Search “self assessment sole trader reddit” in January and it's pure dread — receipts everywhere, deadline looming, “what can I even claim?” Here's the calm version.
Try Amy free for 14 days →The Self Assessment deadline for online returns is 31 January, covering the tax year that ended the previous 5 April — plus any payments on account due the same day (and again on 31 July). Miss it and it’s an automatic £100 penalty, then more.
The reason it’s painful is almost never the form itself — it’s reconstructing a whole year from a carrier bag of receipts in the last week. The people who don’t dread it are the ones whose records already exist.
Online returns and the tax owed are due by 31 January, for the tax year ending the previous 5 April. If you make payments on account, the second one is due 31 July. Register for Self Assessment by 5 October if it’s your first year.
Allowable business expenses — materials, tools, equipment, business mileage (45p/mile for the first 10,000 miles), phone, insurance, accountancy fees, workwear/PPE, and more. The trick is having them logged and categorised, not guessing in January. Mileage alone is often hundreds of pounds people forget to claim.
Not legally, but most sole traders find one pays for itself — especially with CIS rebates or anything beyond the simplest return. Either way, the job is far cheaper and faster for them (or you) if the records are already clean and categorised.
Capture as you go instead of saving it up. With TradesOffice you text Amy your invoices and snap your receipts through the year; everything’s stored, categorised to HMRC’s expense categories, with mileage and CIS tracked. Come January your return is a tidy export, not an archaeology dig. WhatsApp only — no app, £19.99/month, free trial.
From April 2026, sole traders over £50k must keep digital records and file quarterly (then £30k in 2027, £20k in 2028) — so the once-a-year scramble is being phased out anyway. Keeping records as you go now gets you ahead of it.
Text Amy as you work and your return writes itself in the background — categorised, with mileage and receipts already in. Free for 14 days, no card.
Try Amy free →