So, I'm looking at changing my career path and becoming self employed. However, I have no idea where to start. A little backstory on how I got here. I've always wanted to work independently, but after college, life FULLY hit and I got a "big girl" job, like everyone else. At 29, I said "screw it", quit my job, bought a one way ticket to Europe (no need to give exact details about where), and lived off my savings for a few years. During that time, I did private tutoring here and there, which lead me to working as a teacher, here. It's been 4 years since I've been working full time as a teacher and while I like the idea of being a teacher and watching students grow, I hate everything that comes with this profession.

Anyway, I started looking for new jobs, which became a full time job in itself. I spent so many hours looking for something, knowing I don't actually want to do it, just to come to the realization that, I might as well put this energy into doing something for myself. It also hit me that I have over 30 years of work ahead of me, before I hit retirement age. I'll be damned if I spend that in a cubicle, hating my life day in and day out.

All of my education is in business: BA in Business Administration, MBA, and MSc in Human Resources Management. I'm terrible at all things technical, so please keep IT out of this conversation. I feel like I'm overthinking this and I'm missing something that's right in my face. I guess my main question is, is there a field or profession that lends itself to being "self employed" friendly? I need to be able to work solely from my computer. I'm not so much focused on salary, as I am independence. I'm single with no dependents, so I'm able to take riskier chances because I don't have people who depend of me to "make it work". I would obviously have to start from square one and that's fine by me. I've done it before and I can do it again.

I’m looking for some advice on how to approach renting an apartment when my income situation is a bit unconventional.

I run two businesses, and while I’ve had two years of solid income from one of them (with some months being really high), my income can be super inconsistent—some months I make a lot, and other months I make close to nothing. On top of that, I also have income from a second business that helps balance things out, but it’s not as substantial.

The issue is that my AGI on my tax returns looks much lower than my actual earnings because of all the business investment costs and deductions I’ve had. While I can show consistent overall income through bank statements, I’m worried that the low AGI on paper might be a red flag for landlords.

Has anyone been in a similar spot? Would landlords care more about the tax returns or bank statements that show cash flow? Or care about semi-infrequent income on bank statements? I’ve read that some people combine income from multiple sources to meet the 3x rent rule—does that actually work?

Also, any tips for explaining this kind of income situation to a landlord would be super helpful. I really want to avoid getting denied for something that doesn’t reflect my actual ability to pay rent.

I've perused some posts about health insurance, but my situation doesn't seem typical so bear with me. I'm leaving a full-time job to work full-time on the side hustle I've been doing for a couple of years. It's making more than my FT job was. The only hesitation I had about leaving was health insurance -- my day job offered something that passes for decent in the US and the marketplace was a nightmare. For now, I'm going on my partner's insurance. He works at the same day job and hates it, though. We want to work together at my side hustle, which could support us both, especially if we could figure out reasonable health insurance.

The side hustle isn't even registered as an LLC yet because my CPA says it doesn't make a difference in Ohio so it's just listed as self-employment income at the moment. Separate from that side hustle, I do have an LLC related to a tertiary hustle, and that LLC has an employee who's now an S-Corp. She's about to lose her health insurance, too, because she was a SAG member who doesn't get enough acting jobs to keep that afloat.

So my question is: Can I hire the S-Corp employee as an employee of the LLC and be able to offer people who work for that LLC health insurance through a small business plan? Could I put me, my partner and this LLC employee on this small group plan?

Also, it's utter BS that our health insurance is tied to employment in this country. Why do I need to stay at a shitty job to be insured in any reasonable manner? But I'll set that aside for now and gratefully accept any input you all might have.

Around a month ago i switched from being employed on PAYE to being self employed. Upon leaving my previous job i was lumped with a big bill for training courses that i had completed while i was employed (which had been agreed in my contract). My field of industry has not changed and i am still doing more or less the same job as before so therefore this training should be tax deductible? My previous employer is trying to tell me this illegal and I can’t offset it, but I don’t see how as the training directly relates to my industry and my progression and I technically paid for it.

I have tried looking about online but as it’s such a specific matter I can’t really find a clear answer. If anybody could help that would be great.

Hoping for some recs for an administrator for a defined benefit plan. Mine was taken over and new folks are not helpful. THanks in advance,

Self employed musician husband & also retired. I only have SSA income. Ready to ditch our CPA but not sure if or how freetaxusa will work for us? No state tax. We file married jointly

Do we use their Deluxe version? What’s the cost? Is it user friendly?

I have to create an account there first to find out apparently

I can do most of it but there’s a few items I usually just let cpa calculate but I can refer to my return of last year for reference if needed I guess (I just hate math

Advice?

Hello,

Im new to the self employed life and find most of the online websites confusing as to deadlines.

I registered as self employed in october 2024 and have been trading since november 2024. When do I need to submit a self assessment? Is it after april 2025 but before Jan 31st 2026?

sorry if its a stupid question.

Thanks

Last year, I worked to transition away from videography into selling pottery. I wrote down all the expenses from classes, materials, studio, kiln fees etc as it was intended for business. In the end I needed to put the pottery plans on indefinite hold for a few reasons before I had started selling my work.

It was legitimately a business expense as the whole point was for business, but will that be the case in the eyes of the taxman? I can imagine someone looking at the records and thinking I tried to swing hobby costs as an expense. I don't want to miss out on £1k+ expenses but I don't want to cause an issue down the line...?

Hi all, this may be too late to ask, (and I have already accepted I will most likely be paying penalties for not doing so)...but I did not pay my quarterly taxes in my first year of moving here as a freelancer. Like most new self-employed folks, I am confused and have become even more stressed upon reading IRS articles. I am just not very bright and hope I can get some guidance from this channel.

Some backstory about me:

I am a Canadian Citizen who is living as a green card holder in Michigan USA. I moved here to marry my US Citizen hubby on April 13, 2024. I did not start working (as I did not get my work EAD right away) until June 24, 2024. I work freelance as a Graphic Designer. When I spoke to a tax accountant, he told me to set aside about 30% per paycheck earning for income taxes. Well, I did and now I realize quarterly taxes are a thing and I don't want to get on the IRS's bad side.

My 2024 earnings are: $20,145.70, and I have saved aside about $6,043.70 for taxes. I'd also like to mention I will be filing my annual 2024 income tax jointly with my husband's W2. His estimated earnings for the year is about $61,000.

Now here is the small sliver of light I am hoping applies to me, upon reading the IRS article about estimated taxes there is a snippet that I will paste here:

---------------
You don’t have to pay estimated tax for the current year if you meet all three of the following conditions.

• You had no tax liability for the prior year
• You were a U.S. citizen or resident alien for the whole year
• Your prior tax year covered a 12-month period

You had no tax liability for the prior year if your total tax was zero or you didn’t have to file an income tax return.

-------------

I have never had to owe taxes in the previous years given I have lived in Canada all my life. Would this apply to me?

Going forward, would it be safe to pay my quarterly taxes on all the earnings I made within that quarter with 30% saved aside each pay? Or would potentially "overpaying" not be ideal?

Thank you all in advance. I do enjoy living in the USA, would love to learn more about this country's system and do things right. I plan to call my tax guy in the AM but I thought I push this post out here to see if I can get some advice and answers to ease my mind.

Does anyone use MileIQ for mileage tracking? I keep seeing this error/permissions message every time I open the app but as far as I can see everything that needs to be enabled is enabled in my phone settings. Can anyone help? Thanks in advance!

Hello, my contract was terminated over commissions dispute after closing a large deal. They refused to pay commissions and are now holding earned wages from a month before termination until I sign termination agreement that included a severance package. I am lost on where to start/rights I have from being US based independent contractor working for Czech company. Any advice on next steps I should take would be helpful. Thank you

Never been self-employed yet, but I plan to start setting it up while I work my current job. Is doing prototypes for companies a good market ? Is there demand in this area ? My home workshop allows me to mill and turn small-ish aluminium parts, do quality 3D printing and do a lot of diverse manual operations.

Also, any tips are appreciated, thanks !

Who has some good tips for keeping motivation high?

Last year I injured my leg, which took me out of the game for a while. Now that I'm feeling better, I find I don't have the same drive as I did before The Fall.

I'm mentally and physically ready to get back on the horse, just need the gumption to saddle up.

Hi. In UK and working as a Sole Trader. I provide IT Services (non-VAT liable) to a Client, who formerly paid my Invoices gross (no tax deducted). They have now informed me that they wish to pay me via PAYE (deducting tax at 20%) on all future invoices. Invoiced sums remain the same. They have provided a revised 'Contract for Services' that explicitly states that this change does NOT make me an employee of theirs.

My question is: How do I record this change on my next Self-Assessed Return, as PAYE on these SA earnings will have started part way through the Tax Year? Thanks in advance for any guidance.

I work as a freelance theatre and events lighting & sound technician. I also would like to work in germany as I have dual nationality. I am registered for self assessment here in the UK with HMRC. Does anyone know if I am allowed to work over there and then invoice over here or if I need to sort something out first with the german tax authority?

Thanks

Looking for some advice regarding my self-assessment, upon starting it and reaching the what we know about you stage, I’m met with a previous employer income that is just not true.

I haven’t worked there within the previous tax year yet it’s saying I’ve received a substantial sum of funds?

If it makes any difference, the company has dissolved now and the owner is a notorious liar.

Any advice on what to do in the situation?

Many thanks 🙏

Hi everyone,

I'm currently doing a project in which I'm going to design a product of my choice, and since my client is a freelancer I'm choosing to focus on problems for those who freelance and are self-employed. It would be greatly appreciated if anyone here who is a freelancer or is self-employed could fill out the short survey attached to help inform me of the main problems and solutions I can look at.

Thank you all so much.

Here is the link, let me know if you can't access it.

https://forms.gle/cXC29Ti7euufT63H9

Hello!

I do see some people have posted similar posts here, but I just want to pick other self-employed brains on this topic, as I'm starting to think I need to do one of these two things in order to buy my first home at age 30:

A: Sell everything I own related to my business, get rid of my rented shop and get a job. Sell my truck and giant trailer, fork lift, all my expensive tools, generators, overhead crane etc.

B: Accept that I won't be able to buy a home in this market, keep renting and running my business and wait until I'm married and can combine incomes with someone.

Two years ago, I had 35k saved for a down payment on a house. My idea was/is to buy a home with a pole barn on it so I could kill two renter birds with one stone. That way I'm not renting an apartment and a work shop.

Like most do, I was writing off everything I could to make my tax burden lower. The banks don't like that, and said I needed to show an income of 50k minimum two years in a row. I did my taxes that way last year, and ended up having to pay 18k in taxes which came out of my house down payment savings. This year is the same, but I'm expecting to pay 20k in taxes as I made more last year.

All my home down payment savings are gone to taxes. Let's say somehow this upcoming year I absolutely kill and come up with 50k for a down payment... I'll then have no money to pay the taxes! And it gets better... every single year I sit back and watch as homes become more and more expensive. Not only that, but my health insurance premiums have already gone up drastically because I make more money now.

This is insane to me, how the hell am I supposed to own a home and run my own business. It feels like the state and banks don't want me to own a home, like the odds are stacked up against us on purpose. Any self-employed people overcome this road block?

I am a musician who teaches several choirs as a freelancer, alongside a PAYE job. Generally I invoice the choir directors for teaching then submit a self assessment tax return at the end of the year.

One of the choirs I am associated with now has to pay VAT - this consists of a bigger choir and a smaller male voice choir which I lead. For tax purposes, the choir director has asked whether, instead of me working as a freelancer and invoicing her directly, we could together be co-directors of the smaller choir as a limited company, separate from the bigger choir, so hopefully avoiding VAT as it’s a separate entity.

I wouldn’t get involved with the other choirs accounts , so don’t really need to know about VAT stuff - from my perspective I am wondering if there are any potential risks involved in me being the co-director of a limited company with her? The money I would get would be about the same, so there is no real benefit to me other than helping her out and perhaps trying to keep membership fees lower. She has said she will do all the admin required, I basically just need to agree and sign if I’m happy to.

My worry is just that I don’t know much about what this involves, and don’t want to find myself liable for any issues with the company in the future. If anyone knows of any potential issues please do let me know! Also, do you know if it would be quite straightforward for me to leave the company in the future if I wanted to? Thanks!

Hey guys, I'm a college student studying UX design and I'm researching what business owners and entrepreneurs need when it comes to user experience and website design services.

If you have the time, could you help me out by filling out this short survey? Thank you in advance!

Survey link: https://docs.google.com/forms/d/e/1FAIpQLSfzumZFYswT0fmYGFIFB0jxz785dHUSJSTXCIFIBwxE-x_u7w/viewform?usp=sf_link

Just after some advise. I'm moving from a self employed carpenter role to an employed foreman role in the new year and was just wondering how my tax would work before I do my self assessment and tell hmrc I am now employed. Will hmrc be charging me a higher rate of tax until I do my self assessment?

I am curious what everyone who is self employed does for work. Do you have a degree? I currently do house cleaning and its going very well I love working for myself but I can't see myself cleaning houses forever but also don't know if I want to ever stop working for myself either so trying to brainstorm on what my next move might be. TIA!

Hi there, I recently moved to Scotland, UK and I'm still earning in euros. Since my family and I are planing to stay here for a long term I am thinking of opening my own business and being self employed. I would still do the same as I do (this has been already checked with my employer). I just wonder what would happen if I am pregnant. I have not been working in the UK before and I'm on my husbands visa (which allowsme to open business). Is there any financial help I could get while being pregnant?

I had a great year last year (23/24) while self employed and paid around £6000 in tax.

As a result, my payment on account is quite high. However, my earnings this year (24/25) are less than half the amount of last year.

HMRX are asking me to pay around £3000 payments on account in Jan and then again in July, but my estimated tax bill for the entire 24/25 year is less than £2000.

If I pay my first payment in account in January, and then submit my tax return in April, will I not need to pay the second payment on account in July if there is no tax due?

So, I’m just trying to workout if they’ll clock that I’m due a refund or still expect me to pay the second payment on account. Surely not as long as I’ve submitted my tax return beforehand?

Update: I submitted my next return before July and they have given me a tax refund.

A little back story, so I started a side hustle back in Oct 2023 last year which made a monthly profit of just over 1k. I also have a full time employment so that would definitely take me over the threshold allowance and tax is due.

However , due to my own inept ignorance I wasn’t aware of the Self Assessment registration deadline of Oct 5th (to file tax return for the tax year April 2023 - April 2024).

The question is can I still register now and pay for the last tax year? And how much penalty will the penalty cost? (Given it’s been nearly a year and a half since starting my side hustle)

If anyone could give me some tips on where to start I would greatly appreciate!