3 Questions to Ask Yourself before Accepting Your Dream Job

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It was a little over one year ago when my wife and I were looking for jobs in Colorado. We had identified a few areas we wanted to move to in the state and were working on applying to jobs around the Denver area. 

It was the plan that if one of us got a job, we would go ahead and do the move while the other would be self employed and side hustle for awhile.

But then I got an interview at what I thought was my dream job!

The interview was with a streaming service that I will not name, but the topics they normally stream was everything that sparked my interest, from crystal healing to government conspiracies to spirituality and yoga.

The position was for a senior data analyst that would actually end up being less work that I was currently doing, and more focused on things I wanted to build more skill sets upon.

It was perfect…until I went to the actual interview(s).

This story isn’t your normal advice on how to get your dream job. Instead, I will tell you why I didn’t accept the position, and the three questions I found most effective to ask before accepting your dream job.

The company flew me out to Boulder for 24 hours, set me up in a nice hotel and scheduled my interview for that day. 

It ended up lasting all day. I had maybe 5+ interviews total with various different managers, different teams and the CEO. I ate lunch with them and sucked in their culture like a sponge. There were crystals and kombucha everywhere. I was in heaven.

I had to keep my head out of the clouds.

As much as everything about this job was perfect on the surface, not everything checked my boxes.

And my boxes are important to me.

I stopped giving up the things I wanted at jobs a long time ago. I found that the less I cave on certain things, the more I end up with exactly what I want.

3 Questions I asked myself before accepting my dream job

There were 3 very important questions I considered that helped me the most with this job interview, and ultimately the decision of if I would make this huge life change or not.

Question #1: What has my research told me?

Before I flew in for the interview, I looked up the company on Glassdoor and read all the reviews I could. I read everything from interview questions and average salaries reported on certain positions, to the worst of the worst reviews from past employees.

I think it is absolutely crucial to read through reviews of companies on Glassdoor. Others might say it will add too much distraction to the actual potential the job holds. But I think it is so important to see what others experienced while working for any company, in any position at that company.

I want to read what everyone said, from the janitors to entry level and senior level employees. 

At bigger companies, this would have been absolutely impossible. But since this company was more on the startup side of the spectrum, there weren’t as many reviews to sift through. There were maybe 30 total.

And a large portion of those 30 were really bad.

They said the company didn’t value their time and people were forced to sacrifice nights and weekends. They rarely felt satisfied, as it was noted that management kept taking advantage of them willing to work over time.

It gave me flashbacks of my first job as a web engineer working 80 hours a week at a startup. I had told myself I’d never work for a startup again unless it was my own.

Question #2. Would this job check my boxes?

Some important boxes of mine to check were:

  • Flexibility and the ability to work remote
  • No “on call” as in, no 24/7 “on call” support work
  • Decent medical, dental, vision, 401k match, and PTO

They were able to verify that they offered all the benefits I was looking for and did not require “on call” duty as I wouldn’t be in a support role. They even covered a portion of the relocation costs, which was important to me as around Denver was a much higher cost of living than where we live in Missouri.

However, they were unable to fulfill my flexibility request. They said they didn’t have the infrastructure yet to allow employees to work from home. 

This was especially strange to me. Since the beginning of my career in engineering, every company I’ve ever worked for allowed me to work from home when I wanted.

It wasn’t something I was happy with and even though it was something they were (supposedly) going to offer in the future, it didn’t vibe with me.

Question #3. Could I get comfortable in this new culture?

As mentioned above, the workplace had very much of a startup culture. I knew that from the Glassdoor reviews already. And when I got there, the reviews held true. The place was full of people my age and younger, looking like they practically lived there.

The people were all very nice and I definitely clicked with more than one team, even though I’d mostly be working with the data team.

Who I didn’t click with though was the CEO. It was the last interview and meeting scheduled for the day and I thought it would be an easy one. 

I’ve never had such an uneasy feeling from meeting a person in my life, and I’ve met some shady characters.

I brushed off the feeling and tried to interact with him like I would anyone else. Maybe the feeling was nothing.

And then … my feeling proved right.

When he would ask me to tell him about myself, my experience, and why I want to join his company, his responses were very off. He was more interested in my hobbies than my experience. 

Maybe he had a long day and didn’t want to talk shop I guess? I tried to brush this off too. If we just didn’t click, that was fine. Not everyone has to click with the CEO of the company they work at and most people never even meet their CEO.

Companies: stop asking interviewees if they’re married

He continued to ask if I was married, if I had kids and other things that aren’t really people’s business. 

I told him about my wife and that is when things got very weird. He responded with “Oh, so you’re married to a woman?”

Yep! Hence the word “wife.”

We continued talking until one of the female managers came in. He proceeded to tell me “This is [insert name here], maybe you will feel more comfortable talking to her because she is also a woman who has a wife.”

Um … What?

The woman and I both looked at each other with the same confusion, but with a universal feeling of “just ignore him and do what he says.”

We continued to chat after he left. Then I left and got on the plane to come home. The Human Resources manager that day had actually called in sick so I had no one to talk to at the end of the day about the weirdness of it all, nor the next steps that were to come after this day of interviews.

But I wasn’t thinking much about next steps anyway.

I was too fixated on that weird encounter with the CEO to even think about working for that company anymore.

Plus, they didn’t even check all my boxes!

I didn’t take the job… and we didn’t move to Colorado

I talked to the HR manager that next week, and they were prepared to start conversations around offering me the position. We didn’t get very far into those conversations.

I expressed to her that I felt very uncomfortable with the encounter with the CEO and that I was exploring other options. I also had a few boxes I was unable to check, plus they were also not willing to pay me as much as I was hoping. 

She didn’t budge for my request for more flexibility and more money. But she was very understanding and went on to say that in the future if I changed my mind and they had a position open, she would love for me to consider it. 

I don’t regret not taking that job.

I had a very strong gut feeling to not do it. And I trust that gut feeling.

I also like to make money. When I am taking a new job in a higher cost of living area, I won’t be accepting pay that is less than what I currently make in a lower cost of living area. 

Sometimes, not everything goes perfectly to plan and your “dream job” ends up not actually being your true dream job. And that’s okay.

Weird stuff happens, but the important thing is that you learn and grow through it. And stay firm on the boxes you need to check for what you require from a job. 

Every company has its requirements for each job position, but what’s more important is considering your own requirements before accepting your dream job.

Daniella is a 30-year-old Latina software engineer and entrepreneur. She created the site iliketodabble.com a little over 2 years ago to help others grow and manage their income on the path to financial freedom and finally registered an LLC for her side business this year. Daniella and her wife live in St. Louis, MO.

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Money After Graduation Inc. is a financial literacy website dedicated to helping Millennials and Gen Z pay off debt, invest in the stock market, and afford the life they want!

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