[Side Hustle Diary] How I Learned to Spot 'Jobs Not to Apply For' After Being Rejected 46 Times

As I approach retirement, I want to be able to work a bit more at my own pace.

To make that wish come true, I started taking on side hustles at age 50 to learn how to work outside of being a regular company employee.

In my previous article, I wrote about how, after landing my first job, I failed to get any work despite applying to 46 different postings.

I am so happy that so many people read it and gave it so many likes.😊
Thank you so much!

Getting back to the story...
The period where I couldn't land any jobs was painful, but looking back now, I wasn't just failing over and over.

While applying,

'This might be a bit different'

I encountered jobs that made me feel that way several times.

At the time, I had little experience and just wanted any job I could get.

That is exactly why, even though I felt something was off, I still went through interviews and worked on test writing assignments.

This time, I would like to write about the jobs I actually experienced and what I learned from them.

What you will get from this article

・The discomfort I felt as a side-hustle beginner

・Real-life examples of jobs I encountered while applying

・5 things I changed in how I choose jobs

・The reason why the period of 46 rejections was not a waste

📍Jobs that were all interviews and no actual work progress

One job was a posting for AI-assisted article rewriting.

After applying, I was immediately asked for an online interview, which I attended.

At first, the questions were about my experience using AI and my learning background.

I told them I use it for work, and then they followed up with questions about what my goals were and so on.

There was almost no detailed explanation of the business, just a brief overview.
After the interview was over, I thought we would move on to a test writing assignment or a discussion about a specific project, but then...

Next is a second interview with upper management.

Wait, a second interview for a rewriting job?

At that point, I felt a bit uneasy...

In the end, I never heard from them again, but I remember feeling relieved because I felt like any further time spent would have been a waste.

Also, for a different job, there was a similar flow after the test writing, where they brought up a second interview.

Of course, in both cases, they insisted that to proceed to the second interview, I had to register for LINE or Chatwork.

Is it really normal to have a second interview for a writing job?

Of course, I haven't proceeded to a second interview for every single one, so I can't say for sure that they were all problematic jobs.

However, besides the second interview talk, the content of the interviews often involved questions about my personal life, small talk, the interviewer's personal stories, or discussions about my goals for my side hustle, and they rarely explained the actual work clearly, so it didn't seem like a normal job at all.

📍 Jobs that recommended other work

This one still sticks in my memory.

Even though I applied for a writing job, almost nothing about writing came up during the interview.

They asked me again about things I had already written in my application and profile,

I often wondered,

Are they actually reading this?

And in the end, what they introduced to me was social media management.

I am applying for writing jobs.

However,

The process was, "First, register on LINE, and we will discuss and decide which job to assign you through periodic interviews."

That was the flow.

What kind of work is it?

What is the revenue structure?

I asked several times, but there was no clear explanation.

In the end,

The conversation turned to, "The work we introduce is not writing."

That is what happened.

The job description and the actual conversation were different.

After the interview was over, I felt completely exhausted.
It was precious time I had carved out between my main job, housework, and childcare...

📍 A project I honestly struggled with quite a bit

This project was the most difficult to judge.

It was a project where, after a test writing assignment, they said it was not acceptable, and that they would not accept the final submission unless I received feedback in an interview and resubmitted it.

I had no choice, so I took the interview and received the feedback.

However, the content was more concrete than I had imagined, and it was very educational.

This is because they didn't just point out the bad parts but also explained the reasons properly, and they also properly praised the parts I did well.
When writing on my own, it is often hard to tell what is good and what is bad, so this feedback was a good opportunity to look back at my writing again.

Also, the interview focused mainly on writing, and I had the impression that the company was solid.

But there was one condition!

They said that since my writing could not be used as is, I would need to receive paid training in order to take on the project.

Honestly, I struggled with this quite a bit...

I understood the feedback, and for someone like me who isn't yet confident in my writing skills, I thought an environment where I could learn while working on projects would be great.

But, ultimately, what I was aiming for was,

to grow while gaining experience on projects first, and I wasn't looking for any further investment.

So, I decided to decline this time.

What I learned from this experience is,

that it's not just about whether something is suspicious,

but also that 'whether it aligns with my goals'

is also important.

📍 Projects I thought were dangerous

This was not an interview.

After applying, I immediately received instructions for a test writing assignment.

There was a theme and a manual provided.

The deadline was within two days, and I was told to start writing immediately.

However, the escrow payment was never made...

As for me, I absolutely wanted to meet the deadline, and since I was doing this while working my main job, I thought I would start on the parts I could get ahead on, so I began researching and writing. However, unfortunately, the escrow payment was never made.

Even when I sent a follow-up message, there was no reply.

I ended up writing the article feeling half-deceived, but I'm glad I held back from submitting it.

I don't know what would have happened if I had sent the completed article.

I have since used the article I wrote at that time as part of my portfolio.

It wasn't a waste of time, but it was a valuable learning experience.

📍Things I changed based on these experiences

Through these experiences, I gradually changed how I choose projects.

1. Stopped applying in bulk on weekends

I used to apply for many jobs at once on the weekends.

However, when trying to increase the number of applications, my judgment inevitably became sloppy, and I tended to choose ones that seemed suspicious.

Now, I look at projects a little bit every day and only apply for the ones I truly think are good, even if there are only a few.

2. Choose projects with specific job descriptions

"Achieve a flexible work style"

"Welcome those aiming to be freelancers"

Rather than these, I started prioritizing specific postings like:

"Article creation for XX"

"XX characters"

"Published media available"

This is because projects that lacked specificity and were filled with nothing but vague, pleasant-sounding words often turned out to be the ones that felt off, as I mentioned above.

3. Choose clients with a proven track record

I started focusing on projects where I could verify ratings and hiring history.

Precisely because I am a beginner, I wanted to prioritize an environment where I could work with peace of mind.

4. Don't force yourself to fit the target

I stopped applying for projects that were far removed from who I am, such as those limited to people in their 20s or aimed at women in their 30s.

I think there are some articles I could write if I tried hard enough, but when it comes down to it, there are many things I can't fully understand or relate to.
Instead of forcing myself to fit into those molds, I decided to aim for projects I could write based on the experiences I've had over 50 years.
There's no need to try to act young! Haha.

5. Have the courage not to apply

This might have been the biggest factor.

Before, whenever there was a project, I would just apply for it.

But once I had built up a little bit of a track record,

"If there isn't a good project, I won't apply."

I decided that.

I started to focus on quality over quantity.

🎗️ This experience led to my next turning point

To be honest, the period when I was rejected 46 times was quite painful.

But looking back now,

perhaps it was a period where I was practicing how to evaluate projects

before I was practicing how to write application letters.

You shouldn't just apply for every project.

It is also important to choose projects that suit you.

I learned that.

And after this, thanks to an encounter with someone, I would go on to further rethink my application methods.

Next time, I plan to write about what changed after I started analyzing application letters and job postings.

I will continue to write about my real-life experiences of taking on a side hustle starting at age 50.

I hope this will be helpful to those who are struggling in the same way.

What do you keep in mind when choosing projects?

If you'd like, please let me know in the comments.

Likes and follows are also very encouraging.