Derek Sivers built a business empire by accident.
In 1997, he was looking for a place to sell his music album online. When he couldn’t find one, he set up his own little website with a buy button. Soon, friends wanted him to put up their CDs too.
Then, friends of friends came along, buyers started asking for new arrivals, and, ten years later, CD Baby had 85 employees, two million customers, and distributed 200,000 musicians’ work online.
Never having set out to be an entrepreneur, Derek felt done with it in 2008. He sold the company for $22 million in cash, most of which he gave to charity, and went back to his solo artist life.
Whether he was happy with this “little detour” or not, it worked out in the end. But that’s why, in a free class about the whole experience, Derek encourages us to start our own journey with a question:
Why are you doing what you’re doing?
And even though he outlines several options, it’s not an easy one to answer. Because the devil is — as always — in the details.
The Three Forces That Drive Us
In his book Running Down A Dream, another business owner turned independent artist, Tim Grahl, remembers the time he heard Sivers talk about our three strongest motivators: fortune, fame, and freedom.
None of them are right or wrong. You can get more than one. However, only one will drive you. I knew I wanted freedom. Not freedom to travel. I still don’t go many places. Not freedom to work whenever I wanted. I still work set hours [each] day. I simply wanted the freedom to make those decisions myself. I wanted to live a life where nobody could make a claim on my time without my approval.
That’s already a huge step up from how most people live their lives, which is by mere imitation. Who of us hasn’t seen someone doing things that impress them, and instantly started piecing together a poor copy of that person’s life? Often, the copy is not poor because our idol’s life isn’t worth living, it’s poor because we don’t question any of its parts. If we don’t at least adapt it to our own wants and needs, that’s an almost guaranteed descent into misery.
That makes freedom a viable alternative. It’s also the theme Derek chose when he sold his company:
“I really liked the idea of setting up my life in a way that, at any point, I could just disappear. Or I could just be antisocial and go read books for a month, or whatever it may be. So I had to set up my career in a certain way to delegate almost everything, make myself unnecessary to the day-to-day running of my company, so that I was free to go do other things.”
As he explains this, he shows a little slide that says:
Refuse responsibility. Delegate everything.
I think that’s where we should start splitting hairs. Because I don’t believe true freedom is the absence of responsibility. I think it’s something different.
And I’m not alone. Just ask my friend Shaunta.
Rejecting the Zero-Task Lifestyle
I first watched Derek’s class in 2015. Now, next to money, stardom, and independence, he also mentions prestige (try getting a table at Masa) and legacy (there are 2509 Carnegie libraries) as purposes we can choose.
Still, like Tim, I felt freedom spoke the most to me, and so I chose to adopt Derek’s definition of it wholesale. I spent all of 2016 building a passive income business and I’m glad that, today, I control my time, who I work with, and what projects I tackle. But I also have more responsibility than ever. Now, thousands of people expect me to deliver. Readers, partners, customers.
That very much contradicts “not having to do anything,” but I still feel free. Maybe, there’s more nuance to it than “delegate everything.” Reflecting on these same ideas, Shaunta Grimes can’t imagine the zero-task lifestyle either:
Sometimes I think about the possibility of a totally passive income and what it would be like to spend the day on the beach, doing whatever the hell I want to do. But the absolute truth is that I wouldn’t last very long. I’d attract responsibilities like a magnet. It’s just how I am. And, I also find myself rebelling against the idea that freedom only means fewer responsibilities. I guess I’d say I’m partially driven by freedom — but my own interpretation of it. But the truth is, I often willfully make decisions that restrict my freedom.
I think this is true for most, if not all of us. We get bored when we idle for too long. We need a purpose. We want to solve problems. And so, the further I go in my own journey as a solo creative, the more I realize:
Freedom is not about shedding your responsibilities, it’s about choosing them.
When I first struck out on my own, I wasn’t worried so much about the pressure to deliver, to get clients, to make money. I was running away from having a boss, being bored at work, and owing my time to one person, one place. Because those were responsibilities I couldn’t stand having.
I felt much more comfortable with setting my own deadlines, coming up with ideas, and asking people for work, despite having to first learn all of those things. This distinction of what you’ll feel comfortable shouldering might have external consequences, but it comes from an inner place.
Responsibility is freedom, as long as you choose a labor of love.
A Burden We Can’t Shed
Why do people become soldiers? Because they love serving their country. It’s a responsibility they don’t just feel comfortable with — they enjoy bearing it.
Now, passion is tricky because it’s part talent, part love, and part just sticking with it. But if your recurring duties at work constantly make you feel like you’re bouncing around in a pressure cooker, they’re the wrong kind of duties.
The obligations of being a mom are different from the accountability of a CEO and have little in common with the burdens of a remote freelancer. No, you won’t get insta-rich from nailing this choice, but making it will make your life easier. Because we’re all good at being responsible for different things.
We often underestimate the negative impact a responsibility mismatch can have. A lot of us are running around like chickens, work always feels like work, and oh the stress of it all. But if we don’t learn to love the boring days, the exciting ones can never fill this huge hole in our everyday happiness.
The question, “why are you doing what you’re doing?” has many complex answers. But even if we aggregate them into high-level themes like fame, fortune, and freedom, at the end of the day, they all come down to this: “Because my goal comes with responsibilities I feel good about carrying.”
Think about it. Everything is accountable. And — for better or for worse — you’re the one getting all the credit. At the end of your life, you’ll either regret many things or just a few, but it’s all a reflection of how much responsibility you took in deciding what you did with your time. That’s a burden we can never shed, no matter what goals we dedicate ourselves to.
And so it’s not the absence of responsibility that makes us happy, but choosing the right set at the right time — picking duties we love fulfilling and that we feel confident we can deliver on. Maybe, why we do things isn’t as important as those things feeling light enough for us to not crack under their pressure.
Maybe, the better question is:
What kind of responsibility feels the lightest in your mind?
If we answer it correctly, we’ll always feel free. Regardless of our obligations.
Freedom From Within
Socrates supposedly said that “the unexamined life is not worth living.” If all we do is imitate those we admire, we might one day wake up and wonder what it’d feel like to truly be ourselves.
But nowadays, a lot of us pondering this idea associate it with complete and utter freedom — financial independence and a total lack of responsibilities. This isn’t just unrealistic, it’s delusional. Because the concept of responsibility itself will never vanish from our lives.
Only once we accept that we’ll always carry some degree of duty — that, as humans, we’re meant to — can we start choosing our obligations deliberately. These choices will dictate what we channel our energy into and how we design our lives, but they should ripple from the inside out.
Whatever we stand for should make us feel proud, and we should want to approach it with love and care, because when we do, we won’t mind the pressure our goals often put on us. We’ll enjoy our routines and our pace.
Most of all, we’ll learn to be happy and free, no matter how many hats we wear or whose expectations we need to fulfill.
And there’s nothing accidental about that.