The Tax Code doesn’t treat casual gamblers very well. On the one hand the odds are stacked against you winning (those fancy casinos were built on losers, not winners). And on the other hand winning can be worse than losing when the taxman gets a hold on you.
Recent tax law changes turned a bad situation worse. The higher standard deduction means fewer people will benefit from deducting gambling losses since you need enough itemized deductions to exceed the standard deduction before the gambling losses reduce your tax liability.
Then we have issues with state tax returns. If the federal tax return doesn’t treat casual gamblers with respect, state tax returns can be down right rude. Wisconsin, for example, doesn’t allow any gambling losses against wins as an itemized deduction: if you lose, you lose; if you win, you lose.Read More
Once again we see the market throwing a temper tantrum. On the way up it was tempting to handle your investments on your own. Now with the horizon less clear and a modest correction in the books as I write, you wonder if professional help might be worth the extra expense.
Those most knowledgeable about money resist the advice of commissioned (or fee-based) professionals. As everyone know, fees have serious consequences over long periods of time. The lower the fees the more you’ll have 10 years down the road.
But when the market gets schizophrenic confidence in one’s abilities declines. Worse, you can make serious mistakes well in excess of what you would pay a financial professional.Read More
Most of the time the stock market is climbing north. Interspersed between bull markets are those times when rookie investors act as if the sky is falling.
Long bull markets turn normally intelligent investors into casino gamblers; they even use gambling terminology: we’re due for a bear market or as they say at the casino, “Red is due after 8 black spins” at the roulette wheel; as if the ball has a memory. The odds of it coming up red are the same as it was last spin, in case you were wondering.
Of course, long moves in the stock market sets off our sixth sense that this can’t last forever. Before long you’re not fully invested (a religious mantra of many investing circles) which smacks of market timing.
This brings up a good question: Should you always be 100% invested in the market?
If only it were as simple as a yes or no answer.
The truth is many people should NOT be fully invested in the market and some people SHOULD be and it has nothing to do with market timing. The trick is to know when to be fully invested and if not, by how much.
It boils down to your personal situation: where you are on your journey to financial independence, how close to retirement you are (or if you are in retirement), spending habits and viable alternative investments.Read More
The literature is largely silent on what you should do once you attain financial independence(FI). Plenty has been written about building wealth and how much is needed to reach FI and how much you can safely withdraw each year in retirement.
Plenty of debate has also revolved around paying off the mortgage — any debt for that matter — versus plowing the excess payments into investments that pretend to offer a return greater than the interest rate on your debt. While investments can provide outsized returns, the return isn’t guaranteed; the interest on the debt is.
As much as we preach about eliminating debt as part of a smart wealth building program designed for FI, there are some benefits to having certain kinds of debt. Risks are always present, but the advantage may be worth the risk. Buying a home without debt ever would mean most people would never have a chance at home ownership. And you can forget about income properties if you can’t use leverage to start your real estate empire.
A mortgage (all debt) does have one powerful advantage most people overlook. Debt is the #1 motivator when it comes to getting people to sacrifice time with family and friends. Debt motivates you to work harder than you ever would if debt demands were not hanging over your head.Read More
Paying off the mortgage is the American Dream and the first step toward retirement; it’s harder to retire with a mortgage payment blowing a hole through a fixed budget. Owning your home is the foundation of any vibrant financial plan. Until your home is unencumbered (without a mortgage) the bank still owns it in a manner of speaking (and they’ll remind you of it if you miss a payment).
Still, a home mortgage has its benefits. The traditional reasons to carry mortgage debt are bad reasons to carry the liability, but there are still a few good reasons.
We will review the traditional reasons for borrowing against your home and why the benefit is perceived rather than real. We will finish with the three reasons a mortgage can help you build wealth.Read More
It didn’t exactly start with Mr. Money Mustache, but the FIRE community solidified around Pete and his work. Pete retired at the ripe old age of 30 and set a new standard in early retirement.
News feeds have a litany of stories of 30-somethings living the good life as they travel abroad. Coupled with the stories of people paying off a gazillion dollars in debt in four and a half minutes and it starts to look easy.
Except it isn’t that easy! It’s actually damn hard. Personal circumstances play a vital role. Where you live, your health and education opportunities determine at least a part of the outcome.Read More
The reason for starting a side business are legion. Maybe early retirement left you with more free time than you know what to do with. Maybe you took early retirement a bit early with the intentions of earning some side income. Or, personal or family issues limit the hours available for gainful activities.
Micro businesses are a great way to earn more money without a massive expenditure of time. You can enjoy the best of both worlds: reasonable income and freedom.
But there is one factor that causes more headaches than any other: taxes. Micro businesses/side gigs have special tax rules that can cause serious problems, or, if done correctly, virtually eliminate your tax bill.
I’ve published on this in the past, but new tax rules require I provide an entirely new guide. Several notable changes require your attention. A misstep will cost you hard-earned tax dollars; a well thought out plan allows you to keep most or all of your side gig income.Read More
You sold a stock or rental property with a massive gain. You deferred/avoided tax on the complete capital gain by investing said gains in an Opportunity Fund. Then you decide to use the basis from the original investments as a down payment on an income property and conduct a cost segregation study. This equates to a $300,000 deduction on your tax return while avoiding tax on the capital gains!Read More