Bootstrapping Your Creative Web Design and Development Ideas

John Reeve | May 19th, 2010 | , , , ,

A web design, development, or creative agency is a relatively easy type of small business to start. You just need a few computers, some spare office space and a few creative minds who are willing to make sacrifices (you’d need an entire blog post to cover dry seasons, erratic cash flow, client conflicts, etc). Your fate becomes largely your own and the work produced becomes personally rewarding, and your portfolio of professional creative work improves with each project.

What happens when client work isn’t enough and you start looking for more personally fulfilling work? Most designers, developers and creatives have personal projects that are sidelined by our professional work. Finding the time and allocating enough resources to pursue them is challenging but also more rewarding than any client project ever will be. So how do we free up enough time to track down our whimsical pursuits and guide them into becoming a reality?

Intervals, our web-based time, task and project management software, began its life as an internal application for tracking and managing our client projects at Pelago. It quickly became our passion and today Intervals is a full-time and fully supported online application for us. Want to bootstrap your creative ideas and take them from concept to completion? Here are some tips on how to do it, based on Pelago’s experience launching and evolving Intervals.

Exercising your creativity

“Success is going from failure to failure without losing your enthusiasm.”
— Winston Churchill

Designing or developing any type of side project first requires a creative mindset. You can’t expect to hit the ground running because it won’t happen. Many ideas may turn out to be bad ones or may simply be short lived. The important thing is to start brainstorming your ideas hashing them out, one-by-one, to discipline yourself in the art of execution. We all have plenty of ideas, it’s the execution of our creative ideas that separates the talkers from the walkers. For every project that makes it into the Sidecar Projects section of the Pelago web site, there are half a dozen ideas that collapsed under the scrutinizing weight of the creative process. The ideas that don’t go anywhere play an important role in the creative process, their failure molds our minds into a state where it can push the great ideas through the creative gauntlet.

Necessity is the mother of invention

Sidecar projects don’t always have to be unrelated to client work or internal business needs. In fact, some of our better sidecar projects stem from real-world business applications. Take a look at what you are already doing as part of your day-to-day workflow to see if there is anything that needs improving or would be a good launchpad for something bigger. This is how Intervals got started, as an internal time tracking and task, project management application garnered praise, and an encouraging push to take it online, from many of our clients. The Emogrifier came about because we needed a way to mash together CSS and HTML into friendly emails. Creative ideas are lying dormant all around us. We just have to know how to extract them from the dullness of the day-to-day.


Andy Dufresne did not break out of Shawshank Prison in a few days, weeks, or months. It took him 20 years of picking at a hole in the wall. At Pelago, we’ve coined the term “Shawshanking” to describe the process of working on a creative idea a little each day. 20 years probably doesn’t go by very quickly in prison, but the weeks and months fly by at a small business. Devoting a little time each day or week to your creative ideas will see them through to completion while still allowing enough time to focus on completing client work and paying the bills. At Pelago, we try to devote 15% of our time to the pursuit of new ideas. Any time you can devote is time well spent, if for no other reason than to give you a break from the occasional monotony of running a development shop or creative design agency.

Knowing when to say when

“You got to know when to hold ’em, know when to fold ’em…”
— Kenny Rogers

Some of our greatest ideas turn out to be an utter waste of time and energy, which we discover the moment we devote any amount of time to them. But we refuse to acknowledge the impractical implications of our findings and we try to push through them, our stubborn nature getting the better of us. We refuse to admit that there is such a thing as a bad idea, and worse, that it could possibly come from our own talented and creative minds. Knowing when to kill a bad idea not only teaches us how to say “no” to the extraneous and unnecessary, it makes room for the good ideas. No longer encumbered by bad ideas, the good ideas become unstuck and weightless.

Be compelling, not perfect

Most web designers, developers and creatives I know are perfectionists, especially when it comes to their personal work. The inability to know when to stop has plagued many designers in pursuit of developing their creative vision (think of all the poets, musicians and artists throughout history who’ve gone mad). What we see in our minds will never compare to what we can do with our hands, but it can come close. When we take on sidecar projects our goal is to end up with something compelling, not perfect — something in close proximity to our creative vision. Success (and sanity) is much more attainable in proximity to our pursuits than in their absolute completeness.

The pursuit of personal creative projects requires a considerable amount of time before it becomes a discipline in your day-to-day workflow. However, once you’ve found a groove and devoted more of your time to the task you’ll wonder how you ever survived on client work alone.

Photo credit: / CC BY-ND 2.0

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Intervals Blog

A collection of useful tips, tales and opinions based on decades of collective experience designing and developing web sites and web-based applications.

What is Intervals?

Intervals is online time, task and project management software built by and for web designers, developers and creatives.
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John Reeve
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John Reeve

John is a co-founder, web designer and developer at Pelago. His blog posts are inspired by everyday encounters with designers, developers, creatives and small businesses in general. John is an avid reader and road cyclist.
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Jennifer Payne
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Jennifer Payne

Jennifer is the Director of Quality and Efficiency at Pelago. Her blog posts are based largely on her experience working with teams to improve harmony and productivity. Jennifer is a cat person.
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Michael Payne
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Michael Payne

Michael is a co-founder and product architect at Pelago. His contributions stem from experiences managing the development process behind web sites and web-based applications such as Intervals. Michael drives a 1990 Volkswagen Carat with a rebuilt 2.4 liter engine from GoWesty.
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