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I currently work as a full-time employee for a company, but I recently learned that one of our clients wants to pick me up as an independent contractor.

The transition will be well worth it:

Personal Income: $37,000 → $83,000
Household Income: $65,000 → $111,000

But, I have no experience being self-employed. So, I just have a few Tax 101 questions.


  1. Exactly how much should I set aside for paying taxes? I don't mind setting aside the maximum amount, but I'm not certain I know where that maximum is. from what I can see, this is what I'll need to set aside:

    • Federal: With the tax reform, it looks like it's a $24,000 deduction for filing married joint, and 12% for anything under $90k. So... 111k - 24k = $87k. And 12% of that would be $10500.
    • Oregon has something called a "Tax Liability Subtraction". Is that a standard deduction? If so it's $6500 for married joint. Therefore taxable income is $104.5k. The first $17k calls for $1054, and the balance is at a 9% tax, or $7875. Totaling $8929.
    • Medicare & Social Security appear to ignore deductions, correct? And, since I'm self employed, it appears that it's 15.3%, right? If so, then this appears to be $17000

    This comes out to $36,429, or 33% of our household income. Is that too low of a maximum estimate? Would it be safe to go any lower?

    Since my wife accounts for 25% of our household income, can I expect to be able to safely reduce that $36.5k to ~$27.5k ($2275/mo), to determine how much of MY income I need to set aside?


  1. How exactly can I withhold my taxes? I was just planning on saving the money in a savings account till tax season the following year, but then I saw the IRS recommends quarterly estimated tax payments OR withholding. The verbiage on withholding is confusing:

    If you do not pay your tax through withholding, or do not pay enough tax that way, you might have to pay estimated tax.

    Emphasis mine. This verbiage makes it sound like I still need to make incremental payments to some form of withholding account. Can I just open a new savings account, and throw 33% of my personal income (or however much) in there till I get my tax paperwork the following January?


  1. Do you recommend Quickbooks? I've never used it before, but I have used other Intuit services like Turbotax and Mint. My job won't require me to travel much, but it's not out of the question. I also don't expect much business expense except for a small chunk for setting up my home office appropriately.
  • Have you factored in the loss of benefits? Does the 83K factor in holidays, vacation and sick days? – mhoran_psprep Dec 12 '17 at 4:20
  • @mhoran_psprep I didn't forget to factor in those things, but whether or not it will be worth it depends on how much I need to spend on Taxes. I mean, if I need to spend $2500 less on taxes annually, that's an extra $200 in my pocking a month. On the other-hand, if I'm under-paying by $2500, then I might go under my current net income. – MrMusAddict Dec 12 '17 at 19:23
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  1. Proposed changes aren't likely to affect 2018 tax year, so assuming you don't itemize you're looking at $13,000 standard deduction plus $8,300 in exemptions. The self-employment income requires self-employment tax of 15.3% (SS/Medicare) that formerly came partly from you and partly from your employer, your wife still has hers being withheld, so it's only your contractor income that is subjected to this piece.

    Assuming no business expenses (you'll have some), you're looking at taxable income of $89,700 and ~$13,733 in federal income tax due. Your estimated federal payments will be that amount, less the federal income tax that is withheld from your wife's pay, plus your self-employment tax of $12,699 (83,000 * 0.153) divided by 4.

    So if your wife had $1,000 withheld for federal income tax (for the year), you'd be looking at four estimated payments of ~$6,358.

    I'm not familiar with OR tax code, they may require estimated payments as well, and their rate is 7-9%, I assume that's subject to same deduction+exemptions as federal.

    I suggest speaking to a tax-professional, this is just my 2-minute math, but your numbers seem high, likely because you calculated self-employment on your wife's income as well as using incorrect deduction/exemption numbers, but I could have missed something.

  2. Their wording in this section becomes a little more clear in the context of the 'Withholding' section above it. Your employer withholds your income tax currently and sends money to the IRS, when you become a contractor you'll make the quarterly estimated payments to the IRS since nobody is withholding it for you.

  3. Quickbooks seems overkill for the scenario you describe, just track and document your expenses, a simple spreadsheet will likely suffice.

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