A friend of mine is a self-employed consultant.

Sharp, successful, earns well into the six figures every year.

During the business tax filing deadline last March, she left over $18,000 in tax savings on the table.

But two weeks from now?

She’s set to save even more than that thanks to opportunities in the tax code.

She didn’t miss out last time through any accounting mistake. It was just because nobody had ever walked her through what was available as a business owner.

Her story has always stuck with me. Because she's not unusual, and a lot of high earners I speak to find themselves in the same position.

With the business tax deadline coming up on March 16th, I put this checklist together to help you out.

It has the six biggest opportunities I keep seeing people miss out on.

If you earn a significant income from your own business, the next few weeks are some of the most valuable of the entire year.

And a lot of the savings go unclaimed simply because people don’t know it’s on the table.

So let’s get into it.

The Solo 401k is (in my view) the single best retirement account available to most self-employed people.

For some of you, there could be just two weeks left to take advantage of it.

It's open to:

Basically anyone with self-employment income and no full-time non-owner employees.

It lets you contribute as both the employee and the employer, that combination is what makes the numbers so large.

For 2025, the total limit is $70,000 (~3x what a typical W-2 employee can contribute in an employer sponsored 401k)!

There are also higher catch-up limits for those 50 or older:

A sole proprietor earning $250,000 in net self-employment income can potentially shelter up to $70,000 for 2025.

At a 37% marginal rate, that's nearly $26,000 saved from just one account!

Sole proprietors and single-member LLCs with no prior Solo 401k can still open one for 2025, right up to April 15.

For S-Corps and partnerships that have already adopted a Solo 401k the opportunity is coming up now to contribute.

You can still fund employer contributions for 2025, but the deadline is March 16, 2026 (Form 7004 can extend that).

To open one, choose a provider:

Carry, Fidelity, and Schwab all offer Solo 401ks.

You sign a plan document online, pick your account types, and get an EIN for the plan from the IRS website if you don't have one already.

The whole process typically takes under an hour (and is worth every minute).

Want a tax season discount to get started with one of these providers? Reply to this email with "Tax Season!" and my team will follow up with an exclusive Silly Money offer.

Direct Roth IRA contributions phase out at $150,000 for single filers and $236,000 for married filers in 2025.

The Backdoor Roth is the way in for anyone above those numbers, and it's one of my favorite strategies to talk about.

It's a simple two-step process (but not all brokerages support it!):

The result is money sitting in a Roth account growing completely tax-free. Peter Thiel famously used this strategy to shelter $5B from taxes.

For married couples, the deal gets even sweeter at up to $14,000 in contributions for 2025!

Solo 401k owners can go even further with the Mega Backdoor Roth.

After maxing out regular 401k contributions, any room left up to the $70,000 total limit can be filled with after-tax contributions and converted to Roth.

For someone contributing $46,500 in employer profit-sharing, that's up to $23,500 more going into a Roth account (either IRA or 401k)!

This can be invested in just about anything, making it an incredibly powerful wealth building tool.

The 2025 IRA contribution deadline is April 15, 2026, and there’s no extension on this one, so it's worth doing soon.

Open a traditional IRA with any major brokerage like Fidelity, Schwab, or Vanguard, and make the contribution, then ask them to process the Roth conversion. Carry also has tools that can help automate conversions for a smoother experience.

The HSA is available to anyone on a qualifying high-deductible health plan in 2025.

I’ve written a lot about how this is one of the most underrated accounts out there.

It's the only account that gives you a tax break three times over!

No other account does this (not even a Roth IRA).

The 2025 limits are $4,300 for individuals and $8,550 for families, with an extra $1,000 for those 55 or older.

Here's an approach I like to use with an HSA:

Pay your medical bills out of pocket and leave the HSA contributions invested.

Then you can hold on to receipts and reimburse yourself decades later, meaning those dollars keep compounding in the account for as long as you choose.

Most HSA providers let you invest the balance in index funds or mutual funds once a minimum threshold is met, so think of it as a bonus retirement account.

The deadline to contribute for 2025 is April 15, 2026.

Contributions made outside of payroll are reported on Form 8889.

Common providers include Fidelity, Lively, and HSA Bank. You can also use HSATracker.ai to keep track of all your medical receipts, built by yours truly at the Silly Money team.

Self-employed individuals, sole proprietors, partners, and S-Corp owners who pay for their own health insurance can deduct 100% of those premiums.

That covers you, your spouse, and your dependents.

This deduction comes straight off your adjusted gross income, reducing your taxable income before anything else is considered!

For someone paying $800 a month in premiums, that's $9,600 in deductions for the year.

At 37%, that's over $3,500 saved (from something you're already paying for).

This applies as long as you're not eligible for coverage through an employer or a spouse's employer.

It's reported on Schedule 1, Line 17 of Form 1040.

Luckily you’ll never have to give anywhere near that much thought to this.

The right tax provider should handle this in the self-employment or health insurance section.

And as always, a CPA can confirm the right amount based on your specific setup.

Don’t have a CPA to help you out? Feel free to request an introduction to a vetted tax pro by my team here.

Any self-employed person who uses a dedicated space at home exclusively for work can claim this one.

It doesn't have to be a full room, a clearly defined area works just as well.

There are two ways to calculate it:

A freelancer paying $2,500 a month in rent, with a 150-square-foot office in a 1,000-square-foot apartment, gets $4,500 in deductions from rent alone.

So it’s worth pulling out the tape measure.

There's also a useful bonus: a qualifying home office turns any drive to a client into deductible business mileage rather than a commute. At $0.70 per mile in 2026, that adds up quickly!

Sole proprietors and single-member LLCs report this on Schedule C.

The simple method goes in directly. The actual expenses method uses Form 8829.

Sole proprietors, S-Corps, partnerships, and LLCs can all deduct up to 20% of their qualified business income.

That's a big number.

On $300,000 in business income, that's a $60,000 deduction. At 37%, that's over $22,000 saved. From one line on the return. (One of my favorite numbers in all of tax planning.)

Here's how it scales:

The deduction begins to phase out above $197,300 for single filers and $394,600 for married filers.

Above those thresholds the calculation gets more detailed, depending on the type of business.

The right CPA can often find ways to increase the available deduction by adjusting income or wages.

It's filed on Form 8995, or Form 8995-A if you’re above the income threshold, own multiple businesses, or are in certain service-based professions like law. Most tax software handles all of this automatically.

Filing an extension can be helpful if there's any self-employment income involved.

It doesn't change what you owe. It just gives more time to file, and for Solo 401k owners, it pushes the deadline to fund employer and after-tax contributions.

March 15, 2026: S-Corps and Partnerships

April 15, 2026: All Other Scenarios

Here's my honest take: Most of these strategies aren't complicated. They just require knowing they exist.

Some take five minutes. Some take an hour. A few are worth a conversation with a good CPA.

But all of them are available to you, and the savings add up faster than most people expect.

Over time, tens of thousands saved in taxes could compound into hundreds of thousands (if not millions) when invested well.

This is what I mean when I talk about tax strategy as an alpha in investing.

No other strategy provides a clear and legally defined path toward an additional compounding return on capital.

Spend the next week carving out some time to think about your taxes just as you would with all your other investments, because they can be just as powerful.

See you next week!

— Ankur

P.S. If you'd like a tax season discount on a provider that can help you set up and execute a Backdoor Roth or Mega Backdoor Roth, don’t forget to reply with "Tax Season!" to this email and my team will follow up with an exclusive Silly Money offer.

Author Disclosure: I'm writing this as myself, not as some investment adviser or broker-dealer. I'm not a tax professional, this is all purely educational or my personal thoughts - not investment, legal, tax, or professional advice. Financial decisions involve risk, including losing money. Taxes are complex. Please do your own research or talk to a licensed pro before acting on anything you read here.