This month, we wanted to share several important updates that may affect many individuals and businesses over the coming months, particularly around side hustle income, Self Assessment obligations and the growing importance of protecting your business properly through insurance.
As always, if any of the topics below raise questions about your own circumstances, our team would be very happy to help.
Side Hustles, Self Assessment and HMRC: What You Need to Know in 2026
Over the last few years, we have seen a significant increase in the number of people earning additional income through side hustles and secondary income streams.
For some, this may be freelance consulting or online selling. For others, it could involve Airbnb income, content creation, tutoring, dog walking or property-related income. What often starts as a small project or hobby can quickly become a meaningful source of additional income.
However, HMRC is paying increasingly close attention to this area.
Many online platforms including eBay, Etsy, Vinted and Airbnb are now sharing seller data directly with HMRC under new reporting rules. Whilst this does not automatically mean tax is due, it does mean HMRC has far greater visibility over online income than many people realise.
At present, individuals can generally earn up to £1,000 in trading income before reporting requirements apply. Once combined side hustle income exceeds this threshold, there may be a requirement to register for Self Assessment and submit a tax return.
The Government has also announced plans to simplify reporting requirements in future for individuals earning between £1,000 and £3,000 from side hustles, although the current rules still apply for now.
Alongside this, Making Tax Digital for Income Tax is approaching for many self-employed individuals and landlords. From April 2026, those with qualifying income above £50,000 will need to comply with new digital reporting requirements, with thresholds reducing further in subsequent years.
Good record keeping and early professional advice are becoming increasingly important as HMRC modernises its systems.
If you have started generating additional income through a side business, freelance work or online activity and are unsure about your obligations, now is an excellent time to review your position.
You can read our full article here: https://www.richardrileyassociates.co.uk/2026/05/26/side-hustles-self-assessment-and-hmrc-what-you-need-to-know-in-2026/
Protecting Your Business: Our Insurance Partnership with Kingsbridge
Whilst we work hard to help clients manage their finances efficiently and remain compliant, we also recognise that running a business involves wider risks that many business owners overlook.
Even small mistakes or misunderstandings can sometimes lead to significant financial exposure. Professional advice disputes, accidental property damage, cyber risks or employee-related claims can all create unexpected costs for businesses of any size.
To help support our clients further, we are pleased to have partnered with insurance specialists Kingsbridge.
Their team can help businesses, contractors, freelancers and sole traders understand the types of insurance cover most relevant to their operations, including:
• Professional Indemnity Insurance
• Public Liability Insurance
• Employers’ Liability Insurance
• Cyber Liability Cover
• Legal Expenses Insurance
• IR35 Insurance
One of the reasons we chose to partner with Kingsbridge is their straightforward and practical approach. Their in-house team can provide clear guidance without unnecessary complexity and help businesses arrange appropriate cover efficiently.
If you would like to discuss insurance requirements for your business, get in touch.
Welcoming New Members of the Richard Riley & Associates Team
As our firm continues to grow, we are delighted to welcome several new members to the Richard Riley & Associates team. Each brings valuable experience, enthusiasm and personality to the business, and we are very pleased to have them on board.
Holley Victoria Ofiera
Holley joins Richard Riley & Associates with five years of experience in finance across both the commercial property and print solutions sectors. Her background includes purchase ledger, invoicing and credit control, and she particularly enjoys the balance of working with both numbers and people.
Holley is looking forward to continuing to develop her skills within accountancy and learning from the wider team. Outside of work, she enjoys spending time with family and friends and looking after her cocker spaniel, Arnie.
Charlotte Wheeler
Charlotte joined Richard Riley & Associates in February and has quickly become a valued member of the team. She describes herself as positive, reliable and easy-going, with a strong focus on building good relationships both professionally and personally.
After taking time out to raise her two children, Charlotte has returned to work with fresh energy and enthusiasm. Outside of work, she enjoys spending time with family, caring for animals and travelling.
Lorraine Reveley
Lorraine recently joined Richard Riley & Associates following a short period working with us as a temporary assistant. After deciding to return to college while her son was at school, Lorraine studied Business Administration and Bookkeeping before building a successful career spanning more than 30 years in finance.
Her experience includes 23 years working within Merton College Bursary and five years in the construction industry. Outside of work, Lorraine enjoys travelling, reading, swimming and spending time with family and friends, including supporting her grandson at football matches.
Bea Smith
Bea first joined Richard Riley & Associates in late 2024 on a part-time basis while balancing college studies alongside work. She now works full-time as an apprentice and is currently completing Levels 2 and 3 of her AAT qualification.
Outside of work, Bea enjoys teaching herself 3D motion editing and animation using After Effects, combining creativity with technical skills.
We are excited to have all four as part of the Richard Riley & Associates team and look forward to supporting them as they continue to grow and develop within the business.
Staying Ahead of Tax and Compliance Changes in 2026
Now that the new tax year is underway, many businesses and individuals are beginning to focus on the changes and compliance requirements that will affect them over the coming months and years.
With Making Tax Digital approaching for increasing numbers of taxpayers, growing HMRC visibility over online income and continued changes across the tax landscape, proactive planning has never been more important.
Whether you are:
• growing a side business
• managing rental properties
• preparing for Making Tax Digital
• planning for retirement
• reviewing business structures
Or simply wanting reassurance that your affairs are organised efficiently, our team is here to help.
Taking advice early often helps prevent unnecessary stress, missed deadlines and avoidable tax inefficiencies later on.
If you would like to arrange a review or discuss any aspect of your tax or accounting position, please do get in touch.
Best regards, Richard and the team
Richard Riley & Associates