[CEO Friday] How Difficult is It to Be a CEO?

David Barrett —  January 30, 2015 — 2 Comments

Being a founder and starting your own business has become the *it* thing to do lately.  In 2012, more than 500,000 companies were founded, and it’s not shocking that the numbers got even higher in 2013 and 2014.  It’s no wonder everyone wants to get in the startup game.

Interestingly enough, I came across the question of how difficult it is to be a CEO in today’s startup ecosystem.  The question, at length, from Quora

I can’t seem to fully get my head around the role of a CEO. Basically the CEO sets the strategy, vision and makes sure everyone is on the same page. May have meetings with other partners etc. Brainstorm ideas with other execs. Talk to investors. Recruiting / Editing the team.
What else do they do? If you are a CEO or have been one, can you describe what you do on a daily basis? It seems like they just go around, making sure everything is operating in order. They don’t actually have to solve technical problems etc themselves.

This seems to be two questions: what does a CEO do, and is it hard?

As to the first, I think it depends on the organization you are trying to build.  In my case, I’m trying to build an organization that runs itself: ideally the organization would evaluate and prioritize the available opportunities objectively, create and execute plans efficiently, and ultimately go out and do amazing things with minimal need of me.  Accordingly, I view my job as primarily one of auditing the system to make sure it’s functioning correctly (eg, that there are good processes in place, that they are being followed, and having the desired effect), and only stepping in when things are off the rails in a way that the organization can’t seem to fix itself.

So yes, as CEO I do all the things you mention — talk with partners, brainstorm, recruit, etc — but only to the degree that I’ve failed to enable the organization to do all that without me.  On a good day, I do nothing but sit back and watch.

As to the second question — is it difficult being a CEO — I’d say it depends on the day.  I find it’s getting easier over time as the team is able to step up and handle a wider range of issues without my involvement, and able to maintain forward momentum on the most important things without my prodding.  Indeed, the hardest part anymore is trying to resist the urge to over-engage in a system that’s working well enough — even if not as well as I’d like.

In fact, the single hardest part of my job is explicitly stepping back and allowing someone to fail — believing that something is a mistake and will probably be regretted at great anxiety to the organization — with recognition that failure is a cost of discovery.

At the end of the day, I’m just one guy.  Though I know a lot about a lot of things, I know very little about everything.  Accordingly, my goal as CEO is to build an organization full of people who are experts at figuring things out for themselves… without killing each other along the way.

In short, I view my job as CEO not to pursue my personal vision for the local maximum, but to build an organization capable of pursuing a global maximum larger than anybody can see.  This seems very different than what most of the others have written on the thread — especially the “professional CEOs” that seem to thrive in a command-and-control structure (so long as they’re on top).  Personally, I hate working for those CEOs, and if you do too I’d be honored to have you as part of the team.

David Barrett


Founder of Expensify, destroyer of expense reports, and savior to frustrated employees worldwide.

2 responses to [CEO Friday] How Difficult is It to Be a CEO?


    “I view my job as CEO not to pursue my personal vision for the local maximum, but to build an organization capable of pursuing a global maximum larger than anybody can see.”

    And that’s precisely the type of CEO I want to serve. You management team and entire staff are fortunate to have you helping them to all row in sync toward your company’s TRUE NORTH.

Trackbacks and Pingbacks:

  1. Expensify's Founder David Barrett Writes about the Difficulty of Being a CEO, Will You be Next? - Scribe CEO - November 24, 2015

    […] enjoyed reading David Barrett’s brief blog entry on 1) being a CEO and 2) the inherent difficulties of the position. It’s a great, short […]

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