{"id":139,"date":"2022-04-18T11:59:00","date_gmt":"2022-04-18T11:59:00","guid":{"rendered":"https:\/\/moneywithkatie.com\/how-i-organize-my-life-for-tax-season\/"},"modified":"2025-09-05T16:48:06","modified_gmt":"2025-09-05T16:48:06","slug":"how-i-organize-my-life-for-tax-season","status":"publish","type":"post","link":"https:\/\/moneywithkatie.com\/how-i-organize-my-life-for-tax-season\/","title":{"rendered":"How I Organize My Money for a Stress-Free Tax Season"},"content":{"rendered":"<div class=\"sqs-html-content\" data-sqsp-text-block-content>\n<p class=\"\" style=\"white-space:pre-wrap;\">Let me preface this post by saying that if you have access to a CPA and you\u2019re feeling a little unsure about doing your taxes yourself (or, more realistically, you just don\u2019t want to), it\u2019s probably wise to pony up a few hundred bucks and pay your CPA to do them for you.&nbsp;<\/p>\n<p class=\"\" style=\"white-space:pre-wrap;\"><em>That said<\/em>: Regardless of whether you file your own taxes or hire a CPA to do them for you, <em>you need to be organized. <\/em>CPAs aren\u2019t mind readers and the return they file for you will only be as accurate as the information you provide them, so I think this \u201corganizational framework\u201d is useful for anyone who feels like they\u2019re in over their heads. I\u2019m almost certain I\u2019ll end up&nbsp;being audited at some point because we always have so many forms, but having a system in place to organize them ahead of time helped tremendously.<\/p>\n<p class=\"\" style=\"white-space:pre-wrap;\">So your 2024 return is (likely) water under the bridge and you\u2019re trying to get your shit together ahead of time for 2025 so you don\u2019t have to undergo the same #pain as you did this year: Cheers to that! No time like the present. Let\u2019s dive in.<\/p>\n<p class=\"\" style=\"white-space:pre-wrap;\">This post may feel like it was sponsored by TaxAct, but it wasn\u2019t (despite me sliding in their DMs plenty of times)\u2014I\u2019m just including them where it\u2019s relevant since that\u2019s who I\u2019ve used to file for the last four years.<\/p>\n<h2 style=\"white-space:pre-wrap;\">Primary Tools: the Wealth Planner, Lots of Digital Folders, and Caffeine<\/h2>\n<p class=\"\" style=\"white-space:pre-wrap;\">I promise I\u2019m not about to put the hard sell on you; you can create your own version of this Planner if you don\u2019t use <a href=\"https:\/\/moneywithkatie.com\/wealth-planner\" target=\"_blank\">mine<\/a>. I just like to keep everything in one spot, particularly:<\/p>\n<ul data-rte-list=\"default\">\n<li>\n<p class=\"\" style=\"white-space:pre-wrap;\"><strong>My business revenue <\/strong>(income that comes in the form of 1099-NECs and 1099-Ks from sponsors, affiliates, and payment processors)\u2014tracking my revenue myself throughout the year <em>per client<\/em> allows me to verify the 1099s they send me to make sure they\u2019re reporting accurately and I\u2019m actually receiving the amount they\u2019re telling the IRS they\u2019re paying.<\/p>\n<\/li>\n<li>\n<p class=\"\" style=\"white-space:pre-wrap;\"><strong>My business expenses <\/strong>(expenses that you have to track on your own; nobody \u2018reports\u2019 these back to you)\u2014whether it\u2019s my podcast provider, Squarespace fees, cell phone bills, or something else entirely, I track my business expenses throughout the year so I can look back at the end and easily tally up what I spent and where.<\/p>\n<ul data-rte-list=\"default\">\n<li>\n<p class=\"\" style=\"white-space:pre-wrap;\"><em>Note: If you\u2019re self-employed, you can also deduct part of the cost of your home &amp; utilities (assuming you work from home on your business) using the \u2018regular method\u2019 calculation in the TaxAct software.<\/em><\/p>\n<\/li>\n<li>\n<p class=\"\" style=\"white-space:pre-wrap;\">If you\u2019re paying 1099 contractors, it\u2019s also smart to track the outgoing payments for the 1099s <em>you<\/em> have to file. <\/p>\n<\/li>\n<li>\n<p class=\"\" style=\"white-space:pre-wrap;\">The TaxAct software will likely also calculate the QBI (Qualified Business Income) deduction for you, which can wipe off another substantial portion of your taxable income.<\/p>\n<\/li>\n<li>\n<p class=\"\" style=\"white-space:pre-wrap;\">This is an area where I probably could\u2019ve milked it more (travel expenses, food expenses, etc.) but I played it safe.<\/p>\n<\/li>\n<\/ul>\n<\/li>\n<li>\n<p class=\"\" style=\"white-space:pre-wrap;\"><strong>My retirement account deferrals tied to my business<\/strong> (SEP IRA or Solo 401(k) contributions, in most cases)\u2014you don\u2019t really receive any forms that tell you how much you\u2019ve contributed, so I like to track it every month in my Planner so I know what number to report to the IRS as my contribution (this is huge, since these contributions are typically large tax deductions). If you\u2019re contributing to an employer 401(k) or other retirement account, you\u2019re covered here\u2014they\u2019ll report your contributions on your W-2 and you don\u2019t have to do anything else.<\/p>\n<\/li>\n<li>\n<p class=\"\" style=\"white-space:pre-wrap;\"><strong>Our taxable brokerage accounts (wherever we invest money that\u2019s <em>taxable, <\/em>outside of a qualified account like a 401(k) or IRA)<\/strong>\u2014good news! You don\u2019t need to file forms for your tax-advantaged accounts since they\u2019re tax-sheltered, but you <em>do<\/em> need to file your 1099-DIVs from your brokerage accounts (keeping track of these in the Net Worth tab reminds me where we have money so I don\u2019t miss any forms that are typically housed in the Tax Documents section of our accounts). If you have high-yield savings accounts with substantial amounts of money inside them, you\u2019ll also likely need to file your 1099-INT to report your interest income. Interest is taxed like ordinary income (while qualified dividends are taxed like capital gains).<\/p>\n<\/li>\n<\/ul>\n<p class=\"\" style=\"white-space:pre-wrap;\">Having all of this information mapped out in one place will make it easier to both (a) double-check the forms you <em>do <\/em>receive and (b) have an easy bird\u2019s eye view of where you may be missing forms. This year, I had to reach out to several different sponsors who hadn\u2019t sent me my 1099-NEC (stands for \u201cNon-Employee Compensation\u201d) yet so I could file on time. Had I not been tracking revenue per client, I would\u2019ve had a <em>much<\/em> harder time tracking down who hadn\u2019t sent me the proper forms yet. <\/p>\n<p class=\"\" style=\"white-space:pre-wrap;\">Basically, tracking allows me to be the adult version of Grade Grubber Summer from School of Rock.<\/p>\n<h3 style=\"white-space:pre-wrap;\">Quick Review of Common Forms Mentioned<\/h3>\n<ul data-rte-list=\"default\">\n<li>\n<p class=\"\" style=\"white-space:pre-wrap;\"><strong>W-2<\/strong> from your employer if you receive wages from which taxes are already withheld<\/p>\n<\/li>\n<li>\n<p class=\"\" style=\"white-space:pre-wrap;\"><strong>1099-K <\/strong>if you\u2019re using an online payment processor<\/p>\n<\/li>\n<li>\n<p class=\"\" style=\"white-space:pre-wrap;\"><strong>1099-NEC<\/strong> if you\u2019re receiving payment as a contractor&nbsp;<\/p>\n<\/li>\n<li>\n<p class=\"\" style=\"white-space:pre-wrap;\"><strong>1099-DIV<\/strong> if you\u2019re using taxable brokerage accounts<\/p>\n<\/li>\n<li>\n<p class=\"\" style=\"white-space:pre-wrap;\"><strong>1099-INT<\/strong> if you\u2019ve got a savings account (or any other type of account) that pays interest<\/p>\n<\/li>\n<li>\n<p class=\"\" style=\"white-space:pre-wrap;\"><strong>1099-MISC<\/strong> for just about everything else; this year, I received a 1099-MISC form from Chase for the points I received as referral bonuses (roughly $4,000 worth, according to them)<\/p>\n<\/li>\n<\/ul>\n<p class=\"\" style=\"white-space:pre-wrap;\">If you\u2019re paranoid about missing stuff, go into your various email accounts and search your inbox for \u201cW-2\u201d and \u201c1099.\u201d The vast majority of the time, these forms get emailed to you directly or mailed to your house, but knowing <em>where<\/em> you have money will make it easier to go to the source (e.g., a taxable brokerage account) if you notice you haven\u2019t received anything yet.<\/p>\n<p class=\"\" style=\"white-space:pre-wrap;\">It can be a lot to keep track of, so I have a pretty robust file system on my computer for the ones that are received electronically and a physical folder for the ones that come in the mail.&nbsp;<\/p>\n<p class=\"\" style=\"white-space:pre-wrap;\">Here\u2019s what it looks like:<\/p>\n<\/div>\n<div style=\"width: 840px\" class=\"wp-caption alignnone\"><img decoding=\"async\" src=\"https:\/\/moneywithkatie.com\/wp-content\/uploads\/2022\/04\/1FILESYSTEM.webp\" alt=\"  It\u2019s giving \u201cobsessive compulsive.\u201d  \"\/><p class=\"wp-caption-text\">It\u2019s giving \u201cobsessive compulsive.\u201d<\/p><\/div>\n<div class=\"sqs-html-content\" data-sqsp-text-block-content>\n<p class=\"\" style=\"white-space:pre-wrap;\">Once you file your return, you\u2019ll probably receive something called <strong>Form 1040<\/strong> that outlines everything you reported (with other forms attached, depending on your situation). I like to save that as well, as sometimes they\u2019ll ask you to report your \u201c2024 AGI from line 11 on Form 1040\u201d (as a wildly specific example) when filing in the future.&nbsp;<\/p>\n<h3 style=\"white-space:pre-wrap;\">Examples of What My Manual Tracking Has Looked Like Over the Years<\/h3>\n<p class=\"\" style=\"white-space:pre-wrap;\"><strong>Business revenue<\/strong><\/p>\n<\/div>\n<p>      <img decoding=\"async\" src=\"https:\/\/moneywithkatie.com\/wp-content\/uploads\/2022\/04\/21099INCOME.webp\" alt=\"\"\/><\/p>\n<div class=\"sqs-html-content\" data-sqsp-text-block-content>\n<p class=\"\" style=\"white-space:pre-wrap;\">I categorized my business income into different sections and then tracked how much revenue each sponsor, affiliate, or product generates (I redacted names for #confidentiality purposes in this screenshot).<\/p>\n<p class=\"\" style=\"white-space:pre-wrap;\">I\u2019ll usually tally up the entire year of payments from that source in the \u201c1099 EXPECTED TOTALS\u201d column and then cross them off as I receive the forms in the mail.<\/p>\n<p class=\"\" style=\"white-space:pre-wrap;\"><strong>Solo 401(k), SEP IRA, or other self-managed tax-advantaged accounts<\/strong><\/p>\n<\/div>\n<p>      <img decoding=\"async\" src=\"https:\/\/moneywithkatie.com\/wp-content\/uploads\/2022\/04\/4SOLO40128K29CONTRIBUTIONS.webp\" alt=\"\"\/><\/p>\n<div class=\"sqs-html-content\" data-sqsp-text-block-content>\n<p class=\"\" style=\"white-space:pre-wrap;\">Same with my Solo 401(k), noted above\u2014as you can see, I contributed $70,813.30 to tax-advantaged accounts in 2021, and roughly $46,000 of it came from the \u201cSolo 401(k)\u201d row, so I knew exactly what to claim as a contribution so it would match whatever Vanguard sends to my IRS Daddy. (I think I miscalculated my contributions because I wasn\u2019t taking my various business deductions into account, so I may need to go back and remove some\u2026we\u2019ll see.)<\/p>\n<p class=\"\" style=\"white-space:pre-wrap;\"><strong>Taxable brokerage accounts that generate 1099-DIVs<\/strong><\/p>\n<\/div>\n<p>      <img decoding=\"async\" src=\"https:\/\/moneywithkatie.com\/wp-content\/uploads\/2022\/04\/3TAXABLEBROKERAGEACCOUNTS.webp\" alt=\"\"\/><\/p>\n<div class=\"sqs-html-content\" data-sqsp-text-block-content>\n<p class=\"\" style=\"white-space:pre-wrap;\">And since we filing jointly, here\u2019s an example from years\u2019 past of our breakdown of taxable investing accounts. I knew I needed to submit 3 1099-DIVs for me and 3 1099-DIVs for Thomas (our joint account was opened in 2022 so nothing to report, and oddly, Thomas\u2019s cryptocurrency had $0.00s across the board for what we needed to report, so\u2026prayers up to the audit gods that nothing is amiss there). I hid the brokerage account names for confidentiality purposes, but knowing where each account is located helps with the demented IRS scavenger hunt of finding all the correct forms.<\/p>\n<p class=\"\" style=\"white-space:pre-wrap;\">The Wealth Planner separates \u201cTax-Advantaged\u201d investing from \u201cTaxable\u201d investing, so you should be able to quickly see (if you fill it out) which accounts you\u2019ll need to grab 1099-DIVs for.<\/p>\n<p class=\"\" style=\"white-space:pre-wrap;\"><strong>Business expenses<\/strong><\/p>\n<\/div>\n<p>      <img decoding=\"async\" src=\"https:\/\/moneywithkatie.com\/wp-content\/uploads\/2022\/04\/5BUSINESSEXPENSES.webp\" alt=\"\"\/><\/p>\n<div class=\"sqs-html-content\" data-sqsp-text-block-content>\n<p class=\"\" style=\"white-space:pre-wrap;\">And finally, here\u2019s the breakdown from 2022 of business expenses. The rest of this stuff has been charged throughout the year, so I have receipts to back up my expenses: $3,346.02. I ended up being able to deduct about $3,500 of our rent paid this year as well, thanks to the calculation that the TaxAct software did for me (I had to enter total rent paid and the percentage of the home that I use exclusively for business purposes; it was pretty easy).<\/p>\n<h2 style=\"white-space:pre-wrap;\">How our Return Ended Up Shaking Out<\/h2>\n<p class=\"\" style=\"white-space:pre-wrap;\">TaxAct provides this nifty little summary at the end (it took me a few months to aggregate everything and another day or two to double-check all the forms; it was certainly not an easy task this year).<\/p>\n<\/div>\n<p>      <img decoding=\"async\" src=\"https:\/\/moneywithkatie.com\/wp-content\/uploads\/2022\/04\/6AdjustedIncome.webp\" alt=\"\"\/><\/p>\n<div class=\"sqs-html-content\" data-sqsp-text-block-content>\n<p class=\"\" style=\"white-space:pre-wrap;\">We reported $390,422 in 2021 income (so close to $400,000\u2014so close) and \u201cadjusted\u201d down $57,864; this was in the form of deductions like Solo 401(k) contributions and other deductions (moving expenses for an Armed Forces relocation, for example). Your contributions to your employer-sponsored retirement account(s) are already removed from that top line number, so I suppose if you factor those in (about $25,000 between us), we <em>were<\/em> over $400,000\u2014just another feather in the cap of pre-tax investing, no?<\/p>\n<p class=\"\" style=\"white-space:pre-wrap;\">That gets us down to $332,558, from which we were able to deduct the standard deduction ($25,100 that year; 90% of Americans take the standard deduction, and it\u2019s likely you do, too) and the QBI deduction for my business ($29,433) to create our taxable income of $278,025\u2014more than $100,000 less than what we actually earned.&nbsp;<\/p>\n<p class=\"\" style=\"white-space:pre-wrap;\">Again, may I shout it from the rooftops? <em>This is almost entirely due to the power of pre-tax investing.&nbsp;<\/em><\/p>\n<p class=\"\" style=\"white-space:pre-wrap;\">Now for the not-fun part:<\/p>\n<\/div>\n<p>      <img decoding=\"async\" src=\"https:\/\/moneywithkatie.com\/wp-content\/uploads\/2022\/04\/7TaxBreakdown.webp\" alt=\"\"\/><\/p>\n<div class=\"sqs-html-content\" data-sqsp-text-block-content>\n<p class=\"\" style=\"white-space:pre-wrap;\">Since we only paid $22,745 in taxes throughout the year, we owe\u2014<em>womp womp<\/em>\u2014$36,640 this year. Still, we\u2019d owe a whole lot more had we not contributed to our pre-tax accounts:<\/p>\n<ul data-rte-list=\"default\">\n<li>\n<p class=\"\" style=\"white-space:pre-wrap;\">$5,580 to Thomas\u2019s military retirement TSP<\/p>\n<\/li>\n<li>\n<p class=\"\" style=\"white-space:pre-wrap;\">$19,500 to my 401(k)<\/p>\n<\/li>\n<li>\n<p class=\"\" style=\"white-space:pre-wrap;\">$46,000 to my Solo 401(k)<\/p>\n<\/li>\n<li>\n<p class=\"\" style=\"white-space:pre-wrap;\">$2,700 to my HSA<\/p>\n<\/li>\n<\/ul>\n<p class=\"\" style=\"white-space:pre-wrap;\">\u2026$73,780. Had we just claimed all of that as income and <em>not<\/em> contributed it to pre-tax accounts, we would\u2019ve owed closer to <em>$62,000<\/em> this year, not $36,000. Yikes.<\/p>\n<h2 style=\"white-space:pre-wrap;\">Conclusions<\/h2>\n<p class=\"\" style=\"white-space:pre-wrap;\">All in all, I\u2019m grateful that we owe money because it\u2019s a sign of a great year. It\u2019s a little painful to fork it all over at once, but that\u2019s another key thing: Had I been filing <strong>quarterly taxes<\/strong> and setting aside 25%-30% of my business income as I went, I could\u2019ve avoided this all-at-once tax bomb.<\/p>\n<p class=\"\" style=\"white-space:pre-wrap;\">And if I <em>do<\/em> get audited, well\u2026#content.<\/p>\n<\/div>\n","protected":false},"excerpt":{"rendered":"<p>Let me preface this post by saying that if you have access to a CPA and you\u2019re feeling a little unsure about doing your taxes yourself (or, more realistically, you just don\u2019t want to), it\u2019s probably wise to pony up a few hundred bucks and pay your CPA to do them for you.&nbsp; That said: [&hellip;]<\/p>\n","protected":false},"author":178814,"featured_media":2389,"comment_status":"closed","ping_status":"open","sticky":false,"template":"si-template-single-post-self-employed-investing.php","format":"standard","meta":{"footnotes":""},"categories":[37,35],"tags":[42,63],"class_list":["post-139","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-financial-independence","category-investing-and-taxes","tag-self-employed-investing","tag-popular-self-employed-investing"],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v25.8 - https:\/\/yoast.com\/wordpress\/plugins\/seo\/ -->\n<title>How I Organize My Money for a Stress-Free Tax Season - Money with Katie<\/title>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<link rel=\"canonical\" href=\"https:\/\/moneywithkatie.com\/how-i-organize-my-life-for-tax-season\/\" \/>\n<meta property=\"og:locale\" content=\"en_US\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"How I Organize My Money for a Stress-Free Tax Season - Money with Katie\" \/>\n<meta property=\"og:description\" content=\"Let me preface this post by saying that if you have access to a CPA and you\u2019re feeling a little unsure about doing your taxes yourself (or, more realistically, you just don\u2019t want to), it\u2019s probably wise to pony up a few hundred bucks and pay your CPA to do them for you.&nbsp; That said: [&hellip;]\" \/>\n<meta property=\"og:url\" content=\"https:\/\/moneywithkatie.com\/how-i-organize-my-life-for-tax-season\/\" \/>\n<meta property=\"og:site_name\" content=\"Money with Katie\" \/>\n<meta property=\"article:published_time\" content=\"2022-04-18T11:59:00+00:00\" \/>\n<meta property=\"article:modified_time\" content=\"2025-09-05T16:48:06+00:00\" \/>\n<meta property=\"og:image\" content=\"https:\/\/moneywithkatie.com\/wp-content\/uploads\/2025\/08\/CountingBills_Fire-Pink_100x756.png\" \/>\n\t<meta property=\"og:image:width\" content=\"1001\" \/>\n\t<meta property=\"og:image:height\" content=\"757\" \/>\n\t<meta property=\"og:image:type\" content=\"image\/png\" \/>\n<meta name=\"author\" content=\"Katie Gatti\" \/>\n<meta name=\"twitter:card\" content=\"summary_large_image\" \/>\n<meta name=\"twitter:label1\" content=\"Written by\" \/>\n\t<meta name=\"twitter:data1\" content=\"Katie Gatti\" \/>\n\t<meta name=\"twitter:label2\" content=\"Est. reading time\" \/>\n\t<meta name=\"twitter:data2\" content=\"10 minutes\" \/>\n<script type=\"application\/ld+json\" class=\"yoast-schema-graph\">{\"@context\":\"https:\/\/schema.org\",\"@graph\":[{\"@type\":\"WebPage\",\"@id\":\"https:\/\/moneywithkatie.com\/how-i-organize-my-life-for-tax-season\/\",\"url\":\"https:\/\/moneywithkatie.com\/how-i-organize-my-life-for-tax-season\/\",\"name\":\"How I Organize My Money for a Stress-Free Tax Season - 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