I’m a bit late on this one, in the midst of finishing up client taxes and other life busyness. This year I substantially increased the return preparations my company did, and through this process I have a much broader sense of what investors—including high net worth investors—need to be doing to manage the stress associated with tax season.
To effectively manage your taxes, reduce your stress, and plan effectively, there are really two key elements you must master. First, (and most obvious), you must pay them. But secondly, and much less obvious—even for those with a high net worth—is tax administration. The process of managing yoru taxes throughout the year is key to avoiding this first-quarter panic that seems to be universal. If you can effectively administer your taxes, the stress you feel will be reduced. This Stack will focus solely on how you can much more effectively plan and execute your taxes in the coming years.
If you aren’t following these steps below already, this is what you need to do to make next year’s tax season go much more smoothly.
Plan to File & Pay Your Taxes in April (not October)
Your default should be to prepare, file, and have paid your taxes by April 15. Now, of course there are exceptions, of course there are things that might make you need to extend. But I am finding more and more people are just being advised by their accountants to delay. I almost think this is just so accountants have more time to do the taxes because there is very little upside to extending your taxes.
One major downside is even if you file an extension, you are still supposed to pay your full amount of taxes owed by April 15. A lot of people misunderstand this and think that you get to delay payment until October along with filling. This is not the case. You are going to owe interest and penalties on anything you owe after April 15–even if you are filing in October.
Secondly, all this does is push your ongoing relationship with the powers that be (your government) further into the year. Let me be honest here—you are better off paying these institutions what you owe and playing by the rules than letting this hang over your head. Avoid catching the Eye of Sauron in the form of the state, and give them the money and paperwork they think you owe sooner rather than later.
Understand & Pay Your Quarterly Taxes
Many people should be paying taxes directly to the IRS and their state every quarter in addition to their withholdings. Self-employed people are more familiar with this, but if you are getting a tax bill every year of $1,000 or more, you should be paying quarterlies.
Quarterly tax payments are advance installments you make to the government throughout the year to cover your tax bill, ensuring you don’t owe a large lump sum (and potentially face penalties) when you file your annual return. The amount owed each quarter is based on your previous year’s tax filing.
When your return is prepared, if you have owed more than $1,000 in taxes that year, quarterly estimates (and their associated vouchers) are automatically generated for the following year. You need to be paying these.
A final note on quarterlies. While they are annoying and understandably not something you want to pay, they are key to avoiding a huge and shocking tax bill in April. And, effectively managing these means you smooth out your cashflow to accommodate taxes much more effectively. Over the years, this will help reduce the anxiety you feel every April and end the shock and awe associated with receiving an extremely expensive tax bill.
Create IRS and State Tax Logins & Use Them
This I cannot stress this enough. Over the years, I’ve discovered a very small percentage of my clients have logins for the IRS and their state tax collectors. Here is the reality—taxes are most likely your largest expense in life, and if not done right these institutions have the power to administratively and financially destroy your peace and your wallet. By creating logins with the Feds and your state (if your state collects income tax), you have a much better picture of what payments they’ve received and what the history of your financial relationship looks like with them. Ideally, you should not be submitting payment to them via mail and checks. Rather, create these respective logins, and submit it all electronically. You then have a record of what has been paid and exactly when.
You must properly manage your tax planning and get in front of any taxes you will need to pay so every year it’s not a huge source of aggravation. The good enws is taht you can tax plan effectively starting today. Begin with these recommendations and I promise, the coming tax years will be a lot less stressful.
Chisholm Client Update- Your Investments & War
If you’ve worked with me long enough, you know how often I stress the importance of holding steady even in when the sky seems to be falling. It is important to understand that market cycles will include poor government policy, environmental catastrophes, war, oil shocks, large institutional defaults, and all the rest. Yes, there are periods in advanced economies where performance suffers, sometimes greatly,—and while downturns are expected—the trouble is nobody can predict exactly when they are going to happen.
This does not mean I do not get stressed out or worry like everyone else from time-to-time (I am entirely all in on the U.S. economy personally and professionally). But alas, I am now literally old enough to remember some of these “end of the worlds” that never came. And I started my business right after 2008, so I understand that even when the “end of the world” comes, to recover you must hold steady in the market or you won’t recover from that “end of the world” event.
This does not mean you should pretend there are not real human and structural problems on the horizon when it comes to the economies—particularly in the West. But here’s, the thing, we are human, and we will always have self-created problems on the horizon that will impact us in some way or another. And all these good, bad, and ugly events never quite unfold how they are predicted. Keep in mind, the U.S. has an economy that is full of real skill, innovation, and value. Sure, we might need to refocus on manufacturing and building things within our borders, yes an AI disruption of some kind is inevitable, (I will write on this at some point in more detail), but anyone who is telling you the economy is “fake” or going to collapse overnight while we send men to the moon, create an internet out of satellites, and hop in a taxi that is driving itself isn’t paying attention.
So I say all this, to say—stay the course. Use effective cash management to plan for the short-and mid-term which can and will have its upheavals. But do not get distracted by things you cannot control and certainly do not let your newsfeed dissuade you from understanding that nobody knows when the bad comes, that yes market corrections come, but you have prepared as much as reasonably possible. The point of financial success is to live your real life—so go do that (and turn off the screen)!
Rural Life Lately
Our new home on Goshen Grove Farms will be move-in-ready around the end of April. We successfully sold our current house (which we are renting back), and are anxious and excited to move to our land and start living in the home we’ve been imagining and building since we bought the farm.
Here is a view of my office, with what we jokingly call “the Shanty” on the water in the background. Just think, I will be doing my Q2 and beyond reviews from this room with you all! Cannot wait!
Taxes & War by Jenny Logan, originally posted on April 10, 2026 Read on Substack