Google image search: “CEO”

The CEO burden

Jan 23 · 6 min read

I’d always thought of a CEO as the “big boss” of a multi-national corporation with thousands of employees. Yet when I entered the world of startups, it seemed like suddenly everyone was a CEO and I thought that I had to be one too.

In our last company, George and I were forced to give each other “proper titles” (because apparently that’s what investors wanted) and because I did the fundraising, I landed the CEO title.

That was the only actual rationale. With the other being my ego, being a CEO, well that made me strong, important, cool and special.

In the end, it was a dangerous title for me because I tried ever so hard to be a CEO. I tried hard to lead, to be a leader and to do what I thought I should do to be a good CEO.

I didn’t do me, I didn’t do James — I did the CEO thing.

I read all the startup stuff to help me out. I read Fred Wilson’s famous blog post about the three things a CEO does and I read Ben Horowitz’s equally famous; The Hard Thing About Hard Things. I read this stuff as if it was biblical.

Google search: “Startup CEO”

With the heritage and guidance of some of Silicon Valley’s most successful Investors and Entrepreneurs behind me, I did my best to follow suit and their blog posts were my guiding light. I based who I would be as a CEO on others and considering work was such a huge part of my identity, I was really basing a big part of me on what others were doing.

I formed my identity by going from the outside in. “Who should I be? OK. Let’s do that.”

Armed with resources from Silicon Valley’s finest, the latest self-development book and inspiration from regular TechCrunch articles, I was equipped to be a CEO and I was going to do 4 things.

  1. Set the vision
  2. Keep cash in the bank
  3. Recruit and retain the best talent
  4. Be prepared for a painful ride

This was my guidance, yet here is how I interpreted it.

  1. Set the vision — “Know exactly what the company has to do all of the time. Know everything. You have to know everything! If you don’t know everything, you are weak, you aren’t good enough and you will be found out.”
  2. Keep cash in the bank — “Raise money. Raise lots of it, always be raising and do whatever it takes to have money in the bank.” (At this point in my career I wasn’t too well acquainted with this little thing called revenue).
  3. Recruit and retain the best talent “Do whatever you can to keep people and keep them happy. Always be good to people, do 1:1s, listen to people and do what you can to keep people at your company.”
  4. Be prepared for a painful ride — “If this company is anywhere near successful it’s only going to get harder and harder and harder, basically it’s always going to be hard. So get used to it, because a lot of this might be pretty shit.”
Link to original post here.

I created a huge amount of internal pressure on myself to be a CEO and the title itself became a burden.

All of the discourse around being a CEO (as I read it) was about strong, stoic and invulnerable leadership. It was about never giving up and about crusading into the total addressable market with your sword unsheathed, helmet off and head held high. Hazaar!

The current narrative of being a CEO and leadership more broadly is about putting on a suit of armour, hopping on your high horse and going into battle.

Yet, aren’t we supposed to be building companies? Or are we building armies?

I believe that leadership is changing and that the image of the battle-worn CEO or leader is archaic and antiquated. It’s just one picture, that’s getting a little old and faded.


The current modality of leadership does not allow for two of the single most important traits I believe a leader must have today:

Vulnerability and Empathy.

Back when I was doing my best to try and be a CEO, these were the two things I never even thought were an option. I never even considered them, nor did I have them internally available to me. Looking back, in my time as a leader of my last business, I wish I had done two things:

  1. Listen
  2. Say; “I don’t know”

I never truly listened; neither to myself or others. I didn’t listen to my gut, nor that little voice that sometimes keeps you awake at night. I didn’t listen — I just carried on. Honestly, I didn’t really listen to others either, I pretended too but I didn’t. I thought that listening was just a way to get someone to eventually see your way of thinking, because of course as a leader I thought I had to know what we were doing all of the time.

Listening would open me up too much, I might have to admit I was wrong, I might have change something and that required too much vulnerability

For the same reason, I never said “I don’t know.” How could I? As I always had to know, that was my role.

Instead, I piled the pressure on myself to get it right and the burden of being a CEO became heavier and heavier.

The image I had of a CEO at that time was heroic. I was going to go into the house burning to the ground and save the day, and I was going to do it all on my own — or inspire others to do it alongside me.

This image was heroic, but ultimately a fantasy.

I believed leadership was about being the first to face danger, the first to lead the line into battle and the last to go down, fighting.

I played this role to perfection, I could have won an Oscar for my performance. It was truly breathtaking. I went down with the ship, tied to the mast, signing the liquidation papers.

I’ve written about how this fairytale ended many times before, as the suit of armour came off, I realised the wounds were there and they had landed deeper than I thought, finally affecting my mental health. Anxiety ensued and that really did take my breath away.

This notion of leadership, whether CEO or not. Where we keep on fighting and never show any weakness, is as outdated as our current version of masculinity. It’s not relevant in 2019.

This version of leadership piles immense pressure on CEOs and leaders all round and it creates cultures where this brutal approach to work is expected by everyone. It creates a breeding ground for burnout and for shallow connections in the workplace, where we’re hiding what’s really going, where we’re not showing up and being real.

The traditional character traits of leadership are changing. Vulnerability, empathy and compassion are all behaviours which are being added to the mainstream leadership mix alongside conviction, passion and courage.

The commander-like version of leadership is being challenged and it may start to get some competition from the more humble warrior.

Time will tell, but leadership is changing and I believe the image we have of a “CEO” today is going to be very different in years to come.

James x


Written by


founder @sanctus ❤️ On a mission to transform #mentalhealth

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