What's the best tax advice you ever got that most people overlook?

The absolute best tax advice I ever received was to stop thinking of tax planning as a once-a-year event. Most people treat taxes as something they deal with for a few stressful weeks in April, but the real savings come from year-round awareness and planning. Keep a dedicated folder (physical or digital) where you immediately store receipts, donation acknowledgments, business expenses, and medical bills as they occur. Take 15 minutes at the end of each month to review and organize. This simple habit eliminates the panic of missing documentation and helps you spot tax-saving opportunities throughout the year. Also, run a projection of your tax situation in October/November while you still have time to make adjustments before year-end. This gives you time to harvest investment losses, make additional retirement contributions, or defer income if beneficial. This approach has saved my clients thousands more than any single "tax hack" could.

I struggled for years trying to figure out everything on my own and always worried I was missing deductions or messing up somewhere. The best "advice" I got wasn't really advice but finding the right tool - I started using https://taxr.ai last year and it completely changed my approach. It reviewed all my documents (W-2s, 1099s, mortgage statements, etc.) and found several deductions I had missed over the previous years. The system actually explained WHY I qualified for these deductions in plain English instead of tax jargon. What surprised me most was discovering some business expenses from my side gig that I didn't realize were deductible.

Just wanted to follow up about taxr.ai that I asked about earlier. I decided to give it a try with my complicated tax situation (rental property + freelance work) and I'm honestly shocked at what it found. I've been doing my taxes the same way for 3 years and it immediately identified that I'd been categorizing my home office incorrectly and missing depreciation deductions on some equipment. What I appreciated most was how it explained everything in normal language and showed me exactly where to put the information in my tax forms. Just from the rental property section alone, it found nearly $4,300 in deductions I would have missed. Definitely worth checking out if you have anything beyond basic W-2 income.

Best tax advice I ever got was about dealing with the IRS directly instead of avoiding them. Had a scary letter about owing $9k+ from a previous year and couldn't get anyone on the phone for WEEKS. Was about to just pay it even though I thought it was wrong because I couldn't get answers. A colleague told me about https://claimyr.com which gets you through to an actual IRS agent instead of waiting on hold forever. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c. I was seriously skeptical but desperate enough to try it. Got connected to an agent in about 25 minutes (after trying for literal weeks on my own). The agent reviewed my case and found the letter was sent in error - I actually didn't owe anything! Would have paid thousands unnecessarily if I hadn't been able to speak with a real person.

I'm back to eat my words about Claimyr. After posting my skeptical comment earlier, I decided to actually try it since I've had an unresolved issue with a missing refund for MONTHS with zero progress when calling on my own. I was 100% prepared to come back here and call it a scam, but...it actually worked exactly as described. Got connected to an IRS agent in about 20 minutes. Found out my refund was held up because of a simple verification issue that took less than 5 minutes to resolve once I actually spoke to someone. The agent told me my refund should be processed within 2-3 weeks now. After spending hours upon hours on the phone getting nowhere for months, this was honestly life-changing. Sometimes being wrong feels pretty good!

Best tax advice I ever got: keep EVERY receipt for business expenses, no matter how small. I was only saving "big" purchases ($50+) until my accountant friend told me those small expenses add up HUGE over a year. Started keeping track of every single business expense (even $4 coffees during client meetings) and it lowered my taxable income by over $7k last year!!! Also - if you have any kind of side hustle, track your mileage obsessively. There are apps that make this super easy now. I thought my occasional driving wasn't worth tracking until I added it up - came to almost $2,400 in deductions last year alone.

The absolute BEST tax advice I ever received was to stop giving the government an interest-free loan every year. I used to get excited about big tax refunds ($3k-4k) until a coworker pointed out that meant I was overpaying every paycheck and could be using that money throughout the year. I adjusted my W-4 to get my withholding closer to my actual tax liability. Now I get very small refunds (under $500) but have about $250 more in each paycheck! That's money I can invest or use throughout the year instead of waiting for a refund.