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Issue #23: Why Do CEOs Do It?

Last week I had a conversation with another business owner about the stress and amount of hustle that

James Costa

August 22 · Issue #23 · View online
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Last week I had a conversation with another business owner about the stress and amount of hustle that goes into building a business. I also spent a bunch of time reading Ben Horowitz’s The Hard Thing About Hard Things where Horowitz reflects on the issues he found starting and operating a business during the early 00s, and the mental battles he faced. It seems any time you speak to another business owner honestly, we always have something to say about how hard it is. So, if running a business is so hard… why do we do it?
In the first issue of this newsletter, I wrote about remembering where we came from to help us keep motivated in what we’re doing, but I believe this is separate; we can know why we started our business - but is our story why we keep going? For those of us who started our businesses organically (i.e. for fun, or as a side project), our jobs became less about our hobbies as we hired people to keep up with demand. We end up becoming a CEO (regardless of whether we intended to initially).
But back to our question: why do CEOs do it? To answer that, I think we need to first understand the mindset of a CEO in both good times and bad times:
In good times, a CEO might not feel like they’re needed. Things feel like they are stagnating, and they may scramble to do something new (or end up micromanaging their direct reports) because they don’t feel like they’re doing anything. If this time follows a period of things not going well, a CEO will certainly feel good for (what always seems like) a brief moment, but they will often be reminded not to take things for granted. In these good times, a CEO must keep focused: this is a time of preparation as (realistically) there’s always going to be a new problem to overcome. Overall the question that will be running through a CEO’s head during this time is “why am I here?”.
In bad times, pessimism sets in and the pressure of decisions takes a toll. The weight impacts a CEO’s relationships and personal life, especially since it can feel like they’re the only one who can do anything. In the hard times, a CEO will often think about three things: bankruptcy, acquisition / merging, and what the job market would look like for them. Further, they’ll feel as though they’re not qualified to make decisions as outcomes and possibility may feel out of their control. In these bad times, a CEO must also keep focused: how they respond to adversity will define their legacy. During this time as well, the question that will most often be running through a CEO’s head is “why am I here?”.
If in both scenarios a CEO questions themselves, a feeling of confidence in self must be a part of the answer. That confidence is something that separates a CEO who will give up at the first sign of strife, and one who pushes through. A successful CEO understands that stress is a part of their job, but an idea of what the future holds is an important motivator.
Therefore, I believe the reason a CEO “does it” is defined by their vision. A CEO’s vision is the answer to all existential questions they’re faced with. If a CEO doesn’t have vision, then the job becomes much more difficult. Every other position in our companies have a set of goals and responsibilities, and a loss of vision for what a CEO’s are is often when things go off the rails.
Lately I’ve been reading the journeys of various CEOs, and have found it interesting that many of them seem to migrate to a VC role to support the next generation of CEOs. Many believe that their most successful investments are in people not ideas: their gamble is ultimately in those with vision. Regardless of whether that vision is tangible (i.e. a revenue target) or intangible (i.e. solving a particular problem), if you want to know why a CEO does it, ask them what their vision is.
PS: If you enjoyed this week’s issue, I’d really appreciate your support sharing this newsletter. Whether it’s a forward, a Twitter post, or by sewing this week’s article into a quilt, it would mean the world to me.

On Finding Your Purpose: An Extraordinary Letter by Hunter S. Thompson
Tim Urban: Inside the mind of a master procrastinator
Why People Quit Their Jobs
Zero to One: Notes on Startups, or How to Build the Future
8 Steps To Push Past Your Limits When You Think You've Hit Them
“If you are working on something exciting that you really care about, you don’t have to be pushed. The vision pulls you.”
― Steve Jobs
On Saturday night, The Tragically Hip played their final show in their home town of Kingston, ON, Canada. Their lead singer, Gord Downie, is suffering from brain cancer, and while I’ve never really followed the Hip, seeing people come together to support them throughout the tour has been truly inspiring. It shows how strong of a legacy they’ve left, and makes you think about the legacy you’ll leave. I’ve always enjoyed the Stephen Covey’s activity of thinking about your 80th birthday as a way to think about what that legacy might be, and encourage you to as well!
If you have any questions or I can help you in any way, all you have to do is respond to this email.
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