No matter what your goals are, no matter what your financial situation is, some obstacle (or obstacles) sits in your way. To get started, here are my biggest obstacles:

Time I have two successful side businesses right now in addition to my main job. Along with time I set aside to spend with my family, this leaves very little free time for unwinding - and, no, multitasking my writing with watching a baseball game is not really unwinding.

Inadequate side business income I would like to quit my “main” job and focus on my side businesses, but the income from them is too inconsistent as of yet to leave me feeling comfortable doing this.

Significant debt load Combining my home loan and my student loans, my debt load is a lot higher than I’m comfortable with. I don’t have a problem with debt in general, but the size of the debt is immense and feels as though it’s in the way of real financial progress for me.

These are easily the three biggest obstacles in my financial life. These are the things keeping me from building our family’s dream home in the country (for those wondering, it’s very similar to our current house, but wheelchair accessible, on a single floor, surrounded on two to three sides by trees, and far enough in the sticks that we can’t see another house) and keeping me from spending lazy afternoons writing and reading in a writing office with a big glass window overlooking some trees.

I realize what the obstacles are, and I know what I need to do to tackle them. Here’s the game plan for tackling each one.

Practice better time management. I find that when I’m really “in the zone” with GTD, I get a lot more productive. What I do is keep a little notebook in my pocket at all times that functions similarly to the “hipster PDA”. Whenever I have an idea or a task that needs to be followed up on, I write it clearly on a single page with whatever sub-notes I need, then I jump onto the next page. Each evening, I process these ideas and tasks. When I get in a flow of doing this, usually during periods where there is less interruption to my daily routine, I get a lot more done and thus feel less crunched for time.

Focus on maximizing one side business over another. Using this approach, I’m moving from my main job being my primary income stream to one of my side businesses being the primary income stream. Then, I can quit my job (as it’s now a secondary income stream with outrageous and inflexible time requirements) and focus on the side businesses.

Commit to strong debt repayment. Right now, my overall income is far above my monthly spending, so I’m using a portion of that to invest. The rest is going to debt repayment - I want to watch those debts go away, and quickly.

What can you do? Spend a few minutes thinking about the primary obstacles in your life that are keeping you from reaching your financial dreams. They can be anything, from not enough time to too many distractions to situations you just don’t want to face.

Then, consider a plan of attack for each of these obstacles. What can you start doing right now that will move you past that obstacle, or at least start significantly chipping away at it?

Many people start planning without the goal in mind. Starting with the goals is sometimes much more powerful.