In the daily grind, the brain regularly wonders how to get more sources of income. Other than buying the occasional lottery ticket and hoping for a moonshot, a common advice flung around ad nauseum is to monetise your hobby. There's good reasons for this advice. After all, if you love to do something and it is supposedly your "passion", isn't it great if you could make money from it at the same time? Then your job will no longer be a job. 

Of course things are a lot more complicated than that. If everyone could simply convert their hobbies into their regular and constant stream of income, we'll be seeing people do it left right and center. Not all hobbies have money generating potential, let alone be something that can earn you more than what the day job provides. Most will require a significantly high level of skill in order to generate decent returns (e.g. just because I enjoy football does not make me an English Premiere League level player).

It could be considered a bit sad, but when I am asked what is my hobby, I usually struggle to answer the question. I wouldn't consider crossdressing a hobby per say (it is a part of me), but I obsess about it a fair bit, I don't tire from doing it repeatedly and derive a lot of joy in doing it, which kind of makes it sound like a hobby. I've been asked more than once about monetising it, but I knew the the pressure to generate sellable products/services/content would lessen the enjoyment I derive from crossdressing. The only idea that I more seriously considered was monetising this blog via advertisements. Unfortunately after a 2 month wait following my application with Google Ads, Google decided my blog was of low quality content without bothering to provide any explanation why it was classified as such 😑. But oh well, it was worth the shot.

So if I really wanted to monetise my crossdressing "hobby", what were the possible avenues I could take it?

If I significantly improved my makeup skills, this could be a potential side business, although I'd likely have to undercut a lot of the existing makeup artists out there. It is an immensely competitive industry with low barriers to entry, and anyone with a bit of patience and willingness to pick up makeup won't want to seek out a makeup artist unless they're planning for a special shoot. When they do plan for a special photo-taking session, they'll want someone really skilled. There are amateur crossdressers who would be willing to meet a fellow crossdresser, and learn how to elevate their makeup skills in a safe space, but they also tend to be younger with lesser disposable income. Younger crossdressers are also a lot more daring nowadays, willing to come out to friends who could teach them makeup and provide the safe space to dress up, meaning that there isn't a strong need to engage special services to teach them how to transform into a woman.

Youtube and streaming platforms like Twitch, Bigo, etc, are probably a feasible source of side income. The internet allows the potential to reach a huge global audience beyond Singapore. With consistent, quality content pushed out regularly, it is possible to The scene is however, immensely crowded with everyone essentially shouting for attention (figuratively speaking). Another downside would be the need to put myself in the public domain, where everyone can see and hear me. With enough videos/streams out there, I think it wouldn't be too difficult to put two and two together to figure out who my male self is. Maybe at some point when I'm ready to come out I could do it. Or maybe not. I think my transformation from the male self to Isabelle is quite drastic, so it could make for a couple of interesting videos, but that is probably about it.