Investing and taxes are two topics that can seem complex at first, but the more you learn, the more straightforward they become. I was an Accounting undergrad (although I never went into the field), so I’ve been into taxes for a long time. Investing is something I started learning as a teen, and now at 38 I’m comfortable with my strategy.
I do remember in the early investing days, being so confused by the sheer amount of information available out there. On this page, I’m sharing everything I’ve written on investing and taxes. No worries about getting overly technical – I talk about investing in a straightforward, conversational way. Plus I’ll direct you to the best resources I’ve found to start your investing and tax learning journey.
All About Investing And Taxes
Bitcoin – Chasing Bubbles
Ever heard of the Dutch tulip craze? We saw something like that with Bitcoin. You can also point to tech stocks in the late 90’s, housing prices in the mid-2000’s, and any number of other events. Check here for more about bitcoin, bubbles, and how to look at it through the lens of history.
Warren Buffet Investing Wisdom
Every year, Warren Buffet writes a highly anticipated letter to Berkshire Hathaway shareholders. Here I review the letter of 2017, and talk about what it means to you.
The end of each year, and the beginning of the next, is the time to start planning for taxes. There are many tax strategies you can’t take advantage of if you wait for the end of the year. Check out this article all about tax planning.
Ostrich Strategy – Top Tips for a Down Market
What to do when the market goes crazy? Just “go ostrich” – aka stop looking at your accounts. You’re likely to make rash decisions if you’re dependent upon the market going up, up, up to meet your goals. Remember that investing is a long-term game, not a short-term guarantee. Just go ostrich and head out and live your life. Your accounts will still be waiting for you in a few years.
Restricted Stock – Sell as Vested Or Keep?
Whether to sell a restricted stock as soon as it vests, or to hold onto it, is always a hard choice. Neither gains nor losses are guaranteed. Here I talk all about how you can look at the sell vs. keep decision, to determine what’s right for you.
ROTH and Backdoor ROTH – The Good, The Bad, and The Ugly
Ah, the ROTH IRA. People love to sing the praises of the ROTH as if it has no downsides. Well, like everything in life, it’s not perfect. Here’s the good, the bad, and the ugly of the ROTH.
Investment Policy Statement
Your investment policy statement helps to guide your investment strategy, through good times and bad. Developing one just might be the best thing you can do for your future self. It will set forth in writing how you’ll invest, in what, and when your decisions are subject to change. You’ll be able to ward off chasing the next “hot thing” your neighbor’s invested in that’s making a ton of money (see also: Bitcoin post above), and also panicking when the market goes down. And yes, it will go down one day.
Tax Refunds Aren’t Rewards
When it’s tax refund season, don’t let the opportunity to invest in your future slip through your hands. So many people spend their tax refund without thinking, and then it’s gone. Instead of thinking of a tax refund as a reward, remember that it’s just your own money you voluntarily overpaid to the government for them to give it back to you.
Best Investing Books
I’ve read hundreds of books on saving, spending, and investing over the years – and reviewed almost fifty of them for this site. Here’s where I’d recommend you start with your investing reading. These are affiliate links, so I’ll get a small commission if you buy them, but I suggest checking your library first.
Best Investing Websites
Bogleheads Wiki – Getting Started – The biggest favor you can do yourself is head on over to the Bogleheads wiki and start exploring. You’ll learn all about the low-cost, passive index fund investment philosophy.
J.L. Collins Stock Series – Looking for a basic, step-by-step money tutorial that covers everything you need to know? Check out J.L. Collins stock series, where he covers everything from market crashes to social security
Want to get started investing on your own? Here’s Vanguard’s home page.
For More About Your Money
For more about your money, head on over to my main “Your Money” page and learn about smart spending, re-FIRE-ment, and my money musings.
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