I think this weekend is coming at the perfect time--let's plan on drinking wine and thinking deep thoughts about the future, ok? I completely empathize on this; the "The Dream" vs. Real Life faceoff has always been a major struggle for me.

I believe that one of the primary struggles in life - particularly one that consumes people in our general age range and place in life, is this: Is life about striving towards greateness, or about finding contentedness?

My head says it should be about the former. I'm not sure how much of that is innate vs. a product of our upbringing (for example, the basic entrepreneurial nature of American history and the way it is taught to children at an early age). But regardless of where it comes from, I WANT my life to be about striving for greatness.

Here's the thing though: wanting it doesn't necessarily dictate how I live my life. Subconciously, so much of what I do is dictated not by striving for greatness but by comfortability; by what is a natural next step, by what seems to make sense.

At points, I've spent years of my life solely focused on striving for greatness, and let me tell you - when it doesn't work out, it sucks. You realize that you need something else in your life as well; the static happiness that comes from being happy and being at peace.

Striving vs. contentedness. I think each can be addictive, and harmful to your life if you let it consume you. If all you do is push and fight and risk, you will likely seriously damage other important parts of your life. On the other hand, if all you do is find comfortability, you will feel like you are killing your soul, or that you are somehow failing to live up to that American dream of pioneerism, revolution, innovation, etc.

I think the stuggle, therefore, is to find the right balance. It's different for each of us, and it manifests in different ways. Maybe it means having periods of one followed by periods of the other (my current de facto model). Maybe it means figuring out how to manage lower levels of both simultaneously. I'm not sure exactly, but I suspect that you are not alone in your dilemma.

My gut instinct on this is that you are right in your decisions right now, and that you are right to seriously question them. If you just make them and move on, perhaps you do smother your soul with the everyday things in life and forget about greatness. But maybe by questioning it, you remind yourself that there are other things important to you, and you leave a window open so that when you have other opportunities come along you remember how important it is for you to sometimes strive for greatness.

If you figure it out, let me know.

Oh man.

I would suggest that your expecting-father status and future projection towards children(s) education speaks to a strong willingness to commit. Indeed, it's this existing commitment that seems to drive yr risk-aversion.

So, like most things, there's a balancing act. I've been a serial entrepreneur for almost a decade (we're the same age) and being in the flip position (owning a growing little enterprise but being single) I can't say it's any easier over here.

It seems to me that in a perfect world we can find a synergistic interplay between work, friends, family and whatever passes for "fun" in our lives. It's not easy though, as so many situations and preconceptions are geared towards zero-sum/either-or type decision-making.

Anyway, good luck! Keep plumbing the depths and you're bound to come up with goodness.