OK, OK – just being somewhat rhetorical; but also I’d suggest re-visiting your retirement plans. Your life has changed as has your work — perhaps that’s the reason that you’re procrastinating doing the retirement planning?

Dave Ramsey has great advice and is always right!

Cloth diapers will save you a ton. It took me one child to realize this, but with my last 2 kids I’m on board. For cloth diaper saving tips, check my blog.

After reading about where you started, I feel as though you have accomplished so much in such a short time that the matters you describe here are just predictable spin-offs.

BTW, on the taxes: Could you have sent money in to the IRS each quarter based on the unexpected revenue, even if you hadn’t made an estimate at the time you calculated your 2007?

I don’t understand — have never understood — where the IRS imagines a freelance gets a crystal ball. From year to year I have no idea what my freelance work will earn. Some years it’s so little it’s barely taxable; others it’s fairly substantial. There’s no way to know until a client walks in the door. Wouldn’t it make sense that if you got a $20,000 commission you could simply send 28% of it to the IRS the minute the client’s check cleared the bank? You’d probably overpay, but better that than to get hit with a penalty.

Why not take your earnings from this site, and invest in a couple of other writers to contribute with different ideas every couple days so if you need to take a break and spend time with your family, you can do so without feeling like you’re letting down your readers by not having great new content?
Rather than take the time to write yourself, wouldn’t it be better for everyone if you found a few like minded people that would be willing to post high quality posts for you?
How about using the time you saved to make this just be a starting point, so you can help out a lot more people and focus on a different audience. By automating this one by hiring writers, you can maybe have this site more specifically for saving, and then you can start a new site related to investing.

If you wrote a page every day, you’d have a 365 paged novel by the end of the year…
But, if every day you found someone new to write a page for you every day, at the end of the year, you would have enough posters where you’d have 365 pages every single day, or 365 365 paged books every year.
Now that’s not a reccomendation to get that many people writing on this site, but I’m sure since you’re retired now, you could grow 50 sites each with a couple writers on it within a couple years.
That’s more income for you, for all of your writers, and more money in all of your readers pocket, or at least they’ll have help with some need that you can address.

Look, you already know that you can save people thousands of dollars, but by not increasing your ability to reach more people, you’re costing the people that you don’t reach thousands of dollars!
If you can reach out to an extra 1,000 people with your time, You’re saving a combined amount of millions if they take your advice!
Maybe create a professional information product, and put it on clickbank. You will have affiliates making money from selling it, while having your affiliates reach your materials out to MORE people, and your message of saving will be much more inspirational, to many more people.

1. You found you could afford the difference, even with your quiting your 9-5 job.

2. You had a healthy baby.

3. You’re set for the next child, and did it really cost all that much?

4.& 5. You didn’t know how successful the blog would grow.

6.,7., & 8. Okay, here you had good room for improvement :-)

Could you elaborate on your 30 year mortgage regret? Buying a house is one of the biggest financial decisions most of us face (and I would realy love to see your point of view).

I lean towards longer term, but paying back early, even if that means a slightly higher interest rate. I feel it gives a level of financial security should I lose my job. I say this because I am in a job where I have to show up every day to get paid and have no passive income (yes, I should get on top of that). I strongly hesitate to use the words “passive income” when talking about your wonderful blog. You did well organizing your site to sustain some level of passive income (although your continued input continues to draw more people and retain the rest).

Are you writing from the perspective that TSD has provided additional revenue and will continue to provide a steady, if not growing revenue? And with the knowledge that TSD will continue to produce revenue affords you an additional level of financial security?

This is a nice list, but don’t all of these regrets pale in comparison to where you were just 2 shorts years ago. Well done, best wishes.

-CBus

Thanks for sharing, great list. If these are the worst mistakes that you make then you will just fine.

Er, uhm… a 15-yr mortgage has been paid off for 5 years by that time, so you’ll be really happy that there is no mortgage :-)

While the rest of your points I can see as “regrets” – never regret hard work and making sure your ducks are in a row before moving forward.

Congrats!

Have you looked into refinancing into a 15-year mortgage, or was your comment more along the lines of rates being universally higher now compared to when you got your 30-year mortgage?

I would love to see a breakdown of the savings you might see for refinancing in today’s market. I’ve considered it but I don’t really know at what point a (lower rate at reputable bank + fees + effort) > (current rate).