Why Are You Doing What You’re Doing?

A question that deserves a real answer — not once but every day

When I first dipped my toe into the world of tech, self-improvement, and online marketing, I did so out of fear.

I was terrified of an imagined, dystopian future in which I sat in a cubicle next to a huge glass window, overlooking a beautiful metropolis from the 40th floor, yet dying of boredom as each second seemed to pass slower than the last. Nothing about this future was real, and it never would have had to be, but it still scared the shit out of me — so much so that I actively started running away from it.

For the next few years, most of my career decisions were driven by that fear.

I read James Altucher. I found Tim Ferriss. I had to build a Wordpress blog for my statistics class. Slowly, it all started coming together. I would make money online. I would write. I would try to combine the two. Someday. Somehow.

A few years later, I finally did. I became a freelance writer. I started building my own blogs. In 2017, five years after I’d begun running, I finally saw the light: I made about $40,000 — a full-time income — from this work.

It felt like emerging from a long, dark tunnel. While you’re in it, you can see neither what’s in front of you nor what’s behind you, but what might be behind you is scary — so all you can do is run as fast as you can. Then, from one moment to the next, you find yourself in the sunlight, and it’s blinding.

Whether it was a good reason or not, my fear of having “a normal job” was real, and it compelled me to act in a certain way. As it became less likely for my fear to come to fruition, however, that reason faded. Suddenly, it didn’t make sense anymore to work harder just to earn more. I was already free.

As much as I felt proud about having made it this far, I also felt a sense of emptiness. I doubted my decision to continue school part-time. I grew weary of long, 12-hour workdays that lacked purpose. I had to find a new reason.

I read The Daily Stoic by Ryan Holiday three years in a row. This quote stuck:

Evaluate what you are doing, why you are doing it, and where accomplishing it will take you. If you don’t have a good answer, then stop.

Let’s say you’re creating an Excel spreadsheet right now. Why? Maybe, it’s a task assigned to you by your boss. Okay. Why did she give it to you? Maybe, she needs the sheet as part of a larger reporting system your company wants to implement. Okay. Why? Maybe, with a new, more automated reporting system, a whole bunch of employees will save a whole bunch of time. Okay. Why should you care? Well, if you’re partially responsible for a new system that saves people time, you might get a chance to tackle an even bigger responsibility next. Maybe, it’ll come with a pay raise and a new role. Okay. Now that’s an incentive.

Every small task you complete relates to a bigger picture. If you keep asking “Why?” you’ll eventually move from “right now” to “in six months’ time,” and the latter makes all the difference. If you don’t care about where “right now” will lead you, you should change it, and do it fast. If your reason isn’t compelling, it’s probably not the right one. If you don’t have a good answer, then stop.

When I started my entrepreneurial journey, I craved financial self-sufficiency and a basic sense of autonomy at work. I wanted to control my time and be able to choose my own projects. I wanted to comfortably pay for rent, food, and the occasional night out, weekend trip, or fun experience. Everything I did was meant to “take me there.” Once I arrived, however, I needed to stop.

It’s easy to just keep on going after your reason has disappeared. For a while, I told myself I still needed “more” to keep my fear of a 9-to-5 at bay. Eventually, however, I realized I was fooling myself. I didn’t have a reason, and it was scary to admit that. I was afraid I might not find a new one. I was afraid of the hard work it would take to figure that out.

The basic privileges I had created for myself were enough to stay content in everyday life. Why sacrifice that to get more of the same? How can I maintain my freedoms, yet still make progress? Towards what? And, once again, why?

Answering these questions took me all of 2018 and then some. I’m still answering them. I suggest that, as you work on your small tasks each day, you do the same.

Terrie Schweitzer calls this “the dilemma of the privileged.” We’re graced with all this freedom of time and creativity, and, often, we don’t know what to do with it. We default to chasing more of those same freedoms, which usually means more money, slightly more interesting projects, or marginally better experiences, for example when it comes to food and travel. But that’s not why we really set out on this journey.

Everyone wants to make $10 million. I know I do. After I built the foundation that would allow me to get there by playing to my strengths, however, the question underpinning this goal shifted. It used to be, “How can I get there?” Now, it was, “How can I get there while staying happy and healthy?”

Suddenly, I’m playing an entirely different reasoning game. Chutes and Ladders just turned into a chessboard. Options are exploding. Which of the million ways to make a million matter? Which one suits me? What’s a real reason? What actually drives me? These are hard questions, and you’ll find some of your answers can only come from living your life.

Sakichi Toyoda developed the five-why approach to solve problems at the Toyota Motor Corporation. Asking “Why?” multiple times in a row allowed engineers to go beyond treating symptoms and find root causes and long-term solutions to the many issues involved in manufacturing cars. When it comes to your life’s purpose, however, you can’t dig too deep. At some point, you’ll start spinning in circles, doubting your every decision.

“To what end?” as Coach Tony puts it, is a great question. You should answer it frequently, and check if your responses continue to align with one of your biggest goals. When you’re unsure for many days in a row, however, you might also consider taking a break. Take life one day at a time, run experiments, trust your gut, and come back to it later.

I’m typing these words from a couch in a small apartment in London. There was someone here I just had to follow. Doing so reminded me why I spent so long chasing flexibility: I didn’t want to miss once-in-a-lifetime chances because I was tied to one place. If I didn’t use the freedom to jump on them now, then what did I build it for? It feels good to reconnect with your purpose.

Why are you doing what you’re doing? It’s one of the hardest questions you’ll ever ask yourself, but it deserves a real answer — not once but every day.

I wish you the courage to pose it and the strength to craft a response in thought and action. May you always know what drives you, but remember: If at times you don’t, it’s okay to stop and try again tomorrow.


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