Transitioning from being employed to self-employed

Hi there!

I am currently on unemployment under the SEA (self employment assistance) program in Oregon. My assistance runs through November. During the assistance term I get unemployment benefits as long as I devote at least 40 hrs per week on my business. 

We haven't paid ourselves from business earnings, and we haven't paid quarterly taxes. We can get through 2021 without paying myself from the business if we use some savings in December. We project between $80,000 - $90,000 in billings for Q3 & Q4 for our service business. 

My question is: Can we avoid paying taxes on revenue this year by making contributions to my 401k? If so, I expect that we would pay taxes on our unemployment benefits, but is that correct?

 

Thanks!