Your Primary Job in Relationships is to Increase the Other Person’s Self Esteem

Photo by Cristina Gottardi on Unsplash

If you want to have a happy, healthy relationship, your primary objective should be making the other person feel good about themselves. This idea doesn’t only apply to romantic relationships, it also applies to platonic and professional relationships. 

The idea first came to me from a conversation I had with Laura Desimone on the Atila podcast:


Tomiwa (me): What is one thing you think everyone gets wrong about the education system?

Laura: The number one goal of teachers should be to teach students to love themselves. And that’s it.

Me: But… but… What about grades and getting into a good school or getting a good job???

Laura: That part will come. The only reason why people never reach their full potential is because there’s a part of themselves that they don’t love.

*5 seconds of silence as my mind has just been blown and I pick the pieces off the floor*

Me: *thinks* This sounds great in theory, but how do you actually implement that in practice? 

Laura: Well first you have to teach teachers to love themselves.

*Seconds after picking my scattered brain off the floor. It is promptly blown back up again*

That conversation I had with Laura might be one of the top 10 most profound things I’ve ever heard and I think about this conversation at least once a week. So it got me thinking of all my relationships, what function do I play.

First, Let’s do some Self Reflection

Anecdotally, this seems true. The two best teachers I’ve ever had were Ms. Vanderwal, my grade 4 drama teacher and Mr. Stratford, my grade 5-8 gym teacher. Naturally, I forget most of what they taught me (but I do remember the importance of blocking and tableaus). Including my parents, I have to give them a lot of gratitude because I think I got a lot of my self-confidence at an early age from them. Quite simply, what they did best was make me feel good about myself.

Think of your closest relationships. Your partner, siblings, parents, friends, boss, employee, coworker, etc. When was the last time this month you made them feel good about themselves? Matter of fact, After you finish reading this, run an experiment: go and say a genuinely nice compliment to one of them. Remember, that can include partners, parents, siblings, friends, coworkers, bosses etc. If they are overly suspicious and surprised, that’s probably a bad sign. It means that either you’re not good at giving people compliments or that the idea of you giving them a compliment is akin to looking out the window and seeing a pig flying through the sky. Either way, that’s a sign that you need to work on your positivity skills. Or maybe they’re not good at handling compliments (which we’ll talk about later).

By the way, I don’t Know Anything

Essays like this are always slightly juxtaposing for me to write because I feel like I have a lot to say, yet I also don’t know anything. I have “strong opinions, loosely held” on what it takes to be in a good relationship, but I’ve never had a girlfriend and I’m not a parent.

Considering the fact that parental and romantic relationships are the two deepest types of relationships, maybe I’m unqualified to even speak on this topic.

But a lack of qualifications has never stopped me before [grin emoji] 😁. Besides, I think of this more as “publicly thinking out loud, feedback welcome”. That way, if I’m wrong about something, or didn’t consider a different perspective, I can get more people to poke holes in my theory, which ultimately helps me make a more informed perspective.

How to Increase the Self Esteem of Others

The best way to increase someone’s self-esteem is by complimenting and encouraging them. 

First, let’s start with complements. Compliments are tricky because they can easily be abused and become shallow flattery. The key is that the compliment should be specific. I find that sometimes it’s even better to compliment them for something they did a long time ago than something they did recently. 

The second and probably the most important is by encouragement. I am continually surprised by how many people desperately want to do something but  are subconsciously waiting for a “sign” to tell them to go for it. I know someone who started going to the gym regularly simply because I had a five minute conversation with them about what to do with all of their free time . Obviously, I can’t take credit for that, it was all them, but it really speaks to the fact that they were already at the door, the door was open and they wanted to come outside, they just needed someone to nudge them out the door.

This is why I go back to the conversation with Laura. Often, we think that our goal is to protect them and be “practical”. But I think Laura made a good point: If the person has sufficient confidence, they will often find a way to figure out the practicalities.  If you just focus on building up their confidence so they feel like they can do it, their confidence and self-esteem will motivate their brain to find a solution. The mind is fascinating that way. Now, the obvious question is, how do you find the balance between increasing self esteem and promoting delusion?

What’s the Difference between Increasing Self Esteem and Increasing Delusion

Like Aristotle said, virtues are typically the “golden mean” between two traits. On the one hand, You have one extreme of increasing their self-esteem too much. Examples of this include excessive praise and affirmation, complete lack of criticism and shielding from failure. On the other hand you have deep cynicism and criticism. Nothing they do is good enough, you can only ever see the flaws etc. People on this extreme often claim that it’s just “tough love” or “for your own good” and that “you’ll thank me later”.

My theory on questions that involve finding a balance is to optimize for extremes in the micro and the macro will balance itself out. In other words, give them a lot of encouragement and compliments, then when you feel like you’re overdoing it, switch back to criticism. How will you know? That’s tough to say but I would say trust your gut. and the fact that you’re even asking that question, means that you’re being self-aware so you’re already 90% there. Sometimes you might overcorrect to one side but as long as you’re asking yourself those questions, don’t be too hard on yourself.

I also tend to think of it through what I call the Willie Pep strategy. Willie Pep was one of the greatest counter punchers in boxing of all time. I know this because I literally just googled the greatest counter punchers of all time and he was the first name that came up and that will be the easiest for you to pronounce and remember. Anyway, the idea is that when someone comes with a lot of confidence and is overly excited, you counterpunch and give them some critique to make them more humble and make sure they are being practical. However, if they are very low on self-esteem, you counterpunch the other way and give them a lot of encouragement. Now, you have to be very careful, because sometimes someone might be confident and the best thing might actually be to encourage them even more.

Understanding Your Biases, Why you don’t do it Already

Another gem from Laura’s interview:

Tomiwa: How do we teach students to love themselves?

Laura: First, we need to teach teachers to love themselves.

One reason why some people find it difficult to encourage others may be because they weren’t encouraged much when they were younger. It’s possible that they are actually uncomfortable with positivity. It’s like that person you know who gets very uncomfortable when you compliment them. At first you think it’s because they’re “humble” but it might be a lack of self-love and an inability to appreciate the good things about themselves. It’s times like this I strongly recommend reflecting on your childhood and deprogramming yourself. 

Look at the past relationships in your life that affect you the most. Are they self-esteem boosters or drainers. More importantly, ask yourself if you subconsciously learned any negative behaviours from those relationships. As a young guy, I’ve noticed that we guys tend to joke by making fun of each other. Sometimes, it’s just good humor and I find that being able to take a joke from your friend keeps you humble and from being too sensitive. However, some friendships get to the toxic point where whenever someone takes a risk or wants to try something new their friends will discourage them. See Crab in the bucket mentality. This might be disguised as humor but there might be a subconscious fear driving that “joke”.

Finally, by increasing the other person’s self-esteem, you will also increase your self-esteem. Sometimes people find it difficult to raise the self-esteem of others because their self-esteem is already low. This is when “fake it till you make it” can actually be useful. By forcing yourself to be more positive towards others, you will find that you naturally will start liking yourself more as well. Positive energy is contagious.

That’s all I have to say on this topic right now. Like David Ogilvy once said “When Aeschines spoke, they said, ‘How well he speaks.’ But when Demosthenes spoke, they said, ‘Let us march against Philip.’ ”. In other words, I don’t want to just write this article for the sake of writing it. I want to spark a change in your behavior. So after reading this I want you to do something. The next time you talk to someone you have a relationship with, try and raise their self-esteem. You might make them feel better about themselves and make their day. Even if you don’t make their day, at least you’ll raise your own self-esteem.