The Best Leaders Like Their Job

There’s a phrase in business that people say: “The best leaders work themselves out of a job.” 

For years I followed this principle, thinking the right way to run a business was to hire people who were smarter than me. Working myself out of a company I had no plans to ever leave. It took me far too long to realize that this advice was… flawed.

I’m not saying that hiring smart people is a bad idea. Or that building up your team to fill gaps as you take on new responsibilities isn’t worth your time. But if you like “the work,” hear me when I say this: Never getting to do it is a sure-fire path to self-destruction. 

Let me explain.

It’s much easier to take on a predetermined role rather than create one informed by who we are. For years, I let phrases like this tell me who I was supposed to be as a “good CEO” rather than trusting that I have distinctive gifts or talents to offer.

It pigeonholed me into one position—“management.” I delegated responsibilities so I could work on the business, and not in it. Keeping the ship steady in case I ever decided to walk away.

It wasn’t until I felt the weight of the day-to-day business that I even began asking questions like “Why isn’t this fun, anymore?”

I let myself explore what I would do if I left—only to realize my ideas sounded eerily similar to Cladwell. It finally clicked. I had outsourced the very things that piqued my interest in the first place: all the fun parts that spurred my creativity. 

For many founders, building a business is the act of creating. But we don’t have to move onto the next one, in order to do so. Sometimes all we need is a subtle reminder that if something is not working, we can change it. 

Have you ever started a new book only to realize you don’t have to finish it before starting the next? We’re unconsciously living by these little spoken or unspoken rules, but some of those rules can—and should—be broken. 

Being a CEO never barred me from creating content any more than a restaurateur has to stop cooking or a chief technology officer has to stop developing. Said like that, it almost seems silly.

Work itself can get a bad rap, hence wanting to “work ourselves out of a job.” But the truth is that good work is about enjoying the act of creating and creating requires work.

Finding myself as a CEO was never about leaving. Rather, finding my way back to doing what I love.  

Work can be life-giving and soul-fulfilling when we’re clear about what we want. If you find yourself eager to leave a job only to want a similar one, it might be time to slow down and ask, “What do I miss creating?”

Here’s a hint: go back to why you started. 

Let’s Name Your Style

Your style is one-of-a-kind. It can stay the same or keep up with the transitions in your life.  Either way, naming your style direction can help you discover what you like and don't like. Now let's take a closer look at how to break it down.

Style Direction

Choose a place that has your general aesthetic. Think of it as an environment, color palette and feeling that encompasses your style’s personality.

Dress Code

Name your formality - from athleisure, casual, smart casual or professional. Which do you prefer based on your lifestyle & activity 

Preference

Choose a style preference - the fabrics, the fit, the cut or silhouettes that you like.

Want to know yours?