What to do when no one tells you what to do anymore

You left your job and have all the freedom in the world. Now what?

I recently left my day job to go full time on my own projects. So for the first time in a long time I have complete control over how I spend my working hours.

More than that, my portfolio of products earns enough passive income for me to live comfortably on. So I really do have almost no obligation to do…well…anything.

So now I’m faced with this funny problem. What do I do all day?

Freedom

Shout out to Jeremy Finch of The Fire Jar who drew this and all the other illustrations in this post.

I know. Boo-hoo, woe is me. I have no responsibilities, a money factory, and all the time in the world. Cry me a river!

But here’s the thing. I never wanted not to work. I wanted the freedom to work on whatever I want. And now that I have it, I realize that it’s not as simple a proposition as it sounds.

This post summarizes what I’ve learned so far and how I approach deciding what to do on a daily basis.

The curse of agency

At the moment I have far more agency—control over my work—than ever before in my career. For the most part I wake up every morning to a literal blank slate. A mostly-empty inbox, an empty calendar, and an empty todo list.

Free Schedule

The empty calendar is definitely my favorite.

I can code. I can write. I can say “fuck it” and go surfing.

Surfing

Note: actual waves surfed by author are substantially smaller.

In theory this sounds amazing—and don’t get me wrong, it is. But it’s also kind of stressful!

The problem is that every minute of every hour now comes with a new cognitive load. The load of am I doing the right thing? That empty todo list—a mark of your glorious freedom—also carries some serious personal accountability.

When you have a job, the weight of choosing the right thing is largely lifted off your shoulders. Of course you make decisions that shape your work, but unless you’re a founder/CEO, someone else is mostly responsible for your time. You can offload “direction” to the company, roll up your sleeves, and get stuff done without ever having to ask if it’s the right stuff. It’s actually quite freeing!

Those of us who work for ourselves don’t have this luxury. We’re faced with the daily exercise of strategically tasking ourselves. And it’s exhausting! Also—at least for me—it leads to a lot of second-guessing and self-doubt. Not to mention procrastination.

Offloading agency

The situation is improved by doing something counterintuitive: offloading some agency.

I’ve decided that the right amount of agency for me is to control about 75% of my time. While freedom is great, it’s also nice to have a few things I’m obligated to do, and to use those to fill the space when I’m not quite sure what to do myself.

Having external commitments—aka working for other people—is the easiest way to give up some agency. The work can be voluntary or paid, though I find paid work more easily silences the “is this the right thing?” voice in my head, since it’s easy to fall back on “well, at least I got paid for that”. No second guessing there.

It’s also possible to use internal commitments to eliminate agency—for example, telling yourself you have to practice guitar an hour a day. And actually sticking to it, no matter what else is going on.

Guitar

You can simulate offloading agency by pre-committing to do things. E.g. blocking out an hour a day to learn guitar and never skipping it.

Internal commitments require discipline—as well as some mental gymnastics to separate you, the assigner of work from you, the worker. And while I’ve had success with the approach, I find it more challenging to adopt than working for other people. Commitment just doesn’t carry the same weight when it’s to yourself.

Charting a course for your own time

Even after offloading some of your agency, you’re still going to have an overwhelming amount of time that you control. So how do you allocate that time?

The first step is to know what your goals are. Mine are to grow my businesses, do some good in the world, and stay healthy.

Ideally everything you choose to do should be in service of one of your goals. When I work on one of my products it’s clearly in service of the “grow my businesses” goal. When I’m exercising it’s clearly working towards my health. Etc.

But it’s not always a straight line. Sometimes I get pulled into topics and go down what can only be described as a “YouTube/podcast rabbit hole”. I do this because I believe that having a deep understanding of some topic might help my businesses, or help me do good in the world—but I don’t have a story as to exactly how that will happen. And it might not.

Podcast Rabbit Hole

Podcast rabbit holes are a real thing. And they are bottomless.

Writing is similar. Was writing this essay good for any of my goals? I don’t know.

Anyway, once you have goals the next step is to decide how much time you want to devote to each of them. For me, in any given 40-hour week, I’ll aim to spend about 30 hours growing my businesses, 5 hours somehow related to “do-gooding”, and 5 hours exercising.

Typical Week

My idealized week. In practice, I often end up working on the business too much.

Now we’ve taken an extremely difficult question: “what should I do?” and replaced it with an easier question: “what should I do in service of <goal>?”.

It’s still a hard question, but at least it’s scoped down!

Prioritizing with the enjoyment/value dance

How I choose what to do within a goal is through something I’ll call the enjoyment/value dance.

Let me explain.

For every given piece of work I consider two primary axes: enjoyment—how much I like the work—and value—how useful it is for the goal. You can imagine these as two axes forming a spectrum:

Enjoyment vs Value

Now ideally everything you work on would be both super fun and super useful—the upper right corner of the graph—but in practice, that’s rarely true. High-value, high-enjoyment tasks are more like unicorns: rare, special, and worth treasuring.

We can call this the “Unicorn Zone”:

Enjoyment vs Value

You should do everything in the unicorn zone immediately! But in my experience, unicorns dry up quickly and you shouldn’t expect to spend much time here.

Opposite the unicorns are the low-value, low enjoyment tasks. There’s no reason to do anything here, so it forms a dead zone:

Enjoyment vs Value

Most of your work will fall in between these two zones. Things that are fun but not all that useful, and useful things aren’t particularly fun.

Here’s an example of some of the things I do regularly, loosely plotted on this scale:

Enjoyment vs Value

Your graph, will of course look different, based on your goal and interests.

So how do you pick from these?

You might be tempted to prioritize enjoyment. After all—you have agency! What better way to exercise it than to work on things that you love? But this is problematic. If you constantly choose enjoyment over value, then you’re unlikely to succeed in your goals. Remember, we still have goals.

If you’re a developer/entrepreneur like me, a classic trap is to spend all your time building a product and no time talking to customers, doing marketing, sales, or any of the boring business stuff. This is optimizing for enjoyment. But if you only ever write code, your business will probably fail.

So prioritize value then? After all, if we want to succeed we should be working on the Most Important Thing™. But wait—the whole point of going independent—at least for me—was freedom. Surely freedom should include working on things you love, otherwise, why bother with independence at all? You’ve just traded one set of shackles—lack of agency—for another—lack of fun. Plus, if you don’t enjoy what you’re doing you’ll eventually quit or burn out. And then you still won’t succeed in your goals.

The panacea, of course, is the unicorn work: high-value work you love. To a developer/entrepreneur, building a great product—up to a point—can be this. But it’s easy to convince yourself that your product-building is high-value when it only is to a point. You have to do it alongside the less-enjoyable bits like sales and marketing. Kind of like eating your vegetables so you can have dessert. Many of us forget our vegetables and our projects never get off the ground.

Striking this balance is the enjoyment/value dance.

Enjoyment Value Dance

For me, if I’m spending all my time doing things I enjoy, an alarm bell goes off in my head telling me that I should probably be focusing more on the business. And likewise, if I spend too long not enjoying my work that’s also a flag—it means I’ve lost sight of appreciating the journey and gotten too focused on the destination. Enjoyment and value, forever pushing and pulling against one another. Never letting myself go too far in either direction.

Navigating this tension is another challenge in working independently. Staying productive while staying fulfilled.

It’s more complicated, more effort, than you might think.

But I wouldn’t trade it for anything.

Freedom

Discuss this on Hacker News or on Indie Hackers


Cory Zue—that’s me—is a developer/entrepreneur currently working on Saas Pegasus: Django boilerplate for SaaS applications. You can follow my journey on Twitter, or by subscribing to get email updates below.

Jeremy Finch—the illustrator—is the creator of the Fire Jar—which provides small doses of movement, creativity, and reflection. He’s also on Twitter.

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