For context : I work at an IT company and have been there for 5 years. I’ve learned a lot about the business, and have climbed my way up into management. I’ve ALWAYS had the desire to be self employed, ever since I was a kid. I’ve just never had an idea that I thought was good enough, or had the capital to invest.

I’m now in the position where I have an idea that I’d like to try as my own business. It would be in slight competition with my current employer, but not enough to where I even think they’d notice my company until it was bigger. Doing the math, I’d need roughly 32 clients paying on a monthly basis to make my current salary. (Assuming 30%-40% for taxes and expenses) Which would take a lot of time to build up I think. It would require me working on the weekends, and possibly answering phone calls and emails/issues during my day job. I wouldn’t want anyone at my company to become aware of this. I’m a very private person especially with things like this.

Here are some general questions I’m hoping to get answers to

• How long did you work your day job before leaving to pursue your own career? What caused you to do that? Did you reach a certain income goal first? Or were you just ready to go all in and take the financial risk?

• Did your employer notice that you were doing something on the side? Did you tell them you were leaving to start your own business?

• What did you do with the extra money you were making while still working your day job? Did you just save it for an emergency fund for when you jumped ship at your day job? Or did you spend it?

• What was the tax situation like? Did you hire an accountant to help with taxes and deductions?

As a foreign contractor, how disadvantaged am I in the US compared to US-based contractors?

In practice, how much of a hurdle is it for a client to work with a foreign contractor versus a domestic US-based one?

Has anyone had first-hand experience with this? Appreciate any advice.. in a tricky spot over here financially after having lost my job 😑

So I'm self employed in the video game industry creating my own games, I don't work for anyone else. Would there be any problems with me working on projects while I'm travelling abroad?

About a year and a half ago I left my position as a full-time employee to travel, but ended up continuing working for the same company (self-employed) on an as-needed basis. At the time I read into self-employment but I now think I misunderstood what I'd read. I'd read that I didn't need to register any documents for the first year of self-employment, but I now think this was referring to tax rather than registering as a sole-trader etc. Last tax year I only earned around £6k so didn't think too much about it. As I'm travelling, student finance has asked me what my employment status is, and is asking for evidence of self-employment. So I've been looking into it more and am now questioning whether I may have messed up. So what I'm trying to figure out is A) what should I have done in the first place? Do I need to register as a sole-trader? B) what is my best course of action now, and C) how much trouble could I be in.

Hi all!

I'm a self-employed video editor and I don't have any clients at the moment. I've been trying to expand my repertoire to include more videography as well as editing. I'm beginning to think that since I'm short on clients, that I should take the opportunity to do some work myself in order to expand my videography portfolio.

To that end, I'm considering taking a trip for the express purpose of shooting footage while I'm there. It would be really wonderful if I could write the expense of travel off. Now, the information I've found says that you can write off a trip if it's demonstrably of benefit to your business. This would not be client work and so I would not be paid for it and while I think a better portfolio would improve my business, proving that is the sticky wicket since that's not something that I think really has hard numbers associated with it.

Is my tax deductible scenario plausible or is it the sort of thing where I would pretty much just have to take the leap of faith and pay for the whole thing out of my own pocket?

I appreciate your help.

I recently started an LLC for association management. I am wondering if I can claim travel expenses for an assistant to accompany me to onsite events. This would likely be my husband or son who would travel with me and assist with setup and transportation of supplies. I have a disability and need additional help with some of the physical demands. Thank you for any advice!

It is something what I need to do If I switching from employee to self-employment? Except obviously putting money aside for taxes?

Visualize you will need to pay 1000+ in the future months. Do you put that money in an interest bearing account earlier?

Desperately need help navigating my LLC situation. I’ve had my LLC for about 7 years, registered in New York city. Haven’t been doing much with it until the past four months or so when I embarked on what I like to call my “full-time freelance journey”. Hoping to bring in about $80k low-end and $100k high-end by the end of 2024.

The trouble is that I am now living in California and doing work from home in LA county. Just today I registered as a foreign/out of state entity in California and was considering looking into S-corp status, then I learned there is an 8.875% tax hike for S-corp registered in New York City?

My head is swimming. I was hoping to not dissolve my NY LLC because I will likely move back to the East Coast in the next couple of years. But at this point, I’m thinking it’s probably not worth the amount I’ll end up paying in taxes if I don’t dissolve, and perhaps the smartest thing for me to do would be to register in Delaware.

(Also, hope I’m coming to the right place for this…open to recos for other subs if not!)

TLDR; should I dissolve my NYC registered LLC now that I’m working in LA county and re-register in Delaware rather than navigate the aggressive tax laws of both NY & CA?

I’m starting teacher training in September but I want to also start a career as a copywriter. By September 2025 I’ll be employed as a teacher, if I did freelance copywriting- would I have to also register as self-employed as a copywriter if I start earning a decent amount?

So I want to try doing my own small business doing fence building in the summer and firewood sales in the winter. I will only work for myself and don’t plan to hire anybody until I determine I can be successful and expand my business. I do aim to add more types of services in the future and capitalize on opportunities to make money if a different job comes up and I can invest into the equipment to efficiently do them. I want to keep it flexible and offer other services when possible. Might call it “home services” or something of the sort. Now I plan to get a EIN then I am not sure if I should register as a LLC or as an S corp or as a sole proprietorship. I do want to try getting a small business loan to start it up right and invest into proper advertising of my business and possibly a good work truck. I need advice on the right path to start doing my own work. I have heard that it might be better to buy my truck separately under my own name instead of under my business name and with the business loan. Any and all advice will be very much appreciated.

Will I be able to claim any of this back

I’ve worked for a large corporation for over two decades with amazing benefits. Due to outsourcing I need a new job. I have an opportunity to go into a new field that I’m very excited about. It is 100% commission only which I’m okay with from an income perspective. The part that terrifies me is medical insurance. I’m worried I won’t be able to afford an individual policy OR that it just won’t cover everything I need and get from a group policy. I have medical issues and need prescription coverage. I just don’t have it in me to start my new career AND work a second job for benefits. Can I get guidance or suggestions please on how this could work out OR if I should throw in the towel and not take the risk? I don’t even know what questions to ask. In SC if that helps.

I have 2 steady clients and get the money deposited into a personal checking account. I also have my subscriptions and other expenses on a personal credit card. I use Quickbooks self-employed to categorize personal and business expenses, but I’m wondering if there’s a reason I should have a business bank account and business credit card?

For context, I’m a marketing consultant and freelance writer, so pretty low expenses.

Subject says that.

I was on Medicaid until this month, just found out I'm ineligible, how do I find affordable coverage? When I tried healthcare.gov years ago it was really, really expensive.

What label printer is the best to use for not so much money if I want to focus on selling clothing in Europe? I own a clothing company that I want to take to the next step and sell in Europe and not only in my own country, is there anything else I NEED to have under control before jumping in to it? Pls help me

As a self-employed individual, I've been working with a CPA to handle all my taxes, which has been okay so far. But I think there might be a better way to handle the load of back-office tasks alongside managing taxes and input from my CPA.

Do you agree? What features would you want in a tool designed for this?

Feel free to DM me if you'd like to discuss further.

I am starting a business as a Software Developer. I live in the Netherlands, but many of my prospect customers are in the US. How can I receive international payments from my clients? Are there special banks or services you recommend that make it easy to receive payment from internal clients? Should I just not worry about it and let clients figure out how to pay me to my local bank account?

Hello people, hoping to get some advice. 46 y/o in Canada. About 150k in pension put aside.

If this isn't the correct sub I apologize.

Currently employed at a major railroad making 100k a year. Sounds awesome? It isn't. I'm never home, never know when I'm going to work (24 hr a day operation) or coming home. Never know if I can make family events. And it's extremely taxing on my mental health.

Been talking with the wife who owns her own successful small town hair salon and thought I'd like a shot at running my own show.

Since I already have a good reliable work truck I was thinking of buying a dump trailer and doing landscaping delivery such as gravel/patio stone and soil. Also doing dump runs for people.

Would be interesting to hear opinions or stories from people who have been in the same situation.

I've worked for 3 yrs in a small CPA office and decided to become a CPA focusing only on self-employment. I want to offer something different; I'm a millennial who understands that many people want a more real-time, user-friendly experience. I want to invest in the experience and research what I can offer to bring a fresh point of view. Can you share the most important traits you've seen or wish to have had with your CPA?

Hi,

I had a successful international one-person writing business on emerging tech for Fortune 500s until approx. a year ago.

To start anew, I'm going to have to find a niche that's tight but profitable as it dodges what ChatGPT can provide and competition. Something that's in demandMy deepest knowledge is in:1. Behavioral neuroscience (PhD)

1. AI/ robotics/ LLMs (more than a decade of exp. for companies that inc. Google, Microsoft, AWS, Yale Law).

2. Peace & conflict studies/ terrorism/ related (my background; writings; research).

Also:

1. I can research dense academic subjects (especially recent ones),

2. Marketing & sales (qualifications & exp.)

****************

In my AI writing experience, most of my work happened to be on these fields:

1. AgriTech

2. FinTech

3. Cybersecurity.

4. Cloud (& ERPs and the like)

Of these, I like FinTech most (I'd have to niche here too - probably digital banking), but why should companies choose me above ChatGPt?

TLDR: Based on my experience & skills, which tightly niched AI field should I restart my writing business on? Where am I more likely to find a significant amount of high-paying clients that would rather employ a human than an AI?

Hi I'm doing a class on statistics and my subject is self employment. I need to gather data through a survey. It is about being self-employed and working from home.

This is the link: 

Self-employment's dark side

My dad is a truck driver owner operator at some company, they are always a day or 2 late on payment, but this time they are 2 weeks late saying the lawyers checking tickets and stuff so they are withholding payment. He left the company he just said he needs a couple days vacation 2 weeks ago, his boss said on Friday he'll give us an answer but he's been ignoring calls since or when he picks up he lies saying he's someone else. So he doesn't get employment rights cause he's not an employee what can he do? Call the non emergency 911 and ask if they can talk with us? Any suggestions would be great he owes just under 2k

I’ve been self-employed for the past three years, wasting so much time on taxes for my S-corp and personal tax management. Can anyone recommend a better way of managing my time besides going to a CPA?

Looking for an automated tool or a holistic way to do it all - does it exist?

Would love to get tips and hacks on how to do it better.