Derek Sivers

Interviews → The Speaking Show / David Newman

making a shift in your life, goals, a specific plan to only do what makes you happy, being rich

Date: 2020-04

Download: mp3



How do you know when it’s time to make a shift in your life, your family, your personal situation?


You’re OVERWHELMED. You DON’T WANT TO GROW. You’re avoiding your inbox because you DON’T WANT NEW OPPORTUNITIES.

When you’re feeling DONE.

The PATH to the SOLUTION is to VIVIDLY play out HYPOTHETICAL scenarios.

  • increase your rates by 300% or 1000%
  • hire a CEO and become just the CTO or CFO
  • sell your company and retire
  • move your family to somewhere radically new like Hawaii, New Zealand, or Singapore
  • have a baby and be a full-time parent for a few years

Keep going until something excites you - makes you bolt up in your seat and makes your heart race.

I sold CD Baby when I felt DONE. I had no more vision for the future. Granted, selling itself didn’t excite me. I just wanted to be done with it. I quit.

Then I was LOST for a year or two, constantly think of all kinds of HYPOTHETICAL scenarios, until one day I came up with one that EXCITED me more than I’d been in years. It made me JUMP INTO ACTION.

Ideally, we could JUMP right from what we’re doing into something that excites us. But maybe sometimes we need that EMPTY SPACE in between.


Do you believe in goals?


ONLY if they make you JUMP INTO ACTION.

If a goal doesn’t do that, it’s a BAD GOAL, so LET IT GO.

Let go of EVERY GOAL you can. All of the “maybe” and “some day” and “in my spare time” goals. EUTHANIZE them all. They’re TEARING YOU APART.


You write that the whole point of doing anything is to be happy so do only what makes you happy. That seems like a really big luxury - how do you suggest most average folks implement that advice?


Whether age 18 or 48, LET’S START FROM SCRATCH: You have no debts.

You move to Pittsburgh, and rent a 3br apartment for $1000/month. You find two good roommates, and now your rent is $333/month. Add utilities and food. Your cost of living is $800/month.

So, how do you make $1000/month? No matter what you do, you learn the holistic empathetic skills of marketing and sales, communication, and resourcefulness. And at least a little computer programming. You mix that with whatever valuable thing you enjoy doing. (Improving bicycles, designing websites, baking with peanut butter, breeding puppies, helping people get self-sufficient with solar power.) Using the free resources online, you level up your skills, build your network of contacts, build your reputation, etc.

This is a very viable way to live, and you haven’t had to do anything that doesn’t make you happy, right? Even when you’re doing something you don’t love love, like sales, it’s still net happiness because it’s supporting your work that you do like doing. This could go on indefinitely, earning more, saving more, and never doing anything that doesn’t make you happy.

That’s what I did. Even when I was making millions, I lived at my grandma’s house for free, borrowed my uncle’s beat-up car, and ate nothing but peanut butter sandwiches. I got my happiness from my work. I didn’t need to buy anything to be happy.

Or, if you want to GET A HAPPY JOB Be a forest ranger, mailman, or bike messenger. Be outside, getting exercise, listening to music or audiobooks while making a decent living.

BUT... IF YOU MAKE EXPENSIVE DECISIONS: If you spend $100,000 on a university

If you spend $80,000 on a prestigious new car

If you buy a $500,000 home so your annual mortgage is $30,000

... then you made the choice to do something very very expensive. You knew you that to pay for this, would have to more than just what makes you happy! You chose to do work you don’t like to do, and perhaps decades of work you don’t like to do, to pay for this thing you wanted.

When you say, “I can’t just do what makes me happy,” it’s because you chose this trade-off to live an expensive life. I’d say those expenses were NET NEGATIVE HAPPINESS.

But you CAN go back to scratch! You can sell everything you own. You can reverse these expensive mistakes.

That’s the MAIN reason why you should never ACCLIMATE to LUXURY and STUFF : so that you can go back to living for $800/month. Then only do what makes you happy.

And watch out for the DEVIL’S BARGAIN where something enticing up-front has a huge price to pay down the line.


What does “paying attention” really mean as far as decisions, people, life opportunities, and perceived dead ends?


Stopping to reflect - and consider other options.


Talk about your latest book projects - Your Music and People (2019) and Hell Yeah or No (2019) - are they out, for friends only, or going to be wrapped up into “How to Live”?


They’re done and should be for sale on soon.


What was it like to be sitting on $22 million and never having to work again - what alternate universes opened for you? Which were the [tempting] roads not taken?


I gave away the $22 million because I didn’t need it. I already had $4 million. That was plenty.

But I had too much freedom. I could go anywhere and do anything. But I didn’t have to be anywhere, and didn’t have to do anything. I had no ties, no responsibilities. I could build bicycles in Brazil, or catch crabs in Croatia, or be an anthropologist or linguist or nudist, or anything, anywhere. Honestly, it was overwhelming. It was paralyzing.

Maybe that’s the importance of goals versus interests. Maybe we should define a goal as a plan that makes you take immediate action. Whereas an interest is something that might make you click and read for hours, say, “Huh, that’s interesting”, but not DO anything about it.

My very first thought when I agreed to sell CD Baby was: I’M DANGEROUS because now I can DO THINGS FOR FREE, for musicians, that other companies would have to charge money for. I can start something that the world needs, and run it at a small loss, indefinitely, just because I want it to exist. In fact, I guess I’m doing that now, with my writing and speaking and such. I do all this for free. I haven’t earned a dollar since 2008, and I haven’t tried to.