Tim Brown and Roger Martin provide a really nice description of how you might do this in their article “Design for Action.” In particular, the idea of throwing out multiple possible strategies and consciously debating them rather than incrementally working from strategies that are already in place is excellent.

Success leads to success. But here’s something that may surprise you. The size of the success doesn’t seem to matter very much. When you feel successful at something, even if it’s tiny, your confidence grows quickly, and your motivation increases to do that habit again and perform related behaviors. I call this success momentum. Surprisingly enough, this gets created by the frequency of your successes, not by the size. So with Tiny Habits you are shooting for a bunch of tiny successes done quickly. Not a big one that takes a long time.

At the heart of this book are the stories of dozens of people who changed careers. It analyzes their experiences through the lens of established psychological and behavioral theories. Based on the stories and extensive re- search in the social sciences, the book affirms the uncertainties of the career transition process and identifies its underlying principles. But it does not offer a ten-point plan for better transitioning, because that is not the nature of the process. Instead, it lays out a straightforward framework that describes what is really involved and some tried and proven unconventional strategies that will make the difference between staying stuck and moving on.

The book hinges on two disarmingly simple ideas. First, our working identity is not a hidden treasure waiting to be discovered at the very core of our inner being. Rather, it is made up of many possibilities: some tangible and concrete, defined by the things we do, the company we keep, and the stories we tell about our work and lives; others existing only in the realm of future potential and private dreams. Second, changing careers means changing our selves, reworking our identities. Since we are many selves, changing is not about swapping one identity for another but rather a transition process in which we reconfigure the full set of possibilities. These simple ideas alter everything we take for granted about finding a new career. They ask us to devote the greater part of our time and energy to action rather than reflection, to doing instead of planning. Hence, the unconventional strategies.

Transformation, then, happens less by grand design or careful strategy than by the small wins that result from ongoing practices that enhance our capacity to change.

As Jim’s experience illustrates, the experimental method does not necessarily entail an orderly sequence of steps in which one side project leads logically to a next. Instead, small probes are often fragmentary and spontaneous, driven by unexpected opportunities and dynamic situations. Jim’s wife got pregnant and Alaska was out. What next? A different kind of experiment. Like Ben and Carol, Jim went for variety in designing his experiments. But the trend is clear: Small wins may be scattered, but what counts is that together they amount to a sense of progress—away from the stifling situation we are trying to escape.