What’s Your Compass? An Important Lesson from Entrepreneur Derek Sivers

I love writing’s ability to connect with something at your core. There’s nothing quite like reading words that resonate so much with you as if the author had insight into your soul. That connection is something I crave as an avid reader and strive to emulate as a writer.

As you may or may not know, I love to underline phrases and take notes in the margins while reading books. It helps me keep track of lessons learned that I want to keep in mind and hopefully apply to improve myself. Every now and then, I’ll come across a line or passage that’s articulated so beautifully and clearly that it stirs something deep inside me that’s incredibly true about life.

That moment happened recently while reading Derek Sivers’ book Anything You Want: 40 Lessons for a New Kind of Entrepreneur. For those of you who don’t know Derek, he’s a writer, speaker, and entrepreneur best known for founding CD Baby, one of the first companies to sell independent music on the Internet.

Here’s the passage that really struck a chord with me:

What’s your compass?
Most people don’t know why they’re doing what they’re doing. They imitate others, go with the flow, and follow paths without making their own. They spend decades in pursuit of something that someone convinced them they should want, without realizing that it won’t make them happy.
Don’t be on your deathbed someday, having squandered your one chance at life, full of regret because you pursued little distractions instead of big dreams. You need to know your personal philosophy of what makes you happy and what’s worth doing.

Pretty deep stuff, right?

While Derek goes on to list out the personal philosophies he’s adopted over his 10 years as an entrepreneur (which I’ll share in a future post), I want to take a moment to unpack what these few sentences meant to me.

If I asked you the reason(s) why you’re doing what you’re doing in your career / life, would you have a good answer? Or would you just make one up?

If it’s the former, congratulations because that means you probably have a clear vision of where your life is headed and how your current situation fits into that picture. As Derek implies here, only the minority of people can claim this.

However, if you don’t know the motivation behind why you’re doing what you’re doing, you should be alarmed. After all, what’s the point of coasting and doing what others did / are doing if it’s not what you really want? Are you doing X because someone else told you to, or you thought it would make you happy? That doesn’t sound like living to me.

The good news is that it’s never too late to figure these things out. You just need to start having an honest conversation with yourself about about your current situation and how it fits into where you want life to ultimately take you.

If you feel like you’re on the right path already, great. Keep doing what you’re doing. If not, you need to be real with yourself about what makes you happy and the necessary changes required to get there. Like Tony Robbins preaches, I believe you can change your life in an instant.

For those who are lost, I agree with Derek that it’s all about making your own path. You are the commander of your life and responsible for doing everything you can to make it a great one. There’s nothing worse than having lived someone else’s life, only to realize that it too late. You need to dream big and pursue the thing that makes you tick. That will bring you happiness and help you find meaning.

What’s your compass? Are you headed in the right direction? Or is it time to make a change?

If you want to learn more about Derek Sivers, I’d highly recommend checking out his recent podcast interviews with Tim Ferriss (Part 1, Part 2). Get his book too!

If you enjoyed this post, please consider Recommending it and following me.

You can also join my email list & find me on Quora, Twitter, Instagram, and Snapchat. Thanks :)