Keep all of your receipts for at least a few years in case you want to check something with them – either virtual or physical in one place and have things categorized by institution or bill payee, by account and then by time period, usually monthly or quarterly and then by year. Keep the related items together. For example, you can have a utilities folder and then have a subfolder for water, heat, hydro, rent, Rogers, Bell, etc. You can have an investments folder and then have each institution where you have money invested, followed by the account and then by month and year. For a business, you can have a revenues folder and then an expenses folder and have subfolders by types of revenue and types of expenses. There would be a folder for tax returns, CRA correspondence, CRA payments etc. Keep related documents close at hand as well, such as a deed for your house, rental agreement, car lease agreement, mortgage agreement and insurance contracts. You will likely have a physical and a virtual set of folders which is okay – the same setup would apply. It can be a box, filing cabinet, set of folders, an app, a USB stick, a cloud folder, or an external hard drive. The key is to have the documents in one place and in some kind of order so you can retrieve something easily without searching through everything. Items can be stored on the cloud, but I recommend having a duplicate version somewhere within your reach. Statements stored by institutions tend to get wiped out after 6 months to 2 years and retrieving them beyond these time periods is either not possible, or time consuming and expensive. I would download material from the cloud as it comes in and store either on a hard drive, USB stick or in paper form.