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In the summer of 2020, while Greek island hopping, I walked the amazing Santorini coastal pathway from Fira to the dreamy destination of Oia.

Oia sits perfectly positioned perched on the northern tip of the island with the most stunning landscape views—the home of the best sunsets.

After an energy sapping and sweaty hike in 30-plus heat, I arrived in Oia in need of one thing—a coffee.

Soon I felt the caffeine flood my body and I was ready to stroll this cute coastal village, like the curious traveller I am.

Unfortunately, I got stuck walking behind a couple who were strolling arm in arm gazing out toward the cobalt blue waters. Forced to perform that awkward slow pace stroll, stuck behind them, waiting to seize the chance to overtake.

Talk about the art of patience.

As their stroll became a crawl, I seized my opportunity to overtake, sliding past them as they glanced at a gelato café.

As I overtook, I could overhear their conversation and felt puzzled. The female asked the male a question, and waited for his response before she provided her response.

I shook my head—if I was the female, the conversation would have been very different. I went about my day, enjoying the gorgeous scenery, taking photos of the pastel-coloured buildings, enjoying all the Greek summer vibe on offer, but I kept replaying that conversation.

It just didn’t sit right with me.

The young female, wearing her sassy summer dress, asking her partner: “Do you fancy gelato?”

All perfectly normal on the surface, but if you dig deeper you notice a learned behaviour in full operation. So subtle, but with big results. She waited for his response—to guide her decision and the next steps.

I didn’t stick around to wait for his response as I seized the opportunity to move ahead, but let’s dissect this as I constantly see this behaviour. It is known as People-pleasing, the act of putting other people’s needs before your own.

If he responded “no,” what would she have done? Just shrugged and said “okay” while inside screaming “I want gelato?”

Surely if she asked if he wanted a gelato, this was because she wanted one but wanted his assurance or permission. She wanted to ensure she was pleasing him first, before her needs. If he didn’t want one and she did, then surely she would be putting him out by asking to stop for five minutes to purchase the gelato.

That is how people pleasers think, I must please everyone and not put myself first, as that could put someone else out.

If we reframe the situation and turn it on its head, then I would have asked a different question.

Here is how it would play out: “I am going to enjoy a gelato, do you want one too?”

How does this change the outcome?

I am clearly signposting what I want and therefore ensure I get what I want regardless of the response. I am putting my own needs and wants first, rather than asking for permission.

Is this selfish?

Of course not; I am in control of my happiness and make it happen.

Why are we giving this away to other people? It inconvenienced no one in this scenario!

Let’s dissect more familiar scenarios.

Have you ever been in a restaurant for dinner and someone asks “anyone having dessert?” before they glance around the table waiting for permission to say they do?

Then as each person at the table shakes their head and replies, no, the person who asked usually responds with, “I didn’t want dessert anyway.”

Of course they did, or why would they have asked.

Again, if you reframe the situation, the discussion would have played out a little differently:

“Oohhh look at that cheesecake; I am ordering that. Anyone else fancy dessert?”

Regardless of the response, there is one happy diner with a belly full of cheesecake.

I was visiting my sister recently with my family. As we explored the city of her new home, I drifted back from the group as I fancied taking some photos. It was a gorgeous summer day and my family was performing the “looking for a beer garden” march.

I wanted to enjoy the present moment of a new city.

With them ahead in sight, I could see a gelato parlour out the corner of my eye.

“Do I have time to pop in and grab a cheeky gelato fix?” I thought to myself.

Of course I did. I seized the opportunity and the next thing I know, I had a salted caramel/mint choc chip gelato cone in my hand and I had caught up with my family.

They glanced at me, my cone, and shrugged.

As we turned the corner, we were presented with a riverside beer garden. As someone who doesn’t drink alcohol, I was happy to sit and chill knowing I had enjoyed my sweet treat as my family sipped their refreshing drink—their own treat.

If you are someone who struggles with people-pleasing, here are some tips:

1. Ask yourself if you know what you want from life and certain situations. Until you know, you will always be following someone else.

2. Practice knowing what you want. Just yourself. When you are out and around people, decisions and opinions will be shared. In your head, only for you, ask if you are happy with the discussion, your input, and the decision. If you could be convinced you weren’t going to upset or inconvenience anyone, or be judged, would you say anything differently?

3. Now practice for real. The next time you are out and about decide what you want, then announce or ask for it. Watch what happens.

Here are some examples:

1. Dinner Plans. Announce what restaurant you have always wanted to visit.

2. Movie Night. Outline the top three movies you have wanted to watch but always settle for someone else’s choice.

3. Meeting friends. Suggest a time that suits you first rather than waiting to be told a time.

4. It is the weekend. You always end up doing what your kids, partner, or friends want to do. For once decide what you want to do then tell them.

The “worst” thing that will happen is you may need to compromise or discuss your opinion, or choice, a little. But it’s okay as you’re prepared for this.

Keep practicing, as the more you say yes to you, the happier you will become. And the happier you become, the more confident you become.

You can please yourself and still be considerate to others. Sometimes you even need to compromise, but until you say yes to you, you will always settle for someone else’s plans.

~