Today's ProfessionElle

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Ask Alessia: Am I crazy for wanting to go back to school?

Ask Alessia is a column where I get to speak directly to you and answer your questions! I love when you guys reach out to me and share any dreams or doubts or eureka moments you’re having about your lives and careers. It’s my favourite part of doing all this – I truly believe we’re all in this together.

I’ll always change names to keep things anonymous. Get in touch by reaching out on the Contact page or on any of my social channels – links are below!

Today’s question came from Hannah, who reached out to me in my Instagram DMs. I wanted to answer this question because I think it’s something we’ve all asked ourselves once or twice:

I’ve been thinking about going back to school.

I haven’t been happy in my job in a long time. I got a good opportunity at a marketing internship when I finished my undergrad and I always just kind of thought I’d work for a year or two, save some money and then maybe go back to school for a grad degree. But it just never happened.

I used to like my role, and I still like the people, but now I just feel like I’m stuck. I’ve outgrown it and there isn’t a lot of room to move up in this company.

I’m single and still in my (late) 20s so I was thinking maybe this is the perfect time to go back to school and figure out what I’m really passionate about. But is it stupid to go back to school if I don’t really have a plan? I don’t want to waste more time if it’s not going to be worth it.

I get this question all. The. Time. In today’s world, it is so easy to get pressured into choosing a career path when you’re too young to know what you really want. By the time you’re in high school, you’re already choosing electives based on what you think your university major should be, which is supposed to set you up for your undergraduate degree, and then you’re supposed to go get a job and a career and a whole life in that field.

The list just goes on and on and before you know it, years have passed but you’re used to the paychecks and you can’t find an exit route and now you’re smacking yourself on the head for not having just pursued what you loved in the first place.


Sound familiar? I totally sympathize.

As far as I’m concerned, this is one part of our modern day society that is completely dated and needs to change. The truth is, there isn’t a one-size-fits-all approach to education at any level. We all learn differently and at different paces. Some of the smartest and most successful people I know never really enjoyed school because it just couldn’t hold their attention. I, on the other hand, was a total nerd who secretly loved writing essays and I think I’m a pretty smart cookie, too.

Ultimately, the decision of whether you should pursue higher education is a highly personal one and it basically comes down to: (1) what are your goals/what are you hoping to achieve, and (2) will more education actually help you achieve those goals?

Notice I didn’t even mention career goals. You aren’t actually obligated to go to school to help your career – you could theoretically go just because it interests you. If learning is what you truly love, then being an academic is just as meaningful of a life goal as any other – probably even more so than measuring your career by arbitrary benchmarks like salaries, number of promotions, and ranking title. I thought about getting my Masters in both English and Philosophy for exactly that reason – because I loved it. Unfortunately, I also needed money, so I turned to law because it was a little more practical with a higher starting pay. There are days when I regret that decision and there are days when I allow myself to acknowledge that never would have been fulfilled if I hadn’t become a lawyer. But that’s life! We can’t always get everything we want all at once.

But back to you, Hannah.

So How Do You Know if It’s Time to go Back to School?

1. Ask Yourself the Hard Questions

It’s time to sit down and do some soul-searching. If your heart is set on going back to school, this is probably the best time in your life to do it. But the more important question is, what would you be hoping to gain from that experience?

It sounds like you’d prefer more of a challenge in your current role – if that’s all you want, you can always ask for a promotion or look elsewhere to level up. If, instead, you really want to learn something new about yourself or think school can give you some internal insight that working in your current industry cannot, then it might be a good idea to go back for another degree.

2. Make Sure the Program Fits Your Needs

Now that you’ve amassed some experience, you can back to school to make yourself a more appealing candidate for more senior positions in your industry (unless, of course, you’re planning to go back to study something entirely outside of your current industry).

Even if you’re seeking to change industries entirely, going back to school for a professional degree can make sense. Certificate programs are usually shorter (1-2 years) than doing a full Bachelor or Masters degree, and are usually sufficient for an industry-switch if you can also find some good work experience (like a co-op program). This is a way to show future employers that you’re serious about changing your career field and have acquired the skills necessary to do the job.

3. Get Real with Yourself and Get Ready to Justify Your Decision to Future Employers

All of that said, I hesitate recommending that you go back to school if you’re only going because you’re bored, rather than because you have a deep passion for what you’ll be studying or because it help you develop skills for your dream career.

Going back to school in your late 20s is not like choosing a philosophy major when you’re eighteen and seeing where life takes you (aka, me). Now that you’ve been in the workforce for a few years, future employers are going to ask about the gap in your resume if you take off for a while. You need to have a solid answer prepared as to why you wanted to leave the industry to do something else (unless, of course, you go into a program that will develop your industry-specific skills). On top of that, tuition in a good program is rarely cheap and you’ll likely be without the full-time income that you’re used to.

Give yourself some quiet time to sit alone and ask yourself all of the above. Maybe a new perspective is all you need to answer your question.


Overall, the most important thing is that whatever you decide is true to yourself and your goals – whatever you want to achieve in your life and career, rather than what you think you should be doing.

Get in touch and let us all know what you decide!

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