Design, at least for me, has always been a process of making tons of awesome, mediocre, terrible, stupid, interesting things, and then whittling them down and crafting them into a few really great things. Here's a look at my process of doing that.
Have lots of ideas
When you have ideas, write them down. Write down everything. Don't think about how much it will cost, where you'll source materials, or any other details. This isn't the time to talk yourself out of anything.
Think about your customers. A lot. What are they looking for? What do they need? What will they spend money on?
The first 5-10 ideas are always easy - probably because they're the obvious things. The next 40 ideas are like pulling teeth. Think of silly, stupid, and unrealistic ideas when you feel stuck to loosen yourself up. The next 50 ideas usually end up being the best. They're less obvious, more personal, and typically a little weird.
Once I've gathered all my ideas, I'll organize them into groups to look for themes, consistencies, or gaps. I try to look at how ideas relate to each other. This allows me to hone in on a few bigger areas to explore in my designs.
Make a bunch of stuff
After narrowing in on a few themes, try a bunch of different approaches. Don't get bogged down in the details just yet. It's not about making a perfect thing - it's about figuring out which ideas are good and which ones are junk. Try sketching, building little prototypes, and using materials that you normally wouldn't.
During this phase, I'll work both with my hands and on the computer. Switching back and forth keeps me fresh and gets me to try things I normally wouldn't. Something that I tend to struggle with is falling in love with ideas too early. Don't do that. It makes it hard to see things for what they are, and can lead to missing out on something better.
Keeping myself in a constant state of mild discomfort is important to the process. I expect to fail a lot during this time. Expecting failure doesn't make it easier, but I've learned that the work I do tends to turn out better because of it.
Share what you've made
Don't only show people things that are perfect. Sharing early and often keeps you from investing too much time in a mediocre idea. Show your designs, prototypes, and mock-ups to people - friends, family, strangers on the street, anyone who'll look.
Don't go searching for positive reinforcement. You don't want to be stuck with hundreds of bad products on a shelf. You need honest feedback. You put in your time and paid your hard earned money to make them, so don't ruin it because you didn't get real opinions, or because you didn't want to hear them.
Working on new products for Big Cartel's own shop, we recently tried gathering product feedback via email. Since the majority of our employees work remotely, it allowed anyone interested to share some input. Eric, our Design Director, and Vanessa, from our Community team, put together all the designs we were considering and then sent them out to the team. They voted on which designs they liked and felt best represented Big Cartel.
Take time with your designs
Great designs, like puppies, need lots of love and attention. They'll get better, worse, and evolve into new things.
Work on something and come back to it with fresh eyes. Turn it upside down. Look at it from 30 feet away. Do whatever you can to change your perspective. Mock them up and try to get them to look as real as possible. Print them out. See what they look like at actual size.
Now is when I start to fuss over the little details. That last 5% is the hardest, but it's also what separates something that's OK from a really great product.
Make hard decisions
Be brutal. Before you reach the finish line, you need to cut down your ideas to the best of the best. This is really hard to do and it can hurt. These are things that you've put blood, sweat, and tears into making, but try to detach yourself emotionally from them. Think about all the costs and the potential returns, not just the feeling of listing a new product in your shop.
At Big Cartel we do this as a design team. All the possible product designs get pasted into a big file and then we take a couple of hours to look at them together. Sometimes you'll have to cut an amazing item that just doesn't fit with everything else. Don't stress about it.
This isn't the only way to do it, but it's one that's worked well for me.
You can follow along with our progress over on the Design team's Dribbble.