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If You Keep Waiting For The ‘Right Time’ To Have Important Conversations, They’ll Never Happen

Have you ever had to do something you really didn’t want to?

I’m not talking about the small things, like sitting through a compulsory meeting or turning up to that person’s birthday that you said you would.

I mean the bigger things, the ones that you feel you simply have to do.

A couple of years ago, I got offered a job. I know usually that’s a cause for celebration, finally a reason to justify another g&t and a cigarette. But when you work freelance and you’re nowhere near the end of your current contract, the idea of handing in your notice early is a big no go.

A displaced sense of loyalty (to a company I didn’t even work for a few months earlier), and a fear of burning bridges lead to endless emotional chaos, served with a side dish of scrambled brain.

Deep down I knew what I wanted to do.

Even more than that, I knew what I was going to do; I was going to quit my job. I mean, the new job meant spending 4 weeks in Ibiza. It was kind of a no brainer.

But there was one problem.

At some point between accepting my decision to leave my current job and starting this seemingly idyllic new one, I would have to do the very thing you’re not supposed to do as a freelancer: tell my boss I wanted to leave.

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Days passed while I figured out the best time to talk to him, my excuses for not continuing to get more and more outrageous.

What started as, “He seems a bit busy today, I shouldn’t hassle him,” turned into, “I’m 99% certain his girlfriend might be about to leave him and I don’t want to add to his pain”.

I’ve had a few of these moments in my life; times where I have felt paralysed with fear about something I knew I had to do.

They are rare moments, but often hugely important because it feels — whether true or not — that the survival of your future-self relies on doing them.

If you grew up knowing that you were anything that deviated from the hetero-normativity — the “straight jacket” — that society places on us from the day we are born, you’ll probably know what I’m talking about.

Granted, not for everyone. But in my experience there comes a time where you feel like you have to tell people that you’re different, in my case gay.

At 17, it nearly spilled out of me when my mum and I hit the roads for a driving lesson. After stalling the car for the umpteenth time, I just started sobbing. But it didn’t feel like the right time.

I nearly dropped it in to conversation as I asked my sister to “please pass me the gravy” over a family Sunday lunch. Again, it didn’t feel like the right time.

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I had the same feeling, years later, when I knew I needed to end a relationship.

He was a good guy, well intentioned and kind. But you know, sometimes it just isn’t right.

​I had started to feel suffocated, like I was heading towards a future I knew I didn’t want for myself.

But, boom! There it was again! That same feeling of fear when deciding how to tell this poor guy that I just couldn’t stand the idea of spending another night sleeping in his bed.

Do I do it before his friend’s wedding? Well, we’ve already started looking at where we could stay. Do I do it before his birthday? No, I should wait.

I couldn’t for the life of me work out when there would ever be a right time to break up with the guy.

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Professor Stephen Peters is an English psychiatrist. He wrote a book (which I highly recommend a read of) called ‘The Chimp Paradox’, in which he talks about managing the ‘chimp’ side of our ‘human’ brain.

In his book, Peters says that the key to communication is “preparation”.

Ultimately he argues that if you try and have an important conversation, without the right person, right time, right place, right message or right tone, it will inevitably fail.

I remember reading this for the first time and feeling like it was a revelation.

“This is where I’ve been going wrong all this time!” I thought. If even one of these things is out of sync, how could I possibly have thought that the conversation would go well?

It made sense.

In hindsight, coming out to your mum while tears are falling onto the steering wheel in your hands probably isn’t the right time or place.

But as I’ve gotten a bit older, I’m not sure I am able to whole-heartedly agree with this idea as much as I once could.

Absolutely, I do believe timing, place and all of the above are often vital factors when it comes down to ‘perfect’ communication.

But life, I have realised, isn’t ‘perfect’.

My parents found out I was gay by reading my diary, not long after that driving lesson. I broke up with my boyfriend after work on a Tuesday night, standing in his bedroom. And I told my boss I wanted to quit when we were in the smoking area of our office together.

The truth is I felt infinitely lighter after each one had happened, as if finally my life could start moving more in the direction I wanted it to.

As much as the right time, right place, right tone and right message might help these conversations go smoothly for us, I can’t help but feel that waiting for them all to align may only prevent us from becoming as happy as we could be, sooner.