15 lessons from Derek Sivers on leadership, values, and not giving a shit

Derek Sivers has been an incredible (virtual) mentor of mine.

From reading Anything You Want before starting my first company to learning about Leadership from his Dancing Guy video, he’s been constantly giving me value —and he probably doesn’t even know it himself!

Here’s some of the most valuable lessons I’ve learned from him. I hope (and am sure) by the end of this article, you’ll agree with me on him being an incredible mentor as well.

On Starting up

Making a company is a great way to improve the world while improving yourself.

On Leadership

The best way to make a movement – if you really care – is to courageously follow and show others how to follow.

On Focus

Just pay close attention to what excites you and what drains you.

Pay close attention to when you’re being the real you and when you’re trying to impress an invisible jury.

On Knowing Your Why and Values

Know your personal philosophy of what makes you happy and what’s worth doing.

Please don’t think you need a huge vision. Just stay focused on helping people today.

If you think your life’s purpose needs to hit you like a lightning bolt, you’ll overlook the little day-to-day things that fascinate you.

When someone’s doing something for the money, people can sense it, like a desperate lover. It’s a turnoff.

When someone’s doing something for love, being generous instead of stingy, trusting instead of fearful, it triggers this law: We want to give to those who give.

He calls this a Tao of Business.

On Relationships

If you think true love looks like Romeo and Juliet, you’ll overlook a great relationship that grows slowly.

On Saying No

If you’re not saying “HELL YEAH!” about something, say “no.”

When you say “no” to most things, you leave room in your life to throw yourself completely into that rare thing that makes you say “HELL YEAH!”

This reminds me of James Altucher’s line of thinking

On Being Customer Centric

Never forget that absolutely everything you do is for your customers. Make every decision—even decisions about whether to expand the business, raise money, or promote someone—according to what’s best for your customers.

On Simple Living

Live simply.

I don’t own a house, a car, or even a TV. The less I own, the happier I am. The lack of stuff gives me the priceless freedom to live anywhere anytime.

On Not Giving A Shit

It’s a big world. You can loudly leave out 99 percent of it.

No matter which goal you choose, there will be lots of people telling you you’re wrong.

You can’t please everyone, so proudly exclude people.

What have you learned from Derek (or others) that you found valuable? Make a list and let them know.


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