Part of the article may be outdated, as it has been published in 2015. Since 2016 PipsTycoon undertook major changes.
This is how the work algorithm is working now (update 6 Sept 2015):

step 1: you press work

step 2: system looks at your equity and at the market for products/rented products.

step 3: System asks for energy on the formula current energy+energy from highest item available, that you can afford to rent and that you do not have)

step 4: repeat. Usually it is enough, but sometimes you can afford a q1 house AND a q1 car for instance, in which case system first asks for 10 (q1 house), then for 15 (q1 house+q1 car).

step5: you can work.

 

Cases in which you can work with no problems:

  1. you have 25 energy or more (it may increase in time.
  2. you have all products rented or there are none available for you to rent
  3. there is no food available or you already eat.
  4. you are flat broke

in case you have 0 equity (or too little for anything), there is another filter:

  1. if you have game shares/company shares, system calculates their value and considers it as equity.
  2. if you have companies, it asks for 5 energy/company owned

if u do not have anything it calculates how much you earned in wages on last 5 days and calculates how much you could afford if you would kept half of the money. it then requires you to spend that half of money. This is done because many work, and then send the money to a “friend” then “claim” they have no money.