Week one of career coaching and identifying my values.

I'm going to start with the most embarrassing part.

A week ago I had my first session with a career coach. Somewhere in the middle of it, she said something perfectly reasonable about having the free will to make our own decisions. And I, for reasons I still can't fully explain, felt the need to let her know that I don't believe in free will. That we're all just an amalgamation of stardust, moving through life on the back of circumstances set in motion long before we existed.

I'm lucky to be a human and not a cockroach. Or am I? I'm not sure.

Then, not content with that, I managed to bring up being Ayn Randian as something I somewhat admire. What I meant was that I have some admiration for individuals with strong ideals and who aim to create great things in the world. What I actually said was "Ayn Randian", which to many conjures up images of her hero, a distasteful, megalomaniac narcissist who rapes women out of pure desire. Of course, I was completely unable to bifurcate and deliver any form of nuance in the moment.

So. First session locked in. Already made a terrible impression. Less than ideal.

But let me back up.

In the past year I was promoted to a Principal designer, which is as close to the ceiling as one can be as far as the individual contributor track goes. My manager, the good human that he is, asked whether I'd be interested in partaking in the career coaching programme the company offers. Thousands of dollars in free coaching…therapy but with a business angle? I’m in.

The timing could not have been better either, because I've been carrying around a fair amount of existential angst of late.

If I'm being honest, most of the success in my career came from actions in my early twenties. I moved to London with less than a month's rent in my bank account and hustled... HARD. On more than one occasion, I lived in rat-infested squalor, specifically so I could save enough money to give myself the optionality to chase creative projects that would give me an edge over peers.

I also got some lucky breaks. I won a design award early on and was given access to a podcasting studio for no cost thanks to the generosity of others that I did very little to earn.

By some unbelievable stroke of luck, this concoction of random creative endeavours put me on Apple's radar. And in 2018, after a year of interviewing, I moved to the US. And ever since that day, I became a corporate drone.

I didn't record podcasts. I didn't attend events, and I certainly didn't speak at them. I didn't share my opinions. I didn't try to inspire the youth. I just quietly thanked chaos theory for having blessed me with the opportunity to change my life circumstances, and I went to work, and bottled up most of my true nature.

Partly because I knew no one cared what I had to say. And partly because cancel culture was at its peak, and I correctly identified that the surest way to avoid any drama was simply to muzzle myself and push pixels.

The goal was stability.

I met my now-wife a few weeks after stepping off the plane in San Francisco, and for the next half-decade, I kept my head down and worked, without so much as a peep in the public domain. Thanks to this, I hit a goal I'd been aiming for most of my life, and I became a millionaire at the age of thirty-three. A year and a half after that, I’d paid for our house outright. People say the American Dream is dead, but as an immigrant who moved to the US in 2018 to work in tech, it was very much alive. 

I only have one final goal still standing. Which is having enough money in an index tracker for my family to live off the interest. Which, barring a calamity, I should get to by my early to mid-forties. Now, for anyone listening to this, these seem like pretty superficial monetary goals, and I don't disagree; there is way more to life than money.

I'm currently reading The Conquest of Happiness by Bertrand Russell, in it he talks about how a man's goals are often a reflection of that which he lacked as a child. A kid who was ridiculed will seek power. A kid who experienced no love will seek connection.

In my case, that plays out uncomfortably well. Money was a huge issue when I was a kid. My parents would constantly talk and worry about it. So from as young as I can remember, financial stability was my goal. One which, based on my starting position in life, I've succeeded in overcoming.

But to get here, I have been particularly self-interested. Outside of my wife, I have given very little thought to my relationships, and that has come with a price. I have friends but few I would call close. The problem I now face is reconciling a learned behaviour that has shaped most of my life to this point, and moving beyond it to become a more rounded individual.

Which brings me back to the coaching.

To date, I've been laser-focused on becoming the best version of myself, but to go beyond where I am now, I think I have to change focus and start getting the best out of others.

That said, I'm still genuinely unsure I'm willing to make that transition. Taking care of the interests of others comes with burdens and responsibilities that I don't have today. I sleep easy at night with very few worries and very few expectations on me. That is not the case for leaders. I'd be lying if I said there wasn't an element of comfort in staying well within one's limits. Especially given I don't want for anything. I don’t care about fancy cars or watches, and I'm not pining to be the guy in charge of others. Though my innate desire to make progress means I likely wouldn’t say no if it were offered.

The one contradiction that flies in the face of this is my belief that if you're going to live and create, you may as well strive to create the best shit you possibly can. To leave the world better for having existed.

And, as egotistical as it is to say, I think I have better product intuition than most, as well as a grasp of business. Skills which, channelled in the right way, could be advantageous in a leadership position.

But that is not what I do today. Today I employ the whooosah philosophy.

Whooosah is: "This seems like a terrible decision, but it's not my decision to make, so I'm going with it, and I'm not going to rustle any feathers." I like to think that's a stoic approach. Flow-with-the-wind type thing. But really I'm just conflict-averse in the interest of giving myself an easy life, and there's nothing admirable about it at all.

Part of the reason I do this is that any time I do share an opinion and it happens to be the opposite of consensus — even when I'm ultimately right — I get this feeling that everyone in the room is thinking, this fucking guy. I'm also wary of becoming the archetype of the guy who likes the sound of his own voice, the mansplainer. So I think, you know what, just shut up, Rick. No one cares what you think.

Which, as established, worked out beautifully in my first coaching session.

Anyway....

My homework from this week's coaching session was to identify my values. I was told to list my top ten, so here they are..

1. Individual Sovereignty and Freedom  - Because there is nothing more I want in this life than freedom. I think it’s lame that we have to work on things often beneath our skill set simply to get by. I like to believe that at the point at which I am financially free I will be incredibly selective as to the projects I take on, even if they are not financially rewarding. But doing so before you are financially free means you have to contend with a whole heap of other shit, and I have concluded that it makes sense to first become financially free before being idealistic.
2. Stoic and Resilient - Somewhat contradictory to my first point, a part of me feels like even if I lost everything tomorrow, I like to think my mental state would be impervious, that life is just a series of experiences, some of which are good, others are bad, but the destination is all the same. I sometimes think that freedom is either having more than enough, or having nothing at all, which is why I sometimes envy the homeless man who does not need to answer to anyone.
3. Kaizen - Most things worth doing in life take time and sustained effort, but it is sometimes tempting to want things to be immediate; the principle of Kaizen helps to reassure me that the journey is meaningful and that incremental progress over time can compound into valuable outcomes. 
4. Thoughtful and Principled - Ignorance undoubtedly leads to greater levels of happiness; I sometimes wonder if I’d have been better off never reading a book. But the cat is out of the bag now, so if you have any level of awareness at all, it probably helps to at least have some guiding beliefs that help to give life a direction.
5. Competence - I like to believe that in a crunch people can rely on me. This is definitely true in a work context; I am not always the most competent when it comes to certain life endeavours, but I make it a goal to learn and become more competent as challenges arise.
6. Humble and Approachable - I’d be lying if I said I don’t sometimes think I am ‘better’ than others, or that others are sometimes ‘better’ than me. I think it’s somewhat human nature to size yourself up compared to those around you. Despite this, I know fundamentally that whatever edge or shortcoming I have on others is largely contextual and a matter of good fortune, and I will talk to anyone.
7. Quality and High Standards - I think that one of the simplest ways to better humanity is to strive to improve quality and standards of everything, large and small. It is a huge shame to me that furniture no longer lives up to the quality craftsmanship of the mid-century, or that craft in certain creative domains is being lost. But I am optimistic that certain other areas are seeing increases in quality. I would say that the times when I am most proud of my creative output are when the output is pushing the bounds. Otherwise, what is the point?
8. Humour - I try not to take life too seriously; I am a naturally quite serious person, but I like to offset that by poking fun at myself and life in general. I think humour is important as a relief and to question society at large. I subscribe to the belief that comedians hold a valuable role in society to question the zeitgeist.
9. Honesty - If we are not honest, and others are not honest with us, we are simply treading water and being avoidant. I personally struggle with being honest when it’s likely to cause conflict, because I avoid conflict.
10. Work Ethic - Because I get fulfilment and financial reward out of my work, I endeavour to work hard at it. Both because it’s the best way for me to maintain my ability, but also because breakthroughs and insight seem to happen most when fully absorbed in a problem. 

So that is the crux of my coaching homework this week. Moving forward, I will continue to share the exercises I’m working through biweekly along with my commentary. Values feels like a basic introductory exercise. I have thought a lot about my values over the years, but I’m sure we’ll get into the weeds over the next 6 months, and I'll be sure to share anything interesting that arises.