There are moments when I wonder if I’ll ever be happy. I mean truly content.

Do you ever get that feeling? That sinking feeling that you might never just breath, look around and say, “I love it all. And I wouldn’t change a thing.”

I do. I get that feeling. Often.

My life is in transition – quit my job, new house, planning for a business, thinking about life in my 30s – and, although life is always changing, I guess, I can’t help but feel that right now I’m on the cusp of so many new things and a complete life transformation that I have to wonder if all the uneasiness I feel is even worth it.

When it’s all said and done, then, will I be totally satisfied? And what if I’m not?

This isn’t the post where I whine about my life. In fact, I’d like to think that my posts don’t have that kind of vibe (God, I hope not). But this will be the post where I dig a little deeper into my heart and my mind to share this very real, very big, booming feeling that sits in my stomach more often than not. I’m writing it because I bet that many of you have had that same feeling – that sense that no matter what you do with your life, you may never be satisfied. By the end of this post, I hope you’ll have gained a little insight into this big question.

I read this post by Penelope Trunk this week (you all know how much I dig her) and her take on the whole LeBron James fiasco. Although I don’t give a shit about basketball, her insights on the topic of contentment gave me some solace about the state of my mind and forced me to ask myself this very important questions: are you the type of person who is loyal and content or always on the hunt for something new and interesting, possibly never to be fully satisfied?

It’s really not a question of which one is better – happy and stay-put or ambitious and always searching. It’s an exercise in deciding, and accepting, what type you can identify with, if for nothing else than to gain a little added clarity on what makes you tick.

It was painfully obvious to me that I’m the latter: always hunting.

I say “painfully” because I believe that the human mission in life is to experience content; to be truly happy. “Life is a pursuit of happiness”, they say, but what if, like me, you realize that it’s the pursuit, not the arrival, that makes you happy. What if you realize that you may never truly be satisfied. Or happy.

Will I ever be supremely happy?

Simultaneously (I love spelling that word) I was relieved and sad to get my answer. Relieved because I identified that, like LeBron James, the pursuit of happiness is what makes me feel good, alive. Sad, however, that I may be one of those who never quite understands how to roll around in her success and just soak it all in. This is the exact thing people in my life, whom I love, warn me about.

I watched the Simon Cowell-Oprah interview recently and, although I also don’t give a shit about American Idol or Cowell himself, I am fascinated by his career (same goes for Lady GaGa, Drake and the lady who runs the most popular healthy restaurant in Toronto).

The way Simon Cowell spoke about his addiction to the pursuit, his moments of depression and how he, too, is never satisfied had me glued to the television. How can someone with so much fame, money, power and access to the world’s best-of-everything still be searching for more? But apparently, that’s how he likes it. Or, at the very least, accepts he is this way.

I never thought I’d have something in common with a guy like Simon Cowell, but, just like LeBron James, their incessant need to pursue more made sense to me more than the thought of just being content and staying right where I am. And, although I’m the hunter, I do envy and admire those who just simply know how to relish in their lives.

Maybe, someday soon I hope, I can make the latter a pursuit, too.

So, I have a question for you (and you don’t have to leave a comment necessarily, but do think about it): Do you lean towards content and satisfied with you current life or, like me, always on the pursuit?

And then I arbitrarily ask you again: And do you accept that about yourself?

For me, the jury’s still out on that one.

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EDIT NOTE: Just found this video… and decided, this is what I think happy looks like.