By March, most business owners are in a familiar spot: the year is moving, the team is busy, clients are busy — and somewhere in the back of your mind you’re thinking, “wait, taxes are due soon, aren’t they?”
This month’s One Thing is about getting ahead of that feeling before it becomes a scramble. A 30-minute business money check-in — one focused session where you step out of the whirlwind, look at what your numbers are actually telling you, and walk away with one clear decision.
I recorded a short video walking through the full framework. Watch it here, then keep reading for the specific tax moves worth knowing before April 15.
The 30-Minute Check-In Framework
The check-in has three parts: tax awareness, a quick financial health snapshot, and one concrete money move coming out of it.
Part 1: Tax Awareness
For calendar-year businesses, March is when partnership and S-corp returns are due — or at least when extensions and K-1s need to be handled. And for many owners, the business flows right onto the personal return, so the April deadline is closer than it feels.
Ask yourself three questions:
- Are my 2025 business returns on track to be filed or extended on time?
- Do I know whether there’s a tax bill coming?
- Do I know where that money is coming from — cash on hand, a specific account, upcoming receivables?
If you’re not sure on any of these, that’s the signal. It’s not about playing CPA — it’s about knowing whether your cash and your tax reality are actually aligned before the crunch hits.
Part 2: Quick Financial Health Snapshot
Pull three reports for the year so far: your P&L, your balance sheet, and your cash position. You’re not trying to become your own CFO in 30 minutes — you’re just listening to what the numbers are already telling you.
On the P&L: Is revenue up, down, or flat versus the same period last year? Are any expense categories obviously out of line?
On the balance sheet: Are clients taking longer to pay? Are you leaning on debt more than you’d like just to smooth cash flow?
On cash: How many months of core expenses does your operating account actually cover right now?
Part 3: Choose One Money Move
The most important part. You don’t end this session with ten ideas, you end with one committed decision and you need to actually execute. A few examples are:
- Following up aggressively on your top five overdue invoices for the next 30 days
- Cutting one subscription or recurring cost that isn’t pulling its weight — Alan Miltz’s 1% concept is worth knowing here: a 1% reduction in expenses has the same bottom-line impact as a much larger increase in revenue
- Setting a rule where a specific percentage of every dollar that comes in moves automatically to a tax or profit account
- Moving your estimated tax payment into a dedicated account right now, so it’s not accidentally spent before April
The Tax Moves Still on the Table Before April 15
The check-in gets you oriented. But there are also specific tax tactics worth knowing before the deadline arrives. Here’s what’s still available to you.
Solo 401(k)
If you’re self-employed and not maxing one of these, this is probably your biggest missed opportunity. The 2025 contribution limit is up to $70,000+ combining employee and employer contributions.
Never opened one? Under recent rules, you can retroactively open and fund a Solo 401(k) for 2025 all the way until your filing deadline — April 15, or October 15 with an extension.
Already have one? Employee deferrals are due April 15 (assuming you made the election before December 31, 2025). Employer and after-tax contributions can go in as late as October 15 with an extension.
Quick math: A sole proprietor earning $150K could potentially shelter $50,000+ in a Solo 401(k). At a 35% effective rate, that’s $17,500 back in your pocket.
Profit Sharing Contributions to a 401(k)
If you have employees and offer a 401(k), profit sharing contributions are one of the most powerful — and most overlooked — tools in the playbook. As the employer, you can contribute up to 25% of eligible employee compensation as a profit sharing contribution, on top of regular employee deferrals.
- Contributions are discretionary meaning you decide each year whether to make them and how much.
- They’re fully deductible as a business expense, reducing taxable income while building wealth for yourself and rewarding your team.
- The deadline for 2025 contributions is your tax filing deadline either April 15, 2026 or October 15, 2026 with an extension.
Quick math: A business owner earning $200K in W-2 comp could contribute up to $23,500 as an employee deferral plus up to $50,000 as a profit sharing contribution — totaling $73,500 for the year. At a 35% effective rate, that’s potentially $24,500 in tax savings while adding $70,000+ to your retirement funds in a single year.
HSA
If you’re on a qualifying high-deductible health plan, your HSA is one of the most underused accounts out there. Contributions are tax-deductible, growth is tax-free, and withdrawals for medical expenses are tax-free. Triple tax advantage — and most people barely touch it.
2025 limits: $4,300 individual / $8,550 family, plus $1,000 catch-up if you’re 55+. Deadline: April 15.
Pro tip: Pay medical costs out of pocket, let the HSA grow invested, and reimburse yourself later. As long as you keep your receipts, there’s no deadline on reimbursement.
Self-Employed Deductions Worth Double-Checking
Before your CPA finalizes your return, make sure none of these are slipping through:
- 50% of self-employment tax — deducted automatically, but confirm it’s captured.
- Self-employed health insurance — 100% deductible for you and your family.
- Home office — requires dedicated, exclusive-use space. The actual expense method often beats the simplified $5/sq ft option.
- Section 199A (QBI deduction) — pass-through owners may deduct up to 20% of qualified business income. Phases out above $197,300 (single) / $394,600 (married filing jointly).
Should You File an Extension?
Filing Form 4868 by April 15 pushes your deadline to October 15 — and also extends the window for Solo 401(k) employer contributions and SEP-IRA contributions.
Important: it’s an extension to file, not to pay. If you owe, you still need to estimate and pay by April 15 to avoid penalties. But if your income picture is still coming together or you want more time to optimize your retirement contribution, extending is a smart move.
Is Your Wealth Strategy Keeping Up With Your Business?
The check-in and the tax tactics above will help you get cleaner heading into April. But the bigger question — whether your personal wealth strategy is actually keeping pace with what you’re building — is a different conversation.
If you’re not sure whether your tax strategy, retirement contributions, and wealth plan are all working together the way they should, the Strategic Wealth Scorecard is a good place to start. It takes 3 minutes and shows you exactly where your gaps are.
About the Author
Taylor Nissi CFP® is the founder of Pleasant Street Wealth Advisors, a Multi-Family Office serving entrepreneurs, business owners and high-net-worth families globally.
ABOUT TAYLOR NISSI: I’m a CFP® and CEPA who helps business owners running 7- and 8-figure companies align their personal wealth strategy with their business success. At Pleasant Street Wealth Advisors, we help entrepreneurs align their personal wealth strategy with the success they’re building in their business — so nothing falls through the cracks.
Entrepreneurs and business owners.
Serves a national or global client base.
Based in Westchester County NY
High Net Worth individuals