The hard way

In any area of life, if we want to improve it with our full attention, and it’s the absolute highest priority, the progression usually goes something like this:

  1. Identify the problem and choose to prioritize it.
  2. Decide what we are looking for in a solution, what is important to us. Which dimensions do we care about, and which are most important among those?
  3. Look for “sourcing pools” for the solution.
  4. Evaluate candidates from that pool.
  5. Select from those candidates.
  6. Try to integrate those candidates into your life such that they solve the problem.

A few examples: dating, hiring candidates for a job, looking for jobs yourself, picking an exercise program. Even trivial things are like this: looking for a recipe to make for dinner.

The easy way

There’s a different way to do this, which depending on circumstance can be successful or a failure mode. You begin step (1) and identify the problem, but then decide that it’s not a priority. Maybe do a bit of step (2), thinking about criteria, but then don’t continue the process.

Instead, at some point a candidate comes across your desk, for whatever reason – meet someone at a party (romantic partner or potential co-worker), a candidate cold-applies to your company without seeing a job posting, someone posts a job on Twitter. You review this candidate, and yeah! It seems better than the status quo. This posting is more attractive than your current job. You’d rather date this person than be single. Etc.


“Aha! My strategy has paid off. I’m being opportunistic. I’ve avoided all this search cost, and instead the universe has put what I need in front of me.”

You might even think that you’ve done a good job putting yourself in a position to maximize your opportunities: you went to the right parties, you follow the right network of professional contacts on Twitter so you see the good job postings.

This isn’t always wrong. It is often a good long-term strategy to set up your environment such that you maximize easy opportunities, and that you have the slack to pursue the right opportunities when they arise. And search costs are real. You must balance the cost of searching (and the opportunity cost of continuing without a selection) against the expected value of continuing an intense search.

Laziness masquerading as serendipity

But I claim is that this often is a failure mode. The full search is difficult. Executing it well is time-consuming, and if you do it right you may come to realize that your options are worse than you thought. The serendipity mindset is a defensive rationalization that makes you feel good about having found something worse. After all, if you rely on the universe to make this decision for you, you can’t be blamed. And it sets up the wrong comparison: you shouldn’t be evaluating candidates against the status quo but against the other candidates you could have found with a modicum of effort.

When you go for serendipity you probably expose yourself to more variance, but it’s mostly on the negative side. You might encounter something fantastic that would have escaped your search criteria – a job posting that would have been filtered out, but that when you see it turns out to be perfect. But this is mostly cope. If you execute the full search well enough you might end up with the best candidate among the subset who will have you. But with serendipity you end up with a randomly chosen candidate from that same subset.

One consideration on the other side of the ledger: if you don’t really know your criteria, looking at lots of candidates chosen at “random” is a good way to develop your sense of what you value.

We could formalize this problem mathematically, with parameters expressing your search costs, the expected variance in candidates, the efficiency of selection (do people know what they prefer), the heterogeneity of both sides of the market (in terms of attributes and preferences). It begins to look like an Al-Roth-shaped problem.

Just keep it in mind

As a heuristic I think this is valuable. When you find serendipity, you should ask whether you’re falling into this trap.

I think of this as a common failure mode for myself, though I’ve definitely seen both sides:

  • My job at ideas42 was serendipity – I saw the posting on Twitter, but it was indeed exactly what I had been looking for, the perfect job for me at that time.
  • Early in my consulting career, I took serendipity jobs instead of figuring out what kinds of things I wanted to work on. I ended up with a few mediocre projects and a small number of bad ones – where the work and I were not well-suited.