Work that doesn't feel like it

When asked why I choose to own my own business (instead of leveraging my skills in the job market) my list of drivers looks similar to other entrepreneurs I know:

• Freedom
• Financial success
• Making an impact

But there’s one more that seems to matter a lot to me:

Loving the work.

Since 2008, when I left my job and started down a more entrepreneureal path, I've been asking myself the question, “Do I enjoy this?”

16 years later, I still think about that question most days. I use it as a tool to figure out which part of my business needs my attention at any given moment.

It goes something like this: “Spinning my wheels on this is burning me out. Why does this feel like a grind? What needs to change in my business so that operating it doesn’t feel like a grind?”

At times, that question led to me to decisions I’m proud of. Like deciding to start businesses, sell and exit businesses, automate and remove myself from operations, and other "wins" in my career.

It also led me to some decisions I’m not so proud of. Like over-prioritizing the tasks I enjoy over tasks my business actually needs, or giving up too quickly when things feel hard.

Who loves their work?

Strangely, I don’t see or hear many other entrepreneurs cite “loving the work” as something that drives them.

But there are people I admire who seem to spend a great deal of energy chasing this desire to love their work.

Musicians. Comedians. Athletes. Teachers. Artists. Public servants. Journalists. Authors. Actors…

Sometimes, people in those more creative careers end up stumbling into owning a business. But the typical drivers of entrepreneurship—freedom, money, impact—aren’t what led them to business success.

It was their craft. An endless pursuit of their purest form of expression. A competition with themselves to make their next creation better than their last one.

Not very business-like.

The work of business

I’m becoming more aware of this tension:

Years of throwing my energy into building my businesses trained me to sharpen areas of my work that don’t serve me well as a creator.

For example, it’s considered “good” practice in business to do less. Minimum viable products. Ship fast. Spend less time. Squeeze more profit. Automate more. Delegate.

It’s considered “good” practice in business to standardize. Develop processes. Make it repeatable. Scalable.

It’s considered “good” practice in business to be driven by growth. Be data-driven. Find leverage. Strive to reach the next milestone.

This isn’t a playbook for a creator (creators don’t think in “playbooks”).

Can a creator build a business?

Of course we can. The key is to recognize our particular strain of imposter syndrome.

I’ve always had it. But it wasn’t until writing this post that I realized what actually makes me feel like an imposter.

I thought my imposter syndrome was telling me I didn’t have what it takes to be a great business owner. But it’s actually calling into question my instincts as a creator.

A creator shouldn’t care how long it takes to chisel away at a project until it’s perfect—even if that means delaying launching to customers.

A creator doesn’t want (or need) to create the same thing repeatedly (or at scale). Their best work is new.

A creator shouldn’t be angling for how they can optimize their work to double or triple it or unlock hockey-stick growth. Their best work spreads simply because people like it.

Looking back on my years of building and creating reminds me of this truth:

When I’m throwing my energy into creating my best work yet, my business tends to take care of itself.

And when I’m over-heating on the work of business, stressing over growth or shaming myself into the grind—it doesn’t serve well me as a creator.

And that’s not good for business.