For many business owners and professionals approaching retirement, the first half of the year can feel like cleanup season. You’re closing the books on last year, preparing tax returns, and reviewing what already happened.
But some of the most impactful retirement decisions aren’t made in December during year-end planning discussions — they’re made early.
January through June includes several IRA and retirement-related deadlines that can influence taxes, investment growth, charitable planning, and long-term income strategy. When addressed proactively, these deadlines become opportunities to strengthen your plan rather than simply meet requirements.
Here’s what to pay attention to as 2026 begins.
Build Momentum with Early-Year IRA Funding
As of January 1, you can begin making your 2026 IRA contributions. For Traditional and Roth IRAs, you have until April 15, 2027, to fully fund your 2026 contribution. However, many investors choose to contribute earlier in the year.
For pre-retirees, early contributions may provide additional time for tax-advantaged growth. For business owners with strong cash flow in the first half of the year, this can also create discipline to maintain consistent retirement savings before competing priorities arise.
If you’re making a prior-year contribution (for 2025) in early 2026, clarity is critical. When contributing by check, write “2025 IRA contribution” in the memo line. If contributing electronically, confirm that the correct tax year is selected. If no year is specified, custodians may default to the current year.
That small administrative detail can prevent avoidable corrections later.
Integrate Charitable Planning into Your Income Strategy
If you are age 70½ or older, you may begin making Qualified Charitable Distributions (QCDs) from your IRA as early as January.
For individuals subject to Required Minimum Distributions (RMDs), QCDs can count toward your 2026 RMD and may help reduce taxable income. For retirees who give consistently each year, starting early provides flexibility and avoids a year-end rush.
For charitably inclined pre-retirees nearing RMD age, early coordination between giving plans and distribution strategies can be an important part of managing retirement income.
Maximize Flexibility with IRA Contributions and Recharacterization
April 15, 2026, is more than just tax filing day. It is the deadline for making a 2025 Traditional IRA contribution, Roth IRA contribution, and SEP-IRA contribution (if you are self-employed). It is also the deadline to recharacterize certain IRA contributions.
For business owners, this date can represent a meaningful planning window. SEP-IRA contributions, for example, may allow you to make a deductible retirement contribution after year-end and once income is finalized.
Recharacterization offers additional flexibility. It allows you to change the type of IRA contribution you made — such as moving a contribution from a Roth IRA to a Traditional IRA (or vice versa) — and have it treated as if it were originally made to the correct account. This can be helpful if income ends up affecting Roth eligibility. For example, if you contribute to a Roth IRA and later discover your income exceeds the allowable limits, you may be able to recharacterize the contribution before the deadline to help avoid penalties.
It is important to remember, however, that while IRA contributions can be recharacterized, Roth conversions cannot be undone.
What a Tax Extension Does – and Does Not – Change
Filing a tax extension gives you additional time to file your return — but it does not extend most IRA-related deadlines.
An extension does not move the deadline for making Traditional or Roth IRA contributions, taking Required Minimum Distributions, completing Roth conversions, or making Qualified Charitable Distributions for the year.
One key exception applies to SEP-IRAs and Solo 401(k) plans for self-employed individuals and business owners. If a tax extension is filed, the contribution deadline may extend to the October filing deadline.
For many owners and high-income professionals, April 15 is less about paperwork and more about strategic positioning for the year ahead.
Evaluate Roth Conversion Opportunities Early in the Year
Roth conversions can generally be made throughout the year, but the first half of the year is often an ideal time to evaluate whether a conversion makes sense.
Once your prior-year tax return is complete, you have clearer visibility into income levels and can better estimate whether the current year will be similar. Coordinating Roth conversions with other income sources — such as Social Security benefits, Required Minimum Distributions, business income, or capital gains — can help manage tax brackets strategically.
For pre-retirees transitioning from peak earning years toward retirement income, this window can present thoughtful opportunities to reposition assets in a tax-aware way.
Manage Cashflow Across Competing Goals
For families balancing retirement savings and college funding, the first half of the year is a valuable time to revisit cash flow.
IRA contributions can affect adjusted gross income, which may in turn influence financial aid calculations and certain tax credits. Coordinating retirement contributions with 529 plan funding and tuition payments requires careful planning, especially for business owners whose income may fluctuate.
Proactive coordination early in the year can prevent unintended consequences later.
Look Ahead Instead of Looking Back
The first half of the year often pulls our attention backward as we prepare tax returns and finalize prior-year numbers. But some of the most important retirement planning decisions happen when we look ahead.
Evaluating IRA contributions. Coordinating charitable distributions. Considering Roth conversions. Aligning retirement and education funding goals. Each of these decisions, when made early, creates flexibility and clarity for the months ahead.
If you are approaching retirement or running a business, these deadlines are not just calendar reminders — they are strategic opportunities.
At Access Wealth, we believe time is one of your most valuable assets. If you would like to discuss how these early-2026 decisions fit into your broader financial strategy, give us a call. Together, we can use this planning window intentionally and build a more impactful and dependable financial future.
