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First-Time Self Assessment: A Calm Guide for the Newly Self-Employed

June 5, 2026 2 min read

Quick answer:

For your first Self Assessment, register as self-employed with HMRC by 5 October after the tax year you started trading, keep digital records of income and expenses from day one, note the 31 January deadline, and set aside money for tax as you earn. Software that tracks everything in real time makes the first year far less daunting.

Step 1: Register with HMRC

Once you start working for yourself, register for Self Assessment. The deadline is 5 October following the end of the tax year in which you began trading, for example, if you started in the 2025/26 tax year, you must register by 5 October 2026. Registering late can lead to penalties, so do it early.

Step 2: Keep records from day one

Start recording income and expenses immediately. The biggest first-year mistake is letting it pile up; clean digital records from the start make filing simple and your tax estimate accurate.

Step 3: Know your deadlines

Step 4: Set aside tax as you go

Put a percentage of each payment aside for tax, a rough 20-30% of profit is a common starting point. A real-time tax estimate tells you the precise figure, so you’re never caught short in January.

How CleanBooksAI makes year one easy.

CleanBooksAI tracks income and expenses automatically, keeps a live tax estimate, and prepares your figures, so your first Self Assessment is a confirmation, not a cliff edge.

Frequently asked questions

When do I need to register?
By 5 October after the end of the tax year in which you started trading, well before your first 31 January filing deadline. Register on GOV.UK.
How much should I set aside for tax?
A rough 20-30% of profit works as a starting point; a real-time estimate gives you a precise running figure.

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