Ever since I lost my Quicken data on my PC, I’ve been searching for a viable financial planning alternative on my Mac. I started with Mint.com, a free financial planning tool in the “cloud”, which offers some fun new features like bill pay reminders and overspending email notices, but it is still a bit amateur compared to Quicken’s capabilities, especially in its ability to customize categories and run reports. So my financial advisor, who uses Fidelity as a custodian, suggested I try Fidelity’s Fullview product, another online tool that pulls data from a set of online accounts and allows for categorization and reporting of transactions. It did allow me to do some category customization, but the interface was not exactly what I liked. But then an entire billing cycle of one of my credit cards (at least 100 transactions) mysteriously disappeared after I’d gone through and categorized all of them. The help desk said they’d try to retrieve it but it would be a couple of weeks. I lost patience and trust and have since been exploring alternatives: going back to Mint.com and losing some flexibility, moving to something new like Money Guide Pro (another option to integrate investment performance reports with budgeting) or waiting for Quicken for the Mac to be released this month and seeing what it has to offer.

I spent an hour today looking at the alternatives and I’m more frustrated than ever. I admit, I’m still a little pissed about losing all of my PC Quicken data of 1996-2009, but more importantly, I just can’t let go of some of the basic functionality I came to know and love and some other functionality I think is reasonable to want…

1. I really want my customized categories back. Why? I’ve categorized expenses for the same way for the last fourteen years and I’d like the reporting to be consistent.
2. I need an easy way to categorize my business expenses and run a report to generate my expense report. I have a process to categorize those expenses, report on them for my expense report and then exclude them from my spending reports.
3. I want to follow my investments in the same place, ideally in a way that my financial advisor and I can review the progress together.

Quicken for the PC did all these things, with the exception of #3. So it seems logical to me that I can find another program to run on my Mac or in the cloud to do the same. After fourteen years of basically the same functionality, I don’t see why I should have to change. And then I realized … I am the reason that systems in large companies can’t be killed off! I’m one of those “power users” who insist their processes are so effective they shouldn’t be changed by technology.

But what’s interesting is that in my investigation of Mint.com’s supposed missing feature, I realized through some discussion threads there is some reasoning for the standard categories: It makes it a lot easier for them to categorize transactions automatically and run comparison data with other users. Automatic categorization and ongoing benchmarking are arguably better features than category customization. Additionally, Mint.com also has a way to tag business expenses without using a separate category, which could make expense reporting and exclusion from spending analyses even easier. They don’t seem to have much on the investment front, but there really isn’t a reason those two systems have to be tied together. I can still see the full picture, even if I can’t get all the details of the activity within.

If I hired a consultant to come in and run a software selection for me, they would likely advise me to let go of my hangups and use the free product that is likely to make me happier in the long run. They would tell me that it won’t work exactly like I’m used to, but that by moving to something more standard on the cloud, I’m going to get better overall features in the long run. So, I’m going to swallow my own medicine and give Mint.com a try. If I just can’t take it, I’ll see what Quicken releases for the Mac… more soon.