I did this seven years ago as the sole provider for the family. We did not have any savings, so it turned out to be a very busy time for me. I had two years of overlap of the paying job and startup. I am opposed to the common advice of waiting until the children move out to pursue the dream of owning your own company. My father did this and bought a small startup that already had some traction when he was 55. He spent the next eight years working extremely hard under a lot of stress to come out in a good financial position, but his health worsened significantly from that. So, he fulfilled his startup dreams, but it was through witnessing this that I decided "the sooner the better" and pursued my dreams without waiting for the "right time." The two years of overlap I had with the job and startup was worth it. I have plenty of freedom now to spend time and take vacations with my family. I kept this post general because I do not think the details matter. As someone who has done exactly what you want to do, I say 'go for it. The sooner the better. Tomorrow is not guaranteed!'