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We recognize that we need to pad our emergency fund, and maybe cut back so that we are living on less, though. This will help up be better prepared.
If the blogging doesn't work out then you shouldn't have any problem going back into the work force at the same wage you are making now or more.
Do it!
I think it's great that you are looking to jump into a self-employed status. Here's one thing that I would recommend to help reduce risk:
"Make sure you have multiple streams of revenue"
This is key. For instance, if a regular employee lost his or her day job, they would be in a worse situation than you possibly having a bad month running your online ventures. Just make sure you have multiple streams of revenue from multiple online ventures. I don't know exactly what websites you run, but you will most likely want to expand them and create new blogs or websites. Then if one completely fails, you can rely on others. Also if one big advertiser cancels a contract, you will have many others to help lighten the load.
If you do that, you shouldn't need to worry at all. Courage isn't the lack of fear, it's just facing fear head on and not letting it overtake you. You can do it!
I also keep a big savings cushion, not just for emergencies but also to take advantage of any good sale on the stuff that I need. (Frugality and a healthy stockpile can help you weather plenty of lean times.) I save up for major purchases and then sit on that money some more until a good deal pops up. I have no debt, pay my credit card bill in full every month, and avoid payment plans since they'd undermine my flexibility.
One thing you might want to watch out for is the lifestyle inflation when you've just got yourself a big paycheck - like the article said, you can't maintain the utopian view that things will forever be as good as they are now.
First, if your monthly expenses are $1000 ( nice round number) and you know that your online ventures can generate $500, you can generate $500/month with interest, dividends, rental real estate.
A popular method for short term budgeting is using CD ladders. If buy a $10,000 one year CD yielding 5% every month for one year you will have achieved the extra 500 in monthly income..
When I look at investment income versus work income I see how much money I need to save and invest before I could live off my investments..
1. Need to have at least enough income to pay your expenses coming in on a predictable basis.
2. Need to have purchased your own health, disability and life insurance coverage.
3. You have saved up enough "cushion" to get you through the lean months.
4. You have qualified for a HELOC on a personal residence if you own one, or are not planning on purchasing a house for over 3 years.
5. You're absolutely sure that's what you want to do.
Good luck!