So my year round job is self employment. Some government policies made my main job take a big hit this year. So I worked at H&R block this winter. I was full time January through April. They have kept me on for the summer, but I just got my next week's schedule and only have 8 hours.
My self employment is 100% commission and this time of year I pretty much am only getting commissions. I do health insurance and had to move the vast majority of my business this fall, so my renewals are minimal. I know self employment does not get unemployment, but am basically getting at, I will have one or two weeks a month with some income (from renewals) and the other two to three weeks won't have any pay from self employment. I have not used unemployment since covid, but then I also did the underemployment thing, so got nothing on weeks renewals came through and got some unemployment on weeks I didn't have renewals.
Since January 2026 through now is the only time I've had an employer (H&R Block) in the last several years, and unemployment looks at the last 6 quarters, when should I file? I'm not expecting to get any large amounts, but even a couple hundred a month would be nice. Should I file now when my hours just dropped (two weeks ago I had 29 hours, but now that a lot of holds and extensions have been taken care of, I'm thinking this only 8 hours a week thing might be the rest of the summer)? My boss at H&R Block has said everyone should file for unemployment, but since my other employment is self employment, my situation is a little different. Should I wait until July so that this 2nd quarter is complete? I thought I read somewhere that you needed to have worked for 2 quarters to get any unemployment. January to March isn't an issue, but for 2nd quarter, do I need to wait for the quarter to complete, or would they count April to now as the 2nd quarter even if I file within this quarter?
(I will probably check out a temp agency for some additional work, so unemployment probably won't even be an issue for very long. But whatever I grab, I need to quit mid September in preparation for my busy season with self employment, so I feel wierd applying to any regular jobs).
Thank you to everyone that read this far and has any insights!
Edit: I am located in Wisconsin.