2025 was a tough year for a lot of us. Most of us want cash in our hands right now. So naturally, we put off retirement savings, which benefit “future you.” We tell ourselves we’ll save for retirement later. When our profit margins aren’t shrinking, the economy is less volatile, and everything isn’t on fire.

But we’re talking about it right now because an upcoming deadline is forcing the conversation. If you want to make a personal Roth or traditional IRA contribution for last year, you can do it until April 15, or up to the day you file your taxes, if you file earlier. 

This is the deadline when I see people make mistakes, because they’re rushing to file so they can get their refund as fast as possible. 

I totally understand wanting your tax refund in your hands yesterday, if not sooner. But if you move too quickly, you can miss out on an opportunity to save money today and for future you. Because once you file, the option goes away.

So, today, we’re going to slow down just enough to help you make the right retirement call for this year.

There are two retirement savings buckets: personal and business. 

The personal bucket is the one that any human who earned US income, including kids and non-citizens, can fill. You can choose to use a Roth or traditional IRA, or a combination up to the allowed limit of $7,000 for 2025 ($8,000 if you’re over 50). You can open an account and move money until April 15, or until the day you file your taxes if you file earlier. 

And that deadline is firm, even if you take an extension. Fund by April 15, or it’s gone.

Then there’s the business side. This is where it gets interesting.

If you own a company or have self-employment income, you get a much higher allowance for annual savings. For 2025, it’s $70,000 (and even higher if you’re age 50 or more with a 401k). The timing is different too. You can stretch the amount of time you have to capture last year’s allowance when you take a filing extension. 

One catch: your 401k plan had to be opened before December 31, 2025. You can fund it during an extension period, but you can’t open a new one for last year. If you missed that boat, you still have the option to set up a SEP IRA and fund up to $70,000.

If you’re saying, “But Jill, I can’t afford to pay this tax bill AND fund my retirement!” you might be in better shape than you think. Funding a traditional 401(k) or IRA is done pre-tax, which reduces the amount you owe in taxes right now. It reduces your taxable income. The choice becomes and “or”: pay the IRS or keep more of the funds for yourself.

If you can do both -- pay your taxes and save for retirement -- give the Roth option a more serious look. The money you invest can grow forever without ever being taxed again. That’s right, you get all the upside, forever, tax-free. 

And since you’re saving post-tax money, you’re allowed to take back the principal at any time. Your gains have to stay in the account, but the money you save for retirement is much more accessible. If you’re worried that you might need that money back before you’re aged 59 ½, funding a Roth might be a better option. 

And yes -- people still want the cash today versus the cash tomorrow. This is your marshmallow test. These programs are meant to give you incentives to defer your satisfaction till tomorrow -- to not eat the marshmallow. 

As long as you’ve made an intentional choice this year and you’re not on autopilot, you’re fine. Personally, I fund a traditional SEP IRA throughout the year from my business as “minimum” savings -- that $7,000 goal I highlighted last week --  and use my December tax meeting to figure out what amount (if any) to top up before tax time. 

One more note: if you find out you’re getting a refund, consider saving it for retirement, or even using it to cover the cost of converting some of your previous pre-tax savings into Roth. That’s called a Backdoor Roth conversion, and it can happen in personal or business retirement savings accounts. 

If there is any amount you can save for the future and you do not need the tax deduction right now, putting any amount up to $7,000 in a Roth IRA is the no-brainer move.

If you owe money and you’d rather keep it for yourself than pay it to the government, using a pre-tax traditional IRA, SEP, or 401(k) is the way to keep the money instead of paying it in taxes.

Of course, there isn’t only one “right” move. For many of us, 2025 was a rocky financial year. And with the new tax law, you might be looking at a substantial one-time refund. As always, I encourage you to be intentional in your choices and know your options. 

So here’s your simple next step: decide whether you’re doing the personal bucket, the business bucket, or both. Do you need the deduction now (traditional), or the flexibility (Roth)? Then actually move the money and tell your tax preparer you did it. 

Ready to get started? Great, here’s what you do:

Have more questions about retirement options as a business owner? Book a free 20-minute strategy session.

It’s officially tax season. 

If you want to make a 2025 retirement saving contribution, make sure you know which deadlines go with which dates. A quick reminder, the personal contribution deadline cannot be extended. The business contribution deadline can. And any ticking clocks stop on the day you file your taxes.

The expanding war in the Middle East. At the time I wrote this, the White House was peddling a rotating set of six justifications for its illegal action in Iran. Gas prices were going up, the market was dropping, the Strait of Hormuz was closed to shipping traffic, and entire F1 teams were stranded in Dubai. Over 24 hours, the president has moved the timeline for active engagement from two weeks to five weeks to forever. I cannot look at news updates without going full Emily Charlton when Miranda’s facialist ruptures a disc. 

Anthropic and Claude AI. As part of our aligned spending audit, we recently moved from ChatGPT to Claude. Claude’s Opus 4.6 has some lovely capabilities for financial projections that have already saved us significant time, especially in visualization. The jump in Claude’s professional AI capabilities has inspired these two widely-read scenarios (this and this) the second of which actually caused a large dip in software stocks last week. Anthropic softened its safety stance, which concerned me, but then the US government asked them to give up all guardrails, which it refused to do. (OpenAI approved using ChatGPT for mass public surveillance and autonomous weapons strikes.) All this to say, it’s not an option to not engage these tools, and we need to be thoughtful and aware in our choices.

Estrogen patch shortage. While I’m so glad the word is out on the short- and long-term health benefits of patching up, we are now facing delays in having estrogen patch prescriptions filled. CVS seems to be out entirely, leading to days spent chasing alternative sources and moving prescriptions. Men, trust me -- you want to help fix this asap, if only to keep this section of the newsletter from going further off the rails.

ICYMI, here are resources you should know about:

Here’s some good news: the new Zillow home price forecast says it’s going to be a buyer’s market for the next 2 years. If you’re thinking about buying a home soon, remember that you get the best mortgage as a self-employed person by showing income on your federal tax return. So, if your strategy has been to avoid taxes by showing low or no income from your business, it might be time to pay to get access to the best lending opportunities.

Fintech companies have created a way to access wages early without penalties or having to take a loan that has to be paid back in full. Unsurprisingly, this is an employment benefit that is wildly popular right now -- even more so than 401(k) participation. We have this service available to my team within Gusto, and (also unsurprisingly) they strongly encourage its use. Just watch your interest rates, as long-term borrowing can quickly put you back in loan shark territory, albeit with less risk to your kneecaps.