You basically had three separate questions:
- … do you decide to stop moonlighting and embark on your new path full-time?
- when and how do you decide to stop moonlighting and embark on your new path full-time?
- how should you make the switch?
Let’s take them one by one.
… do you decide to stop moonlighting and embark on your new path full-time?
Who says that you need to stop moonlighting and embark on your new path full-time? That is not a necessary condition of moonlighting.
Also, that depends totally on the kind of work you are doing in your moonlighting endeavors. If it is a creative passion you are pursuing (e.g. writing, painting, music, photography), you can pursue it on the side. For example, here’s a list of writers who managed to pursue writing along with their day jobs. There are more examples from India: Arnab Ray (scientist-cum-blogger-cum-author), Deborshi Barat (lawyer-cum-writer), Ravi Subramanian (banker-cum-author). The reason for holding on to your day job may be manifold: purely economic, for stability, for feeding another side of you etc. The need for self-discipline is super high of course in such a dual career. But then, self-discipline is also required for sustaining any creative pursuit over a lifetime.
[Aside: Speaking of discipline, here’s one fictional author who does not seem to have any discipline whatsoever]
However if your aim is to start a business (some technology you are developing that would require your full attention, or even transforming your creative pursuit to something that can sustain you economically), then one must think about making the switch. Which brings us to the next question.
when and how do you decide to stop moonlighting and embark on your new path full-time?
There is no one answer for this. Also it depends a lot on your line of moonlighting work. Also depends on the stage of life, and the amount of risk you are willing to take. Some people make the switch once they have made a mark in their moonlighting career. Some people make the jump directly. Some examples:
- Writers: [Moonlighting option] Publish a best-seller. Generate enough money to write the next book. Example: Chetan Bhagat. [Non-moonlighting option] Opt out of campus placement in a leading management college. Take up writing full-time and go on from there. Example: Rashmi Bansal
- Tech entrepreneurs: [Moonlighting option] Develop a fantastic website that starts generating money. Quit your day job when you are sure that you can sustain yourself. Example: Chandoo [Non-moonlighting option] Drop out of college, and create one of the world’s largest tech companies. Example: Steve Jobs.
- Photographers: Get enough confidence about your photographic excellence through tens of thousands of Facebook LIKE-s and Flickr comments. Do a few gigs for money and rank in some national competitions. Quit job after you decide that you can sustain yourself. Example: Devendra Purbiya.
In summary: When and how do you decide? Many a times, it is based on sound economic and rational thinking after gaining significant moonlighting experience. For some, it is purely emotional.
how should you make the switch?
Once you are well on your way in your moonlighting career, I think the answer becomes evident on how you can make the switch. Again, the specifics of this depends a lot on what field you want to moonlight in.
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