The most fun a designer can have in their early careers is working at a bootstrapped tech startup.

It’s really a blast building a product from the ground up. As the company’s sole designer, it’s your responsibility to make sure what you ship is beautiful and intuitive. But when you’re the only artsy kid in the room, things can get tough. Here’s some hard-learned tips that have kept me going through the ups and downs.

Can’t Stop, Won’t Stop, Don’t Stop.

If you work at a startup, don’t let me catch you at the coffee shop without your moleskine. A doodle a day keeps creative block at bay. Keep pushing, iterating, and thinking of how to do it better.

Stuck? Ask for feedback from your coworkers. Hit print, make four copies: one for yourself, two for sharing with coworkers to take notes on, and one for the final decisions after you’ve synthesized the results.

Once you’re done with paper, pencil, and photoshop mock-ups, it’s time to prototype, get feedback, iterate, and repeat. Don’t ever stop. If your product is still under development, everything can change completely at any moment. Being able to throw your designs away and start over is essential to your success.

Go Outside Your Comfort Zone.

Learn a new thing or two, balance your visual design with interaction design. Codecademy and Code School are great places to learn some javascript and jQuery. If that’s over your head, Jessica Hiche’s Don’t Fear the Internet is an amazing resource to learn some HTML and CSS basics. Need a text editor? Go with Sublime Text. If your pixel polishing is lacking spend some time on Dribbble and Behance. Whatever you do, don’t get trapped in your own little design bubble—push your own limits and you’ll be amazed at how quickly your skills improve! Which leads us to…

Challenge Yourself When Others Don’t.

The hardest part is that your decisions will never be challenged enough. There’s no senior designer or creative director who will throw away your designs and tell you to start from scratch.

Sometimes, the team will be enamored with your very first version of a design. Don’t let it go to your head—you’re not done just yet. The only person who is able to really keep refining the design is you. And you need to. If you don’t, mediocrity will result. Great design doesn’t happen on accident. It doesn’t happen on the first try, either.

iterate

When you’re pushing a design, wherever you stop—that’s what the product will look like. Sometimes feedback from your non-designer coworkers is not enough. This is why user feedback is so important. There’s no better way to tell if your designs work or not then to test them on real people.

Some days, the juices are flowing, the team is mind-melding, and everything falls into place. Engineers are executing perfectly, and you feel a sense of wonder at how much your team can accomplish in just one day.

Some days, there’s simply no wind in the sails. Go for a walk, pour yourself a cup of coffee, and draw it up again from scratch.

Startup Life isn’t easy, but it’s definitely worth it.

—Will

Don’t forget to follow me on Twitter, and on Dribbble too!

What do you think? How do you go about being the sole designer at your company?

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