Making those big life decisions

Or, how to ask yourself better questions.

“How did you sleep?”

It was a strange question from the barista. Not that we hadn’t spoken about our sleep challenges before, but it was strange in that it wasn’t one of those mornings I’d grunted hello at him and nodded lifelessly when he asked if I wanted my usual double shot oat latte.

In hindsight, he may have been asking because I’d ordered a chai latte the day before, and the last time I had one after lunch, I reported back that I couldn’t sleep until midnight (I know, it’s weird). But on that particular morning, I felt well rested — great even — and I smugly told him so.

When he didn’t say much in response, that’s when I noticed his messier-than-usual hair and slumped posture. The Sad Ben Affleck vibes were overwhelming.

“Did you sleep okay? I asked.

That’s when it all came out. He’d been sleeping terribly for weeks. His nights were all playing out like this: he would fall asleep quickly, then jolt wide awake at midnight and not get back to sleep until after 3am, sometimes 4am. It had gotten to the point where he could correctly guess the time based on the type of bird chirping outside the window. He was exhausted.

I asked if there was anything on his mind keeping him awake. He said there were lots of things, but they all came down to this one big thing: having to make a decision about whether his young family should pack up their lives and start fresh in another country. It was all becoming too expensive to lay solid foundations in Sydney.

No wonder he couldn’t sleep.

And he wasn’t the only person I’ve spoken to these past few months who was at a crossroads of varying degrees. To an extent, I’m at one too, albeit not as life-changing, trying to work out what to say yes or no to work-wise and in which way I’d like to take my career.

When it comes to making big decisions, I used to be one of those people who subscribed to the “If it’s not a fuck yes, it’s a no!” philosophy. I am no longer that person. I realised it too quickly shut down possible outcomes I hadn’t considered. Making a big decision shouldn’t solely rely on a strong yes or no answer to a question; it’s about asking the right question in the first place.

Let me explain what I mean.

Take a work scenario where you’re considering a new opportunity. Is the question you need to ask yourself, “Do I want this job?” Or is the better question, “Am I interested enough in this job to continue the conversation?”

If we went with the “If it’s not a fuck yes, it’s a no!” approach, and felt undecided and weren’t fuck-yessing all over the idea, that would mean shutting down the opportunity during the first discussion.

But if we asked ourselves the better question, “Am I interested enough to keep the conversation going?”, the answer might be a soft “yeah”. Not a fuck yes, but still a yeah. And that yeah, over time, might eventually lead to a big old fuck yes. It has for me in the past.

Like I said it’s all about asking the right question.

(Side note: One philosophy I personally subscribe to is “If it’s a fuck no, it’s a fuck no!” I’ve – politely – said no to job opportunities during the first interview or said no to a second date at the end of the first because my “fuck no” radar was up. I always, always, always listen to the “fuck no”.)

Which leads me to a conversation I recently had with Byron Bay-based meditation teacher Caitlin Cady. I met Caitlin a few years ago when I interviewed her for the Women’s Health podcast and loved our chat so much I’ve stayed in touch with her over the years and still listen to her voice regularly via her guided meditation app, Heavily Meditated.

We were musing about purpose specifically – how to find one and whether we even need to have a purpose – but part of what she said felt so relevant to making big decisions that I want to share what she said here.

Caitlin told me: “I’ve noticed there are a lot of people, especially in younger generations, who are totally paralysed by not knowing what to do with their lives. The very best advice that I could give is to just start doing something, because sitting around thinking about what to do will make you more paralysed.

“If we sit here ruminating, we don't actually ever have to give it a crack. Whereas what I'm proposing, and how I've found a way of living my life that makes it feel meaningful and satisfying, is being willing to experiment, iterate, fail, and learn. And then try again and take what I’ve learnt and give it another go.”

And if you get that thing you decided you wanted, and it doesn’t turn out exactly how you thought it would, I asked Caitlin, what then? That’s when she suggested asking yourself a different question (hmmm, there’s a theme here).

“Rather than chasing an external goal — like a new job, new place to live, new relationship, etc — ask yourself, what's the feeling that you're trying to feel by chasing that goal? Pay attention to how you want to feel and set a goal that supports the feeling,” Caitlin said.

The idea comes from the work of author Danielle LaPort. Here’s how Caitlin explained it: “She tells the story of someone who thinks they want to travel, but what they actually want to feel is a sense of adventure and exploration and experimentation, and to learn about different cultures. Then they meet someone, a romantic partner, and everything is totally aligned, except that the romantic partner is afraid of flying and will not travel. So then this person goes, well, this relationship is not for me. But in reality, this romantic partner loves to go to foreign film festivals and loves to go out and eat different cuisines, and so on, but just won’t fly.

“Danielle’s much more eloquent in the way that she describes it, but her point is that all of the feelings that this person wants to feel with their partner — the spirit of adventure and exploration — all of that is available in that relationship. But the external thought of what the person thought it needed to be is different to how it could be.”

I thought about this question — how do I want to feel? — when I was considering an opportunity to work on a brand that I loved. For months, I’d overlooked the niggling feeling that it wasn’t right because I had really wanted to make it work. But when I asked myself, “What is it about this particular job that I hope to feel?”, I realised I didn’t need that job itself. I could feel creative, connected or part of a team in other ways. I could make money other ways. And so, I couldn’t ignore the red flags anymore. The initial fuck yes, became a fuck no.

So my friends, if you’re feeling stuck and have a big decision you’re contemplating, might I suggest asking yourself a better question? It might make the situation a whole lot clearer.

Until our next 3am Huddle,

Lizza x

Photo by Jake Weirick on Unsplash