002: my old boss thinks I'm cooked
past assumptions, my ABCs of working in family, coming out of semi-retirement
My name came up during a boozy black tie dinner my uncle attended last month.
He was in a group of three, including the host. The remaining gentleman blurted before the host could say anything.
‘That guy? He used to work at my startup, and then went back to work for his family. Haven’t heard from him in a while. Feels like he went into semi-retirement!’
Sheepishly, my host introduced my current boss to my old boss.
past assumptions
I had a bunch of questions when I first joined the family office:
1. What is a family office anyway?
2. What is expected of me here?
3. How is it like working for family?
4. If I join, does this mean this will be my last job forever?
It’s silly to mind read myself five years ago but these are best guess of the assumptions I used to vaguely hold in my mind:
A family office preserves and grows wealth.
The better investor I become, the more money I’ll make, the more respected in my family and my field will be, the more control I have over my life.
I’ll manage my bosses just like I’ve manage other bosses in the past.
I need an exit strategy. Again, the more money I have, the more control I have over my life.
I’m a more trustworthy narrator if I tell you my latest assumptions.
But first, let me explain what changed.
my ABCs of working in family
In these past five years working for the family office, I felt greater autonomy, belonging (aka relatedness, purpose), and competence (aka mastery) now than when I started.
Autonomy
I joined my family a few years after my elders sold the listed family business and started investing the proceeds.
I was spared from specialising into one sector and encouraged to look broadly at new economy sectors and asset classes that could futureproof our family’s portfolio.
I started in venture capital and ended up spending a lot of time in crypto. It was the best decision I’ve ever made, not in terms of the most money I made for my family, but in terms of the degree trust I’ve built with them.
Now I’m ready to try something new. Like this Substack!
Belonging
I could go into all the strategies I use for managing upwards but at the end of the day, it’s realising whether family is worth fighting for. That’s a story for another day..
Competence
I personally think losing less of the family’s money year after year is nice, but no return comes without risk. Making more money year after year is great, but how sustainable is it?
I prefer to measure progress based on a few things. Am I explaining new concepts effectively, especially to my family? Am I attracting sophisticated peers and deal flow organically, especially in emerging domains? Am I developing better taste?
Perhaps the score will take care of itself.
coming out of semi-retirement
So here comes my latest assumptions:
A family office is one of many platforms for self actualisation of family members from different generations
The more holistic my understanding of skills required to help my family flourish for the long term, the more focused my quest becomes to cultivate those skills, the rest will take care of itself
I need to be intentional in what and what not to do to cultivate strong bonds within my family. Relationships can achieve sometimes even the strongest of governance structures cannot.
Control is an illusion. Keep my options open but commit to something and give it my best efforts. A portfolio approach applies not only to finances, but also to life.
Should be fun revisiting this in another five years!