Before I get into the long story, I just want to summarize by stating I am looking for tips on how to best avoid tax issues, make things easier on myself, and not reinvent the wheel. I started a web design company as a side business back in 2006 and made good money to help with the costs of having a family, since then I am still the only employee but last year I suddenly went from not having a major profit to suddenly having a net income from my business of $60,000 in addition to my normal day job. Now most people would say "man I wish that was me!" but here's the issue. I know my business and I'm good at it, however handling the finances correctly and understanding the taxes due, not so much. My invoicing is usually done via excel, payments via PayPal or check, and the only record keeping is from the automated recurring billing system, quick mileage notes for client meetings, and PayPal exports at the end of the year. As you can tell I'm not making things easier on myself. Now with the sudden jump in income I find that I owe around $12,000 in taxes (I didn't know that I should have been doing estimated tax payments) and have no money from business. I've come to my senses and realized this is not how I should be doing things. So far I've come up with this plan for 2013 to try and make sure this doesn't happen again: 1. Get a better bookkeeping method. 2. Do estimated tax payments 3. Make wage payments to myself and keep business money as business money otherwise. My main problem is constantly using my business income to support my family. 4. Possibly get some training on managing my business better. 5. Don't make these mistakes again What are your guys recommendations for a bookkeeping system for this type of business? Should I be using QuickBooks and creating invoices from it? Is paying yourself the best way to go about this? Are there any other recommendations you would give me?