Wikipedia defines collaboration as 'working together to achieve a goal.' Collaborative activity involves a number of people (if you're working on your own you're not collaborating) engaged in co-ordinated activity to achieve an agreed objective.
So why collaborate?
Collaboration can be fun in its own right and producing something worthwhile with your friends or colleagues can be immensely satisfying.
When working on your own, neuroses, insecurities and fear may become your worst enemies. Unfortunately, you have to do everything yourself, even the boring bits.
Some tasks are too big or complicated to achieve on your own, especially when you are working with a limited timescale.
Of course, if collaboration was simple, everybody would be doing it. However it's not common for people to collaborate outside the workplace. This is because there are a number of blocking factors that may prevent people from collaborating. Some of these factors are listed here:
Your big fat ego. This is the part of yourself that does everything for the wrong reasons and attacks people when they don't fall into line with your expectations.
Your neuroses, insecurities and fear. When you collaborate you may project these onto other people and see your own worst self in someone else.
Power games. Often a collaborative group will be dominated by whoever is playing the power card. This may be ego driven, or may be a genuine attempt to bring order to a chaotic situation. There's nothing wrong with good leadership as long as it is asked for and not forced onto people. A good leader brings out the best in themselves and other people. Some groups can operate without leaders, others require leadership, every situation is different.
Issues of trust. People may not trust collaborators to take responsibility for their own actions, to do their fair share of the work, to treat each other with respect, to work hard or to be honest. These may all be valid issues, and trust may have to be earned. An interesting phenomenon to think about, though, is that to mistrust people causes them to behave in an untrustworthy manner (if they're a certain kind of person). This is a kind of projection. It's worth noting also that you can't necessarily expect people to work hard, especially if they're not getting paid. Look at what people ARE doing, rather than focussing on what they aren't doing. It is hard to deal with people who abuse your trust though, and it's worth testing people out with something small before you get involved in collaborating on a large scale project.
Poor time management. Time management doesn't necessarily mean working to fixed hours or to a fixed schedule, but it does mean ensuring that tasks are completed in a timely manner and dependencies (where someone is relying on you to finish something before they can do their bit) should be taken seriously.
Expecting people to take an equal share in the work or to work just as hard as you. Some people have lots of time to spare, some people less so. Some people are specialists, some are foot soldiers, some people are just helping out with their contacts or their name. Some people are fun to be around but just plain lazy. Some people are doing something, but it's hard to understand what, until they're gone. Everyone has different requirements and commitments.
Not listening. If you don't listen to each other then you can't co-ordinate your activites, develop a collective vision, maintain group morale or provide each other with feedback. Contrary to the popular myths, some people can actually speak and listen at the same time. If you want to ensure that someone is listening to you, ask them to repeat what you have just said back to you in their own words. Sometimes you don't have to listen. It's useful to make sure what you have to say is interesting, relevant, positive and well thought out if you expect people to listen.
Being uncooperative. Some people are uncooperative because they are playing power games. Others because they don't understand what they are doing. Sometimes it's hard to tell the difference. Some people dislike being told what to do, others don't like telling people what to do. Some people say they'll do something and then don't. It is important to understand a person's motivations for being uncooperative before tackling the situation. Ensure that it is not in fact YOU that is being uncooperative (see point 2) How to deal with uncooperative people is an essay in its own right, so I won't go into too much detail here.
Abusive behaviour. Contrary to proper myth, being verbally abusive can help to achieve some objectives (some people, eg. the police, the army or slum landlords would argue that physical abuse is also a powerful technique for getting things done). However many people don't respond well to being abused, and it's worth bearing this in mind. Ideally one should have some other outlet for one's frustrations. There is a difference between being abusive in a jocular or comedic way to really meaning it. Some people have trouble telling the difference, and in these situations it is best to err on the side of caution. For example, 'Jesus, pull your finger out, stop talking about it and maybe actually do something for a change you lazy fucking idiot' may be seen as motivational to one person and as a deal-breaker to someone else.
Poor project management. Once you have set your objective, you have to make it happen. Some people need to be constantly motivated beyond this point (which can be tiring). Others don't like to follow plans, other still don't like to be managed. Ideally the entire group collaborates to manage the project. In industry project management is sometimes considered to be a dirty concept, arrogant pencil pushers pushing people who they see as tools to do things they'd never do if they weren't getting paid. There is more than a grain of truth in this.
Again, project management is a topic in its own right, but in a nutshell, you can break your plan down into activities, roles and resources, assign items to timescales and then track progress through observation and by obtaining constant feedback. People tend not to accept being managed, so it is better to encourage them to manage their own timescales, set their own objectives and requisition assets and resources themselves as they see fit. Don't be upset if they don't do this, fully actualised people are few and far between and they're often too busy to spend time collaborating on other people's projects. There is usually an initial resistance to implementing project management protocols, but if they're creative, useful and easy to implement, then once they are finally adopted, you'll never go back to being disorganised and confused ever again.
Not understanding your motivations. If you don't clearly understand why you are doing something it makes it more difficult to get it done. It is important to understand the motivations of the people you are collaborating with too.
Not connecting the idea of wanting to do something with the actuality of doing it. There's a jump involved here that is a little daunting for the uninitiated.
Losing motivation early in the project. Before you see things starting to happen it's easy to give up. Sometimes this is OK, for example if it turns out that what you wanted to do isn't really what you wanted to do. Don't be angry if some of the people you are working with give up. If you want to continue, spread their workload around the rest of the group and then look for a new collaborator.
Not having a clearly defined objective or goal. You can't collaborate if you don't know why you're collaborating or what it is you're supposed to be doing. A goal can be based on an external requirement or may meet an internal need, say to innovate or to create something new and unusual. A goal may or may not be negotiated between the team, sometimes the goal is provided by a client or 'thought leader', sometimes the team is formed around an existing goal or objective, and sometimes the team forms first then generates objectives internally. Once the objective is negotiated, the next step is to formulate a plan of action, recursively break down the plan into easily achievable steps, set a timescale and milestones, define responsibilites and dependencies, and assign tasks and roles. Sometimes objectives are fixed once the project is underway (waterfall model) and sometimes objectives can shift as new infomation appears, or as the environment changes (iterative model).
Lying. Don't do it. Be honest. White lies are okay if you're dealing with someone who is hypersensitive, easily confused or a liar.