Questions About Late Taxes, Autographs, Messenger Bags, Retirement Scams, and More!

What’s inside? Here are the questions answered in today’s reader mailbag, boiled down to summaries of five or fewer words. Click on the number to jump straight down to the question.
1. Retirement scam
2. Penalty for late filing
3. Wool dryer ball question
4. Unhappy, but with savings
5. Charcoal grills last longer?
6. Old tax paperwork
7. Recommendation for messenger bag
8. Rebuilding trust after debt
9. Using a gifted iPad
10. 529 and an irresponsible child
11. Autograph collection
12. Low energy and motivation

We spent this past weekend renovating our youngest son’s bedroom. Due to some room rearrangement in our home, the room that used to be my working office is now vacated and thus we’re transforming it into a bedroom for him.

What did that mean? It meant cleaning the carpet, fixing some holes in the drywall, getting the room prepped for painting, and things like that.

Part of the challenge with this is that our youngest son isn’t entirely enthusiastic about having his own room. He shares a room with his older brother and his older brother, while incredibly kind about things, is ready to have his own room.

So, part of this weekend has involved nudging him to be excited about these changes. We looked at paint options. We talked about room arrangements. We talked about wall decorations.

Through all of this, I really think he’s warmed up to the idea, and it’s been nice seeing him feel more and more positive about the change.

On with the questions.

Q1: Retirement scam

I have found myself involved in a romance scam and withdrew $300k from my retirement, that was not returned and now I owe 100k in taxes and don’t have either. What suggestions would you give me ? I am single and 63 years old.
– Laura

The first thing I would do in your situation is contact a tax attorney and see what he or she can do to help. I can’t really offer specific advice without knowing your situation in detail, so I would suggest going to the appropriate kind of professional here, and that would be a tax lawyer.

At the very least, you likely have some area for negotiation with the IRS for a reduced tax bill.

The thing to remember about the IRS is that they’re usually very cooperative if you’re the one being proactive in a difficult situation. If you go to them, explain your situation, and work with them, the solution is going to be much better than if you try to trick them or avoid payment. Don’t play games with the IRS – you won’t win, and the penalty for losing is pretty tough.

Q2: Penalty for late filing

Is there any way to avoid penalties for paying your taxes late? My taxes are a nightmare this year with lots of 1099s for contract work and I’m utterly lost.
– Max

Max sent this to me just a couple of days ago, so he’s in a bit of a bind. I answered him directly, but wanted to include the answer here.

The only way to avoid penalties in a situation like this is to pay the closest estimate you can to your total tax bill on April 15 or contact the IRS to set up a payment plan if you can’t afford to pay that approximation. Here’s the info on payment plans.

You can easily file an extension that will give you another six months to file your taxes, but that still means you have to have an approximation of your total tax bill paid to the IRS by April 15.

Again, as with the first question, don’t play games with the IRS. You’re better off being proactive and trying to work with them rather than avoiding the problem.

Q3: Wool dryer ball question

Do wool dryer balls work or are they just a scam? Person on local Facebook group keeps talking about them.
– Aimee

Wool dryer balls are a reusable substitute for dryer sheets. You can use a wool dryer ball hundreds of times rather than a use or two for a dryer sheet, and the effects are the same – softer clothes, less static cling, a little less lint, and so on – with a bonus of slightly reduced drying time.

They seem to do this job just fine. We use them and they basically do exactly as I described above. I would say that the reduction in drying time is very minimal, maybe 5 minutes for every hour of drying. Although I don’t really know how to measure it, it definitely seems like less lint is produced when using them.

Are they “worth it”? You can easily find a set of six wool dryer balls for about $10, and they each claim to work for about 1,000 loads. I find their effect to be additive, so if you use all six at once, you’ll have less lint and softer clothes and less cling and a bit faster drying than if you use just one. I think using five or six at once is substantially better than a single dryer sheet – probably one or two balls equals a dryer sheet. So, if you’re looking at a straight dryer sheet replacement where you’re using just one ball as a mediocre replacement for 1,000 washes, that’s 6,000 uses for $10, which is cheaper than dryer sheets. However, if you use, say, six balls at once, you’re getting 1,000 uses for $10, which is $0.01 per use, whereas dryer sheets are about $0.03 per sheet (but you can use them a few times), so that’s about equivalent in cost.

In other words, I think they’re “worth it,” but it’s not a big huge savings or a major difference in your clothes drying experience. I think it’s either a slight improvement or a slight savings depending on how many wool balls you stick into each dryer load. This is, of course, assuming that the dry time improvement is so small as to be negligible, which I believe is the truth, and I’m also not counting the possibility that your clothes might last a little longer, which is definitely possible due to less lint but not a major change. They’re also more environmentally friendly (by far). On the other hand, you do have to remember to retrieve them; I find that they always come out in a dryer load, go up to my bedroom with me, and are discovered when folding clothes, so I have to take them back to the dryer and sit them on top so they can be used again.

In other words, wool dryer balls are probably just a small incremental improvement.

Q4: Unhappy, but with savings

I’m 28/M/single. I have been saving about 40% of my income each year since starting my job in 2014. I have about $60K in 401(k) and $35K in savings.

I hate my job with the burning fire of a thousand suns. Everyone in my workplace is an awful human being who would backstab literally anyone else for a $0.50/hour raise. They literally spend all day playing Office Survivor. The boss is a troll who [enjoys] it. I do everything I can to avoid all of it without getting fired. I do this mostly by saying I don’t want to do anything but what I’m currently doing and saying I am not interested in raises.

Theoretically this is the kind of stable job that a person should keep for a long while if possible. [This company] is large and stable and isn’t going anywhere. I don’t anticipate being fired for any reason as I do my job and stay on the good side of the politics.

I actually don’t mind the work either. It’s just every single element of this job except for the 2-3 hours a day when I can get lost in the task is excruciating.

What is the wisest path out of here?
– Mark

So, it seems like you want to stay in your career path in general, but you just want to escape your current job. The tone of your email sounds like you’re somewhat on the risk averse end of the spectrum concerning your job/career – you’re not really into making unplanned leaps of faith. That’s a good thing – neither am I.

If I were in your shoes, I would look for anyone I know well in my field that’s at a different company and have some conversations with those people. What’s the environment like there? Is it “Corporate Survivor” or a decent office environment? Is the work similar to what you do right now?

If you find some potential employers that sound better, ask your friend to keep an eye out for a position that might be right for you. Just explain that the office politics are really intense at your current job and that’s not really your thing – nothing else should need to be said.

If you don’t have any strong relationships with people at other companies in your field, start building them as soon as possible. Try to find a way to go to a conference or convention or two in your field. Look for local professional groups in your field. Start a professional social media presence on LinkedIn and any other services that people in your field use. The big key here isn’t to escape tomorrow, but to start building a light at the end of the tunnel.

You can always quit and just try your hand at getting another job in your field. You have enough saved that you could live for several months without work, but you have to be spending that time actively looking for work.

Q5: Charcoal grills last longer?

My brother claims that charcoal grills last longer than gas grills because they’re better made for the task as all you really need is a thick piece of metal. He basically thinks gas grills are a waste of money. We are thinking of buying a grill. Which is more cost efficient, gas or charcoal?
– Alex

It depends on how frequently you grill and how well you take care of your grill.

A charcoal grill will be much less expensive initially, but the ongoing cost of charcoal is going to be much greater than the ongoing cost of propane. If you grill frequently, the cost of lots of charcoal will really add up and end up exceeding the cost of a propane grill.

The biggest issue with grill lifespan is the care you put into the grill, and the biggest factor there is minimizing exposure to inclement weather. Do you leave the grill exposed to the elements? Do you keep it covered? Even better, do you keep it in a garage or other sheltered area when not in use? Those steps will drastically extend the lifespan of either type of grill.

Your brother is right that the average charcoal grill is simply made and has fewer points of failure than a gas grill, but neither item is all that complex.

My advice would be this: if you grill very frequently during the summer, a gas grill will probably be less expensive over the course of several summers. If you grill infrequently – every other week or less – you’ll probably get more value over several summers out of a charcoal grill. Flavor might be a factor for some, but I think much of the flavor comes from wood chips in either type of grill.

Q6: Old tax paperwork

The standard advice seems to be to keep tax paperwork around for seven years. What should I do with tax documents after seven years?
– Martin

Seven years is a great general rule for how long to keep tax returns, as noted by the IRS themselves. They give different guidelines for specific tax situations, but they’re all in the 3-7 year range, so 7 years is a good general rule.

After that, it’s up to you. If it’s easy to store older documents, there’s no reason to trash them, but it is exceedingly unlikely you’ll need anything older than seven years unless you have a non-tax reason for keeping those documents.

I have an encrypted drive that keeps electronic copies of all of my old tax returns, but with the other documents, I keep them for a minimum of seven years and literally burn them in a campfire when we don’t need them any more. I don’t go out of my way to make sure that I burn a document exactly seven years after filing; rather, I just have manila envelopes labeled “2010 Tax Return Docs” or “2013 Tax Return Docs” and I burn those envelopes when I notice they’re more than seven years old. Paper shredding works well, too, but a handful of paper documents like that work very well as kindling.

Q7: Recommendation for messenger bag

I have a new job where I work remotely. I will be working from home sometimes, but I plan to work in various locations within a few miles of my house to change things up. I need a messenger bag that will transport my laptop, a few books, various charging cables, etc. I want to buy one that will last for a long time and not look like trash but I don’t need a “premium” bag, either. What do you use?
– David

I actually use a North Face Surge II backpack for this, which I’ve been using multiple times a week for almost ten years now and it’s still in wonderful shape. (This isn’t the exact model I have, but very close.) I also have a GoRuck bag that I received as a gift that still looks practically new; I’ve used it a few times but I’m still mostly using the North Face Surge II because I never bothered to migrate all of my odds and ends, which will probably happen when the Surge wears out.

Having said that, I recently saw an AmazonBasics backpack that another work-from-home-most-of-the-time friend of mine uses as a portable office and I was very impressed; it was the nicest sub-$50 backpack I’ve seen for that purpose and it would also work well as a weekend travel bag.

If you’re specifically looking for a messenger bag, I have two friends that utterly swear by their Timbuk2 Command messenger bags. They carry their laptops in them, along with a bunch of other stuff, and it seems to work well for them. I used to use a messenger bag in my previous career and I never found them comfortable; I’ve always preferred a backpack.

Q8: Rebuilding trust after debt

A few years into our marriage, my husband went through a period of very reckless spending, racking up almost $10K in credit card debt. We had a difficult time and we went to counseling. Since then I haven’t seen any financial problems at all and he seems to not spend very much but I still feel like I don’t trust him to use a credit card or make good financial choices. I find myself watching the mail like a hawk and poring over credit card statements and being more judgmental than I should about one or two little purchases a month when I know I do the same thing. Not sure what I can do to rebuild financial trust.
– Norah

The truth is that it will probably be very difficult to rebuild full financial trust. Your experience with your husband building up a lot of debt had an impact on you and it’s one that you had to invest a lot of work in rebuilding – that $10K had to come from somewhere!

The first thing I’d suggest is to think about whether he has kept the trust since it became clear to him how important this was. He promised things with words, and he seems to be fulfilling it with actions. Before the financial crisis, did he really realize how important this was to you? After the realization, did he change his behavior, and has that behavior changed?

Another thing I’d rely on is time. Give it more time. Time does heal most wounds, even though some healing is slow.

You can help that healing by reflecting on how your actions and thoughts are demonstrating mistrust in your husband when he’s clearly shown through action that he’s made changes for the better. Make the choice not to check the mail like a hawk and not to pore over his statements. Let it breathe, through your actions, and see what happens.

Q9: Using a gifted iPad

My kids got me an iPad for Christmas. I simply don’t use it, but I want to use it. They have asked me about it and I try to “fluff up” my use but it mostly just sits on the table. I guess I don’t know what you’re supposed to use it for. I am thinking about selling it while it still has value but I want to really try it first.
– Alice

I can’t really comment on your specific situation, but I can tell you how I use my own iPad.

When I’m working, I have it set up as a second monitor on my desk. It displays my to-do list and sometimes displays notes that I want to look at while I’m writing.

I take it with me when I go to the library for research and take notes right on the screen with an Apple Pencil. I use the Notability app for this.

I often use it to read books and magazines and articles. I find the Pocket app really useful for article reading, and individual apps for magazines are great. I have the Kindle app on it because I have a fair number of Kindle e-books, but the iPad isn’t my number one place for reading those (I use my actual Kindle device and my phone 95% of the time).

I use the iPad a lot in the kitchen, where I set it on its stand and look at recipes while cooking. Sometimes, I’ll play a Youtube video if I don’t understand a technique I’m trying in the kitchen. I’ll do the same when I’m doing a home repair or something like that – I’ll just take the iPad to wherever I am and play a video to help me through it.

I like watching streaming video on it for entertainment sometimes, though I honestly don’t watch much television in total in my life. I do this sometimes while relaxing on the couch.

Q10: 529 and an irresponsible child

My husband and I started funding a 529 college savings plan for our son when he was 3. He’s now 17 and considering college. Our 529 plan has $26K in it. All sounds good, but here’s the problem: our son is extremely irresponsible. He has zero seriousness about his studies, goofs off all the time, gets fired from every after school job, and has directly said he can’t wait for college partying. I don’t want the 529 to contribute to this. I want to help him get an education when he matures. What can I do?
– Darren

First of all, kudos to you for having a rational and clear view of your child’s character rather than reflexively defending your child in every situation. Taking a realistic view of things and making choices accordingly is almost always the best choice.

Assuming you are the owner/custodian of this 529 plan and your child is the beneficiary, you are the one that controls whether or not money is taken out of that plan. You can simply refuse to allow it to be withdrawn for college expenses.

You absolutely need to have this conversation with your child before he makes some life-changing decisions under the assumption that you’ll be providing 529 money for him. You shouldn’t wait until he’s in college and the bills are rolling in, because then you’re saddling your child with a financial situation much different than what he expected. Talk about it now. Make it clear that the 529 will stay untouched until he shows reasonable maturity.

Q11: Autograph collection

I have a collection of baseball, football, and hockey player autographs from the late 1970s and early 1980s. They’re mostly signs programs from events. I want to sell them. Advice online says that I have to get them certified but I don’t have money. Suggestions?
– David

If you have some high value autographs – Hall of Fame caliber players or players who had a large fan following, particularly deceased players in this group – you can potentially get an auction house interested in your collection. This is particularly true if the programs are from memorable games. You might want to contact Leland’s Sports Memorabilia, which I’ve dealt with in the past successfully.

If your collection is mostly obscure players, the collection likely has limited value to begin with and you won’t recoup your investment. People don’t really value autographs from players who were only in the majors for a few seasons and hit .220.

I would not invest in certification out of pocket for these items, especially if you have limited funds.

Q12: Low energy and motivation

Love your advice. My problem is sort of a meta problem though. Most days I just completely lack any energy. I get out of bed and can get through basic work and life stuff but then I’m just dead and all I want to do is hit the couch. I know I should go to the doctor but I can’t afford a big medical bill. It’s a giant catch 22.
– Andy

You already know the answer here. Go visit the doctor if you feel devoid of energy and see if there’s a medical issue going on.

There are definitely lifestyle choices I make that greatly affect my daily energy, but I also know that if those basic things aren’t working, I should probably see the doctor. For me, things that are key include getting plenty of sleep (ideally going to bed early enough that I rise naturally instead of an alarm clock), eating plenty of fruits and vegetables in my diet, getting some exercise every day, drinking plenty of water, and meditating every day. Those steps make a giant difference.

One thing you might want to consider doing is seeing if there are any free clinics in the area. Doctors often run free clinics for people who lack decent medical insurance so that they can get basic care. Also, remember that this might be something simple like a vitamin deficiency – a B12 deficiency, for example, can cause some of the symptoms you mention.

Got any questions? The best way to ask is to follow me on Facebook and ask questions directly there. I’ll attempt to answer them in a future mailbag (which, by way of full disclosure, may also get re-posted on other websites that pick up my blog). However, I do receive many, many questions per week, so I may not necessarily be able to answer yours.

Trent Hamm

Founder & Columnist

Trent Hamm founded The Simple Dollar in 2006 and still writes a daily column on personal finance. He’s the author of three books published by Simon & Schuster and Financial Times Press, has contributed to Business Insider, US News & World Report, Yahoo Finance, and Lifehacker, and his financial advice has been featured in The New York Times, TIME, Forbes, The Guardian, and elsewhere.