sneak Preview (+ Giveaway!)

Subscribe now and you’ll get the best posts of all time.


  • Francesco says:

    Cosa posso dire se non pick me!

  • Angela says:

    I tend to have creative peaks and valleys. I have periods of intense creativity where the results are virtual sell out shows. Then I am in a creatively barron valley with very little production for long periods of time. It’s hard on the brain to say the least. So far I haven’t been able to find the ballance and each dry spell leaves me wondering, “is that it? Is that all I have? Is it time to give up on my persuits of making my art a career?”

    I have just downloaded the Unconventional Guide to Art + Money and am slowly going through it…struggling all the way but hopefully making progress. I have started revamping my website to focus more on sales. Working for myself will hopefully provide income to live sustainably as a full-time traveler living in my camper. I truly appreciate what you are doing to help us creatives! Thanks!!

  • Leanne Fournier says:

    Great post Chris and especially relevant for me as I’m in the process of rebuilding my “ship” (and yes it’s taking some time). I write entirely for other people so the balance between creativity and delivery is often complicated by client preferences and needs. I always take a giant step back, get both the client and myself out of the way, and focus on the audience who I’ve gotten to know by the fact-finding I do before I start writing. This dictates whether the approach should be wildly creative or more straight forward. I can then cut through all the clutter to arrive at the right approach that I’ll rationalize and sell to the client. This always keeps the process moving along with the client and I both knowing where we stand and what’s going to be delivered.

  • Leanne Fournier says:

    Apologies had a typo in my email for the comment just submitted. Yikes!

  • Stephen P Brown says:

    I struggle all the time, as a composer (Not as a conductor – it’s “easy” interpreting someone else’s work). Still, I have a daily 6am composition time slot and when it’s a struggle, I often delete or save and just start again, read or write some blog posts, add a pre-internet composition to my website (or some other ‘support’ tasks), and know that there’s tomorrow. I think I’ve gone three days max without writing a single note, because something always makes sense eventually. Fortunately, my livelihood doesn’t depend on my compositions, so… phew! Are they perfect? No. That’s why I’m on a quest – to make my compositions better. I focus on one or two elements to improve each time. Even little editing issues aren’t always accurate, but the more I notice the more I remember for next time (or add to my editing checklist). I have a pre-determined schedule I need to stick to (150 new pieces in 7 years? That’s one every 2.7 weeks. Gulp. )(Yes – that idea came from your Every Country quest!) which helps me create AND get them out the door.

  • Tisha says:

    I used to struggle with perfectionism, which would eventually lead to not working for very long periods of time, and then I would put loads of pressure on myself to create something amazing when I was totally out of practice. I found a balance by doing two things. The first was to drop the perfectionist attitude, because it’s the number one way to get burnt out and not finish what you’ve started. So, when I find myself working for way too long on something, I literally tell myself, “It’s done, move on,” and then I proceed to take my own advice. The second thing I do, which has been monumental, is to learn discipline. I think that there is this idea that creative people have bursts of inspriation and then nothing, and so on. But if a person can learn discipline, and work even if they are not particularly inspired, the work becomes more frequent, eventually easier, and the inspiration will show itself sooner or later. I’ve learned to schedule my creative time, marking off the days on the calendar that I’ve worked and I never let more than two days go by that I don’t do something. Both of these things have really added balance to my life.

  • Laura G. Jones says:

    Oh, issues with the creative process… what writer hasn’t had those? I’m seriously dedicated to achieving that balance for myself, and there are three factors that make the biggest difference to me.

    1. The Why.
    Why do you want to create this? I’ve found no greater weapon against creative distress but clarity on exactly why this is helpful, and for whom. Starting from your soul.

    2. The How.
    This is the part where you need to have the courage to step out of conventionality and do something “crazy” that works for you. In my case, I stopped blogging and went to a newsletter-only format. Crazy. But I create SO much better, and provide better value. So it works for me. At least for now.

    3. The What.
    I hate, hate, hate what pressure does to the creative process. Just like you said, seeking perfection doesn’t do any good. So I do something completely woo-woo and pass that on to God (in Elizabeth Gilbert’s words, my “genius”). I don’t put immense pressure on myself to deliver the information. I just open up, relax, and allow God to work through me. When faith is there, I’m amazed at what I can put out into the world.

  • Larry Hochman says:

    I was listening to a great training with Eben Pagan and John Carlton. JC was talking about how Navy SEALS are experts at observing their surroundings…they color code it. It made immediate sense as to what we do here.

    Creativity comes from being a great observer of what’s going on around you. Taking in data from the outside world and pairing it with your own experience…coming up with great stuff. Psychologically, this is “convergent thinking.” It’s where some of my coolest stuff has come from.

    Thanks for an eye opener, Chris. 🙂

  • Lucy Chen says:

    When it comes to the art business, I’m most struggling with how to sell more of my paintings and prints.

  • Bonnie Pang says:

    I have been constantly struggling with my creative process ever since I got into art school and take drawing very seriously. Most of my issues are with motivation and perfectionism. During my down periods I tend to think my art is never good enough or does not suit the market, then I would go into a downward spiral and stop drawing rather than pushing myself to improve.

    Things have gotten a bit better when I find art/creativity related books, blogposts and podcasts to read and listen to (such as this site!). Knowing that there are many others who share the same problems makes me feel a lot better.

    I’m also learning to improve my mindset and give up being a perfectionist. If I really feel stuck, I would leave it alone and go to work on other tasks, then come back when I feel better.

    Hope everyone can find a way to get the right balance! 🙂

    *I wonder how can I get my profile picture to show up?

  • Maria says:

    hmmm, this is called business planning! and this is why the education from well known Universities is not that worthless afterall, even if you pay a small fortune to get a degree..there are specific steps that an entrepeneur must apply in order to create a successful business with long viability.

    I hold two degrees in Marketing and Maritime Business and although I’m due to open my own business in a short period of time I can’t stress how important for an aspiring business man/woman is to obtain fundamental business knowledge and skills! if we could find some common qualities between the successful examples that Chris includes in his new guide, those would be strong entrepreneurial skills!
    Therefore, before the creative process begins, it is absolutely important to have a degree! not for the title, but for the skills obtained!

  • Maria says:

    p.s. Not everyone can be the ”captain”! A ship needs seamen, engineers and officers as well..without them she cannot sail! if you want to lead the vessel then you need to understand that the creative part is just a small fraction of the whole picture..educate yourselves, be strong and confident and gain the best skills in order to show the world how magnificent your art is! world needs this kind of entrepreneurs.
    The main reason that many businesses end up to close after some years of operation is because their owners had a vision but not the skills! so, if you do want to be your own boss, become the person who can deal with anything!
    I think this guide includes just that; a miniature of a business degree and I can’t wait to buy it! I believe it will help hundreds of people starting their own business successfully.

  • Andrew Elsass says:

    Whenever I hit a creative/or motivational block, I remind myself of these two things:

    The first I read in an Atlantic article by Megan McArdle: “Most writers manage to get by because, as the deadline creeps closer, their fear of turning in nothing eventually surpasses their fear of turning in something terrible.” I try and crank that fear up as much as possible by imagining visitors going to my site and dismissing it and me because it hasn’t been updated in X amount of days.

    Another thing I think back to, and I don’t remember the exact source other than I saw it retweeted a long time ago, was the “Steps to the Creative Process”:

    1.This is awesome
    2.This is tricky
    3.This is awful
    4.I am awful
    5.This might be ok
    6.This is awesome

    When I hit steps three and four, I use that as an indicator to keep pushing through, knowing that once I put in a little more time, whatever I am working on will turn the corner to a place where I am happy with it.

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