The Harder You Try to Be Original, the More You Sound Like Everyone Else

For as long as I can remember, I tried to get myself a girlfriend.

A long time ago — I really don’t remember the year — I tried online dating.

I wasn’t much of a person who goes out, so I thought it would be much simpler.

After all, I used my computer a lot.

So it only made sense.

This was way before swiping left and right.

Personally, it was more challenging than it is now.

Back then, there were 2 main ones.

We’ll call them OK and Fish.

These were the ones where you had to fill out a whole bunch of info and answer questions about yourself.

Then they would “match” you with their top picks.

Of course, thinking that, I thought these matches were the ones for me.

So why when I messaged them, they never responded?

My experience with those sites were pretty shit.

So I temporarily gave up on it.

But I kept trying.

Years later, I tried it again.

Don’t remember if I made new accounts or used the accounts I made previously.

Anyway, the second time around, I managed to get myself a date!

But this was my first date using these dating sites.

So after the date, when I asked to go out again, she said no.

I’m pretty sure I stopped trying after that.

Then, years… much later, in 2019, I had this insane amount of confidence.

I had been working out throughout that year and had been in the best shape of my life.

And truth be told... I was a little lonely.

So I tried online dating again.

Of course, by then, it wasn’t about dating sites anymore...

It was about dating apps.

And the most popular one at the time was Tinder.

There was some others as well.

There’s this one, I’ll call Bee, where it was like Tinder, except it was up to the woman to choose if they wanted to match with the man...

Or something like that, I don’t remember.

Anyway...

I didn’t have luck with Bee.

Just didn’t think women were all that interested in my profile.

And Tinder wasn’t that much easier either.

I must’ve fixed up my profile dozens of times, trying to say the right things to grab a woman’s attention.

The harder I tried to force the right answer, the more I kept circling the same kinds of answers.

I thought repetition meant I was getting closer.

Sometimes, it only meant I was searching the same place harder.

That was the first thing I needed to accomplish.

Forget getting a date.

I needed to get someone’s attention first.

I’m trying to remember where I got the idea at first, but something reminded me of an episode of Mad Men.

I wasn’t trying to think about advertising.

The connection just showed up.

Mad Men was a show about the advertisers back in like the 60s or 70s.

Anyways, the only reason I knew about this show was because...

...with absolutely no interest or anything in advertising and marketing, I took a college course on Creative Advertising back in 2012.

At the time, I had no idea any of that would matter to me 7 years later.

So... back to that episode...

In that episode, there was this powerful scene.

I can’t do it justice by talking about it.

If you want, here’s the scene:

The main character, Don, had to pitch an idea to Kodak on how they were to advertise their new technology of their “wheel.”

It was like slide show mechanism in the shape of a wheel.

Kodak wanted them to talk about the future and make the wheel exciting.

But Don had a different idea.

He decided that it wasn’t a wheel...

It was a carousel.

And instead of talking about their future tech...

He decided to talk about...

Nostalgia.

And how powerful taking someone back to a different time in the past was.

So... I took that concept and applied it to my Tinder profile.

It wasn’t a dating idea.

It was an old advertising idea that suddenly fit a completely different problem.

It was so many years ago, and I can’t remember exactly all that was on it.

But luckily, my awesome wife saved it.

So my profile said:

If you can relate to these things, we can get along:

• had a book specifically for all the phone numbers of the people you knew

• calling to ask your crush’s parents if you can talk to them

• yelling at someone that you were already using the only phone line in the entire house

• MSN Messenger

• remember watching ‘The Hit List’ and ‘106&Park’ for music

After putting that on my profile — and some other things — I was finally getting women to swipe right on me.

Once I noticed the connection, then I could actually build the profile around it.

The connection gave me a direction.

But it still needed to become something another person could recognize and respond to.

But of course, you can’t see who swiped right on you unless you pay.

I didn’t pay.

So mission 1 accomplished: get attention.

I eventually got a couple matches.

But I had no idea how to message!

So mission 2 was to get a response.

Because it didn’t matter if you matched with someone...

If you don’t say the right thing, you’re not getting a reply back.

At least, that’s how it was for me.

Looking back, I was working on attention grabbing hooks before TikTok was a thing.

Because I had to say something that was not something typical a woman sees often — like “Hey” or “You’re pretty.”

And on top of that, start a conversation going.

I couldn’t always explain what would work yet.

But I was starting to notice what felt predictable.

As I said, the first few matches I messaged, did not reply back to me.

But I think I eventually got better at it, because pretty soon, I got them to reply back and converse.

Mission 2 accomplished: learn to message.

Then I came to the next challenge: getting the date.

Of course, there were a few women I was messaging with who eventually ghosted me.

I always thought it was something I said, so I was always looking to improve what I said.

So I kept staring harder at the words, even when the words might not have been the whole problem.

Asking for the date during a good conversation I think was easier.

Because if you already like someone enough to have a chat... on a dating app... then why would you say no, right?

And that’s how it went.

I don’t remember how I asked the first one to say yes, but it was enough to get the date.

Mission 3 accomplished: get the date.

We agreed to meet at this mall she was close to.

I always made sure it was at a public, open place.

Their safety and them FEELING safe MUST be priority.

I got there and I waited...

And waited...

And waited.

After some time, I called her, because I got her number from our chats.

Turns out... she forgot about our date.

Well, that made me feel special…

She rushed to meet me.

And I was feeling pretty bummed about it.

But made the best of it.

We were walking around the mall, talking... got some bubble tea — or boba... talked some more...

And by the end of the date, we went our separate ways.

I texted her a few hours later and wanted to know if she wanted to go out again.

She said no.

And that was my next mission...

Mission 4: get the second date.

But I realized...

Based on my date a few years earlier with that girl from the dating site and the one I just had...

I had to not end the date and message after about a second date.

I decided I had to arrange the second date ON THE FIRST DATE.

And what a game changer that was.

The realization didn’t finish the job.

It just gave me something new to test.

Because doing it all over again: matching, messaging, getting the date...

I went to dinner this time with this other woman.

Think it was her that wanted to go eat Korean.

And I knew a spot.

So we went there.

And during the date...

At an appropriate time...

I suggested we go somewhere else for our second date.

As they say in sales, I “assumed the close.”

I didn’t ask if she wanted to go on a second date or not...

I assumed she wanted to go on a second date.

So I suggested a movie date next.

She said yes.

Mission 4 accomplished: arrange second date on first date.

We went out again and watched Jumanji.

Went to dinner right after.

And after the date, we messaged each other.

I thought all was going pretty well.

She said she was going on vacation with her girls.

Whatever, that’s cool.

But what wasn’t cool was that somehow...

I wanted to save something from her Tinder profile so I opened Tinder.

Why did I see her profile inviting other guys to “party” with her and that she was from “out of town.”

Now, I know we never mentioned anything about being exclusive to each other or anything...

But I still felt ways about it.

But surprisingly, I didn’t even take it badly.

I looked in the mirror...

Said “You’re awesome”...

Opened Tinder started swiping.

One night, I was house sitting for my cousin who went on a vacation.

And I particularly remember swiping right on someone right before I slept.

The next morning I woke up, I saw that she matched with me!

And did it all over again.

Messaged...

Got the reply back...

Chatted...

Then got the first date.

We went out to like a restaurant/bar called JACK AStor’S.

She was 7 minutes late.

But that date was different than the others.

During the other dates, I was the one who was talking more and keeping the conversation going.

But this one...

She was the one who kept the convo going.

It was quite refreshing.

During that date, we arranged the second date.

And at the end of the night, I walked her to her car, hugged her, and we parted ways.

Since this was right around Christmas, I didn’t contact her for the week so that she could spend time with her family.

Of course, I was worried she would forget about me.

But I didn’t wanna seem needy.

Looking back, the useful shifts rarely came from having the entire process figured out.

I kept running into a problem, noticing something I hadn’t noticed before, and then testing whether it actually worked.

At first, online dating looked like a series of problems I could solve by trying harder.

Fix the profile.

Write a better message.

Keep the conversation going.

Get the date.

Arrange the second date.

And to a certain extent, that worked.

I got better through repetition.

But the biggest improvement to my profile didn’t come from fixing my profile for the hundredth time.

It came from an episode of Mad Men.

An episode I only knew about because I took a Creative Advertising course 7 years earlier…

…despite having absolutely no interest in advertising or marketing at the time.

I wasn’t sitting there deliberately thinking:

“How can I combine nostalgia-based advertising with online dating?”

The connection just showed up.

Then I took the connection and deliberately built something with it.

That difference matters.

Because creation is not one mental process.

There is the process that helps you discover what might be worth building.

Then there is the process that helps you construct it.

Both require effort.

But they do not require the same kind of effort.

And a lot of digital builders unknowingly use construction-mode behavior while they are still trying to discover the idea.

They evaluate before there is enough to evaluate.

They edit before there is an argument.

They research before they know what they are actually searching for.

They try to consciously force an original connection…

…then assume they lack creativity when their mind keeps producing different versions of the same thing.

But the problem may not be a lack of creativity.

You may just be using the wrong mental mode for the job.

Creative fixation happens when your attention becomes trapped inside one way of understanding a problem.

You’re still thinking.

You’re still working.

You may even feel like you’re making progress because you keep producing new words, new drafts, or new versions.

But your mind is searching the same small area over and over again.

It’s kinda like when I fixed my Tinder profile dozens of times.

I kept trying to find the right words.

But the harder I forced myself to find the right answer…

…the more I circled the same kinds of answers.

• Search-Space Narrowing:

Once your attention locks onto an initial idea, example, or interpretation, related ideas become easier to retrieve. Your mind starts searching near what is already active instead of considering completely different directions.

• The Familiar-Answer Loop:

The first solution creates a frame around the problem. More effort inside that frame may produce additional variations, but not necessarily a different perspective.

• Invisible Fixation:

People often do not realize when they are fixated. From the inside, it just feels like the problem requires more concentration, another rewrite, or one more piece of information.

• Derivative Output:

Recent examples can occupy so much of the mental search space that the builder unknowingly repeats their structure, language, and assumptions — even while trying to create something original.

This is why effort can become misleading.

The work feels difficult, so you assume the responsible response is more pressure.

But sometimes, the pressure is keeping the same mental frame active.

You aren’t failing to find the answer because you stopped thinking.

You can’t find it because you haven’t stopped thinking in the same direction.

The incubation effect describes what can happen after you have already spent time with a problem…

…and then temporarily stop directing your full conscious attention toward it.

That does not mean the mind magically creates a completed answer while you do nothing.

It means stepping away may weaken the grip of the ideas you were fixated on, create room for more distant associations, or help you return with a different mental frame.

It’s kinda like when the Mad Men connection showed up.

I had already loaded the problem.

I knew I needed attention.

I knew my existing profile wasn’t working.

I had rewritten it dozens of times.

But I wasn’t deliberately trying to remember an advertising lesson from 2012.

The relevant memory appeared after the problem and the raw material were already inside my head.

• The Problem Must Be Loaded:

Incubation is not aimless waiting. Its effects are connected to problems the person has already encountered and spent time trying to solve. Kinda like how Dr. House solves his patients’ cases.

• Pressure Can Stop Without the Process Ending:

A low-demand period can remain psychologically connected to the problem even though the person is no longer consciously forcing a solution.

• Fixation Decay:

Temporarily leaving the problem may reduce the influence of misleading ideas, failed attempts, or assumptions that were dominating attention.

• Associative Movement:

When conscious control relaxes, distant or previously overlooked information may become easier to connect with the original problem.

This is also why walking can feel different from sitting at a desk and demanding an answer.

Walking appears to help more with the expansive part of creativity — generating possibilities and finding fresh directions.

It does not appear to provide the same advantage for narrow, focused problems with one correct answer.

In other words:

Movement may help open the search.

But focused control is still needed to choose and finish.

So stepping away is not automatically productive.

But staying at the desk is not automatically disciplined either.

Sometimes you have already done the part that conscious effort can do.

Continuing to apply pressure after that point does not prove you are serious.

It may only prove you do not trust the parts of creation you cannot directly supervise.

Associative combination is the ability to connect information that is not normally connected.

This is where a lot of originality comes from.

Not necessarily creating something from nothing…

…but recognizing a relationship between things that previously seemed unrelated.

It’s kinda like taking a pitch about Kodak technology and using it to improve a Tinder profile.

Advertising and dating were not the same subject.

A carousel and an online profile were not the same product.

But the emotional principle underneath both situations was useful:

Nostalgia creates connection.

That was the bridge.

• Remote Association:

The mind can search across memories, concepts, experiences, and observations that were originally stored in completely different contexts.

• Spontaneous Generation:

One part of creative cognition appears to support wandering thought and the loose association of ideas.

• Executive Selection:

Another part helps restrict the search, manipulate the idea, reject what does not fit, and select what is useful.

• Originality Through Recombination:

A useful idea can feel new because previously separate knowledge has been combined in a way that fits the current problem.

I did not deliberately create the memory of Mad Men.

But once the connection appeared, I had to do something with it.

I had to decide whether nostalgia actually fit the profile.

I had to choose the memories.

I had to write the examples.

I had to turn a loose connection into something women could read and relate to.

The connection was discovered.

The profile was constructed.

That is the relationship most builders miss.

They either try to consciously control everything…

…or they romanticize inspiration and wait for a complete idea to arrive.

But creative work does not require choosing between intuition and discipline.

It requires knowing when each one becomes useful.

Between discovery and construction is what I think of as the Recognition Gate.

This is the moment when a loose signal becomes noticeable enough to capture…

…but not developed enough to judge as a finished idea.

It’s kinda like remembering the Mad Men episode.

At that point, I did not have the completed profile.

I only had a connection:

Nostalgia might help me get attention.

That was enough.

The connection did not need to explain or prove itself immediately.

It only needed to pass through the gate.

The rule here is:

Capture first. Evaluate later.

The job of Constructive Mode is to turn the selected signal into something real.

This mode:

• questions

• tests

• organizes

• removes

• articulates

• edits

• completes

• publishes

It’s kinda like taking the nostalgia idea and turning it into specific memories:

Phone books.

Calling your crush’s parents.

MSN Messenger.

The Hit List.

106 & Park.

Once the signal appeared, openness was no longer enough.

I needed constraint.

I needed judgment.

I needed craftsmanship.

And eventually, I needed evidence from the real world that the idea worked.

That is the identity shift.

You are not one mind performing one creative task.

You are a builder moving between receptive and constructive modes.

One mode expands.

The other compresses.

One recognizes possibility.

The other creates the asset.

And the more capable builder is not the person who applies the most control at every moment.

It is the person who knows when control is useful…

…and when it is crowding the very process they are trying to access.

Your job is not to consciously manufacture every valuable idea.

Your job is to prepare your mind, recognize what emerges, and become disciplined enough to build it.

The idea may arrive as a signal.

The asset still requires craftsmanship.

Realizing that your mind has two different creative modes can feel relieving.

Because now you know you aren’t necessarily bad at coming up with ideas.

You may have just been trying to force an idea to appear using the part of your mind designed to judge and finish it.

But understanding that difference is not enough.

Because you could also take this entire realization and turn it into:

“I guess I should go for more walks.”

Which would be nice.

You might become a very relaxed person.

But you’d still have the same unfinished newsletters sitting in your notes.

The goal is not to stop trying.

The goal is to create a better rhythm between discovering an idea…

…and deliberately turning that idea into something useful.

The operating sequence is:

Load → Release → Notice → Select → Construct

Each stage has a different job.

And most creative frustration happens when you ask one stage to do the job of another.

You try to construct before you’ve noticed anything worth constructing.

You keep loading more information when your mind already has enough material.

You reject the signal because it doesn’t look like a completed idea.

Or you stay in discovery forever…

…collecting interesting thoughts without ever building anything from them.

This sequence prevents both extremes.

It gives the mind enough freedom to make a connection.

But it still requires you to turn that connection into an asset.

If this helped you see your own attention a little differently, I think you’ll enjoy The Psychology of Digital Builders.

Every week, I break down the hidden psychological patterns that determine whether creators, knowledge workers, and digital builders turn what they know into newsletters, frameworks, products, and other online assets...

...or quietly spend years consuming instead of building.

I’d love to have you building alongside us.