I’m enjoying independent life too much to go back to a full-time role.

Someone saw one of my LinkedIn updates last week and asked if I had gone back to a full time job. No way, I said. I’m pretty much still a Grab or Uber driver by another name.

A heavy week. A discussion with the risk folks of a major insurer. Two runs of my AI risk management course for a banking association. A full day of a similar thing for insurance professionals. A few new engagements agreed before the week was out.

Interestingly, I’ve started to explain what I do now, not what I used to do. A lot of art. A lot of training. Lots of building. A fair amount of writing. From AI governance to financial regulation to the deep technical stuff.

One of the slides I have been started using to introduce myself.

I’m essentially a gig worker. Someone needs training. Or a piece written. Or some other odd job. And I’m there. If the destination fits.

Some reflections on independent life. And what gig work has to do with portfolio theory.

From Grab to portfolio theory

Much of what I do is not so different from driving Grab or Uber. But I know the risks of this kind of life. And so I’ve reached back to an earlier part of my career to manage these risks. I used to run investment risk for Singapore’s foreign reserves. It turns out the same rules apply to a very different portfolio - my own independent life. So 5 simple reflections from this perspective.

Never let one client own you.

Concentration risk is the enemy of an investment portfolio. It’s also the enemy of independence. The moment you have a single paymaster, everything bends to that relationship. You’re a pseudo-employee without the benefits of a real job.

So I spread it broad on purpose from the start. This week alone - a major insurer, a banking association, an insurance body, and a handful of new engagements agreed: a governance institute, a university, an international regulator programme. My LinkedIn now has close to 10 live affiliations. And a few more coming soon, including an adjunct gig teaching AI financial forecasting.

And I tell people I don’t just do training. I can help write and build too. And I don’t just do AI governance. I can do financial and investment risk. And a variety of financial regulatory topics. And I can go as deep into AI technicals as you want me to.

Charge the risk premium.

Higher risk, higher yield. Grab has peak pricing. Every gig has its own return and its own risk, and the price should track both.

I try not to judge a gig by the fee in front of me. I think better to price it across its full lifetime. Some work pays nothing or little now and pays much more later. Some work pays well now and costs you your freedom. And occasionally, there are the requests that just want to borrow what you have for free. Forever. For something called exposure that I do not care for.

I’ve become a lot clearer-eyed. And I try not to confuse being busy with being paid.

Have some dividend-yielding assets.

Much of what I do only pays when I am in the room, and it stops the moment I stop. That’s the biggest issue with such gig work. You can be fully booked and still be selling hours one at a time, forever.

So I have been building the other kind. This past week my ebook store went up. At learn.simplyboring.ai. 5 ebooks now. Another 10 in the works. Write it once, sell it many times. It is slow and unglamorous. But an ebook is the closest thing I have to an asset that pays dividends while I am doing art.

Hold something uncorrelated.

Every portfolio needs a position that does not move with the rest. Mine is the art. It pays almost nothing, but that’s not the point. This week, tired after four days of delivery, I started a whole new watercolour style anyway - because I cannot keep still, and because painting is the one thing I do that has nothing to do with AI.

I have no illusions that the interest in AI will last forever. Everything cools. The frameworks get commoditised, the novelty wears off, someone builds a tool that does the boring parts. The AI side of me will become irrelevant one day. When that day comes, I hope the art, the platforms, and the odd non-AI thing can help me hedge.

Rebalance when the work comes.

My life is now full of peaks and troughs. Sometimes, there are too many gigs. Sometimes, close to zero. And so when the email comes, the instinct is to grab all of it. Partly greed, partly the old fear that it might dry up tomorrow.

Now that I am at month 8, I can see a clear need to rebalance. I cannot keep taking every gig at the same price. I need to do fewer, and charge more for the hard ones. And say ‘no’ more often. Which I have now realised takes some skill. Even Grab drivers decline gigs, or wait for peak pricing. And the irony is that I have not rebalanced my own investment portfolio for months. And that’s also something one needs to keep watch on when independent.

So, a gig worker

A Grab driver and an independent like me are not so different. Both are just managing a portfolio. Mine is now 2.5 companies - Quaintitative (I know, confusing name) for the work, Simply Boring AI for the products, and a stealth one I am building with Stephen Tracy.

Almost 8 months in. The portfolio is taking shape. I still cannot keep still. And I don’t think that is going to change.

#IndependentLife #Quaintitative #PortfolioThinking #AIRiskManagement #Transitions #Reflections

Independent Life and Portfolio Theory