I advocate making excruciatingly detailed plans for projects, studios, and the like, using databases, diagrams, and lists aplenty. Yet I also advocate going with your gut when evaluating work, and following your creativity. After all, what's life if you don't take some risks?
Some people plan much of their lives in advance. That is a necessity for those who wish to pursue professions such as medicine or law, which require the fulfillment of a very specific sequence of achievements, concluding with the granting of a license to practice the chosen profession on a willing yet unsuspecting public. Such people move straight from high school into the prescribed, step-by-step process of obtaining their license. They commit much time and money to their pursuit, and their path is yet further determined by their need to repay student loans.
There are good things to be said for this approach. For one, a person does not have to expend thought and energy sorting through what one wants to do; that much is established. This minimizes distraction and maximizes focus, which is requisite for leaping the substantial hurdles of these paths. Another positive is that these professions tend to increase an individual's opportunities for achieving financial success.
The opposite extreme can be seen by looking at those people who move from one path to another depending on which way the wind blows them. Those individuals are not always drifters, either; some of them are bright and motivated but find that their interests are turned by tides of history and circumstance.
The advantages to this way of living are that one often acquires a broad perspective and a variety of skills. If you have been a sailor, a stockbroker, a cheesemaker, and an orchestra manager, you have experienced more points of view than most people do. Eventually, a person may settle into one path and pursue it with a frame of reference that is far more broad than those held by others in the field. In fact, such broad experiences could well lead a person to make some great breakthrough in his or her field. Conversely, he or she might keep moving from business to business, and never put down roots in any particular field.
In my life, I have fallen somewhere in the middle of those two extremes. When I was a teenager, I discovered that I had an intense interest in music. Shortly thereafter I discovered what would become my entrée into audio: synthesizers. The strength of my attraction to music acted as a focusing influence akin to, but not as rigid and formalized as, a decision to pursue law or medicine.
At the same time, I've tended to follow interesting opportunities that have presented themselves until they ceased to be interesting, at which point I would strike out in another direction. Through luck and skill, I have never lacked for interesting opportunities, but I have sometimes felt that I was doing little more than drifting.
The part that always struck me as curious was how often my career appeared to be following a logical and well-timed path. So many times I have answered a knock at the door and found myself in the middle of a situation that was just coming into fruition. Interestingly, in hindsight, I seem to have had clear vision all along the way. If I did have such vision, I was not aware of it at the time. Regardless, after some years of this, I have come to believe in myself, which has served me well more often than not.
The moral of this discourse is that each person is ultimately responsible for finding his or her own path in his or her own way, and it is best to be unafraid to do so. If you are someone that flourishes only in structured situations, observe, embrace, and pursue that. Strive for balance, yes, but don't fight your nature. If you are simply unable to lock yourself into one direction, figure a way to make that work, perhaps by freelancing in a few different areas.
Examining one's direction should be an ongoing effort, and questioning oneself helps avoid becoming close-minded and stuck in a rut. Self-evaluation and self-doubt, however, need not go hand in hand.