If you are just starting this, I suggest you start at The Introduction – Part 0. Alternatively, you can jump to Our Early Retirement Plan: Where We Are Now (Part 1), Our Early Retirement Plan: My Personal Income (Part 2), or Our Early Retirement Plan: My Wife’s Plan (Part 3).

In part 2, I explained how I can live a retired lifestyle even while I’m technically bringing in an income. In part 3, I detailed how my wife could retire early. Today, I’d like to go through some obstacles we have in attempting to retire early.

• Children and Rising Expenses – Right now we are DINKs (double income no kids). We hope to have children some day. Children aren’t cheap, and there’s a whole slew of costs with them that I haven’t even begun to explore. I know that day care is expensive. I hope to be a stay-at-home dad at least part of the time. That would reduce some expenses from the outset. Additionally, there are some options available to the military for day care.
• Education – With the aforementioned children, there’s going to be an education expense. This is one area where I don’t necessarily believe in frugality. I want to have enough money saved so that if our children can get into a great school, money won’t be a problem. My wife is of the opinion that the child should earn their way through college so they don’t become Lazy like dad. I think we can find a middle ground with this. Again, this is speculation since there are no kids at this point.
• Health Care – This is one of the biggest reasons why people can’t retire early. Fortunately, the military has a great plan that we’ll be eligible for called TriCare. We haven’t looked at the costs of this in detail, but I think it’ll be a cost-effective solution for us.
• Expensive Housing – Whether we choose to stay around San Francisco or move back to Boston, housing is not going to be cheap. This is going to be one of our biggest expenses. Though we could look to live in an area of lower cost of living, I’m partial to the two areas I mentioned because I know I can surround with smart people there. Besides the opportunities that brings, it would be good for potential children to also be surrounded by the same smart people.
• Other Uncertainties – I’m sure there are going to be other obstacles. Life pops up with surprises when you least expect it (of course they wouldn’t be surprises if you expected them).

These are some things that are hard to account for at this stage. Thus any plan that we make has to add quite a bit of padding