Over the weekend, I had the pleasure of helping out¹ a reader with difficulties implementing OmniFocus and Moneywell with the hurdles that he had in his path. In the advice that I shared, the thing that I tend to tell people (especially when people ask about OmniFocus) is that apps like OmniFocus and Moneywell aren't just apps — they are interfaces to a system. With OmniFocus you have it interfacing the GTD system² and Moneywell interfacing Dave Ramsey's Envelope System.

So while it is possible for somebody to pick up these apps and to use them with great success without prior knowledge of the systems, I feel the best way to start using apps like OmniFocus and Moneywell to better your chances of having beneficial long term effects is that you should understand the system first. Understand what start dates are for. Understand why you use different envelopes when budgeting. Once you not only understand the concepts, but also accept its uses, then that is one less hurdle to jump over. It's a matter of learning the app and its integration with the system.

Of course, like most systems out there, systems usually are implemented on the lifestyle-level. Systems aren't something that you "turn on" when its time to be in that mode. You should try to acclimate it into every part of your life as much as possible. If you're anything like me, that is the only way to guarantee consistency in receiving the benefits these systems provide.

Lifestyle Changes

I remember having a discussion with a couple buddies of mine about the Paleo diet, and a question surfaced whether there are cheat days. My knowledgable buddy said "No. This isn't just a diet, it's a lifestyle". As soon as I heard that, I was overwhelmed. As I thought about it, for somebody to go full fledge on this diet, you do have to change your lifestyle. The same can be said about any kind of "productivity" system and finance system.

Of course, being a member of this category myself, you've might've failed a few diets in your life. A lot of times I've become excited about changing my lifestyle with different systems and/or mindsets in which I would go "all in". However I would fail to realize what "all in" entailed until I the moment came where I wanted to take a time out from this change and return to "normal" for a few minutes.

My mistake was that "all in" was too much for me. "All in" is a complete lifestyle change and I needed to wean myself away from what was normal. On a financial sense, that means I had to wean myself from the impulsive spending that I was used to ever since I had first started working at the age of 16. That's a lot of years of seemingly hard-coded personality traits and habits to separate from. So I found it best for me to start "simple".

Start Simple

There are a lot of resources out there about power-tips for OmniFocus/GTD, finances, etc. Sometimes you might even find some here. But honestly, for anyone just starting out — ignore these tips at all costs. I know — the inner geek in us wants to power our way through and automate everything. But if you have no reason to tweak your system and you're just starting out, then you're just tinkering with something that hasn't been established.

OmniFocus

• Start slow.
• Take out a piece of paper
• List everything going on in your life. Although David Allen says to spend a great deal of time dumping all of this out, I say stop after a 15 minutes. You can always return later.
• Pick out what's a project and what's a task. Put one-off tasks in a special "One Off Tasks" Project. Name it whatever you like.
• Create projects for all the other projects.
• List out all the steps that you can think of for the individual projects. Don't spend too much time.
• Enter into OmniFocus. "One Off Tasks" will be a Single Action List, and other projects will just be regular parallel projects.

Now take a look at what you have, that's your basic backbone for OmniFocus/GTD. If this is your first time doing this, I'll tell you it's not perfect. But perfect isn't the point right now. Be simple. Don't worry about perspectives and all that — that can come later. If you're working in iOS only, then forget about Perspectives all together until the day when/if you get a Mac.

Moneywell

• Start slow.
• Take out a piece of paper
• List out the general areas where you spend your money. Don't spend too much time.
• Group them together
• Decide how much money you want to spend every week/2 weeks/month/etc. on these areas.
• Enter into Moneywell.

Now you have your backbone for Moneywell. Don't worry about the Spending Plan, scheduled payments, or bucket transferring yet. If you're working iOS only, don't bother with learning the Spending Plan.

While beginners really shouldn't follow those instructions to a T, as I glanced over a lot of the descriptions, the point to get out of this is don't worry about setting up your backbone perfectly. Because you won't. Set it up simple and acknowledge that it isn't perfect. Acknowledge that there's room to improve and be eager to find and implement those improvements.

The reason I suggest not to spend too much time on planning is because since this is a lifestyle change, you also have to learn and develop the mindset. If you spend all your time setting up something when you're new at it, you may end up building a monument of inexperienced data. A tower that is bound to crumble. Start with small huts of data before you build your Burj Khalifa.

Use The Damn Thing:

Now that you have the backbones for your systems, you can now do what you've been wanting to do this whole time. Use the apps!

As you use apps like OmniFocus and Moneywell, your first few months of using it will be similar to field testing. The only way you can learn what changes you need to make is to live it first — use it in the wild. As for me, you'll soon realize that you accidentally entered in a lot of projects as one-off tasks. Or maybe you realize that you overgeneralized a bucket in Moneywell. Now you have your data in terms of changes to make.

Tweak As You Go

The more you use these apps, the more tweaks you will find you that you need to make. What you're doing is honing your system. As you hone your system, you actually improve the experience of the apps themselves. The difference from tweaking through experience than tweaking via power-tips and tricks as a beginner is that with the former, you actually understand why you're changing it. The more you use the apps and its associated systems, the more these power-tips will actually make sense. You then have my permission to go as crazy-automated-super-power-user as you want.

So just remember — start slow; build simple; tweak as you go. That's the secret to implementing apps like OmniFocus and Moneywell.

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