6 Questions You Need To Ask Before Staring A New Career


While we all love the excitement of starting a new career, it can come up with a lot of decision making. Changing careers can be scary and exciting, filled with new potential and fear if this is the right decision.

Career planning is a topic that we all need to discuss at every stage of our life.

Unlike other generations, millennials and Gen Z tend to not stay on the same career for their entire lives.

I’m a huge fan of career change. I just did this recently.

I think it’s so important to constantly re-evaluate your career path. It’s not just something that you do when you’re 18 and choosing a college major, or 22 when you’ve entered the job market. Because as you enter the job market, surprise, surprise, you learn that it’s okay to change your mind after you graduate when you’re 30, 40, or even 50 years old. You are not stuck with the decision you make when you are 18 years old.

And there could be a number of reasons you changed your mind. You may no longer be fulfilled by your career, maybe your job isn’t what you expected, or maybe you discovered a new career path that sparked your interest. The latter is very common. I think high school and college are quite limiting in career choices and when you go out into the job, you discover there are jobs you never even knew existed. And that includes entrepreneurship.

However, before you go off to start a new career, you need to ask yourself these questions. Firstly, not everyone can afford to quit their job and start again with no consequences. But more importantly, if you don’t ask yourself these questions, you could be in this situation again. If you rush into a new career without asking these questions, you could be unhappy in your new job and face a new set of problems.

So that’s what we cover this episode of the Millennial Life Admin podcast. For more details, make sure to listen to this episode!

To truly get the most from this article, I highly recommend you journal these questions when it comes to your future career. These are the 6 questions you need to ask yourself:


1. What is the total investment required?

Do you need to save up for it or take on debt? 

When looking at choosing a new career path, you need to evaluate what it’s going to take to get started. You might need to take on a course, buy supplies, or even go back to college. Ask yourself how large is the investment and if you can save up for it or if you have to go into debt for it. For instance, if you’re looking at starting an online business, you might need to take a course, however, if you’re looking to law school, that will come with debt. Look at the expense required.

After that, ask yourself the most important question when it comes to the investment, is it necessary?

If you’re looking to be a lawyer, engineer, or something that requires a professional designation, then yes you will need to go to school. However, most with most careers, you don’t need a formal education. It’s important to learn, but with the world of the internet, there’s probably a course out there that can teach you the skills online at a lower price or even for free. Employers look at experience, not necessarily formal education.

I ask myself this question all the time. I constantly think about going back for my Masters’ degree. However as I’ve looked through job postings, I’ve seen that a Masters’ degree is not a requirement for my career anymore. While it would definitely help, it’s now an asset instead of a requirement and can the qualification can be replaced with experience.

This is my personal experience from my evaluation of what investment is necessary. For me, a Masters’ degree would cost approximately $16,000 and I would have to go to school full time for 2 years which would mean I would have to take on another $100,000 debt to cover my living expenses for 2 years (probably a little less since I make $50,000 now), but it would be a lot of money. Alternatively, I could move home. But all these costs come with consequences, evaluate the true cost for you.


2. What is an entry-level salary for the position in your location?

But don’t just “Google” it. I love Google, but remember that it has its limitations. When you are researching an entry-level salary, a classic example I see university graduates make is they assume that the surface level salary that is given by a university or Google, will automatically apply to their situation.

No, job salaries are different depending on where you live. A software developer makes a very different salary in Winnipeg than they do in Toronto or San Francisco.

So instead of Googling the entry salary, look for an actual job posting with it.

My two favourite sites to look at salaries are Glassdoor and LinkedIn. Find a job posting on LinkedIn, and look up the company in Glassdoor to see what the actual salary is. Many companies do not post their salary and many people end up assuming what it should be. I love Glassdoor because they are reviews from real people and list the real salaries of companies.

When doing your research, I encourage you to dig a little deeper. If you are looking to go into the field, research the salary of the specific niche in that industry. For example, if you want to be a lawyer, what kind of law do you want to work in? A corporate or criminal lawyer has different salaries than an immigrant lawyer. A software developer specializing in gaming makes a different salary than one that works in developing apps for small businesses.

Do the research.


3. What is the total cost of the investment compared to the earning potential?

And after that, look at the cost of not making this investment. What is your max earning potential in your new role? Now that you have the investment cost and the earning potential, look at how long it will take to pay off the investment and the opportunity cost of making or not making the change.  

All the same, steps apply for when you when to invest in starting a business. What is the investment required – education, course, material, what do you expect to make in your first year, how long until you break even? What is the demand for that product/space? 


4. How volatile is the job market? 

I’m constantly looking at the future of jobs. And as I write this, we are currently in the middle of COVID19 which has deemed many jobs unessential. Some industries will be able to weather the storm of the global crisis, but this will change the landscape of the job market for a long time.

Jobs are also being phased out with technology and the demands of the world. Many jobs are being streamlined by new technology, but you also need to consider where the world is going. For example, a job in Engineering sounds like a lucrative career, however, it depends on what type of engineering you choose. Software engineering is on the rise, but when I was in school, oil engineering was the hot industry. And now it has crashed.

To hear more about job security, listen to Episode 2 of the Millennial Life Admin Podcast all about emergency funds!


5. What is the skillset that you are developing and is it transferable?

This is my favourite question. I’m constantly looking at what will make me in-demand in the future. The world is changing so quickly and I’m constantly evaluating the skills I’m developing.

There are jobs now that didn’t exist before like careers in social media. However, many of the skills are the same. People who excel in social media also have excellent skills in communications, advertising, and public relations. The same goes for advertising, instead of making commercials for TV, many companies make commercials for YouTube.

You need to have skills that are flexible and adaptable.

This is actually a reason I left my last job. I realized the skill set I was developing would be very limiting to me in the next 10, 20, and 30 years so I had to make a change.

Write down the skills you will develop in your new career and examine how transferable they are for the future.


6. Does this job fit my lifestyle and needs? 

This is the question I feel like no one considers. Everyone looks at the salary (which is definitely important!) but there is more to a job than the salary.

These are additional lifestyle changes you need to evaluate:

– Are you willing to move?
If you are looking to be a software developer in Winnipeg, the opportunities may be limited. You may need to move for your career. I think about this all the time because I used to work for the Federal Government, and while there are jobs in Vancouver, most of them are in Ottawa. And having lived there for a year, I am not willing to move back (it’s a lot of snow, guys).

– How will it affect your partner or kids? Your decisions will not only impact yourself. If you need to move, look at how it will affect them. Maybe your partner has a flexible career or maybe they need to stay where they are. Look at how it will impact others.

– Does it fit your personal needs? Do you like to travel for work? A lot of people love traveling for work and it can be a great opportunity to see the world. Personally I don’t like traveling for work a lot because I like being really immersed in my travels, and when I’m traveling for work, I’m mostly in the hotel. But it depends on your job.

– How do you like to work? Maybe you are yearning for that laptop lifestyle or work from home career. With COVID-19, many people are working from home including me (I alternate one week in the office, one week at home because of my type of work), and while a lot of people love it, I personally hate it. I used to work remote and I hated it then too. But that’s because I’m very social and love working with my clients and team in persona.

Look at how it affects your relationships and if it meets your personal needs.



At the end of the day, starting a new career can be exciting, but it can also come with intimidation. Answer these questions to make the most out of your new career!

Author: Kimberly

Hi there! My name is Kimberly and I created MLA as a personal development, career, and finance resource for millennials. MLA focuses on helping career-driven millennials create the personal development habits to achieve work-life balance and manage their money. Throughout this blog, you’ll find articles that give specific and detailed advice because I’m not into the fluffy advice. There’s plenty of that on the internet. Here you will find tangible advice on how to find a rewarding career (that you love!), where you can help others, and learn how to save and invest your money for the future. I hope you’ll follow along!

Leave a Comment

Your email address will not be published. Required fields are marked *