Always Ask the Question

Awhile back, I was talking with someone about entrepreneurship and building a business and they shared with me a story about someone who managed to get her product into a big catalogue simply by asking the owner if they might consider offering it amongst their other merchandise. The takeaway from this interview was, “Don’t hold back, always ask the question.” There are so many questions we don’t ask, either of ourselves or of others.


Questions are dangerous things because once asked, they hang there waiting for an answer. And sometimes answers, if given honestly, may present us with clarity we’d just as soon not have. As re-booters, it is these inconvenient answers that are so important to our reinvention process. “Am I ready for this? Can I take it on? Am I brave enough to try?” If we can’t see ourselves or our situation clearly and honestly, we’re just spinning our wheels. The enlightenment, the ah-ha moment, that can follow from a surprise, scary answer can change the course of our lives (or at least our thinking).


Recently, I was talking to a fellow about a serious decision he is preparing to make in his relationship. “I don’t want to be the bad guy,” he confessed, agonizing over when to pull the relationship rip cord. We went round and round about this for awhile and then I finally asked him, “Well, what if you are the ‘bad guy’*? Is that something you can’t live with? What would it mean if you were (or at least that is how others might perceive you)?” As the reader of this post, you may substitute any condition/status/interest/opinion. Perhaps, deep down, you are (gasp!): gay, fascinated by serial killers, talk too much, drawn to some weird religion, into D/s, Democrat, Republican, still play Dungeons and Dragons, hate being a caretaker, love reality tv. Or maybe we need to be willing to ask ourself whether the person we’re dealing with is who they present themselves to be? What if my confident, opinionated husband actually has no direction or ambition at all? What if my boss isn’t the loyal stalwart they claim to be? Am I willing to acknowledge this as a possibility? It’s not that you have to tell anyone else, but at least tell yourself. The point is to explore whatever it is we shudder to admit about ourselves and be honest about the answer. As long as you’re not hurting anyone else, can it really be that bad?


For me, admitting that I wanted to be a writer was a really big deal. Even saying it out loud, today, feels scary–especially in a place like Washington where everyone has ambitions and where there are “real” writers who publish real books and make real money. Saying that I am a writer may not be as scary as admitting I might be a Republican or like to watch reality tv (and I’m not admitting to either, fyi), but so what if I were? Absent a few roles where you’re harming other people, surely our ego can withstand the possibility that yeah, in this particular instance, we are selfish or indecisive or have engaged in some behavior that would put us in a less than an ideal and flattering light. This is true of us all!


Is it the end of the world? No!


What the act of articulating such answers does is free us up to live our lives from a more authentic place. Heck, we may even summon the courage to stop fighting this part of ourselves. Maybe you have no ambition and are ok with living your life in a drift-less state. Articulating and admitting such an answer to yourself may help answer why you feel so stressed all the time when your spouse asks you what have you accomplished. (Whether or not your achievement oriented spouse can continue to live with you is a different matter.)


I know so many people who haven’t been willing to ask themselves the important questions: what do I want? What sort of person am I really? How does this support or conflict with my image of who I am? Is what I’m doing, is the direction I’m currently heading the one that truly suits me? And we have to be brave enough to listen to the (sometimes terrifying) answers that burble up. But then, we have to summon another dose of courage and ask ourselves—if we are displeased or unsettled by the answers we receive—if I am this way, is that really so bad? Why do I fear this?


Whoa, Nelly, these are some big ass questions. The answers may throw you…but they also might open new worlds of possibility.


So, circling back to the top of the post, there’s our successful entrepreneur encouraging us to always ask the question. Here I am encouraging you to truly listen to the answer. Whatever it is, it can’t be so bad. It just can’t. You’re you, you’re fine as you are. You can handle it…


* Note: for purposes of this post, I am not saying that this person’s characterization of themselves as being the “bad guy” is even correct. Maybe they’re not the bad guy at all, but they’re doing something hard but necessary. What’s important for purposes of this example is how they perceive it.


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