“Where do you see yourself in five years?” Don’t you just hate that question? If we were any good at answering this question, we might be better off picking lottery numbers or buying undervalued stock and then phoning in our answer via satellite from our own private island. Wait. Why would I even need to answer the question? I digress.

Wise decision making is virtuous, and I am not advocating for recklessness. However, I am arguing that any presupposition of security in life’s decision making is an illusion. Projects fail. Markets change. Economies rise and fall. Insurance plans get cut. Opportunities are missed. Scandals unfold. Life happens, and it’s messy. More often than not, following after the false god of security leads to a series of sacrifices where each compromise builds on the last until we find ourselves locked away in a comfortable jail cell of our own making.

I once had breakfast with someone who had an idea and opportunity for a new business. He was clearly enthused about it. I asked him what was holding him back from pursuing it. He replied that he could not jeopardize the security of his family. In one of the rare moments I had something sharp to say in response I asked, “Which does your family need more… the illusion of security or you fully alive?”. I think I’ve had a good retort like that maybe three times in my whole life.

Why not live as though my job is insecure and experience the freedom this provides? Why not spit in the eye of all the ways a career should go and set my sights on adventure or helping others or achieving the supposed impossible or creating beauty — something that matters more than the empty promise of job security? Taking chances means you are likely to work to make ends meet out of necessity. It is living in near complete dependence on a system that could lay you off on a moment’s notice that seems nuts to me. I’ll grant you that even being able to consider such questions is born of a privileged station. However, if we are so privileged, dear reader, I believe it is incumbent upon you and me to ask these questions and make the most of that privilege.

Morbid as it may be to imagine, if you could have a conversation with yourself on your own future deathbed, do you think a nice steady career development track would rank high in that conversation? Then why are you on that track — real, imagined, or put upon you?

Maybe career is best understood simply as our history and not our future. Perhaps a career is only the series of twists and turns that were the envelopes holding your paychecks before today. Tomorrow is tomorrow and not wholly determined by yesterday.

Am I suggesting this perspective is an easy one to embrace? Nope. But I am suggesting it is a good one to embrace, a freeing one to embrace. Am I advocating that everyone embark on adventure to start their own business? Certainly not. Maybe the most freeing thing you can do is work for less money in a different occupation. Maybe it’s to climb the ladder for a while so you can retire debt as quickly as possible and then move on unencumbered. Am I encouraging breadwinners to shirk responsibility in light of the needs of their family? Absolutely not. However, I am advocating a stare down with the ideas of need and security so as to watch them flinch and shrink away as their true nature is revealed.

In this particular season of my life where I have been blessed with the opportunity to struggle after something more than a nice safe career I can be cavalier about saying these things. I hope, though, that by having written these words down they will press against me when I inevitably stray over the border into the fiefdom ruled by the feudal lord of career.