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willyd123

AwesomeA - This is a great question. I did some research and I could not find a clear answer. But I believe you would consider this donation as two components - 1. the discount portion of the gain and 2. the remaining amount of the gain. For the discount portion, I believe that you need to always re...

willyd123

I've tracked this since 1995... 1995 $180,282 1996 $227,727 1997 $312,335 1998 $413,125 1999 $672,846 2000 $720,729 2001 $725,517 2002 $773,543 2003 $1,104,246 2004 $1,496,559 2005 $2,114,260 2006 $2,820,771 2007 $2,933,113 2008 $2,460,812 2009 $3,446,791 2010 $3,275,024 2011 $3,399,804 2012 $4,073,...

willyd123

The point I tried to make which is that the premiums you pay via payroll deductions that your employer takes for the medical plan are pre tax (i.e., they reduce your taxable income). So plan 1 has premiums which total $1,690 annually ($65 X 26). If you are say in the 24% tax bracket, the actual net ...

willyd123

I would go with 1. because the premiums are pretax which means the difference between the two plans is ((($65-$42) X 26) X (1 - your marginal tax rate) and the HSA contribution is tax free (assuming you use it for qualified medical expenses).

willyd123

I think what "cas" wrote about only being able to contribute 2/12s of the annual HSA maximum is correct assuming that the person moves from a HDHP to a non-HDHP after he retires in February and stays on a non-HDHP for the remainder of the year. However, If he continues on an HDHP then he can make th...

willyd123

You are permitted to contribute to both a tIRA and a Roth IRA in the same year but the combined contribution cannot exceed the 2019 limit of $6,000 (+$1,000 catch up if 50 or over).

willyd123

I am in a very similar situation except that I am retiring in the first week of January. I asked my company's payroll person (and they agreed) to deduct a full 2020 401(k) contribution of $26,000 as well as a full HSA contribution of $8,100 from my January 15, 2020 check (I am getting an abnormally ...

willyd123

It is definitely a planning opportunity I would consider. The only unfortunate thing is that presumably she will be in a pretty low tax bracket and thus the contribution she makes will not have a huge tax benefit at least initially. The good news is that if she continues contributing and investing o...

willyd123

BHs - I have an Apple iPhone 6 and despite having changed the battery, the battery life is so short that I think I really need to upgrade. I do want to stick with an iPhone and I think we should probably stay with AT&T. So two questions: (1) What is the lowest version of an iPhone I should get balan...

willyd123

Hello - Here's a basic summary of who's eligible. Under the law, an eligible individual: -Must be 18 years of age or older -Must be covered under a qualified high-deductible health plan (HDHP) on the first day of a certain month -May not be covered under any health plan that is not a qualified HDHP ...

willyd123

Hello - I'm not sure I understand your first question. Contributing to an HSA will reduce your taxable income regardless of whether you have enough deductions to eclipse the standard deduction amount. HSA contributions are not itemized deductions. HSA contributions are deductions from income like 40...

willyd123

Thank you. Very helpful.

willyd123

BHs - I watched an interview with Kathleen Murphy of Fidelity Investments on CNBC this morning where she was discussing Fidelity's move to zero commissions. She mentioned that in addition to this move, Fidelity also pays higher interest on cash (a topic that is regularly posted about in this site) A...

willyd123

I am 100% invested, no cash. Some HSA administrators require a minimum cash balance be held but LivelyHSA does not which is who administers my HSA. Utilizing an HSA like a retirement asset rather than a spending asset at least until you enroll in Medicare can be financially very beneficial.

willyd123

It is definitely legal and the company won't come after you. They probably won't ever even know you did this unless they really did their research and they'd have no reason to do that anyway. You should definitely spend all you can before you leave.

willyd123

I am in a similar position as you are. I have looked at this nine ways from Sunday, have run many models, read many of the BH posts on the topic, etc. And here's what I plan to do (would love other BHs to poke holes): I plan to do conversions from age 60 (I'll be retired) to age 69 when I plan to co...

willyd123

This is one of the areas I manage for a Fortune 500 company: Quantum - The quantum or size of the award is going to be highly dependent on the role, size of the business, industry, etc. For our company, only some Directors would get RSU awards, and the amounts would be nominal (maybe $20,000 in gran...

willyd123

Hello - Situation: I am nearing retirement and am comfortable that I have adequate assets so now I am focusing on how to tap the assets to meet expenses. Last year my equity ETFs and mutual funds that are held in my after tax accounts generated about $75,000 in dividend income. This along with my pe...

willyd123

By the way, you should write an email to your head of HR that you would really appreciate it if they would consider adding back a HDHP option for people like yourself.

willyd123

Again, it is all about the organizations objectives and ultimate plan design. In our case, the actuarial value of the HDHP is actually higher than the old traditional plan which means the new HDHP plan will actually pay more of the total plan costs than the old plan. With our company's plan design, ...

willyd123

I am responsible for designing the benefits plans at my employer. Two years ago, our company went to a design that includes ONLY HDHPs. However, we designed the plans to do as much as possible to address the affordability issue by providing substantial front loaded company funded seeding into employ...

willyd123

I will be leaving the corporate world on January 2nd. I got them to push my bonus that would have been paid in late 2019 into 2020 for tax reasons which is the reason I plan to stay until then.

willyd123

I will be leaving the corporate world on January 2nd. I got them to push my bonus that would have been paid in late 2019 into 2020 for tax reasons which is the reason I plan to stay until then.

willyd123

Hello - A company contribution to an employees' HSA should not show up in your pay stub as income but rather as an employer paid benefit in terms of the records. When your payroll department issues your W-2, they will need to include both your and their contributions that went to your HSA through th...

willyd123

Not sure if we are helping or confusing but I can tell you that I'd much rather contribute to an HSA due to it's triple tax favorability than a Roth. Yes, the tax deduction is a one time event (of course) but the Roth never provides a tax deduction.

willyd123

The main difference is that if you contribute to a Roth, the contribution will NOT reduce your taxable income when you make the contribution. On the other hand, your contributions to an HSA DO reduce your taxable income. So with an HSA, you get a tax deduction when you make the contribution and you ...

willyd123

Hello - Some people save receipts for qualified medical expenses for years so that if at any time in the future they want to pull money from their HSA they can do so up to the smaller of their total expenses backed up by the receipts or their HSA balance. By way of an example, assume that you opened...

willyd123

I've used LivelyHSA for about two years and have been very pleased. They, just like Fidelity, do not charge fees. With Lively, you can also invest 100% of your HSA assets (they don't have a minimum cash holding requirement) and you invest through their partner TD Ameritrade who offers plenty of comm...

willyd123

Hello - 1. Given that myself and kids will not be on HSA starting August and I have already contributed about $4000 to our HSA plan, will we be penalized come tax time since we did not have HSA throughout the year? If you are covered under a high deductible health plan for a portion of the year you ...

willyd123

Thanks again to both of you. Always good to get reactions from others on these things. To Homestretch, On my pre-Medicare medical coverage plan, as you probably know there are no great choices but after thinking about and analyzing the various options (e.g., no coverage, ACA plan, short-term plan, r...

willyd123

Good point from you both on the impact to Medicare. I always think about that in terms of age 65 and always forget the two year look back. I will probably pay more due to the conversions (if I do them) but the increment is not real huge so I'd factor that in but I don't think it'd be enough to chang...

willyd123

Hello - I think picking one administrator that you plan to use for your and your wife's HSA for the long haul makes a lot of sense. So I'd research Fidelity and Lively and any others and determine which of those you think would be best and move all of your and your wife's HSA assets there. And then ...

willyd123

Hello BHs - I've gotten so much from reading the thoughts in this website I was hoping to tap this group again on an issue I am grappling with (Roth Conversions). Situation: Age: 57 (married) Planned Retirement Age: 58 After Tax Assets: ~$4.8M Retirement Assets: ~$1.7M I’ve done a fair amount of thi...

willyd123

Hello - I have my core HSA with Lively. I like Lively because they don't charge fees, you can invest all of your assets (no minimum amount that has to be kept in cash) and you invest via TD Ameritrade where you can find low expense ratio and no commission investments. I am still employed and I have ...

willyd123

Agreed but theoretically, if a person wasn't enrolled in any medical plan, came down with a medical issue and say this occurred a few months prior to the ACA open enrollment period. At that point, couldn't they enroll in an ACA plan and be fully covered from that point on? I am not advocating for th...

willyd123

Very helpful. Thanks to all...

willyd123

Hello BHs - I will be retiring early soon and am getting prepared to manage the absence of company-provided-subsidized medical, dental and vision coverage. I am clear on how to handle medical coerage but I have not spent any time thinking about Dental and Vision coverage. As background, my wife and ...

willyd123

Thank you very much.

willyd123

This question has probably been asked before but I couldn't find the answer... If you go onto a non-ACA-compliant medical plan (aka "temporary plan" which have pre existing exclusions, plan payment caps, etc.) and you came down with a serious illness, would you be able to drop the temporary plan cov...

willyd123

I happen to be in a pretty similar situation except that I am 58. You can absolutely retire. You haven't even mentioned Social Security which will be here for you despite all the fear mongering. Many people don't factor in these benefits into their planning but if you and your wife's earnings histor...

willyd123

Hello - In terms of a boat, you might try The Moorings. You can select a boat as well as crewed or not, etc. We had a 7 day trip scheduled but we canceled due to the hurricanes. In terms of your time on land, you may already have a place figured out but in the event you do not, we love staying at Gr...

willyd123

Ah, very good. Thanks.

willyd123

Hello BHs - I am trying to help a relative who just started working as a contractor in April. I used a tax calculator and the results show that she would owe $3,725 in self employment taxes (Social Security and Medicare) and another $1,294 in Federal income taxes for all of 2019 assuming she continu...

willyd123

Have any of you seen any data from any organization of any repute that might suggest an age beyond which you would likely not be impacted by future reductions to benefits that may be legislated?

willyd123

Bacchus, Svensk and Jack all make great points. Thanks.

willyd123

Silk -

That's actually what I am doing, trying to complete my financial plan as I am planning to retire soon. One of the inputs is the cash flow from Social Security which is why I am trying to figure this out.

willyd123

Hello BHs - This is a worn out topic I know but just wanted to get your thoughts on SS benefits and when to commence. According to the Open Social Security Model, I should: - Have my spouse file her retirement benefit to begin 2/2027 at age 62 and 1 month - File for my retirement benefit to begin 1/...

willyd123

I can tell you for sure that employers do in some cases pick up the investment fees (and / or admin fees) or portions thereof. My employer picks up 2/3s of the investment fees for example.

willyd123

Hello - I sincerely hope you are right about no fees being charged but that is very surprising because Health Equity typically does charge fees for investing. Maybe your employer is picking these up on behalf of the employees which companies sometimes do. In terms of your investment choice, if you a...

willyd123

Hello - My role at my company is to manage the RSU plan, among other things. Very few companies will violate the plan provisions directly as this creates all sorts of legal risk. However, in my experience it is quite common that if a company wants an employee to "move on" on the company's desired ti...

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