Hitting Tax Deadlines Is Smart, and Year-Round Tax Planning Is Even Smarter

Meeting tax deadlines is crucial, but good year-round habits — including making full use of workplace benefits — can help lower your tax bill and your stress levels. When you purchase through links on our site, we may earn an affiliate commission. Here’s how it works. Profit and prosper with the best of Kiplinger's advice on investing, taxes, retirement, personal finance and much more. Delivered daily. Enter your email in the box and click Sign Me Up.You are now subscribedYour newsletter sign-up was successfulWant to add more newsletters?Delivered dailyKiplinger TodayProfit and prosper with the best of Kiplinger's advice on investing, taxes, retirement, personal finance and much more delivered daily. 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Tax season can be a lot, but it also offers an opportunity to turn taxes from a once-a-year burden into a series of small, strategic moves to help you build financial confidence and momentum for the future.For most tax filers — especially those with workplace financial benefits such as a 401(k) or equity compensation — tax awareness usually pays off most when practiced throughout the year, rather than just focusing on deadlines.What's more, workplace benefits, such as retirement plans, health savings accounts (HSAs), employee stock purchase plans (ESPPs) and financial wellness tools, can be used to simplify the process and strengthen your overall financial planning.Become a smarter, better informed investor. Subscribe from just $107.88 $24.99, plus get up to 4 Special IssuesProfit and prosper with the best of expert advice on investing, taxes, retirement, personal finance and more - straight to your e-mail.Profit and prosper with the best of expert advice - straight to your e-mail.With steady habits and smart use of workplace resources, tax season can shift from stressful to strategic as you find ways to keep more of what you earn. Here are five year-round behaviors that can help make a real difference.Many individuals may not realize just how much workplace benefits can help them navigate tax season. You should look into:About Adviser IntelThe author of this article is a participant in Kiplinger's Adviser Intel program, a curated network of trusted financial professionals who share expert insights on wealth building and preservation. Contributors, including fiduciary financial planners, wealth managers, CEOs and attorneys, provide actionable advice about retirement planning, estate planning, tax strategies and more. Experts are invited to contribute and do not pay to be included, so you can trust their advice is honest and valuable.Additionally, access to financial wellness resources — such as on-demand education, coaching or support from financial advisers — can further empower you to navigate tax season with greater confidence and success.Employers often partner with providers to deliver educational sessions, checklists, explainers or equity-specific guidance. These resources can help transform confusion into clarity so you can integrate your workplace financial benefits and tools into a broader plan.It's always helpful to have a clear view of your financial situation, so try kicking off tax season with a quick, stress-reducing organizing session. Gather key documents such as your W-2, 1099s, equity-related forms, last year's return and records of deductible expenses — many may live on your workplace benefits portal.While the 2025 tax year has closed, there may be opportunities to still make some moves through your workplace benefits.For example, look into any IRA and HSA contributions and review your employer 401(k) settings — these typically remain open until Tax Day. And, whenever you have any major life changes or equity events, revisit your workplace benefits choices to ensure they still align with your goals.Even the most money savvy among us may lack a strategy when it comes to minimizing taxes on investment returns, including any investments you may hold through workplace retirement accounts or equity awards.Tax-aware investing is a practice of structuring your investments to help minimize taxes and maximize after-tax returns.Popular methods include placing income-generating assets in tax-deferred accounts, such as 401(k)s or IRAs, using municipal bonds and tax-efficient funds in taxable accounts and harvesting losses to offset gains when possible.It's important to discuss with a tax professional and financial adviser to help make sure any of these strategies fit your needs and align with IRS rules and requirements.That said, taking a tax-aware approach year-round can potentially help you to grow and keep more of your investments.To shift the focus back to your workplace benefits, it's also important to understand how different types of benefits are taxed (or aren't) in general.For example, is your retirement account traditional (funded with pre-tax dollars, requiring you to pay taxes on withdrawals) or Roth (funded with after-tax dollars, with no tax on withdrawals)?And different types of equity compensation — incentive stock options (ISOs), non-qualified stock options (NQSOs), restricted stock units (RSUs), employee stock purchase plans (ESPPs) — come with different tax treatments and paperwork. Holding periods matter, as does the timing of any stock you sell.Understanding what all this means can help you navigate decisions more confidently, calculate your taxes accurately and avoid surprises. Check with your employer for educational content or access to benefits support.Looking for expert tips to grow and preserve your wealth? Sign up for Adviser Intel, our free, twice-weekly newsletter.Your tax outcome can be an opportunity to realign goals and get more intentional about the year ahead. If you find that you owe taxes, consider the most effective way to pay.For example, selling investments to cover the bill may result in capital gains taxes and affect your long-term strategy. To identify more tax-efficient methods for generating liquidity, you might benefit from connecting with a financial coach or adviser and from speaking with a tax professional.On the other hand, if you receive a tax refund, consider how you can put it to work for your longer-term financial wellness and overall goals.You might consider using the funds to pay down high-interest debt, strengthen your emergency fund, or increase contributions to a workplace retirement account or 529 plan.Even small amounts set aside with intention can help you build financial momentum.Tax season doesn't have to be overwhelming. With the right preparation, intentional use of your workplace benefits and year-round tax-smart habits, you can simplify your experience, avoid surprises and make meaningful progress toward your goals. Simple steps can help you build better habits to stay proactive and prepared.And remember: While workplace tools and resources can help you make more informed decisions, it's always wise to consult a qualified tax professional about your specific situation.Tax-loss harvesting. IRS rules stipulate that if a security is sold by an investor at a tax loss, the tax loss will not be currently usable if the investor has acquired (or has entered into a contract or option on) the same or substantially identical securities 30 days before or after the sale that generated the loss. This so-called "wash sale" rule is applied with respect to all of the investor's transactions across all accounts. show lessMorgan Stanley Smith Barney LLC ("Morgan Stanley") and its Financial Advisors and Private Wealth Advisors do not provide any tax/legal advice. Consult your own tax/legal advisor before making any tax or legal-related investment decisions. show lessWhen Morgan Stanley Smith Barney LLC, its affiliates and Morgan Stanley Financial Advisors and Private Wealth Advisors (collectively, "Morgan Stanley") provide "investment advice" regarding a retirement or welfare benefit plan account, an individual retirement account or a Coverdell education savings account ("Retirement Account"), Morgan Stanley is a "fiduciary" as those terms are defined under the Employee Retirement Income Security Act of 1974, as amended ("ERISA"), and/or the Internal Revenue Code of 1986 (the "Code"), as applicable.

When Morgan Stanley provides investment education, takes orders on an unsolicited basis or otherwise does not provide "investment advice", Morgan Stanley will not be considered a "fiduciary" under ERISA and/or the Code. For more information regarding Morgan Stanley's role with respect to a Retirement Account, please visit www.morganstanley.com/disclosures/dol. Tax laws are complex and subject to change. Morgan Stanley does not provide tax or legal advice. Individuals are encouraged to consult their tax and legal advisors (a) before establishing a Retirement Account, and (b) regarding any potential tax, ERISA and related consequences of any investments or other transactions made with respect to a Retirement Account. CRC 5182475 02/2026This article was written by and presents the views of our contributing adviser, not the Kiplinger editorial staff. You can check adviser records with the SEC or with FINRA.Profit and prosper with the best of Kiplinger's advice on investing, taxes, retirement, personal finance and much more. Delivered daily. Enter your email in the box and click Sign Me Up.Kate brings more than 20 years of experience in financial services, technology and benefits. Prior to joining Morgan Stanley, Kate held management and elevating leadership positions at several financial service institutions, including E*TRADE, First Republic Bank and PNC focused on B2B, B2C and B2B2C lines of business.