Living With Insecurities: The Wisdom of Enough8 min read

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On numerous occasions, I’ve deleted phone numbers simply because the other person wasn’t enthused about chatting with me. Maybe they took too long to reply, or worse, ignored my message. I’ve even had instances where I deleted a contact simply because they just didn’t seem interested in continuing a specific conversation.

While this might look like “high standards” or “not chasing anyone,” it’s closer to insecurity – the nagging sense of not being good enough. I can tell because rather than that confident feeling that I was “filtering out those who don’t value me,” they were more anxiety-driven. I did them because I didn’t know if they liked me, would embarrass me, or something else. I was feeling uncertain.

Why Am I So Insecure?

While insecurity itself isn’t a mental illness, overwhelming and persistent insecurity can often suggest underlying mental health problems such as narcissism, anxiety, paranoia, addictive or dependent personalities, and trauma.

If you ask me, I’d say my insecurity stems from my childhood and the social conditioning I experienced growing up. My parents weren’t poor, but they always reminded us that we weren’t rich either. On top of that, constantly being told that I couldn’t have what I wanted, or that I’d embarrass them if they took me out, really messed with my mind.

Heck, throughout my teenage years, I despised the clothes I wore. I wanted to look cool, but without anyone even reminding me, I told myself I wasn’t rich enough for that. Gosh, I really hated those clothes and shoes.

I remember when I gained admission into the university and saw a fellow young guy with a BlackBerry Z10. I felt super-intimidated, despite his standing in the same queue as me submitting the same files for the same registration process. It’s funny how the first time I operated the Z10 I was disappointed with it – the same disappointment I will feel when I first had sex.

Insecurity can be bad as it adversely affects various aspects of your life. In relationships, it may lead to possessiveness, constant need for reassurance, or even emotional manipulation, straining the bond with your partner. At work, insecurity can make you hesitate to share ideas, take on important tasks, or ask for promotions you deserve. Socially, it may cause you to isolate yourself, missing out on friendships, experiences, and opportunities that could enrich your life. 

Over time, unchecked chronic insecurity can erode your self-esteem, fueling anxiety, narcissism, depression, and a distorted self-image, ultimately preventing you from living authentically and reaching your full potential.

How To Be Less Insecure

It was not until my 400 level when I took my self-development seriously and started challenging my insecurities – those internal monologues – that I began to see improvement in different aspects of my life.

It takes more than just positive affirmations or meditation to be less insecure. You have to do a lot of internal work: I had to read a lot of books. I had to actually learn skills and feel confident in my abilities. I had to make some money. I had to buy myself the sort of clothes I preferred. I had to wear perfume. I had to actually prove the voices wrong.

I’m over 6 years into the self-development journey and at this point, I can say I am pretty much over the things that triggered my insecurity in the past – The pizza and shawarma didn’t make my taste buds explode. Sex and money just like the damn pizza only feel great while it lasts, and then it’s back to boring, or seeking something else. 

I’m looking around and I am almost feeling nihilistic. I am now running away from the soda and meat pies that I used to crave in secondary school (because I don’t want to risk my health). I am now running away from the ladies I used to drool over in porn and on the streets (because I don’t want to risk my peace or health). I am now running away from the jobs I used to idolise (because f*ck working all those hours for someone who won’t pay you enough).

Does this mean I have overcome all my insecurities? Am I saying that I’m now 100% free from them? Hell no. Haven’t you been listening? They have been the fuel inside of me, driving me to seek improvement.

  • I started reading about communication because I was insecure about talking to strangers.
  • I started developing high-income skills because I was insecure about how much money I had.
  • I started working out and dressing better because I was insecure about how I looked.

Almost all the achievements and qualities people admire in me today came from battles with insecurities. The larger the insecurity, the bigger the praise.

Yes, I can make enough money to take care of my basic needs (thanks to my skills), but I still feel insecure about not knowing how to leverage it to become financially free. Yes, I can certainly talk to ladies (thanks to my sharpened communication skills and charm), but I still haven’t been able to get that bodacious, intelligent, and sophisticated lady to be my girlfriend

Do you see the pattern?

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How To Get Rid of Insecurities

It seems that whenever I overcome an insecurity, it transforms into an even bigger one. Ask yourself, how many percent of society today are financially free? How many of them have very beautiful, intelligent, and sophisticated partners?

The truth is, even Elon Musk and Chris Hemsworth have insecurities they are dealing with from time to time. The ladies are not exempted, from Taylor Swift to Oprah Winfrey.

While it is important to actually do something about your looks, communication skills, and financial status you need to know when it is enough. 

  • Maybe you don’t have to be swole, or botched. Maybe just staying fit, dressing well, and wearing nice perfume is enough.
  • Maybe it is okay to date a lady who is not a 10/10. Perhaps a 7/10 is enough. 
  • Maybe it is okay to keep working for money till you’re well into your 60s. As long as it is enough to pay your bills, and afford you the chance to still enjoy your life.

Maybe the aim isn’t to get rid of your insecurities. Maybe true victory is being able to sit with your insecurities unperturbed. It is saying, “That is enough”. Maybe you need to learn how to live with your insecurities.

“True story, Word of Honor: Joseph Heller, an important and funny writer now dead, and I were at a party given by a billionaire on Shelter Island. I said, “Joe, how does it make you feel to know that our host only yesterday may have made more money than your novel ‘Catch-22’ has earned in its entire history?”. And Joe said, “I’ve got something he can never have.”. And I said, “What on earth could that be, Joe?”. And Joe said, “The knowledge that I’ve got enough.”. Not bad! Rest in peace!”

– Kurt Vonnegut

Conclusion: Everyone Is Insecure About Something. It’s Only Natural.

This is not intellectual gymnastics to justify an inability to “succeed”. It is just a reminder to do things with less angst while savouring the process – like role-play and sex before climaxing.

So next time, when they don’t respond promptly to the chat or agree to meet up, you don’t end everything there and then. Because, many times the real issue isn’t the behaviour, but the underlying expectations that were not fulfilled. 

No one expects their 5k Facebook friends to message them every day. But, there are usually high expectations from a crush, lover, or family. No one expects to buy an entire planet. But there is high expectation to buy that new iPhone. 

Everyone feels insecure about something from time to time. It is only natural for a social species. However, the ability to differentiate necessities from mere expectations is an invaluable skill.

When you’re tongue-tied facing your crush, ask what necessities or expectations are holding you back. Are you less human or are you just holding yourself to high standards and self-rejecting?

Learning to be okay with enough – enough intellect, looks, money, pleasure, comfort, effort, etcetera – is perhaps the secret sauce to living a richer and happier life. 

Books on Insecurity

Here are some books I recommend to help you deal with insecurities 

  • Rejection Proof: How I Beat Fear and Became Invincible Through 100 Days of Rejection, by Jia Jiang
  • The Subtle Art of Not Giving a F*ck: A Counterintuitive Approach to Living a Good Life, by Mark Manson
  • You Are a Badass: How to Stop Doubting Your Greatness and Start Living an Awesome Life, by Jen Sincero


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I enjoy writing long-form SEO content for self-help and personal development blogs. I can also do simple graphics design and copywriting. I’m an author, coach, logician, introvert, and storyteller. I love simplicity.

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