3 Questions You Need to Ask to Discover Your Dream Job

This ain’t your standard list of questions type of blog post!

We’re only talking about three today, but these questions dig deep. If you answer these sincerely, they’ll help you discover your dream job (or business idea).  

It’s easy to focus on what isn’t essential in the long run when you’re not clear on the deep stuff about your dream job, like why you want it. 

For me, it was always reverting to focusing on basic needs. Like “will this make enough money to pay the bills?” or “will the benefits package be enough if I have an emergency?” or other fear-based questions like that. 

But even if I had these basic needs met, or if they thoroughly exceeded them, I was still unhappy. I felt like something was missing. Like the work that I was doing was unfulfilling. So even if a job I took had an excellent salary or benefits, I’d be longing for something else. It was like the job was great on paper, but it didn’t make me feel truly fulfilled. 

I was miserable in my career that had a bangin’ benefits package and a salary that the 13-year-old version of myself who lived in a trailer with no heat or running water could only dream of. 

So, I had a hard time figuring out that my JOB was what was making me so unhappy in the summer of 2018. I told myself there was something wrong with me as a person, not the fact that I was in a career that didn’t make me happy. 

“It couldn’t be my career,” I told myself, “getting a job with a good salary and a 401k is what I’m SUPPOSED to do”. I wouldn’t allow myself even to think that my job didn’t align with me. 

But once I started to think about what was *actually* important to me, everything changed. I only thought money was the most important thing to me because of my childhood full of poverty. 

Do you wanna know what truly changed my mindset?

Thinking about what I would be like on my deathbed. More particularly, if I would look back on my life and regret. 

Would I regret not making more money? Or I would regret not finding something to do that would truly fulfill me.

Yup, you guessed it! I would regret not going after something that would fulfill me.

So, if you’re feeling the same way right now, then this episode is for you. These three questions are going to be perfect for when you’re looking at another career or when you’re ready to think about potential business ideas. 

QUESTION #1: Does the company your applying to (or your potential new business idea) align with your values?

This is the number one aspect of job hunting or business planning that I think gets overlooked. I talk a lot about how my primary reason for getting started was because of financial freedom. Still, I’ve changed since then, and I now only focus on being purpose-driven. 

If you want to start a business

I focus FIRST on the real motivation and purpose and let that drive every decision I make. So if you’re starting a new business, then make sure to get clear on your motivation and that what you want to do aligns with your most important values. 

If you focus on your values and your purpose in your business, that will drive action you take. So the question is, will these actions you take align with you?

This will be a way to determine if this is your dream business.

If you want to apply for a different job

But, let’s say you’re on the opposite side of the coin, and you know you don’t want to start a business. That’s perfectly fine! You can still find meaningful and purpose-driven work inside of a company. 

So, before you even think about basic needs stuff like salary or benefits package, first look at their values and what truly drives them as a company. 

If that already doesn’t align with who you are, then you’ll know this isn’t your dream job, no matter how high the salary is. You’ll know that if you take this job just for the money, you’ll compromise who you are. After a time, that compromise will eat at you until you become miserable, just like I was. 

That’s why it’s important to know what your values are before you start looking for a job. If you need some extra help with this, then I encourage you check this post out that is all about finding your core values.

Now, don’t get me wrong here, you still need to make sure things like salary and benefits packages are excellent, too. You DO need to be able to pay bills and put food on the table.

What I’m asking you to do, though, is to prioritize your values first. THEN if you are aligned with the job (or business idea), compare things like salary, schedule, etc. 

These questions to discover your dream job aren’t here to not be realistic. They’re here to help you make sure you actually FIND your dream job, not just a job that looks good on paper.

QUESTION #2: If you had 15 million dollars in the bank and still decided to work there, would you?

This is probably my favorite question to ask yourself to discover your dream job. It’s double-sided. It helps you make sure that this possible career (or biz) move is the RIGHT one. Not only that, it’s an excellent way to add some self-discovery in there, too. 

Why?

Because when you take away the fear of not having basic needs met, you’re left with more creative and deep emotions that are important to you. 

Let’s say you had 15 million in the bank, but you still decided to go to work every day. You’re probably not going to go to a soul-sucking job that pays well, right? You’re going to do something that is fulfilling and that you look forward to doing. 

I know it’s easy to blow this question off when money may be tight. But please don’t skip over this one. After you answer it, you’ll feel it in your gut if this is the dream job (or business idea) for you!

QUESTION #3: Think about the worst day you could have there. Would you quit? You can only quit on the best day. 

There was a time in my career that I was feeling intense burnout. At the time, I wasn’t sure if it was just my health, my marriage, or my job. I was totally lost and unsure of what to do. The only thing I DID know was that I didn’t want to feel like that anymore. 

So to decide what was making me feel that way, I asked myself, “Would I quit on the best day?” concerning all three. 

For example…

• My health: “Would I quit trying to eat healthy and workout on my best day?”
• My marriage: “Would I get a divorce on my best day with my husband?”
• My job: “Would I quit on my best day here at work?”

I only answered “yes” to one of the three. Wanna take a guess which one? Yup. It was my career. I hated it so much that even on the very best day I could possibly imagine working there, I’d still quit. 

I’d never quit on the best day of my health or marriage. So that narrowed it down pretty quick for me. 

Why is this a question you need to ask yourself to discover your dream job?

What I love about this question is that it’s powerful either way you look at it. Let’s think about this in the opposite direction.

If you’re about to apply for a new job or go all-in on a new business idea, then think about the absolute WORST day you could possibly have.

Now, I get that you won’t know everything until you actually get into it, but just use your imagination. 

So, I’m talkin’ like a going-home-crying type of bad day. 

The real question is, would this new job be WORTH that type of emotion? Would you still stick with the job not because you had to but because you wanted to?

If you loved and believed in what you’d be doing so much that nothing would stop you from doing it, that’s the million-dollar answer. 

If you answered yes to that? Then you’re on the right track, my friend. 

Are you going to use these questions to discover your dream job? Let me know in the comments below!

xo,

Monica

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