1) Open a business checking account.
I intend to do this so that I am forced to save more by actually cutting myself a "paycheck" twice a month. All of my money, besides monetary gifts of less than $100, will be deposited into this account. When it's time to pay bills (my rent at the first and other bills on the 15th), I will tally up exactly what I need and transfer that amount to my personal checking. Any business related expenses will come directly from this account. Quarterly, I will check how much I've saved and see what possible business related purchases I should make. If there are none, I plan on investing 50% of the saved amount. I don't want to invest it all and have no cash for a rainy day, and I don't want to have it all sitting in my checking gathering dust.
So this innately is a simple thing to accomplish. Open a bank account. That, I did.
I have been able to cut myself a paycheck for a while now. I didn't open a business account, just a basic checking account. I use the debit card to make tax deductible purchases. I transfer a set amount of money twice a month. All very simple and easy.
The other half of my task has been much harder. Making business related purchases to offset my tax bill hasn't happened at all. And there has been absolutely no saving of any money whatsoever. With vacation and random downtime I haven't had that much extra income. Plus, what is left over goes to paying the previous year's tax bill. So I have nothing saved for this year's tax bill or for a rainy day.
These issues can be called a cash flow problem. Because my money comes in various amounts at various times, it is hard to understand what my income actually is and what I should pay when. Plus like most people, when times are tough, I often want to stick my head in the sand and hope the problem goes away. Not actually helpful.
I aim to have a monthly check-in - where I pay bills, reconcile my bank statements, and assess my progress on my financial goals. I do most of these things on a regular basis, just not at a set time. I do it approximately monthly or every other month. I think monthly is best. Bank statements do only come once a month. The one thing I don't do at all is assessing goal progress. If I don't know where I am supposed to be each month, it is easy to leave it to the last minute, like saving for my taxes.
Now before anyone suggests it, I have tried Mint to keep track of these things. According to Mint, my money in is a good amount less than my money out, so that demotivates me. This inequality is caused by Mint not recognizing my deposits as income. Since my income is random, I can't set-up Mint to see certain checks as income. There's a lot of maintenance that I don't care to do.
Anyways, consider this the plan: First Saturday in every month (starting this Saturday) will be money day. I need to establish goals for the year, and monthly progress goals for each one. Also on this day, bills will be paid and statements will be reconciled.
Fingers crossed.