Flipping a coin is not as rational as playing Stephen Covey's game of creating a personal mission and selecting a choice that will best fulfill that mission. This process seems logical enough, but also might lead to great unhappiness. We could end up living our lives "in quiet desperation" instead of ecstatic happiness and fulfillment. We might marry for money instead of love.
One of my favorite artists, David McManaway, started out making paintings (he believed this is what "artists" should be doing). When he was bored with paintings he would start combining found objects at the side of his studio. Soon he found that all he wanted to do was his "jomos" (as he called them). Now, 50+ years later, he's had a productive and creative life (and I suspect, he rarely has been bored). And he still doesn't do any paintings.
One reason we may pick the wrong choice is because we are attached to the people and places that we know. One of my sisters told me of an article she read about how we need to grieve when we choose the "road not taken." Yes, it is sad to change or leave, and that loss does not magically go away when you turn our backs on where we were (and loved) and what we've done. Sometimes we just need to embrace our past and kiss it goodbye.