11 Good point about the tax consequences, but isn't there a way to avoid some of these issues? I thought I read something about a post-termination transition period where you can still distribute AAA balances tax-free?

4 Yes, that's correct. After S corporation status ends, there is a post-termination transition period (generally 1 year after the last day of the last S corporation tax year) where shareholders can still receive distributions from the former S corporation's AAA tax-free to the extent of their stock basis. This can be really important for planning purposes. Some shareholders mistakenly believe all their distribution options end when S status is revoked, but this transition period provides a window to distribute accumulated S corporation earnings without dividend treatment under C corporation rules.

14 I dealt with something similar and we ended up going this route. The key was proving that we never operated as an S corp (no distributions, no K-1s issued, etc.) and that it was an honest mistake in the election. Saved us from having to do the split-year filings.

This is really helpful advice. I hadn't thought about documenting the strategy formally. Is there a specific format you'd recommend for this kind of business plan? Also, does the board approval need to happen annually or just once when implementing the strategy?

There's no required format, but I'd recommend including projected capital needs, specific growth milestones, timeline for expansion, and how the retained earnings will be used. Make it clear this is a temporary strategy until the business can support you full-time. Board approvals should definitely happen annually. At minimum, you should have annual minutes documenting review of the compensation strategy and business progress. Each year, note how the retained capital is being used toward your stated goals and reaffirm the strategy. This creates a pattern of consistent business purpose rather than looking like an afterthought if questioned.

YES! My brother-in-law got absolutely hammered for this exact situation. Ran his consulting S-corp for 2 years taking zero salary and only distributions. Got audited, and the IRS reclassified ALL his distributions as salary, meaning he owed back payroll taxes plus penalties and interest. Cost him over $30k when all was said and done. They specifically target S-corps for this issue because it's such a common tax avoidance strategy.

Have you had any issues with Wave at tax time? I tried it last year and my accountant complained that the reports weren't detailed enough for some of the deductions we wanted to take. Did you add any paid features to make it work better?

I did have some limitations with Wave during my first tax season, particularly around categorizing certain business expenses properly. I ended up using their paid receipt scanning feature ($8/month) which helped tremendously with organization and made my accountant much happier. For detailed job costing and tracking profitability by service type, Wave definitely has limitations. I supplement with a simple spreadsheet for that analysis. The payroll integration with OnPay has been flawless though - all my quarterly filings have gone through without issues and the reports are accepted by my accountant without complaints.

I switched from QuickBooks to Xero last year for my pool service company (5 employees) and it's been excellent. The inventory tracking is better for tracking chemicals and supplies, and the mobile app is way more user-friendly for entering expenses on the go. Their project tracking feature works well for tracking costs by customer property too.

Thanks for sharing your experience! That's helpful to know about the mobile app and project tracking - both would be really useful for my lawn care business. How was the transition from QuickBooks? Did you lose any historical data in the switch?

Thanks for bringing this up! We are claiming the Child Tax Credit for both kids, but I'm not sure if we've maxed it out. My husband does get 1099s and I know he needs to do the quarterly payments but honestly we never knew how to calculate them properly. Is there a simple formula to figure out roughly how much we should set aside from each check?

A simple rule of thumb is to set aside about 25-30% of his 1099 income for taxes. This covers both income tax and self-employment tax (which is roughly 15.3% alone). For proper quarterly payments, you can use the IRS Form 1040-ES worksheet, which helps calculate your required payments based on expected income. The due dates are April 15, June 15, September 15, and January 15 of the following year. Setting up a separate savings account just for taxes can be really helpful - deposit that percentage from each check immediately before you're tempted to spend it.

This is great advice! I'm a contractor too and opened a SEP IRA last year. Was able to contribute almost 20% of my income and it dropped me into a lower tax bracket. Saved me thousands.

Just be aware that SEP IRAs have an earlier deadline than traditional IRAs! For 2024 taxes, you need to set up and contribute to a SEP IRA by the tax filing deadline (including extensions) in 2025. Don't wait until last minute like I did!

You know what, that could actually be part of the problem. I didn't realize the W-4 had changed that significantly. I did fill out a paper form when I started and I remember putting "0" for allowances, but maybe that wasn't even the right field on the new form. I definitely didn't check anything about multiple jobs because my first job had already ended when I started this one. Do you think that could have somehow triggered zero withholding?

That could absolutely be the issue. The new W-4 doesn't have a place for "0 allowances" anymore, so if you were filling out an old form or using old terminology on the new form, it might have confused your payroll department. Even though your jobs weren't simultaneous, the Step 2 checkbox helps the withholding system account for your total annual income. Without it checked, the system might have been withholding as if this was your only income for the year, and depending on your pay rate, that might result in little or no withholding if the projected annual amount would be under the standard deduction.

That's a good point. If they gave you a W-2 but treated you as an independent contractor for withholding purposes, that's definitely something the IRS would be interested in knowing about. Companies can get in big trouble for misclassifying employees.

They definitely gave me a W-2, not a 1099. And they are withholding Social Security and Medicare taxes correctly - it's just the federal income tax that's showing $0. So I don't think I'm being classified as an independent contractor. It seems more like some kind of specific error with just the federal income tax withholding.