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

I 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…

Millennials And Their Different Career Expectations

Millennials (or Generation Y) are the current 18 to 30 year olds and in less than 10 years, they will form the majority of the workforce. To be precise, 75% by 2025.

“Why should I care?”, you may ask.

Well, these guys are different. They have different values and traits, especially when it comes to their career. Or as Dan Pink puts it in Drive:

This generation is redefining success and is willing to accept a radically re-mixed set of rewards. They don’t rate money as the most important form of compensation. Instead, they choose a range of non-monetary factors from a great team, to the ability to give back to society through work. And if they can’t find that satisfying package of rewards in an existing organisation, they’ll create a venture of their own.

As a millennial myself, I could not agree more with these statements. Several other studies conducted on this generation in various locations are also in agreement. So do Deloitte and PwC.

So because your future hires care less about salary and more about a “sense of purpose” in their work , forward-thinking employers are starting to adapt their hiring approach to communicate their “why” more clearly.

Here are a couple of steps your organisation can take to join in too:


Every company (regardless of the size or industry) has its own unique culture. Communicate that to your potential employees and let them be the one choosing to work for you.

Not in a texty job ad, but through photos and videos that Generation Y is constantly exposed to on the world wide web. Web pages with videos get 100% more views than those just with text.

Really think about “why should they choose to work for me over the company next door” and clearly communicate that to them.

Transparency pays off… at least when it comes to employment!

Be Where They Are 

Showing more is great, and in fact 86% of UK businesses have made efforts to improve their employer brand one way or another over the past year. Yet most of these initiatives are only showcased on their own career websites. That’s not where millennials spend time!

To attract the new generation of workforce, employers need to be where they are. That is, Facebook, Twitter, Instagram and websites with genuinely useful and entertaining content tailored to millennials.

Feature those videos you produced to show what it’s truly like to work at your awesome company where qualified millennials spend time and you’ll see the magic happening: Not only will you end up with more visibility but you’ll also get candidates who already know what it’s like to work at your organisation.

Following these steps will put you in a much better position to receive more qualified applications and eventually better-fitting candidates for that dream team you’re building— both in terms of culture and skillset.

Why? because candidates have already done half the job to screen themselves for your organisational culture and if they apply, it means they really want to be a part of your “why”.

It’s a win-win