Real or physical obstacles, including money issues, are fairly straightforward and usually can be dealt with using one of the strategies posted on the 20th of last month in Real Change Step 2: Finding Resources.
Mental roadblocks on the other hand, are often far more challenging, typically because there is no readily apparent outside solution. Overcoming mental roadblocks requires one of two things: a very powerful mindset (which I could write an entire book about) OR a very simple tool pirated from the business world (which I can teach you right here).
All mental roadblocks can be stated as a belief you hold.
"I am afraid I might fail."
"I'm too old to start something new."
"I can't think of anything of value I have to offer anyone."
The simple tool is a version of the well-known "Cost-Benefit Analysis," only flipped around to become the "Benefit-Cost Analysis."
For any belief you hold, write down the Benefits. For example, the Benefits of being afraid to fail are: I don't have to worry about embarrassing myself, I get to stay safe, I get to stay comfortable, I won't lose anything, and so on.
Then list the Costs: I continue to disappoint myself, I disappoint others, I will never realize my dreams, I won't impact the world the way I would like to, I won't be recognized and admired the way I would like, I may be missing my best chance at happiness, and so on.
Now, make your choice. It is easy to weigh the impact of the belief and decide whether the Benefits outweigh the Costs. If so, stay with the thought. It serves you well. However, once you decide that holding onto that belief is simply too costly, you can actually remove it from your mental inventory forever. If it comes back, do the analysis again.
Believe it or not, you can apply the Benefit-Cost Analysis to any decision you are weighing in your head. Once you master it, you will be able to rapidly move past any mental obstacle that gets in the way of achieving real change.