“To travel hopefully is a better thing than to arrive”
Robert Louis Stevenson “El Dorado”, 1878
This week is something a little different. It started out as a reflection piece to myself which I decided to share… I hope you enjoy it. MJ
Once I am my own boss I’ll be happy.
I was laying on my back in the middle of the road. My Vespa was lying beside me, the engine still running. I did a quick scan of my body and realised that the only damage was to my pride. Thankfully it was 5.30 a.m. so the roads were deserted. But they were as slick as an ice rink thanks to the torrential rain that had turned the tarmac into glass. I was rushing to get to work - to be the first in at the desk.
I had bought the Vespa off a colleague on my desk - a guy who was moving up in the world and no longer needed to economise his journey into work each day. I wanted to be him. I wanted the title, the clients, the aura and the respect he got on the desk each day.
Whilst I can't totally speak for him - he probably wanted to be his boss - our boss - who he worked in lockstep with. 25 years on - he is the boss - not at the same company but the boss none the less - I wonder if it feels like he thought it would?
Once I leave finance, I’ll be happy……
For the longest time, I thought I would never leave JP Morgan let alone leave finance.
I loved it. I loved the rough and tumble of the JP Morgan trading desk - the characters, the banter, the camaraderie and the cut-throated edge to the way we all operated.
But Marshall Wace came calling, then after a time Och Ziff and each time I went in search of something new - something different.
When I left Wace, I did so under the impression my role was being marginalised in favour of algorithmic trading and that the firm didn't value me - in hindsight I could not have been more wrong. I joined Och Ziff hopeful that my “skills” as a trader would be better appreciated and I suppose in some ways you could say they were, at least in terms of how they paid me - but I don't know if the firm ever really placed any value on humans - based on the culture they cultivated.
So when I left OZ I did so with excitement and a feeling of freedom - able to explore and innovate and reinvent myself.
Of course the reality turned out to be a lot different. Being an entrepreneur was (IS!) hard. Starting a business is difficult, and I learned the hard way through Nucleus Wine that scale matters. Through Wine Owners, I learned that a shared vision isn't optional - and neither is an addressable market whose habits you can actually shift.
At the same time I was cultivating a budding seed that I wanted to be a Venture Capitalist. Sourcing deals, raising capital, building relationships with entrepreneurs and helping them along in the journey - making money in the process - it all sounded wonderful.
All I needed to do was get a few good investments and then I could raise my fund and I would be a venture capitalist and I would be happy.
But I was too naive to realise that the payback cycles for venture were measured in years, not quarters. The panic started creeping in - first as restlessness, then as a tightness in my chest every time someone asked, 'So, what are you doing now?' The answer, I decided, was an MBA.
With an MBA I will underpin my story as an investor and a business person, I will exponentially expand my network in NYC and everything will be back on track and I will be happy.
As the MBA is coming to a close I am offered the opportunity to join a fast growing consumer start-up - Ample Hills - that I am already an investor in. I’m going to be the COO, I’m going to help grow this and sell this and then I can raise my VC fund and I will be a Venture Capitalist and I will be happy.
Except it didn't grow - it failed and instead I thought it was all my fault. Every investor I'd brought in, every person who'd believed in me - I imagined them all shaking their heads. Should have known better.
So now there I was wondering what it was that would make me happy.
I thought I wanted to go back to being an investor but was afraid no one would invest with me. So I told myself I just need to go slowly, I need to trust my instincts - but be more thorough.
If I could just find a few good investments then I would be back and I would be happy.
One investment became two. Two became five. Slowly - painfully slowly - I was raising small groups of investors again. At the same time, I started helping other entrepreneurs. Coaching them through the decisions I'd botched myself. And they were paying me for it.
Could this be it? I become a venture capitalist and an executive coach, and then I'll be happy?
A friend who I trust and who IS a venture capitalist tells me I am good at this and that I should raise my own fund. So I start to do this - at first with my best friends - but then they decide they don't want to do this, so I go it alone.
Another friend, who is also a big investor and who has offered to back me in my new fund challenges me - “Is this going to make you happy? You seem pretty happy now with the way you do things - why change it?”
Of course he is wrong - how can he know what makes me happy - I want to be a venture capitalist and then I’ll be happy.
But his seed of doubt finds fertile soil in my mind and when I tell my wife she says - “Of course he’s right - you should keep doing what you are doing!”
So I keep on investing and coaching. I just need some of my investments to do well and I need more coaching clients and then I’ll be happy.
Another friend tells me I should write. It's how you build your brand, it's how you get your name out there. So I start to write. Once I build my personal brand, I will get more investment opportunities and more coaching clients and then I will be happy.
I keep at it and my calendar fills up with meetings - coaching meetings, investment meetings, mentoring meetings.
My calendar is not my own. It's owned by my clients. By the entrepreneurs I support. By my children and the activities I sign them up for.
Is this what it actually feels like? Is this happiness? It isn't any different than how it felt before. Or at least it isn't much different. A different set of responsibilities. A different set of questions. But still- questions. Still - responsibilities.
Some of the investments start to work out. Some of them start to return some money to me, to the investors who supported the ideas.
The coaching and the writing start to expand and I get other opportunities. To speak at events, to help clients in other parts of the world.
But now I need to make bigger investments and I need to find higher paying clients and I need to get more speaking and presenting opportunities.
Because of course, then I’ll be happy.
The point I am making to myself, but that I decided to share is that “...and then I’ll be happy” isn't a thing. It isn't a place or a destination. It's not a utopian level of being or enlightenment or awareness that the next ________ will unlock.
Because here’s what I’ve learned - but still often forget. Happiness is in the process. It's in the tough meetings. The investments that fail. The uncomfortable conversations and the lessons that follow - the ones that sting before they settle.
The happiness is in the control of your calendar and the feeling of inadequacy of not having gotten done what you wanted today.
It’s in holding your daughter's hand on the walk to school on the one day you take her.
Or your sons’ hands as you walk in silence to their school each day - knowing that the days of doing so are numbered.
It's in the small interaction with Eric, the guy in the doorway of the boxing gym on the way to meet your wife from the subway.
It's in the constant struggle to get the boys to do their math homework each week.
The happiness is everywhere and all around us - we just have to stop long enough to see it. It's not that we need to fight the urge to want the next thing. It's that we have to enjoy the fight itself. And we have to fight the urge to believe that when we get there - wherever 'there' is - it will feel different. That we'll be happier. That it will be easier.
Because I've been 'there' a dozen times now. And every time, 'there' just becomes 'here' - with a new set of problems and a new version of 'then I'll be happy' waiting in the wings.
So now, when I catch myself sprinting towards the next milestone, I think about that morning on the Vespa. Lying on my back in the rain, engine still running, wondering when I'd finally arrive.
I'm not sure I ever will.
But maybe - just maybe - that's the point.
