5 Does anyone know if you need a business license to report tutoring income? My university's tutoring program told me the same thing about being an independent contractor, but I'm worried that I needed to register as a business with my city first.

21 Just a heads up for anyone reporting tutoring income - don't forget about self-employment tax! I made the mistake of only reporting the income on Schedule C but didn't complete Schedule SE my first year. Got a letter from the IRS about it later. Even though you don't get a 1099 for under $600, you still owe self-employment tax (Social Security and Medicare) on that income if your net earnings are $400 or more. It's about 15.3% on top of regular income tax.

The annualized income method (Form 2210 Schedule AI) is actually really helpful for people in your situation. Instead of making equal estimated tax payments, you can make payments based on your actual income for each period. Since you didn't have any income until April (which is in the second period), you wouldn't owe anything for the first quarter. Just make sure you're accounting for both income tax and self-employment tax in your calculations.

Quick tip: if you're using tax software like TurboTax or H&R Block, they can actually help you calculate your estimated payments using both the regular method and the annualized income method. Just enter your projected quarterly income and it'll show you the minimum required payment for each quarter.

To actually answer your solo 401k question with a specific citation - check IRC section 401(c)(2)(A) which defines earned income for self-employed individuals, and 1.401(k)-1(a)(4)(ii) of the Treasury Regulations which specifically allows self-employed individuals to make employee deferrals based on this earned income. The confusion comes because the tax code uses weird terminology. For a sole prop, you're technically both the "employer" and the "employee" even though you don't pay yourself a W-2 salary. Your contribution limit as an "employee" is the standard 401k limit ($22,500 in 2023, $23,000 in 2024, plus catch-up if eligible), capped at your net earnings. The "employer" contribution is up to 25% of your net earnings after deducting half of SE tax. Fun fact: the IRS does refer to Schedule C income as your "compensation" for retirement plan purposes even though it's not technically compensation in the W-2 sense.

Has anyone mentioned the record keeping headache of having multiple solo 401ks??? I have three separate business activities and originally had separate 401ks for each. HUGE mistake. The Form 5500 filing requirements alone made me consolidate everything. If your businesses are truly separate, then yes get separate EINs. But consider using ONE 401k plan that covers all your businesses. Most providers like Fidelity or Vanguard can handle this - you just need to make sure the plan documents indicate it covers all your sole proprietorships. This way you get the administrative simplicity of one plan while still maintaining separate business identities. Just make sure you track contributions from each business separately for your own records. The IRS doesn't care which business made which contribution as long as the total stays under your combined limit.

16 Former non-profit financial director here. One thing to keep in mind is that executive compensation at non-profits is supposed to be determined through a formal process called a "rebuttable presumption of reasonableness" which requires: 1) Review and approval by independent board members 2) Use of comparable salary data from similar organizations 3) Documentation of the decision-making process The board should be able to provide some explanation of how they arrived at the compensation figures. You have every right as an employee to question this, especially if the organization is claiming financial hardship when it comes to staff benefits. Look specifically at Parts VII and IX of the 990 form, which detail compensation and functional expenses. This might give you more insight into where money is being allocated.

21 My wife works for a similarly sized non-profit hospital and we went through the shock of seeing the executive compensation last year. One thing to understand is that those huge spikes in certain years might be from vested benefits or one-time payments. For example, if they have a Supplemental Executive Retirement Plan (SERP) that vests after 5 years, the whole amount shows up on the 990 in that year, making it look like they got a massive payday. It's still a lot of money, but spread over the vesting period, it might be somewhat less shocking. Check if your organization posts their audited financial statements too - sometimes they have notes that explain unusual compensation arrangements better than the 990 does.

Something else to consider - the W-4 form changed significantly a couple years ago. It no longer uses allowances (0, 1, 2, etc). Instead, there's a multiple jobs worksheet or you can use their online calculator. If you're still thinking in terms of "claiming 0" you might be using outdated forms or concepts. The new W-4 has a specific section for multiple jobs that helps account for exactly your situation. Check if your employers are using the current form and if you've filled it out correctly for your multiple income streams.

Has anyone mentioned the "two-earner/multiple job" worksheet yet? When I worked 3 part-time jobs during grad school, my tax person showed me this worksheet on the W-4. It helped a ton with calculating the right withholding. Not sure if it still exists with the new W-4 format tho.