Merchant of the Skies

Technically this isn’t missable but it’s far easier to do at the beginning as, otherwise, running yourself out of cash is painful and low reward (if this is you case just start a new game in another slot, sail until you run out of energy and need a tow, pay for it, keep doing it until you bankrupt).

You can also do this at the end of the week right before payday, at the beginning you can spend yourself down to around 2g right before. But payday only costs around 25-30g early on so you’ll have to make a point of doing it. Sailing until you’re close to an island but will need a tow is probably easier. Tow cost is based on distance so the closer you are the more of the “emergency bailout” you’ll have to get back on track.

Make sure you have a hold full of sellable items to make this easier after. You only get one bailout before you lose (or so the game
claims) so be careful not to bankrupt a second time. Your loan is for 1000 gold so it can be helpful early on.

Anyway, as soon as this happens the game alerts you about it and the consequences and the achievement pops.

This Achievement can be easily done at any time by depositing all your gold into the bank on the west end of the map and letting the week end. Your weekly pay will be taken out of your investment and the achievement will pop.