Feature Article

Congress created one of the best tax savings vehicles in 2003. It wasn’t the individual retirement account (IRA). It wasn’t the Roth IRA.It was the health savings account (HSA). The HSA is the only tax-preferred savings vehicle in which a taxpayer potentially gets both an upfront tax deduction in addition to tax-free and penalty-free distributions. The IRS wrote the HSA rules to give taxpayers maximum flexibility in how they use their HSAs for medical expenses. Strategic use of the HSA can lead to lifelong tax savings opportunities. Let’s review the basic rules as to how an HSA operates, the little-known rules that create tax savings opportunities, and examples of how the HSA can be used to provide tax-free and penalty-free distributions when the taxpayer has a cash need.

If you’re thinking about extra forms that might have to go in with a 1040, Form 8082 is probably not the first thing that pops into your mind. But if what you need to do includes Form 8082 – Notice of Inconsistent Treatment or Administrative Adjustment Request, and you leave it out, there might be no way to recover. That appears to be the result in the Second Circuit decision in Laurence Gluck’s appeal of a Tax Court decision. There is also a lesson about like-kind exchanges that may have continuing significance despite changes in the law. With a deficiency of more than $1.5 million, it seems like a pretty big deal. It turns out that Laurence Gluck is one of New York City's largest landlords, so it may not have been that big a deal for him. On the other hand, it makes it surprising that the issue tripped him up. Click here to continue reading.

In Part 1 of this series, we took a deeper dive into IRMAA planning and minimizing tax on your Social Security benefits. You play a large role in shaping your retirement years in terms of lifestyle and financial health. Think of taking advantage of the many techniques to lower your tax during your retirement years as another aspect of self-care. By treating your financial health and well-being as carefully as you treat your mental and physical well-being, you can ensure that you have resources to attain your financial goals and support yourself in the style for which you’ve planned. In my practice, I see a wide range of client behavior surrounding retirement – from no planning to thoughtful, long-range planning. Looking ahead, whether you’re working with your tax professional and financial team or whether you’re planning on your own, pays off enormously. Please read on for some additional tips and techniques for tax savings involving charitable giving, Roth IRA conversions, and minimizing capital gains taxes – and two more examples.

We've all heard the messages to pay yourself first, save a percentage of your income, build your nest egg, and some of us heeded the messages. Whether you’ve saved a lot or a little, we have many ways to reduce taxes in retirement, and by doing so, we maximize the power of our retirement savings. Accumulating retirement funds is step one. And there are tax-advantaged ways to save for retirement: employer plans (401(k), 403(b), 457), individual retirement accounts (IRAs), self-employed retirement plans (Keogh, SEP, SIMPLE, Solo 401(k)), and non-retirement accounts. While you’re saving, you may have accumulated multiple “buckets” of assets, some in taxable accounts, some tax-deferred, some nontaxable. Looking ahead toward retirement withdrawals/distributions (the funds you’ll need for essential and discretionary living expenses) adds tremendous value, and tax planning is a big part of the picture. Read on for more specifics and stay tuned for Part 2 with additional tips and examples.

If you’re like most tax professionals, you’re probably working tax-prep season hyper-focused and -vigilant, refusing to hit pause except on absolute demand. You’re keeping a sharp eye on the ball, the players, and the end goal: maximizing your resources and providing impeccable service to your clients. Now, when you have lots of familiar, practiced work to do in little time, working like this can produce great results. However, tax-prep season is ending, and tax-reduction planning season is beginning. Therein, hyper-focus, hyper-vigilance, and workdays, weeks, and months without meaningful rest can backfire and steal from you the results you hope to produce. That’s because reactively responding to external demands and deadlines (set by clients and the IRS, for example), requires something different from you doing proactive designing and selling high-end tax plans. Consider this, as you shift from tax-prep to tax planning, you: ● Soften your focus on computers, numbers, and speed and sharpen your focus on talking with prospective clients about their finances, their hopes and worries about their business and family, and how you might best serve them. This requires a shift from grinding and discipline to presence and attunement. ● Soften your focus on meeting immediate deliverables and sharpen your focus on developing long-term strategies for products you offer and your business overall. This requires a shift from following rules, structures, and guidance to thinking creatively and working socially. ● Soften your focus on external deadlines and client demands and sharpen your focus on your own ambitions and drive to get things done. This requires a shift from aligning your priorities with others’ agendas to aligning your priorities with your own dreams and goals. Making shifts like these can be challenging, particularly if tax-prep season devours you and you enter tax-reduction planning season depleted and drained. However, taking time now to recharge and reset can help you pivot and produce powerful results in the end. Did Tax Season Devour and Deplete You? When it comes to personal performance in business, I like to contrast two modes of working: Depleted Mode and Resourced Mode. These modes aren’t binary; rather, they’re two ends of a continuum that we all constantly move along. Generally, when you find yourself highly distracted and distractible, pushing yourself to keep going, and working excessive hours to make up for lost time, you’re in Depleted Mode. Tax-prep season unfailingly produces this outcome for the best of tax pros. Exhaustion (or simple tiredness), frustration, and a taxed mind (pun intended) live here. When you’re drawn into your work, interested in the results you produce, and loving what you do, you’re in Resourced Mode. Enthusiasm, creativity, and connection live here. Resourced Mode offers an ideal environment to tax pros for engaging with the demands of tax planning season. You’ve probably seen yourself operate in both of these modes and along the continuum. Many tax professionals start the tax-prep season in Resourced Mode but end in Depleted Mode after months of hyper-focus and -vigilance, both of which you can only sustain in short bursts. There’s nothing wrong with Depleted Mode; most people land themselves there through hard work and commitment. (Incidentally, you can build systems and structures to reduce or avoid Depletion Mode over time, but that’s a topic for another day.) Many people produce great work in Depleted Mode, and that can trick them into thinking it’s effective for every kind of work. You can do tax prep in Depleted Mode, for example, because the work is familiar, somewhat predictable and consistent, and ultimately requires less mental engagement. However, Depleted Mode renders fewer productive results in tax-planning season because there you need deeper thought, mental space and physical energy to develop a strategy, a connection to people, and effectively sales. Ultimately, even in situations where Depleted Mode works decently, Depleted Mode can lead to: ▪ Procrastination: Being overworked and under-rested drains your mental capacity and leads to internal resistance on projects that require more mental energy. ▪ Distractibility: Quick changes of focus habituate your brain to prioritize distractions instead of focused work, so you might find yourself putting “easy” work ahead of “valuable” work. ▪ Agitation: Fast pacing can create agitation, or a constant background sense of worry, which can hinder progress when you try to settle into something that requires deeper thinking, such as tax or business strategy (which requires divergent, non-linear thinking). ▪ Lower pay for more work: procrastination, distractibility, and agitation make it difficult to approach valuable work (higher-paying, more satisfying), leaving you to do easy work instead (lower-paying, less satisfying) so you feel as if you accomplish something. ▪ Cyclical depletion: In Depleted Mode, you produce less per hour, make up for it by working more hours, and stay in Depleted Mode by overworking yourself. Still working in depleted mode? Click here to learn how to shut down the grind and turn on the productivity.

Federal, state, and local governments, as well as private organizations, have collectively given trillions of dollars in financial support to individuals and businesses during the pandemic through a maze of government and private programs. These benefits will help taxpayers to a greater extent if they are tax-free, but are they? In some cases, we have a definite answer. For many, it is the classic tax law answer: “It depends.” We’ll review the general tax law rules applicable to deciding, then show three ways you can use the tax law to exclude these benefits from a taxpayer’s income.

Lucky and talented folks win all sorts of prizes and awards. Often, the winnings have nothing to do with the winner’s business or profession, but sometimes there’s a professional or business connection. You might view your career arcs as a series of applications, interviews, hirings, promotions with one or multiple employers. But some career paths – musicians (both instrumental and vocal), songwriters, and composers come to mind – involve frequent auditions with a healthy dose of competition. The renown and visibility afforded to competition winners often open doors to career advancement – more and better engagements, management contracts, and media/recording opportunities. Competition prizes and awards are taxable. But these winnings might also be subject to self-employment tax that can be up to 15.3 percent on the taxable amount. While most professional musicians are in the business of being musicians, very few consider themselves in the business of being competition participants. The distinction is important and allows for tax planning and savings opportunities. To learn which is better for tax planning, keep reading.

The best tax planning will often be found where both the form and substance of a transaction align in the client’s interest. One such planning activity focuses on reducing self-employment tax, and while the attempt is admirable, the substance of the transaction might be stronger than its form. Generally, if you’re a partner in a partnership, your distributive share of income is subject to Self Employment Contributions Act (SECA) tax, also known as self-employment tax. This can be up to an additional 15.3 percent on your earnings, unless an exception applies. Many tax pros attempt to mitigate this tax by simply making the spouse of the main business partner a limited partner in the entity. The thought is that an exclusion applies for SECA tax when there is a “limited partner’s” share of partnership income. But be careful! When the underlying substance overrides the form of a transaction, the taxpayer generally will lose. The IRS recently highlighted such a problem with form in its draft partnership tax instructions by saying “For purposes of self-employment tax, however, status as a limited partner is determined under Section 1402(a)(13); whether a partner is a limited partner under state limited partnership law is not determinative.” Simply calling a partner “limited” is not enough. The limited partner exception from self-employment tax creates a significant benefit when applied, but rulings focused on the substance of the partner’s interest have narrowed this exception. Let’s review how to properly qualify as a limited partner in light of the IRS’s recent emphasis in this area. In the process, we will also look at the specifics of how particular forms should still win the day by avoiding SE tax. Keep reading for more.