Why I’m still working entry-level jobs in my 30’s

Why I’m still working entry-level jobs in my 30’s

“Thank you for your interest in our entry level job…. We regret to inform you that we've decided to move forward with other applications. Good luck to you on your search!”

I have applied to over 500 jobs in the last 5 years.

Rejection and e-mails like the one above are a common thing in my world.

They look something like this:

It’s embarrassing because you might think that I would have a better way to get reliable income at this phase of my life.

However, I don’t. Despite having a wealth of experience, a large network, and two degrees, I’m often in the same job pools as kids right out of college.

Mostly things end with a nice “we regret to inform you” email, sometimes they ghost me completely, and other times I go through several stages of the interview process to be ghosted or rejected.

If you think this sounds frustrating, then you’re right.

If you can relate to this experience, then you might be a millennial.

Is it any shock that 51% millennials are underemployed? It’s not for lack of effort, lack of education, poor experience or otherwise. It’s because life is expensive, and we can’t afford to spend six months to a year searching for the perfect job.

We have to eat. We have massive amounts of debt. We have bills. Cost of living keeps rising along with inflation.

So, we take what we can get. We take the "good enough for now" job. Then we hate it and eventually quit or sometimes get fired.

Then we start all over again.

We rarely get the 5-10 years of experience required in a given field to move up to intermediate or high-level positions.

Why? Well, a few reasons.

1. We can’t stand the job, so we quit.

2. We get sick on the job or injured and have to leave.

3. We can’t perform and get terminated.

4. We get bored because the work is tedious.

I don’t enjoy most entry-level jobs, and they don’t pay that well.

Sales is one exception. I got into sales after a career in teaching because it was the only field where you could make over 50k in an entry level position if you simply hustled and had a slight amount of social acumen.

I’ve been a Lyft driver, a freelance editor, a tutor, a factory worker, and I’ve sold nearly everything that could be sold both in person and over the phone.

Do I enjoy this? Sometimes.

Am I good at it? Usually. I’m a hard worker, and I excel at work. I’m usually a top performer in sales roles, and I always meet or exceed expectations in other roles. If I believe in what I'm selling then I'm excellent. If I don't believe in it then I'm good but not the best.

But, so what?

I’m still looking for the job that can actually turn into a career. People rarely find actual careers, though. Most of us are stuck with jobs that pay the bills and we find out fulfillment elsewhere.

I have not found a job that allows you to sit around writing, sharing ideas with people, researching things you’re interested in, reading about cool stuff, and making videos and music.

You can definitely make money doing the things that I listed but it won’t be at a job. You have to make that type of job yourself.

Does work really look like this for anyone? 

When I was in my 20’s, I figured that I would rack up some the student debt, get a decent job, and eventually pay it off.

I’m not blaming anyone other than myself, but it would have been nice to have some required classes in personal finance in university. I can write an essay or a lit review in my sleep (almost literally), but I only learned how to properly save and budget within the last couple of years.

In 2020, I made about 75k selling health insurance. That’s the most money that I’ve ever made in a year. While the money was nice, the work sucked. I worked my ass off and it was mostly thankless, repetitive, and stressful.


For context: my life has actually been pretty amazing. I’ve lived in Taiwan, South Korea, San Francisco, Los Angeles, Arizona, Nevada, and the Pacific Northwest. I’ve backpacked in Australia, went scuba diving in Thailand, sipped organic café in Colombia, and more. I’ve met nearly all of my heroes.

I wouldn’t have it any other way.

The only thing that has allowed me to do this is entry-level jobs, periods of self-employment and unemployment, teaching English as a trade, debt, and my ability to not care about a Kool-Aid chugging corporate job world life.

Not getting sucked into a long-term soul sucking career has allowed me a ton of freedom. I would be a much less interesting person if I had stuck it out with a job since I turned 18.

I have unprofitable passions. Therefore, I job hunt. 

Employers don’t like to hire the perpetual job hopper. They see all the downside. Job jumping has massive upside for someone who is creative, likes to travel, has bouts with mental health issues, and doesn’t like to commit to more than 1-2 years in the same exact role.

Does it mean that I have to slog through the job seeking process every year or two? Yes.

Does it mean that I don’t have to suck up to a boss that I despise for 5 years only to climb up a single rung of the corporate ladder? Also, yes.

Maybe one day I’ll finally figure out. Until then, I’ll continue the cycle of working, paying my bills, saving money, investing, and working out a way to end the cycle as soon as possible.

Employers: if you see an application from me or another millennial, don’t write us off. We are doing their best to deal, and we'll work hard. If you pay us well and actually value us then you'll get our creative juices, life experience, social marketing skills, and more.

I'll keep on the hunt until I find something that I don't wish to leave. Until then, I will continue the cycle of entry-level jobs mixed with self-employment and freelancing.

My lifestyle is more fun than being stuck in the corporate world for three to four decades of my life for the chance to retire at 65 with little to no retirement.

I taste mini-retirement every 2 years, and it's sweeter than the bitter taste of letting my dreams die for the promise of a 401k.