This whole conversation makes me glad I'm just focusing on my job search instead of trying to juggle gig work too. Seems like a lot of extra complications.

One last thing - make sure your gig work doesn't put you over the maximum earnings threshold for the week. If you earn too much, you might lose your entire UI benefit for that week.

Thanks everyone for all the helpful info! I feel much more prepared to handle the tax situation now. At least I know what to expect and how to set up withholding if I ever need unemployment benefits again.

Just wanted to add that if you're using tax software like TurboTax or H&R Block, they usually have specific sections for unemployment income that make it pretty straightforward. You just enter the info from your 1099-G form and it calculates everything automatically. I was worried it would be complicated but it was actually one of the easier parts of my tax return.

I don't think they have a specific format requirement. As long as you can show the date, employer, position, and method of contact you should be good. The spreadsheet approach mentioned earlier covers all the bases.

Just wanted to add that I've found it helpful to take screenshots of the "thank you for applying" pages even when they don't send confirmation emails. Also, if you're networking on social media like LinkedIn or Facebook job groups, screenshot those conversations too. I learned this when Washington ESD asked me about a connection I made through a Facebook group and I almost couldn't prove it happened. Now I document everything, even informal networking conversations that might lead to opportunities later.

The anxiety around job search documentation is real but try not to let it consume you. Focus your energy on actually finding work rather than stressing about perfect record keeping. Document what you can and keep applying for jobs.

I completely understand the anxiety around documentation - I went through the same thing when I first started claiming. Here's what has worked for me: I created a simple Google Sheet with columns for date, company name, position title, how I applied (Indeed, company website, etc.), and any confirmation info. For applications without confirmation emails, I take a screenshot of the "application submitted" page or the job posting itself. I also save job postings as PDFs in case they get removed later. The key is consistency - do it right after each application while it's fresh in your mind. You're already doing great by being proactive about this!

Just want to add that I did something similar in 2024 and my experience was actually pretty smooth. I think it depends a lot on which field you're going into and whether ESD considers it "in demand." I got approved for retraining in healthcare IT after about 4 weeks. Make sure ALL your documentation is perfect - I included labor market info from WorkSource showing the job growth in my new field compared to my old one. Also found it helpful to meet with a WorkSource counselor first who helped me prepare my application. They know exactly what ESD is looking for!

As someone who just went through this process last year, I'd strongly recommend getting your application in ASAP! I was in a similar situation - laid off from manufacturing and wanted to switch to cybersecurity. The whole process took about 5 weeks for approval, but it was totally worth it. One tip that really helped me: when you fill out the application, be super specific about why warehouse jobs are declining in your area. I included actual statistics from the Bureau of Labor Statistics showing job losses in my old field vs. projected growth in IT. Also, make sure your chosen program leads to industry-recognized certifications - ESD loves that because it shows clear employability. Once approved, you're golden - no more job searches while in training, and you can focus 100% on your studies. The relief was incredible! IT is definitely considered "in demand" so you should have a good shot at approval. Best of luck!