Building a portfolio of small bets

Standing atop the shoulders of an unknowable lineage stretching millennia

Afterthoughts: My Beautiful Friend by Elena Ferrante

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We all of to support ourselves; we all have to make a living. The conventional road is to invest in our skillset and market ourselves as the perfect candidate for a job with a company or a project. Others who share a certain nerve and gumption will start ventures of their own. Both of these routes are perfectly serviceable and acceptable. They do, however, require a certain element of focus and precision day in and day out. Unless there is an intrinsic love for the work, it can grow a little stale and tiresome.

The alternative is this fairly new notion of having a portfolio career.

A portfolio career is a working style where you combine multiple streams of income—often creating a mix of full or part-time employment, freelancing or working as a consultant. For example, you could combine consulting with part-time work, developing your own product or service and freelance writing.

While this approach invites uncertainty, the inherent variety invites a lot of spice into the work. This can be a very energising thing and stave of the feeling stuck in a routine that a lot of people find themselves in.

What I am interested in, and what I propose, is an offshoot of this traditional conceptualisation for a portfolio career. I take the perspective of an investor, and see time and energy as my primary resources. Like an investor, you want to invest in projects or things that will maximise your return over the long-term.

The most idealised version of this is to work on building products or services that once-built require no or little maintenance but can continue to provide value in the free market which in turn you capture. Once one is built, you move onto the next. In essence, what you are trying to aim for is to build a portfolio of small bets. Conventional wisdom that is associated with good investors making good investment applies here. Over time, you will accumulate a dizzying array of small bets. The chances of one or more of those bets taking off are probabilistic. The key factors are patience, the number of small bets, and the inherent quality contained within those bets.

You could strike gold and make it rain with your first bet, but it might be the 100th. However long it takes, I think it a great strategy for building resiliency into the way we make a living. We slowly decouple ourselves from having to work in the traditional sense by building up income streams one small bet at a time.

What makes it more appealing to me are three things:

  • Complete ownership over each small bet
  • The projects are small enough that the variety in the work will be welcome
  • Slowly detaches our need to trade our time for money

I recognise this approach to making a living is fraught with uncertainty and will therefore not be for everyone, especially to those with dependents. But in principle, I think adopting this approach even in a small way will pay dividends sooner than you might expect, emotionally and socially if not financially.

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