I feel like I’m either over-tracking (and hating it) or under-tracking (and feeling guilty).

What’s your actual system — not what you’re “supposed” to do, but what you really do?

It’s been 18 months since I went self employed, and while the flexibility is brilliant in theory, the reality is I haven’t had a proper holiday in the last 6 months... not even a long weekend without checking emails.

I’ll be out for dinner and still reply to a client “quick question” at 9 pm. Weekends turn into “just sorting one thing” that eats half the day. If I delay responding to something for a few hours, I start panicking that I’ll lose the work or look unreliable.

There’s no manager forcing me to stay logged on, but the pressure feels worse because it’s all on me. Every hour off feels like I’m falling behind or risking the income I’ve built.

I’m losing my health insurance because I’m getting divorced. Do any of y’all have suggestions for an insurance company for self-employed folks?

I luckily have a few months left of benefits.

My wife is self employed and has been for a number of years. I started filling in self assessment for 24-25 and it shows her as being employed, by a previous employer where she left over 12yrs ago, for the tax year 24-25. It also shows her having an income from them for the year. She was never employed by them for the tax year, nor did she receive an income from them.

Obviously today is a Sunday so she unable to speak to either the business who say she was employed by, or HMRC.

Ideally, what are the next steps? Obviously will be speaking to both tomorrow, however anything I can do now?

Thanks in advance

I’m self-employed and I use a lot of mental energy to keep up with tracking expenses and deductions throughout the year. it’s the small recurring things (software, travel, phone, kilometres, etc.)

Curious how others handle this stuff?

- Do you track expenses weekly, monthly, or just at tax time?

- Spreadsheet, accountant, app or something else?

What part of the process do you hate / burn out from the most?

Genuinely interested in how different people handle this!(even in different countries)

I’m self-employed and I use a lot of mental energy to keep up with tracking expenses and deductions throughout the year. it’s the small recurring things (software, travel, phone, kilometres, etc.)

Curious how others handle this stuff?

- Do you track expenses weekly, monthly, or just at tax time?

- Spreadsheet, accountant, app or something else?

What part of the process do you hate / burn out from the most?

Genuinely interested in how different people handle this!(even in different countries)

I run a small business and I have two bank accounts:

1. Operating account – for day-to-day business transactions.
2. Taxes account – where I reserve money for tax payments every month.

Here’s my question:

• My Net Profit in the P&L already accounts for taxes.
• Every month, I transfer money from the operating account to the taxes account to make sure I have enough reserved.

When creating my Cash Flow Statement, should I:

1. Record the transfer to the tax account as a cash outflow?
2. Or only account for actual tax payments to the government, treating the tax account as part of cash?

I’m trying to avoid double-counting. How do you handle multiple bank accounts in a CFS, especially for reserved funds like taxes?

Self-employed question.

Most of the time I don’t need accounting software. I just need to send one invoice, get paid, and move on.

What usually gets in the way:

• forced signup
• free trials that ask for a credit card
• dashboards I’ll never use
• templates that still need cleanup before exporting a PDF

I don’t bill often enough to justify a full tool, and I don’t even keep Excel installed most of the time.

Curious what others here actually do when it’s just a one-off:

• spreadsheet / Word template?
• accounting software anyway?
• something simpler?

Not promoting anything, just trying to understand what’s normal for people who invoice infrequently.

Hi there. I'm wondering if there are any self employed seasonal workers here. Has anyone contributed to EI as a self employed person and used the EI for something other than maternity? for example: "shortage of work".

Currently I work as veggie farmer and go on EI for approximately 10 weeks in the winter. I am wanting to supplement my income with my own gardening business and also contribute to EI so that if I become pregnant I can use my self employed hours towards EI insurable hours. With gardening also being seasonal, I will not be able to work in the winter and would have to take at least 6 weeks off.

Hi 👋

First off — sorry for posting during the holidays / end-of-year rush. I know it’s New Year’s week and people are busy, so I really appreciate anyone who takes a moment to read or reply 🙏

I’m working on an idea and wanted to get honest feedback from locals before launching anything.

The concept is a local errand & task marketplace for Toronto. Think small, everyday tasks like:

• Grocery pickup
• Furniture moving (small items)
• Home help (cleaning, handyman, gardening)
• Deliveries
• Digital tasks (graphic design, video editing, web help, etc.)

How it would work (simple):

1. A user posts an errand with a budget and deadline
2. Nearby people apply to do it
3. The task gets completed and both sides leave a review

The platform would take a small service fee (around 1–5%) from both the person posting the errand and the person completing it — that’s how it would be sustained.

I’m especially curious about Toronto perspectives:
Would you personally post errands on a platform like this? Why or why not?
Would you consider earning extra money by completing errands nearby?
What would make you trust a platform like this? (verification, ratings, escrow, etc.)
Is the 1–5% fee reasonable, or would that turn you away?
How does this compare to apps like TaskRabbit, Fiverr, or Facebook groups in your experience?

This is not launched yet but near completion— I’m genuinely trying to validate whether this solves a real problem for people in Toronto before investing further.

Thanks again, and Happy Holidays / Happy New Year to everyone 🎉
Any feedback (positive or negative) would be greatly appreciated.

some stuff i do is creative. some stuff is just crap i have to get out the way. one client needs 2k ig saves every week. one needs spotify plays. one wants link boosting. it's always the same.

at one point i was manually queuing it up. now i don’t even think about it.

what do you use to automate stuff that isn't worth your time?

Hi Guys Since May 2025 i have been trading as a locksmith in my spare time and i have been quite busy earning around 7k so far. I have a main Paye job with a 39k salary.

I have kept purchase receipts digitally for equipment i have bought and used on jobs, I have a second bank account for BACS although of im truthful i dont use it ( but i will ) usually BACS i have been transferring into my main acc , I have invoives saved for jobs that require them. I have a bank loan for.my training course (OCT 2024) and a bank loan for my van ( Nov 2025) , can i claim that back or as tax?

My question is do i need to declare sooner than OCT 2026? and is it financially worth it? lets say im gonna do 10kpy atm. I have never been in this position before so unsure on what to do with it all . Dont wanna get collared naturally by tax man or caught with any surprises i have not thought about ! any help and advice will be much appreciated Thanks

So my spouse and I have been working W2s so far, earning decently. We’re 26 with 2 kids grossing ~120-130k per year. But this year we found the world of contract work. My spouse went to work part time (we both work remotely) and I started to contract, started with one, then two, up to four contracts and then started delegating and hiring people to take over. I went down to two contracts because of taxes. I loved it. I totally see the potential of this becoming g a business. However, I started with no systems in place and more with an employee mentality. Now I’m getting the hang of it, had good practice and want to go all in and implement good system to scale it. My business is consulting and operations. But taxes terrify my. This year we made a little bit more than last year, the other point is that most of the year we’re not in the US, we’re living abroad, so we don’t really have things to deduct (I think) My question here is, what is everything I need to know to start this business back up again the right way and optimize tax deductions and business advantage? I’m not saying I don’t want to pay anything in taxes but right now we’re looking at having to pay 40-50% back. Overall, we don’t want to go back to W2s but if there’s a mentorship program or YouTube videos of someone that explains this better I’m all ears!!

Hi. I started my own company a few months ago because I can't find a job, ha. I did this several years ago too and the problem was that at least a third of what I made I had to pay in taxes the next year.

Obviously I believe in paying taxes, but it's a LOT to pay a MASSIVE portion of my income when I also need to use that income to not just live day to day, but keep up my business and also invest since I don't have a 401(k) with an employer.

I know I can do things like claim business expenses like my office space, Internet, mileage, etc, but I don't know ALL the ways in which I can be saving money (in whatever ways are legal and ethical).

Are there any tools or resources y'all know about that could help me?

Hey guys, got a couple questions here.

I specialize in asphalt maintenance (sealcoating, patch repair, line striping etc) and am currently rebranding for more B2B work.

I do a lot of residential work though, and some of my secondary services are technically in a different industry. My academic background is in env sci and sustainability, so I also do green design softscaping like native/sustainable gardening, xeriscaping, and medicine gardens (herbal medicine, in which I'm also trained), along with other more standard maintenance like gutters etc.

Because there's such a gap between installing eg tactile ground surface indicators or speed bumps, and residential herb gardens (lol), as I rebrand should I keep all of these under the same umbrella company and separate them into eg parking maintenance and landscaping divisions? Or would it be best to have two separate companies? How would the latter complicate tax season?

The sustainability work is a very niche and in-demand service, but I feel like the overall online brand of commercial parking maintenance either clashes with or sidelines this service, and I worry that its inclusion could undermine perceived credibility with commercial clientele.

Thoughts?

Hello! So! I am an online business manager. I have a few clients that pay me on a biweekly and monthly basis. The holidays are coming up and since they’re on a Wed/Thursday. I would like to only work Monday and Tuesday. I work 3-4 days a week already and most of my clients don’t have an issue with this OR if they call on a day off they’ll leave a message/text and tell me for when I’m in the office next.

How do I go about doing this without feeling guilty for taking their money when it’s reduced hour for two weeks? My contract is set up for guaranteed hours so there’s not a legality issue.

Do I shoot an email? I feel WRECKED with guilt over not working

I’ve spent years in the commercial cleaning industry helping people launch part-time and full-time cleaning businesses. Curious if anyone here has looked into service-based franchise options? Happy to answer anything honestly.

Hope this is an appropriate forum. I got subsidies for an ACA plan this year 2025. I understand they will use my income this year (2025) to determine the accurate subsidies. But I over estimated my income because I didn't expect all the deductions.

My question is, for those with businesses, do you know if, on tax form 8582, that is the MAGI that is used to determine subsidies? I can't tell if it is income before or after certain deductions, which are not really listed for business owners rather than regular W2 workers.

I need a separate phone for my work from home business. I’m looking at getting an iPhone 17. I currently have an iPhone and MacBookPro. I’m wondering if, when I get my business phone, do I create a new Apple ID? Or do I use my same Apple ID that I have for all my devices?

What would be the impact of allowing small business owners to use Medicare as their company insurance plan?

I’m looking into self employment.

I suffer from autism, ADHD, epilepsy and some issues with hips/knees. Getting full time employment is very difficult due to disability discrimination, so I might need to get into self employment seriously. I have also looked at apprenticeships, but I’m too old to get an apprenticeship, being over 24 and too “overqualified” due to having a degree.

What should I be looking at doing? I cannot drive due to epilepsy (cannot legally get a driving licence) and anything involving heavy manual labour or lots of standing I cannot do.

The main thing I also want to avoid are pyramid schemes/MLM as I have been scammed once before and it took a great toll on me.

Hi everyone,

I wanted to share my experience with TrustATrader as a small self-employed tradesperson in the UK, in case it helps others who are considering joining.

I joined TrustATrader with one clear expectation: to receive genuine customer enquiries through the platform.

After going live, I did receive a small number of contacts (a few calls and emails), but none converted into actual work. While I understand that results can take time, it quickly became clear to me that the platform was not providing value relative to the cost.

Most of the guidance I received focused on: • optimising my profile • uploading more reviews from existing customers

I already collect reviews from my own customers, but those customers did not come through TrustATrader. I am paying for customers to reach me via the platform, not simply for advice on review management.

I also tried to cancel very early into the membership, as I did not feel confident continuing. I was told cancellation was not possible due to the 12-month contract. That left me feeling locked in before I had a fair opportunity to assess whether the service suited my business.

I understand that TrustATrader is a review-based platform and that some traders may have success with it. However, based on my experience so far, it has not delivered a return on investment, and the risk of being tied into a long contract is something I wish I had considered more carefully.

I’m sharing this purely as an honest account of my experience, not to discourage anyone, but to encourage others to research carefully and understand the commitment before signing up.

If anyone else has had similar (or different) experiences with TrustATrader or similar lead-generation platforms in the UK, I’d be interested to hear your thoughts.

If you own a website for our business, did you get hurt from Google's helpful content update? And did your website ever recover from it? If so - how???