This is a conversation between me and my future self, if my financial path wouldn’t have positively forked 2 years ago. The transcript is available here.
What would your future self have to say to you?
Taxes
It’s almost time to pay Uncle Sam for the privilege of living in the US.
Since my business partner and I just finished our corporate taxes last week, I thought it would be a good time to finish my personal taxes. I’ve got a relatively complicated tax situation. I’ve got personal taxes, my side-hustle taxes, and our side-hustle taxes. I had my side hustle taxes done and my personal taxes were just waiting for the final numbers from our corporate filing. We’re an LLC, run as a partnership, filing as an S-Corp.
I was all set to get about $100 back from my personal and side-hustle #1 taxes. That’s a perfect tax year. No more money out-of-pocket and no free large loans to the government.
Side-hustle #2 ruined that. It started taking off in September, so we’d never paid any estimated taxes. When I added those numbers in, I owed a bit under $2000.
Ick. I hate owing.
Thankfully, I set aside 25% of all of my side-hustle income just to cover this.
It was still too much. What could I do to lower my tax bill?
My IRA!
I’d only contributed $100 to my traditional IRA last year. Contributions are tax deductible and you can make them until April 15th of the following year.
That’s great. I had money sitting in a savings account, earmarked to get wasted by the government, and I had an unused tax deduction that I could still contribute to.
That got it down to a $1000 tax liability.
Was there more? What could I do?
When I paid off my car last year, I started sending half of my car payment to an account earmarked for the next car. I had $1700 sitting there, so I sent $1200 of it to my IRA, leaving $500 to hopefully cover any car repairs that come up. Hope isn’t a good financial strategy, but I’ve also got a straight brokerage account that’d doing pretty well, so I can cash that out, if necessary.
Down to $800.
Contributing a bit over $3000 to my retirement saved me more than $1000 right now. That’s sweet, but I still owed money.
Did I miss something on my first side hustle?
$67 to oDesk? How did I manage to keep my annual oDesk bill down to $67? I had a full-time guy in the Philippines for a while last year, and I regularly hire writers for my niche sites.
So I hit oDesk and ran some reports. I was off in that deduction. By $2400. I have no idea where that $67 came from. Including it dropped my side-hustle profit considerably, and brought my total tax bill to a net $7 refund.
There is a reason I never file my taxes as soon as I finish with Turbo Tax. I always wait a week or two, and I always come up with something I missed. This time, the wait saved me nearly $2000.
Mortgage Race
I spent last week at the Financial Blogger Conference. Saturday night was the big debauch, a 90s themed hip-hop dance party.
Yeah.
Instead, Crystal, Suba, and I hosted a super-secret pizza party to let some of the less “dance party” inclined attendees discuss things like the sanitary concerns of group body shots, sex toys, and horror movies.
During the course of the party, Crystal and I decided to race to pay off our mortgages.
Her balance is just under $25,000.
My balance is $26,266.40.
We both technically have the cash to pay off the balances right now, but we are both dealing with secondary housing issues. She’s building a new one, and I’m updating an inherited house. Neither of us is willing to use our cash reserves to pay off the balance right this moment.
Now that my credit card is paid off, I’ve moved that money to an extra interest-only payment on my mortgage, effectively doubling my mortgage payment, which puts my projected payoff date as about the end of next year. Crystal’s aiming for June, so I’ll have to hurry.
We do have tenants lined up for February, and all of the non-expense related rent will go to the mortgage.
I think I can win.
Update:
I forgot to mention the terms of the bet. The loser has to go visit the winner. When I win, Crystal’s going to fly to Minnesota to experience snow.
Can I Sell My Lottery Payments for a Lump Sum?
This is a guest post.
Winning the lottery is everyone’s dream. You hit the lotto, cash in your ticket and kiss all your troubles goodbye, right? Actually, that might not be true. Just look at the number of lottery winners who’ve ended up worse off than they were before they hit it big. There are several problems here. One problem is that people often spend their money unwisely, without learning how to manage it properly. Lottery annuity payments were designed to help with this. However, those annuity payments might not actually be enough to make a significant difference in your life. If that’s the case, you might be wondering if you can sell your payments for a lump sum. The answer is, yes, you can. But there’s a catch. Actually, there are a couple of catches.
Buyers Matter
First, let’s talk about buyers. They’re the ones who’ll be paying you a lump sum for your lottery payments. Now, you can’t expect a buyer to offer the full amount you’re owed from the lottery, but you should be able to expect a significant percentage of the winnings. That’s not the case with many buyers. They recognize your desperation and have no qualms about taking advantage of your situation. That’s not true for all buyers, though. You need to recognize qualified buyers from those better left alone. Obviously, that’s tough to do on your own. Most people have never been in the position of having to sell lottery payments before, and it’s easy to get lost in a world with which you’re not familiar.
Sell Only Part of It
Another important consideration is whether you need to sell all of your lottery winnings or only a percentage of them. You can easily sell just a specific portion of your winnings, enough to cover your immediate needs, and retain the remainder as regular ongoing payments. This ensures that you have the money you need right now, as well as a financial cushion for the future.
Work with a Go-Between
The ideal solution to your quandary is to work with a firm that acts as a go-between. The company will vet and investigate buyers, ensuring that you only have the cream of the crop to choose from. Not only that, but working with a reputable firm will also ensure that you get the highest percentage possible of your winnings, rather than leaving you with a mere pittance.
Of course, not all such firms are the same, and you need to recognize a reputable company. Look for a firm that’s been in business for a number of years – one with an established reputation and a list of satisfied clients. Second, make sure the company doesn’t work for the buyers – the firm should work for you, the seller. This ensures there’s no conflict of interest. A company that works on behalf of the buyer has no incentive to go above and beyond to ensure you get a fair deal. One that works for you certainly does.
Smoking Saved My Life
Lately, I’ve been traveling for work about twice per month. The trips have generally been to my company headquarters, about 5 hours east of my house, though at the time this goes live, I will be ending another trip in the Chicago area.
Earlier this month, I was out there to conduct some training webinars and enjoy the company Christmas party. After the party, my insomnia kicked in and I couldn’t sleep. At 6AM, I decided to give it up for a lost cause and pack my stuff for the 5 hour drive home.
On no sleep.
The morning after a nasty ice storm.
I do not have a death wish.
Really.
I got packed, ready to go. Then crawled back in bed with the nap timer on my phone set. Thirty minutes later, I checked out of the hotel and got in my car.
I really don’t want to die, though this trip scared me a bit. It’s a long 5 hours, 4.5 of those hours are on one road, driving across southern Wisconsin. Tedious is one word that comes to mind. Mind-numbing and lullaby-driving are two others.
Instead of getting on the highway, I drove to Wal-mart. I stocked up on cigarettes and Rockstar.
Now, I quit smoking 6 years ago when we found out brat #3 was coming a bit faster than we expected. It was purely a financial decision at that point, but breathing turned out to be a nice change, too.
Nicotine is a stimulant with immediate effects. That means, if I start feeling drowsy, I can smoke a cigarette and I quit feeling drowsy while I chug energy drinks.
Good plan, Jason.
It worked. I made it home, then fell on the couch and didn’t move for 4 hours. Then I ate dinner and went to bed.
Unfortunately, even after quitting for 6 years, by the time I got home, it felt like I’d never quit. So I get the joy of quitting again.
By the time you read this, the craving should be gone and I should just be getting ready to climb in my car for a long drive on not enough sleep.
The Value of Hiding Money From Your Spouse
I have a confession, but it’s probably not going to be a big shocker if you read the title of this post.
I hide money from my wife.
Some of you just started screaming at your monitor that I’m a horrible person.
That’s cool.
You’re wrong, but the fact that I got that reaction out of you makes me smile.
Ok, I might be a little bit horrible, but not because I hide money.
My wife has an admitted shopping problem. If she thinks we’re broke, she shops less. That’s a win and allows me to save up for our long-term goals and provide for our financial security.
I don’t lie about it. If she asks how we’re doing, I tell her. At least in general terms.
But I didn’t tell her about my annual bonus, until we had a bunch of car repairs come up that would have swamped our emergency fund.
I also haven’t told her about the cash I’ve been stockpiling.
A couple of years ago, the power went out here for four days. It wasn’t just our house, it was 75% of everything within 5 miles of our house.
When the power came on in some places after a day or two, the phone lines were still down, which meant gas stations couldn’t process credit cards.
Quick, look in your wallet and tell me how much cash you have on you….
Most people live on their credit or debit cards.
Could you buy food or water if your plastic was gone?
I could that week, but not for long, so I started taking the cash payments from my side hustle and putting it aside. I’d come home, give my wife a little cash, keep a little cash for myself, and put at least 80% of it away. I absolutely refuse to touch that money for anything.
Part of the “set it aside and forget about” means not revealing its existence. It would be too easy to dip into it to pay the pizza guy or when we go to Rennfest.
So I don’t talk about, and it gets to sit all by itself in the safe, comfy and warm. It’s my security blanket, and nobody gets to touch my binky.
