Seven fatal flaws I need to fix
Since departing Clarity, I’ve been reflecting on what I learnt from the experience, and which lessons I’ll apply to my next venture.
I’m proud of the business I built. To grow from zero to $20m ARR in a little over a decade is a huge achievement.
But I made plenty of mistakes and experienced plenty of failures.
Many of these failures were a consequence of mindset and personality wrinkles which I’m working on ironing out ahead of my next venture.
- Shiny new object syndrome
I get bored and distracted far too easily. I see exciting opportunity everywhere. And, to paraphrase Oscar Wilde, I can resist everything but temptation.
This frequently led to me investing time and resources in new initiatives and side projects, rather than doubling-down on those parts of the business that were performing.
There’s a big lesson to be learned about focus and what Neitzsche called ‘a long obedience in the same direction.’
2. Lone-wolfing
I’m a introvert. I prefer working independently. I’m not a natural team player.
However, in retrospect, I now wish I’d had a business partner: someone with real ‘skin in the game’; someone truly vested in the business and its successes (and failures) in the same way that I was.
This led to two issues: 1) I didn’t have anyone to really challenge my decisions / thinking / assumptions; and 2) I felt extremely lonely and isolated when things weren’t going well.
3. Shadow-lurking
I should have done a better job of being a more visible leader internally and externally.
To some extent this was a result of my natural shyness and crippling sense of ‘imposter syndrome’, but I should have worked harder overcome that.
In a people business especially teams need to feel and see the influence and drive of its leader.
And, similarly, I could have been a more public cheerleader for the business, and for our amazing team and clients.
My team deserved more from me. And the business needed more from me. I operated too much in the background.
It’s a poor excuse, but being public — whether is speaking, presenting or even just engaging on social media — is something I find extremely stressful.
I’m training that muscle (and this blog is evidence of that!).
4. People-pleasing
A major personal fault — and one that holds me back a lot, I think — is my innate desire to be everyone’s friend. I’m too much of a people pleaser.
This meant I avoided uncomfortable conversations. I shied away from providing candid feedback. I was much too worried about upsetting people or giving people a reason to dislike me.
I must get better at being more direct in my communications. I don’t need to be everyone’s drinking buddy.
5. E-Myth extremism
I was overly-influenced by the classic business book The E-Myth by Michael E. Gerber.
It’s a bit old-fashioned now, but essentially Gerber’s book provides a framework for building a business that’s inherently scalable.
I applied the E-Myth principles quite rigorously from day one.
This mindset led me to a strategy that boiled-down to two overarching principles: 1) ensure that Clarity wasn’t in any way predicated or reliant on my individual skills / experience / network etc., and 2) hire exceptional talent and give them an unusual level of autonomy and latitude.
Whilst I think the principle here was right and effective in many ways, I went too far — I gave people too much freedom, and this backfired at times in big ways and small.
Next time I’ll strike a better balance.
6. Big-picture myopia
The bigger we became the less attention I paid to the small stuff.
Ultimately this led to me becoming very distant and removed from the day-to-day realities of the business. I stopped paying close attention to the details and became totally consumed with big-picture thinking.
In some instances my lack of attention to the details compounded into non-trivial problems.
History is littered with examples of entrepreneurs — like Elon Musk and Steve Jobs — who obsess about the details, whilst remaining clear-eyed on the big picture.
I’ll take a leaf out of their books next time.
7. Immortality mindset
I used to pride myself on my ability to work superhuman hours; to fly across continents and appear unfazed; to be the last man standing at parties.
This was all just ego and BS. And it took a serious toll on my health and wellbeing. And it impacted my personal relationships and family life.
I’m now convinced if you’re going to be a successful entrepreneur (particularly as you age), it’s critical to strike a healthy balance.
It’s blindingly obvious to me now: I can only be successful if I’m healthy — physically, emotionally, mentally, and spiritually. This is the foundation for everything else. Lesson learnt.
