Should I convert my SGD to some form of USD as a safety nest for the exchange rate, for an expected overseas payment of USD100k by mid of 2020?

Thanks 😁

My viewpoint (which could be unique to me) is as such: As we don't know for sure how exchange rates will move, I usually tend to change my money in two batches, one closer to the date that I need the money, and one that is a bit further away, (e.g. 3-6 months before)

If the rates improve in 2020, I would at least be able to convert one future batch of funds at a better rate. A consolation there.

If the rates worsen in 2020, I would at least have converted one batch of funds at a better rate. Like wise, some consolation at least.

If the rates stay the same....then all is well.

It's a psychological thing, but it works for me.