Before we meet I highly recommend that you gain a clear understanding of how much money is typically coming in, how much is going out, what assets you own, and what you owe. Just knowing this can be a huge relief.
Good news: there is an online tool, called Mint, that does a good job at helping you put together all this information. It will even send you a weekly report on how you are doing as well as allow for an up-to-the-second snapshot of your situation. There are other options too. You can see some of them in this comparison. I use Mint but there are also other good options out there. The main thing to know about Mint is that it is bankrolled by financial firms who pay Mint to promote their products through its recommendations. As long as you comparison shop for any financial services (don’t just take their recommendations!) you’ll be fine and it’s a good service.
For those concerned with their credit scores, there is a solid free tool called Credit Karma. Credit Karma does a good job at roughly predicting credit scores and how quickly they will change over time. It will show you your trends over time and also how different aspects of your credit score compare with the population as a whole. They also give you a report card with a grade in each category. For instance, I received an A in Open Credit Card Utilization since I only use about 10% of my available credit card limit in a given month but got a C for Average Age of Open Credit Lines since I am only at an average age of 7 years due to opening an account and closing an older one. Like Mint, Credit Karma appears to make their money from product placements/endorsements so, be careful and skeptical of their recommendations and don’t choose any without research and comparison.
Lastly, the credit score they project will not be quite the same as any of the three major bureaus (Transunion, Equifax, and Experian). Each of the big three uses proprietary methods to calculate your credit score. You can (and should!) obtain a copy of all the data (except the scores) listed in your credit report from each bureau once annually. You can make that request here. People who are very proactive about credit usually rotate the companies (request Transunion every January, Equifax every May, and Experian every September for instance) so that they can review and correct mistakes every 4 months. This isn’t necessary but sometimes the reports contain errors so it can certainly be beneficial.
I recently ran across a great NYT tool, The 1% More Savings Calculator. Play with it. It really helps show how much small changes in saving today can make an enormous difference down the road.
In addition to the tools above, here are some helpful books in case you want to read more:
Ramit Sethi has a very good book on money as well.
The canonical book on investing is Burton Malkiel’s A Random Walk Down Wall Street. It is a bit less practical but very interesting/intellectually fulfilling and the most important and forceful single argument in the the movement criticizing active mutual funds and the fees they charge.
Millionaire Next Door is a great book that looks at the lives of millionaires and shows that they usually aren’t opulent and part of why they are wealthy is that they tend to be practical and rather frugal.
Perhaps the best known-highest impact guy in the personal finance world is a radio show host named Dave Ramsey–his show is great! His main book is well regarded in the field.
Also very well-regarded in the field is John Boggle’s book on mutual fund investing. I am a big fan of his and curious to know what you think if you read it.