How many times can I re-write a newsletter in a week? Come on, man. Nobody wants to think about the federal government this much. 

I’ve written about uncertainty before. But this week, it’s uncertainty and an annual tax deadline, which means we have to make money choices.

Retirement savings, in this economy? The stock market and tariff rollercoaster over the past week may have you thinking twice about whether you want to defer any additional funds right now. Today, let’s take a step back and look at whether compensating yourself via retirement savings is still the right move.

Use this information for educational purposes only. I am not your personal tax or financial advisor. 

First, reconsider your cash needs. As of 12 PM PT on Wednesday, April 9, most “assorted reciprocal tariffs” are on hold. But the base 10% global tariff and an upgraded 125% tariff on China remain, as do steel, aluminum, and auto levies. You may need your reserved cash to stay in business and pay import duties until you can recover them through sales. Entirely fair.

(Aside: China called 47’s bluff because they can. Lest you think this delay is a US win, China will be just fine with not buying American Treasury bonds and sending its diplomats to fill the power vacuum left by the America First strategy. US small business owners facing 10x import duties, not so much.) 

Another consideration is your emergency fund. While you should have a backup bank line of credit, if you’re in your first two years of business or you haven’t shown profits, that may be difficult. While we don’t yet know whether we’re in a recession, since last week, the risk of entering one this year is up from 25% to 75%. If you are concerned about covering payroll or your own bills, you may decide that paying the taxes due for 2024 and keeping the funds available in a high-yield savings account is the right move. Also fair.

If you’re ready to skip out on retirement savings because you’re nervous about putting money into the market right now, please read on. Retirement savings has two aspects:

1. Depositing money to save on your current or future year taxes

2. Investing that money for growth

Depositing money into your IRA or 401k is not the same as investing in the stock market. Making a contribution to a traditional IRA or 401k account by your tax deadline checks the box for receiving the current year tax deduction. If you don’t like the current market conditions, you can leave the money in the cash or money market option. Do you want to pay more taxes into this dumpster fire of an administration or save the money for yourself? I thought so. 

Also, if your investment strategy has been all S&P 500 index or Magnificent 7 stocks, it’s time to broaden your portfolio strategy. You can invest in funds for almost anything at a low cost through your online broker or in your 401k. Besides equities (stocks), you can choose from other asset classes like cash, fixed income (bonds), real estate, and commodities (raw goods). How you mix these for yourself is your personal investing strategy. If there’s a country or industry you think will be a winner over the next few years, buy its ETF. Or you can focus on impact investing. Funds allow you to purchase one share of one thing and get access to dozens or hundreds of publicly-traded companies. 

And yes, the market will continue to go up and down.  If you made an investment in the last seven days, it’s looking pretty good right now. And, I bet you spent much of this week wringing your hands over whether you should have cancelled that deposit. Volatility and uncertainty remain high, and will until at least the midterm elections in November 2026 unless Congress steps up. In the best of times, even professionals struggle to “time the market,” meaning knowing precisely when to buy or sell. The lesson of the last 24 hours is that it’s hard to predict whether any single market day or hour will be amazing or horrible.

The classic solution is dollar-cost averaging (DCA), which means investing some amount of money in the market on a periodic schedule. If the market’s up, your money buys fewer shares. If it’s down, it buys more. My personal strategy is to deposit a small amount into my SEP IRA each month and top it up at tax time, if profitability and cash flow allow. 

For more support on today’s topics, I pulled these newsletters from archive:

• November 2024: Uncertainty / getting past functional freeze 

• February 2025: Retirement savings strategies

If you’re moving forward with your contributions, remember that personal IRAs must be funded by the earlier of April 15 or when you file your 2024 taxes. Business IRAs and existing 401ks can be funded until the earlier of filing your return or your extension deadline. If you’re new to all of this, or want to brush up, check out my blog post on how to save for retirement when you’re self-employed. 

Next week, you’re getting the planned newsletter. Because the client deadlines are also real.

On the topic of retirement, I have a new partnership for my subscribers from Betterment, a financial services provider with excellent educational tools, holistic accounts beyond the 401k like 529 plans and high-yield savings, and a social impact fund investing option. Betterment 401ks are fully integrated with Gusto payroll. If you’d like to learn more, please reach out to our dedicated account rep, JJ Osterman, to schedule an appointment. Mention that Jill James referred you.

Tuesday, April 15 is the deadline for 2024 state and federal income tax payments and Q1 2025 estimated payments. After April 15, you can be penalized for 2024 underpayment, even if you’ve taken an extension. 

If you’re not able to pay in full, or you want to conserve cash to help with tariff payments, you can set up a payment plan by contacting the IRS or your state tax authority before the deadline. You can simply say, “I can’t make my payment in full, I’d like a payment plan.” They can’t determine whether you could, but choose not to. 

April 15 is also the last possible day to make 2024 personal IRA contributions to a traditional or Roth account.*

*unless you’re in a declared FEMA disaster area like Los Angeles County, Western North Carolina, or more recent flood areas in Kentucky and West Virginia. Specific details here.

Brevity: I can’t monitor the news all day, nor is it good for me. I’ve been keeping up with the day’s business and economic events by spending 20 minutes per day with the Marketplace podcast. Fun fact: four separate friends consider host Kai Ryssdal their “radio boyfriend.” Move over, money honeys.

Levity: Upon visiting with his child, Professor Scott Galloway had this to say about my alma mater: “I can’t imagine people I’d rather not party with.” (Start at 3:51.) You can zhuzh up the dorms and put a glass dome on the underground library but the vibes are still the 300 out of 300 party school ranking we earned in the ‘90s. And I returned for grad school voluntarily. Never change, UChicago.