My Seventh Year as a Bootstrapped Founder

Before my son was born, I struggled with the question of how much time to take off. Obviously, taking a month off would be fine. But if one month is okay, why not two? Why not four? Why not a year?

I resonate with this. I didn't feel this nonchalant i.r.t. time when my first 2 were born, but I did feel this way when my 3rd was born back in Nov. I questioned a lot why I work so much, and felt like I've been missing things with my other kids that I shouldn't have been missing, even though I only work 9-5 most days, and I see them any time I go grab a snack or grab coffee, or when they randomly burst into my office to ask me to come check out a magna-tile tower they made. Somehow I still felt like I had been missing out on precious time with my littles, and it was hard to want to go back to work.

But I think it depends on your financial stability at the time, because even though I was running the same business when all 3 were born, I only very recently felt stable enough to not have to work. I still remember the intense stress of feeling like I had to go back to work with the 2nd -- which was around the time I quit my job to go full-time.

I admit, I failed my wife during that 2nd time because I went back to work too early after he was born, and I would learn years later that she felt very abandoned. This time, with the 3rd, I was able to take over 8 weeks off (closer to 10 if we're counting sick time).