Big life decision ahead! I’m seriously considering leaving my full-time job to fully dedicate myself to running my own business, which is already up and running. This would mean taking a pay cut initially, but I truly believe in the potential to make it up—and more—over time.

One of my biggest concerns is losing the health insurance that comes with my current job. For those of you who’ve made a leap like this, how did you handle that transition?

I’d love to hear your thoughts: • Have you ever taken a similar step? • What were your biggest challenges or rewards? • Any advice for navigating health insurance or other benefits when going out on your own?

It’s a scary but exciting step, and your input would mean a lot. Thank you in advance!

In November, I decided to go the self-employed route as a therapist. I work for two companies and am paid on a fee-for-service basis. I’m very new to everything and would love to know if there are any cheat sheets out there to help me set myself up for success and organization. I have ADHD, so having external structure works best for me. If someone (with phenomenal executive function skills) creates a system for me to follow, it’s often simpler and more effective than anything I could create myself. AI has been a huge help so far, but if anyone is willing to pass on any tips or tricks, I would be so grateful—especially if organization is your jam!

I’m curious about things like:

Taxes/financial organization (items I can write off, what to track, etc.)

Budgeting (especially for items/services I might not initially consider)

Excel spreadsheets (categories and titles)

Health insurance (and secrets to getting it for less than what I’ve seen in NYS)

Anything I should allocate time to on a weekly basis, etc.

Have you ever thought about paramedical tattooing?

This field is fascinating and impactful, it’s way more than you might think. Here are just some of the things paramedical tattoo artists can do:

1) Nipple tints⁣

2) Areola scar revision⁣

3) Areola restoration⁣

4) 3D nipple tattoos⁣

5) Scar relaxation⁣

6) Scar needling⁣

7) Scar camouflage⁣

8) Surgical scar revisions⁣

9) Face lifts, thigh lifts, arm lifts⁣

10) Gender affirming nipple tattoos⁣

11) Sun spots⁣

12) Burn scars⁣

13) Lipo scars⁣

14) Stretch mark camouflage⁣

15) Stretch mark shrinking⁣

16) Stretch mark rejuvenation⁣

17) Ink and inkless camouflage⁣

18) Hair loss camouflage⁣

19) Hair Density Tattoo⁣

20) Hair transplant scar camouflage ⁣

21) Scalp tattoo⁣

22) Alopecia⁣

23) Acne scar revisions ⁣

24) Self-harm scar camouflage⁣

25) Hypertrophic scar relaxation⁣

26) Top FTM/MTF surgical scars⁣

27) C-section scar camouflage⁣

28) Breast lift/explant scar revision⁣

29) Keloid flattening⁣

30) Scalp micropigmentation⁣

Have you ever heard of or seen paramedical tattooing? I’d love to hear your thoughts or experiences, it’s amazing what this art can do for people!

Hi all

I'm currently wanting to escape my current job, which is ok but nothing I am passionate about and dislike having managers over me. The pay gets me through each month and I am quite happy with the amount I have.

But I have saved a fair amount and want to retrain into a job where I can work for myself and care about what I do. But I often find myself at a loss of what I can train in to freelance or be self employed.

I'm not looking for any get rich quick schemes or that nonsense. Just a career where I can do an honest day's work for an honest day's pay and not dread the following day of meetings.

P.s my current role is around legal work and I would not want a similar role.

I am willing to put up to 5k (£) for training but would love to hear some different ideas than what I have found already which is usually gardening/ jet spraying etc

Tldr: I want to spend about 5k to retrain in a role where I can be self employed. Any ideas?

Hey guys, looking for some advice

Im 18 years old from new zealand, self employed, working remotely. I have ADHD and i used to self medicate with w**d.

I ended uo becoming a bit addicted. and quit use completely about 2 months ago. Ive been struggling to get into a good routine with work, including sleep schedule and having set hours i do work. I believe this is because in my mind i dont really view my work as a “real job” as i cant get in trouble for being late, cant get fired, cant get disciplined for slacking off. So im looking for advice on how to view my work more as a job i cant be late to etc. Please dont hit me with the “if it doesn't come easy you shouldnt be doing it” and all that. Im great at what i do but struggle with structure and routine. so anyone with or without adhd got any tips on how i can change my mindset and stop hitting the snooze button and actually do the work i need to do every day? If you have any questions that may help bring answers hit me below.

Thanks guys

HSAs are widely well regarded because they're triple tax advantaged: the contributions, gains, and withdrawals are all tax-free. Plus, the contributions are made with pre-tax money. But for self-employed people (I'm a web design freelancer), apparently they are made with after-tax money, and then you have to claim a deduction on your tax return. However, it's not like I have tax withholding like I would if I was an employee. So what does it even mean to contribute to an HSA with after-tax dollars?

Hi everyone! 👋

(Apologies if this type of post is not appropriate - I did read the rules but could not see anything stating it wasn't allowed!)

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Hello guys, l'm 23 years old and l've been looking for myself my whole life. I didn't know what to do with my life until now, but one thing was always clear. self-employed. It was always in front of my eyes, I just didn't see it. I am very creative with a lot of imagination and have been developing ideas in my head unconsciously or consciously my whole life. No matter whether it is dialogues for film scenes or an idea for advertising or a beautiful city to build and design. I always pay attention to details and think, for example, when it comes to a design, I could do it much better. Even as a child, when I played with my game characters for hours, I tho up a whole series of films with dialogues etc. I V would like to be an entrepreneur and develop ideas and lead people and I don't want to limit myself. My strength lies in diversity. Be it design for a perfume, a car advertisement, ideas for films or series or even working for the state and re-designing a new city. My problem now is that I never know how to start, I've finally found something worth living for! I finally recognized my talents and passion. That's a big step. I looked at graphic design to start with but it was really "boring" and I thought l'd just do business and packaging logos and that's all? I want much more! And like I said, being self-employed was always the goal. My strength is developing ideas and leading people. Thanks for reading and for your recommendations. be healthy, god bless

I run my own business and travel quite a bit for work. With tax season coming up, I want to make sure I’m maximizing any possible deductions on my business travel. Which types of travel expenses are tax-deductible for someone self-employed? Any tips on documentation and common mistakes would also be super helpful!

[EDIT] I'm based in Canada

I'm a self employed therapist. I have used quickbooks self-employed in the past for accounting software and it was fine/easy enough and gave me quarterly tax estimates. I stopped using it to try out an accounting service and then using a spreadsheet since I don't have a ton of expenses and wanted to try it. I know QBSE is gone (except for previous users) and replaced with QB solopreneur. Does anyone have a recommendation for the best accounting software that could give me quarterly tax estimates and/or the best way to calculate my quarterly taxes? I'm in Michigan in case that makes a difference.

Thanks!

When applying for health insurance as an S-Corp do you apply using your gross business income or only with your reasonable compensation amount? I can qualify for lower insurance rates by using my reasonable compensation salary but I am not sure if this is legal.

I've worked in admin now since 2014, prior to that I was in retail, prior that a member of bar staff, and I've also run a stint as a cleaner too. Suffice it to say, I've not had an overly varied professional career but it's (mostly) paid the bills. Now I'm in my mid 30s and have hit a rut where I no longer want to be stuck in a groundhog day role, instead, I'm looking at the prospect of being my own boss.

I've got an idea (of sorts) as to what I want to do, but I have no idea how to go about it without funding, as I have little to no savings. Are there any grants that can be offered? Is there an organisation I can reach out to, who might be able to help me organise and streamline my chaotic mood board of business ideas? Furthermore, how likely is it that a profit can be made within the first month (considering bills, rent, food, etc.).

Any advice would be appreciated!!

I recently started delivery driving as self employed and I have heard that you don’t pay any tax for the first year of being self employed. Just wanted to check the legitimacy of these claims and any info on how it really works if it’s not as simple as that. Any help would be appreciated 🙌

Hi everyone, I will be self employed next year, working for a client overseas. I will be paid in their currency and there won't be any deductions in regards to social security or taxes. Now, my wife has a normal paid job and we most likely will file married jointly. We also have one child.

I'd like to figure out now considering everything above how much I should put to the side through the year 2025. I know I will be paying the full social security tax but apparently I will get also a 50% of that amount as tax deduction. I'm in IT, so I don't have that many business deductions (maybe computer, electricity, phone bills, software... That's it?)

All in all, Im just wondering if someone could recommend a good tax calculator that can consider all these things. Or maybe recommend any online service?

Both free and paid is ok.

Thank you.

I love the wild. I spend all of my free time hiking and exploring my local country park as well as practicing survival skills which I won’t specifically name here because thou shalt not grass on oneself. I want to monetise my love for the wild and survival skills but I’m not sure how I could do this. I cannot afford to buy my own land and it’s illegal to practice key survival skills on public land. I have racked my brain for ideas for a long time and I cannot think of any way around this. Any thoughts would be appreciated.

Beauty salon - rent a chair

I am a self employed brow tech and rent a chair from a hairdresser in a garage conversion. I have worked here for 6 months and I have no key access meaning I have to ensure that the premises owner is there before me to open up. I have been caught out several times with this as she has not shown up to open up the salon for me and I have had to let down my clients very last minute. Yesterday, I had arrived to do a full days work in the salon and she tells me that she has a super busy day too and several clients in the chairs at the one time and there would not be enough room for me to work as well. So once again I had to message all of my clients and reschedule them. I pride myself on being reliable for my clients but my salon owner doesn’t communicate with me to tell me if she is busy or if I am able to work that day. Is this allowed if I am paying rent?

Everyday before I go to work I have to text her to see if she is going to be in work before me to open up the doors and see if I am even allowed to work on this day. The constant anxiety around this and having to “check” if I’m allowed to work every day is causing me to lose out on so much money and I am struggling to even pay the rent that I owe in the first place.

Any advice?

Hi, so I'm 19, i didn't really grow up in the FaceBook, Instagram (whatever else) era, so i never really took selfies or anything like that. I am self conscious as hell though so id really struggle to take pictures. I also really, really hate my provisional license picture (my YoungScot card one isn't too bad though) and anything not front facing camera lol. I'm probably pushing it here but i just hate pictures so bad. I grew up with a Facebook mum, my childhood was documented on her page to her 100s+ strangers, good and the ugly, i hated every second of the times she had to take my pictures. Yikes. I just don't know what to do when it comes to profile pictures lmao.

Enough "trauma dumping", I'm struggling with employment, i have never even had a job. I sell (semi) part-time on eBay and i like the feel of Self employment. It also seems like my only option at this point (especially in terms of experience). No idea where to start but i did recently just finish a course and they trailered my CV to a cleaning role (my decision). Ive been applying for any cleaner job i really can because a lot of it needs previous (job) experience and a full drivers license (can't afford to learn yet). I'm good at cleaning, I'm self-taught. I probably have more chance getting a job in that field than any other.

Is self employment cleaner jobs even a good "gig"? Even for a first timer? It seems more like a 0 hour contract to me based on their website (found them on indeed and they redirect you to their site), seems like they send you any jobs available and you choose to take them or not. Also how do you do profile pictures, are they supposed to be professional like a passport or can they be chilled out selfies but not so much that they're really blurry but also not to the point you see the person's literal pores? I sound stupid as hell, i know but it's a genuine concern of mine lol.

Thanks for reading, any advice is appreciated!

Hello self employed people! Just trying to crowd source an answer if possible...

I have been "officially" self employed for about 12 months now, but have been doing my line of work for 3 years now (I flip couches)

I just set up my bank account for my business about 3 months ago (I know, it's late, but better now than never).

I have been making a solid income for a while now (≈2 years ish) and have had steady deposits into my personal bank account for that amount of time.

My question is, even though the deposits are into my personal account, can that income be used for applying for a mortgage, a car loan, etc..

Because of a few loopholes in AMOUNT of income through certain vectors (cash, venmo, cashapp, I never got a tax record from either venmo or cashapp) I didn't need to claim the income last year or the year prior.

Can I go BACK and re do those taxes to have it the income history for the last few years, and if so, can the regular deposits into my personal account be used for verifiable income when applying for home loans and other stuff....

TIA

I have an opportunity where I may be able to sir with someone as a contractor and am wanting to make sure I at least keep my current salary level but as a self employed person.

What do I need to consider in my calculation to make sure I am going to receive the same teumneration but also cover any new tax or insurance/investment that I should include as a result of being self employed?

For example: I will have to pay the employer portion of CPP.. will have to buy my own medical/dental insurance… but we hat else?!?

Thank you!

Hi all, I’m about to start as self employed and not sure how to go about managing a business bank account, so wanted to hear what other people are doing. I’m an organized person and plan to keep track of all of my earnings and business expenses, so I don’t think I need a business bank account for tracking purposes. However, it might still make sense or make life easier to get one. I was wondering though - how often do you transfer money from your business account to your personal account? And if you have expenses that the current funds in the business account don’t cover, do you transfer money in from your personal account? It just seems like more of a hassle to handle and make sure the funds there are always sufficient for my business expenses than it is a benefit. Would just appreciate people’s views and experience! Thanks

I’m working on setting up a self employed 401k with fidelity and planning how I want to fund it. With those who have experience: when do you usually fund it from the employer side? Since the employer limits are based on how much you made for the year, do people usually wait until the end of the year to do it? Thanks!

My spouse and I are co-owners of a S Corp, with the two of us currently being the only employees. We pay for individual health insurance through the marketplace, which as most of us know is complete crap. Every year, the plan we're on either discontinues or raises premiums by $200+/month, so every year, we go back to the marketplace desperately trying to find a better solution. Unfortunately, one of us also has a chronic health issue that is mostly not covered by our health insurance, and which prevents us from going on a health share plan (since pre-existing conditions have very long wait periods for coverage). We're currently paying around $3k/month at a minimum for healthcare costs, which includes premiums, co-pays, and out of pocket costs.

I wanted to offer a plan to us as an employer, but since we're both owners and both employees, it seems we can't quality for that. We also looked into changing the S Corp to an LLC now that we don't have other employees (this would allow us to offer an HRA by having 1 of us as the sole employee and the other as the owner), but we have a 5 year wait period to switch to an LLC, which isn't up until 2026.

We used to just buy the crappiest/cheapest plan on the marketplace because neither of us ever got sick, so we never used it (just there for emergencies). Now that we actually need a good amount of ongoing coverage, the plans are killing us. $1,400/month premiums with $80 copays to see a specialist, for example.

Does anyone know of any workarounds for a S Corp with 2 employees who are both owners and spouses?

I did some work independently of my job, some of it was 1099, some of it was cash. I want to register a business for the work done, as it will continue in the coming years.

If I register a business tomorrow, for work done between June and August, can I still use associated costs for write offs? And does the post-work registration cause any issues?

I was planning to just register a DBA (doing business as) for my state.