The Humbling Art of Choosing Well

by Juliet Grayson

Starting a new relationship is hard. Whether it’s romantic, professional, or even a friendship—there’s always that early hope, that wish to trust, and the uneasy truth that we don’t really know who we’re dealing with.

A few years ago, I was looking for a new admin assistant. I can still feel the stretch it required in me—interview after interview, sifting through CVs and stories. Over three years, I started about nine different people. Some simply weren’t good enough and didn’t have the attention to detail that’s needed in this job. One outright lied – saying they were settling locally, then announcing a move to Scotland just weeks in. Two more just left.

As a psychotherapist, I had assumed I’d be able to sense who was honest and reliable, who was a good person. But I couldn’t. I got it wrong again and again. Though finally, I found someone who is a really good fit for me and my organisation – sharp, grounded, with great attention to detail—and we rub along together well enough. I’m delighted with how it’s worked out with him.

It reminded me of a mental health placement I did in the early ’90s, when I was training as a therapist. I spent two weeks at a residential facility for adults with severe and complex personality disorders. Most of the clients were court-referred. I remember chatting to someone I assumed was a psychiatrist. Only later did I learn they were actually a patient with paranoid schizophrenia. It was a jolt. I realised then that I didn’t have the superpower I’d hoped for. That moment taught me humility. I don’t always know. I don’t recognise the person I can trust who will do the job well – and I don’t recognise the person I can’t trust!

So if it’s that hard to find an assistant, how much more delicate is it to find a life partner?

Before the internet, I used lonely hearts ads to search. I met hundreds and hundreds of men. But eventually, I met someone—and it’s now 30 years since we got together. And mostly, it’s been an excellent match.

That’s why I say to people starting new relationships: Don’t give up. Keep looking. Persistence pays.

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