Every tax season I tell myself "this year I'll be organized and file early."
Late march this year, I was staring at a pile of receipts and trying to figure out which expenses are actually deductible. Last year I paid way more than I should have bc I rushed through everything at the last minute.
The bookkeeping side has been my biggest headache. I've got sales from multiple platforms, PayPal fees and random business purchases scattered across different accounts.
How do you ensure you file your business taxes in good time or this is just a personality issue?
Anyone else procrastinating on filing taxes for their online side hustle?
byu/IndependentWrap6 intax
Posted by IndependentWrap6
9 Comments
Monthly book keeping
Not a personality issue, it’s a systems issue. Set up automated bookkeeping and reconcile weekly, not yearly. Open a separate biz account so receipts don’t drown in personal stuff. Honestly, if taxes stress you out, hire a bookkeeper, it pays for itself in refunds.
You can help yourself out for 2026 by opening a business credit card – all business expenses go on this card, no exceptions, no personal expenses. Make your life easier, because as you’re discovering, going through months-old receipts line by line to determine what’s business-related is a horrible task to have to complete
Not once, not twice….several times. But when the fines came, i learnt my lesson!
> How do you ensure you file your business taxes in good time or this is just a personality issue?
keep good records throughout the year. your problem sounds like you are scrambling to compile your records for the tax year once tax season starts. if you actively keep good records throughout the year you’ll be in better shape to do your taxes.
i have one client who owns several businesses, keeps amazing records, and it takes me less than 90 minutes to prepare his tax return.
As well as the other good advice here — DO IT IN FEBRUARY. Or March. But don’t extend to October 15th, that just makes it harder on yourself, harder to remember what was what.
Online bookkeeping program connected to your “business” bank account. Reconcile and categorize transactions once a month. You don’t need receipts unless you paid cash. Review categorization once before doing taxes. I own an S-corp, so for me it’s a little different, but I will eventually go back to being a sole proprietor & I will still do this.
I’m afraid it’s a personality issue. It’s not as if you have some sort of record keeping system in place which is merely insufficient. You instead have no system at all, and for whatever reason will not implement one.
A number of my own clients are very good their business, but they are poor at record keeping. They recognize that, and take steps to mitigate the problem. There are already some good suggestions in the thread, so now it becomes a case of actually following through on them.
This is all about time management and systems setup. You need to invest in either a bookkeeper or get some bookkeeping software like Quickbooks. If you setup the rules correctly and link your accounts it takes about 20-30 minutes total each month to go and categorize expenses and reconcile. If you do this correctly at the end of the year you will have accurate reports that will allow you to easily migrate information to your tax return come March or April. Yes it costs a little bit but the savings from penalties and the peace of mind it will give you will be worth it long term. You have to decide where you are going to spend the money on software to help you organize which you can take a deduction on or on interest and penalties as a result of being late every year and extra stress which helps nothing and decreases your productivity and you thus make even less. Hope this helps you.