A huge challenge everyone who decides to be self-employed needs to face is that there are suddenly no constraints. At school, university, or work, there are always deadlines and you had to carry pre-specified work using a pre-defined toolbox. But if you’re self employed, you can build anything, work on any project, using any tool, framework, or programming language.

This freedom is both a blessing and a curse.

There’s something magical to working with constraints. Constraints breed creativity and can act as powerful forcing functions. Without them, there are just too many options and oftentimes nothing, at least nothing remarkable, is done.

“Telling yourself you have all the time in the world, all the money in the world, all the colors in the palette, anything you want — that just kills creativity.” - Jack White

This is particularly true for aspiring entrepreneurs. Most get stuck and never ship anything as a result of the lack of constraints.

“Constraints liberate even the most able minds.” - David Heinemeier Hansson

So what should you do as an aspiring entrepreneur? Since no one else imposes constraints, you need to do it yourself.

A great way to do this is to set up a challenge for yourself. A properly defined challenge can be a tremendous aid in beating procrastination and getting beyond analysis paralysis. Moreover, it can also help to build your personal brand as long as you write about it publicly, which you should do in any case to add accountability.

Examples of personal challenges are:

• 12 Startups in 12 Months by Pieter Levels which was later adopted by Jon Yongfook, Sean Walker, and CJ Trowbridge among others.
• Hardcore Year by Andrey Azimov. (12 months to get to $1,000 in monthly recurring revenue.)
• Road to Ramen by Basile Samel. (6 months to get to $700 in monthly recurring revenue.)

The 12 Startups in 12 Months challenge is the best of the three listed above since it focusses on the process not on outcomes. You can’t control how much money you’ll make while you can certainly control how many products you ship. This is analogous to how restricting your food intake to 1500 calories a day makes more sense if you want to lose weight than having a goal like “I’m going to lose 20 pounds until next year”. Similarly, a goal like “I want 1000 followers by the end of the year” doesn’t make much sense since it’s often based on luck. A better goal would be to tweet, engage and communicate daily. It’s always a smart decicion to focus on goals that you can control. Otherwise you’re setting yourself up for failure and will end up demotivated.

After all, one of my favorite mantras is “be impatient with actions but patient with results” which is somewhat in conflict with a challenge based on a result you can’t control.

I’m currently toying with the idea of setting up a similar challenge for myself and will write more about it once I’ve decided what exactly I want to do.

Creative practice doesn’t really arise from some unseen, divine inspiration that strikes an artist and that he or she subsequently carries out in creative work. Rather, art emerges from a negotiation between a creator, an initial vision or context, and a set of material limitations that help lead the idea from abstraction to concreteness. Creativity is always found under conditions. - Ian Bogost