The "Work On Yourself" Trap


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Hey friends,

Big rant this week for the singles and not looking. Do let me know how this resonates... always appreciate you writing back.

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At a dinner last night, I overheard a familiar refrain: “I need to work on myself before I start dating.” It’s practically the anthem of the personal development community.

I sat there, fighting the urge to interrupt their conversation.

(hearing one more saying “let me work on myself” and I will screaaaam)

Because this particular piece of advice isn’t just misguided.

It’s counterproductive.

Here’s the truth about this “work on myself first” mindset:

The Relationship Paradox

“What gets wounded in relationships can only be healed in relationship” - Terry Real.

We all get our wounds or relationship patterns from our upbringing, our relationship with mostly parents, attachment issues and so on.

And you don’t get past them by just working on yourself in isolation. You get past them by seeing them play out again and again in the relationship and then choose differently.

Most relationship wounds only heal through relationships. Not through meditation retreats. Not through self-help books. Not through solitary reflection.

When you tell yourself you need to “work on yourself first,” you’re removing the very environment with the right stimulus where genuine growth happens. It’s like saying you need to get better at swimming before getting in the pool.

Not gonna work.

My take: I don’t know how shitty I am in relationship until I am in one… and I’d rather find out sooner by being in one to unlearn those shitty patterns.

I’ve seen wise couples 30 years into their marriage. Still working on themselves.

The work never freaking stops, so stop using that as an excuse to not going to date.

The Hidden Psychology

Let’s call this what it really is: fear disguised as responsibility.

“I need to work on myself first” sounds mature.

But dig deeper and you’ll usually find:

  1. Fear of rejection
  2. Fear of hurting others
  3. Fear of facing your patterns
  4. Fear of being hurt again.

These concerns are valid. But avoiding relationships doesn’t eliminate them—it merely postpones your confrontation with them.

The Competence Fallacy

Your relationship skills don’t improve in isolation.

Ask yourself: How would you know you’ve “fixed” your attachment issues without testing them in actual attachment scenarios? How would you identify your relationship triggers without encountering someone who triggers them?

This isn’t theoretical. You can’t read your way into relationship competence.

Also: you will never fully heal.

So drop that ambitious healing agenda and accept that healing is ongoing.

Just because you encounter something that feels a bit raw and vulnerable doesn’t mean to stop.

It means “slow down and pay attention”.

“If you cannot feel it, you cannot heal it”, as the saying goes.

One of my exes, a phenomenal lady, once said that she would have to attain enlightenment first before she can love.

I said “Nah, stop getting triggered by me first.”

We laughed.

(She is now happily married, and we are still good friends)

The Time Allocation Reality

If finding a partner matters to you, it needs dedicated time and intention—just like anything else that matters.

When you tell yourself you’re “working on yourself first,” check your calendar. If you’re not blocking time & resources specifically for meeting potential partners (sourcing, vetting etc..), you’re not prioritizing relationships.

You’re avoiding them.

Which is fine if that’s your focus.

AND

If deep down you do want to end up with someone,

and you don’t put in the time, energy, attention, resources?

Ain’t gonna happen.

In theory, you can keep working on your products (i.e yourself) and then the market will find you.

In reality you need to keep putting yourself out there in intimate relationship, get feedback and then iterating.

The Growth Acceleration Effect

Ironically, relationships accelerate your personal growth. The right partner will:

  • Call out your blind spots faster than any book. (I thought I’m good until the lady screamed at me for forgetting to put the toilet seat down AGAIN…)
  • Bring out your insecurity without shaming it.
    • As a guy, I gotta work through a shit ton of insecurities all the time “my d*ck is too small, I don’t last long enough in bed, I don’t make enough money, etc..”
  • Motivate self-improvement more effectively than willpower alone
    • (I definitely exercise and dress better once I’m in dating mode. Vanity goes a looong way as motivation brah)
  • Provide embodied examples of what healthy relating looks like
    • (for eg, stay open-hearted during conflict, or inform “I’m being triggered, I need 15 minutes”)
  • Create the psychological safety needed for real change

The Path Forward

If you recognize yourself in this pattern, here’s what actually works:

  1. Name Your Patterns: Tell potential partners about your known issues so they can help you identify them. Like “I tend to get overly attached” or “I tend to dissociate in most heated moments” or “I play hot n cold”
  2. Set Growth Metrics: Define what “growth” actually means with specific behaviors, not vague feelings. “I will not scream at you”, or “I will find one lovely thing to appreciate about you daily”
  3. Keep Dating & Iterating: I admit: most of the time, most of us are better off being single than being with a bad fit. But you need to get out there, engage, get feedback.

“If you know you are only 30 mistakes away from what you really want, how fast do you want to fail?” - Fran from WeThinkDeeply.

The Relationship Growth Loop

Real growth happens in this loop:

  1. Date and interact
  2. Notice your patterns
  3. Work on specific issues
  4. Apply new awareness in relationships
  5. Repeat

Breaking this loop by “working on yourself first” actually slows your growth.

If you don’t want to "date", just say “I’m looking for growth partner that I want to do this work with for a life time”.

Whatever your terms you prefer.

Just Don’t Stop.

The Uncomfortable Truth

Let me be direct: When you claim you need time to “work on yourself” before dating, you’re usually procrastinating on facing your deepest fears.

And that’s the opposite of personal growth.

The real work isn’t becoming perfect before entering relationships. It’s being brave enough to be imperfect while in them.

Last,

if you struggle to be good enough

a few line from the poet Mary Oliver that saves my life.

“You don’t have to be good

You don’t have to walk a hundred miles in the desert repenting,

You just have to let the soft animals of your body

love what it loves”

Go take some rest, listen to the body, and keep going

with all my love,

Khuyen

#rantover

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