The question that keeps you up at night IS the sign you’re looking for


Have you ever woken up every morning with the same question burning in your mind? Do you constantly wonder if it’s worth changing paths, environment or career day-in and day-out but continue convincing that part of your mind to quiet down? Do you think you could make a decision to act if  you had a sign, or a clue, or some sort of guidance from someone more experienced than you that could “show you they way?”

About 10 years ago I had those thoughts swirling in my head. I had a good, secure well-paying job and a bright future. Though, for some odd reason, I woke up constantly with those questions burning inside me day-to-day and week-to-week.  “Why can’t I just be content with what I have?”, I would ask myself. “What’s wrong with me?!”

I convinced myself changing paths would be a form of quitting – and I was no quitter. Some friends would explain to me how “life is hard. No one likes what they do. Everyone has those questions – it’s normal, but you keep working until you get over them. Eventually they go away. Anywhere you go you’ll ask the same thing. Everywhere in the world is the same. You’re just running from your problems. Deal with it.”

It sounded like mature advice to me so I tried to overcome the doubts and concerns I had about my current path. Unfortunately, letting go of the questions turned out to be pretty impossible.

I got it in my head that I wanted more, something different, something challenging and I couldn’t kill that thought. I wanted to move to SF and be part of the startup community. I wanted to create things people used. I wanted to meet others that created the things I loved to use. Friends on the other side of the advice fence validated those thoughts telling me “it would be a great fit. Quit what you’re doing now and just go!”

How could I decide which piece of advice was right? Both had their merits and both came with a fair share of doubts. Growing as a person by learning to be content didn’t really feel like a great life-goal and quitting to follow a curiosity seemed irresponsible. As Kenny Rogers would say, “You’ve got to know when to hold them, know when to fold them” but how do you know when that is?! Why didn’t Kenny answer his song’s question?!

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As my freshly shaven cheek chafed against my frosted collar while walking to work on a frigid winter day in DC I decided enough was enough. If there isn’t a clear logical answer to stay or go then I would break the tie on weather. I don’t care if it’s right or wrong – I was going to make the move. I was done with the cold. I quit my job, got on a plane and flew to a city that I had never seen with no work waiting for me on the other side. When what I’d done truly sank in at 30K ft I went to the bathroom and threw up.

Of course, I will never be happier that I came. Without a doubt, it was the best decision I’ve ever made. I realized this as I was walking home from my first job at a cool new startup in SF. I paused to catch the sunset of a spectacular view from the street, groceries in hand, when it hit me – I hadn’t had a sleepless question-filled-night or pensive morning in – well, since I arrived.  Sure the process was scary, but the questions were gone. I still had tons of work to do and was working extremely hard, but, now, I had an open mind to do it. Life felt right again.

It was important to me to try and distill a lesson from this experience so I would never have to go through that period of agonizing unknowns again. After all, staying back in DC could have been the right answer too. Sometimes you are running from problems and need to face them in order to grow. On the other hand, it’s important to follow your dreams; life is short. So, do I know now how to make the right decision again when the time comes? What did I learn from all this?

The answer IS the question.

Yeah. It really is that simple. No, the “answer” isn’t any old “question.” It’s the questions that burn inside you. The ones that wake you up and put you to bed. The ones that you debate between constantly and ask advice for every chance you get. The ones spawned out of an interest to learn something different. Those are the questions I’m talking about. Those are the question that MUST be answered. They are answered through creating your own experiences.

Well, what if I follow that logic and I’m wrong?

That’s the beauty of these gut-wrenching questions. As I learned, even if I was wrong,  the questions I had went away – they got answered. My mind was free and a freer mind can do so much more than a plagued one. So, you see – it’s a win/win. Either be half the person you are because you are preoccupied mentally every day with a burning question or be half the person you are because you made a bad decision. Only attempting the latter will leave you net-positive with no more questions and an ability to work towards living fully and clearly once again.

The mission to create space in your mind for thoughts to grow is paramount to moving forward positively in life. It is accomplished by oscillating back and forth between curiosity and answers. I realized there is a version of life that does not have the burning question running through my head every day (that was the fallacy in some of the advice I got early on.) Yes, life has its challenges and problems and it is important to work through them, BUT it’s a waste of life to circle around the same question. It deprives your mind of answers it needs to free up space so it can grow and more forward.

What do I tell those that ask me what to do next when they have a difficult question burning in their minds and causing tons of stress? I say the question IS the answer. Your body is your sign. Whether you are wrong or right it is important to know if you are indeed wrong or right. That knowledge is the catalyst that sets off the ability to ask and answer even more important questions, building answers upon one another to form clarity. Finding that answer clears the mind for more to fill.

Why am I writing this story almost a decade after it happened? Sadly, it happened to me again this past year. I’ve given this advice to so many people looking for direction yet I lost sight of it myself when the questions began to form in my mind again. It grew so subtly over time. This time, I made the excuse that it was different since I was older. That this time there was more to lose. And, yes, the concept of not being a quitter became more of a focus than learning, growing, exploring and building. I am writing it because I was wrong again and this is a message to me as much as it is to you. Your deepest hardest questions are only asked when your mind knows that it needs to find an answer. Your questions ARE the answer.




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