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I've read many articles and texts over the years about running companies and personal finances. Every time, I sink down in my chair, mentally exhausted from the utterly confusing, cryptic material I've attempted to digest. And so I yet again forget about doing whatever I was going to do, such as running some kind of business.

I have a fear of getting sent to prison.

If I simply create a database table on my computer, with three columns: "label", "amount" and "timestamp", where I input every single amount I either get or buy (using minus on the amount fiends to denote the rows which correspond to the latter), with a short description such as "Food from X" or "Money from ad deal for Y", and really stick to this, will I be "safe" in case I ever get into some kind of financial trouble?

Would a court or the cops be content if I were to give them a "dump" of this table, perhaps formatted according to some standard format that they tell me, but containing nothing more than the three fields I mentioned?

Is there perhaps some kind of service which could automatically "calculate the taxes" or whatever if I just hand them my "financial log" or whatever it should be called?

My brain truly seems unable to comprehend how to "fill out tax forms" or anything related to the entire economical system currently in place world-wide. On the other hand, it is capable of creating such a database and to output it as any (open) file format or printed on paper.

Would not this at least show some kind of "good faith" if I ever find myself in trouble with the law for failing to send in some report or form or whatever?

PS: I'm not joking about my brain not being made for this. I actually like databases and numbers and money sums and the idea of keeping track of them like this, but "everything else", such as complicated (or any) rules for how to actually "use" these numbers are way beyond my ability to think. (Beyond me just finding it to be "deadly dull", which is also true.)

blahdiblah
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Lg Dolbier
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4 Answers4

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If you're not comfortable "filling out tax forms" then hire a Certified Public Accountant (CPA). Depending on how easily they can convert your records to actual income statements, it may not be that expensive, but if you just hand them a list of transactions and make them categorize them it will take more time. It may be cheaper to hire a bookkeeper (even on a contract basis) to review your transactions once a month and organize them so that you don't waste time filling out tax forms.

Note that "courts" and "cops" aren't really concerned with your bookkeeping - it's the Internal Revenue Service (IRS) that will make sure everything is accounted for properly. You likely won't go to jail just for being incompetent; only deliberate acts like falsifying records or not paying your taxes are criminal acts. The rest will just cost you money and time to clean up.

Nosjack
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D Stanley
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You've got a couple of things going on here... and I'm not sure all of it is financial.

First up, the big one:

"I have a fear of getting sent to prison."

Uh, no. You don't get thrown into prison for messing up your taxes. I've messed up my taxes twice. Want to know what happened? I got audited... and then had to mail the government a check for the difference.

That's all.

The IRS isn't looking to send people to jail - they're looking to simply collect taxes. An extremely small number of people are sentenced for tax fraud - about 600 per year, in a country of 360 million. It's also not something you can do on accident - it's deliberate/intentional/willful.

Next:

"Is there perhaps some kind of service which could automatically "calculate the taxes" or whatever if I just hand them my "financial log" or whatever it should be called?"

Yep. There are businesses that will take care of this for you. Honestly, the easiest thing may be to simply google '[Your location] Accountant' or '[Your location] CPA' and schedule a consultation with them - just talk about what you're thinking about. They'll tell you the best way to proceed from there. Because, honestly, I think half the problem you're dealing with right now is uncertainty/worry, and talking with one of them would help alleviate that.

Kevin
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A business is a team effort

Your log is just fine for your part of the bookkeeping job, as long as you keep it honestly.

Your bookkeeper does the bookkeeping, all nice, neat and to GAAP standards. Filing taxes (not your job) is as easy as plugging in numbers out of the bookkeeping.

I’m not intimidated by anything, and I do bookkeeping... too much. However I work better when I’m not doing bookkeeping and focusing on the stuff that makes the business win. As businesses get bigger, this becomes mandatory. You don’t think Elon Musk or Jerry Yang do their own Quickbooks, do you? LOL, of course not, they have people to do that.

And the good news for you is, those people are much cheaper than you think they are.

In fact, I’ll make a bet. I bet you do not personally file your own personal tax forms, tabulating the income and expenses, hand writing the numbers onto the tax forms, and mail them in on paper. I bet you sit there on your computer, frazzled and stressed out, and go to TurboTax or H&R Block or some equivalent and try to find the numbers it asks you for. Now if you make enough money to think about opening your own business, I bet you’re paying way too much taxes because you’re missing deductions you’ve earned. Getting a bookkeeper to handle both your personal and business taxes may well pay for itself.

Certainly, “taking that load off your mind” will free your mind to do a better job pursuing your core business, and make more money.

Master yourself.

Understand that every human being has very strong feelings about money. There is mental programming burned into your brain even stronger than politics, and it is mostly subconscious. It’s placed there in childhood years, and from observation and experience (not book teaching).

People can be very powerfully affected by that, to the point where dealing with money in a certain way offends a values system they don’t even realize they have. Say, someone as a child watched money tear the family apart - endless fights, a gruesome divorce that was largely about money, etc. If that person values family, it’s gonna make them subconsciously think of money as toxic - and they may well “push it away” - not taking financial opportunities (“who needs it”), pushing money out of their wallet and bank account (“there’s never enough”), etc. Ironically they set themselves up for the same problem!

So with all due respect... when a smart person is inexplicably blocked from being smart with money, it’s worth looking into what might be behind that. The takeaway is that is very fixable, but the fix is not in our bailiwick here on money.se.

Trust me that accounting will make sense. In the meantime, take your lessons one at a time. Trying to gulp down a bookful of lessons in one go, is probably a bad idea anyway.

Don’t be evil

To stay out of jail, it’s that simple. Do your level honest best without being sneaky or clever. Don’t do anything that would cheat another person, including your fellow taxpayers. Don’t do sneaky things like pretending a huge flatscreen TV is a business expense. Keep it clean and honest, and jail becomes an impossibility even if you make honest mistakes.

Lesson of the day: keep finances separate

The takeaway for today is that you must think in terms of wearing two hats. Your personal life is your personal life. Your business life is a completely different “life”. The two do not mix.

It’s sort of like being a trustee. If you had a family member who had a mental disability and could not manage their own financial affairs, and it became your job to do that, then you would use their money to pay for their stuff. And your money to pay for your stuff. If your cable bill was due, you wouldn’t grab the trustee checkbook to pay it; that would be stealing.

You have the same mentality toward your business. Dolbier Widgets Unlimited gets a totally separate checkbook and credit cards. Pay cable bill with personal money, never grab the DWU checkbook to pay a personal expense. Likewise never pay for business needs out of your own pocket.

If you need to add money to the business, your bookkeeper will tell you how to do that. If you want to take profit from the business, again, your bookkeeper will tell you how to do that.

When you do that... and your business gets to a certain point, you can ask your bookkeeper to “throw a switch” and give you a liability shield. That makes it almost impossible to sue you personally due to problems with your products. In order to throw that switch, you must already be doing the above.

Harper - Reinstate Monica
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I mostly agree with everyone here, but just wanted to add: if you do have a business, there are accounting rules you have to follow for the business, including an adequate accounting system that enables you to correctly comply with all applicable laws.

If your question is simply about your own personal taxes, then as folks have alluded to, if you're an employee, you'll get a tax form at the end of the year that is necessary for reporting and paying your taxes.

If you don't have a business, but you receive income other than W-2 income, then there are a range of applicable rules that may apply, in addition to what your bookkeeping system looks like.

C.S.
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