Upskilling In Your 5 to 9 For Your 9 to 5

February 6, 2025
Whether you’re early in your career or midway through, it probably seems like there aren’t enough hours in the day to take a course but quitting your job to go back to school isn’t an option either. And upskilling while on the job is no longer a “nice-to-have” but is becoming increasingly essential as a recent report by the World Economic Forum points out. So, if the only option you’re faced with is to “learn while you earn”, we’ve spoken with a career coach who has some tips on making this a reality. Before we get into the details of how you can best manage your work and personal life with continuing education, Ibiyemi Balogun, Founder and Lead Career Coach at Foot in the Door Consulting says it’s important to understand why upskilling is important and what to consider before you embark on taking a course or certificate.
Why Upskilling is Important
Ibiyemi says upskilling is important because it allows you to:
- Transition industries more smoothly: If you’re looking to change jobs and work in an entirely different industry altogether, you’ll have an easier time getting hired if you have knowledge about that industry that you don’t have from your current industry and/or role.
- Meet people who can aid your career transition: Networking is key to getting your foot in the door as the old adage “it’s not just what you know, it’s who you know also” still pays off, especially if you’re trying to move into a different career field altogether.
- Get better at your current job and apply for promotions: Maybe your goal isn’t to change your career altogether but to apply for that management position and move up in your career. Upskilling and obtaining a credential from a recognized institution is a way of showing your current employer that you are committed to bettering your career, and makes you a more valuable asset to the company.
- Branch into a side hustle teaching a specific thing: You might be looking for a way to get out of the 9-5 race and work for yourself but this isn’t something that happens overnight - especially when you’ve got bills to pay and food to put on the table. So, if you learn a new skill and develop that on the side to the point where you can eventually do that full time, that’s another way upskilling can transform your trajectory.
But, before you “add to cart” your chosen course or certification to upskill, take the time to find out “why” you’re doing it in the first place, advises Ibiyemi.
Things to Consider Before You Upskill
- Choose the right program before you upskill: Take the time to reflect on where you’re currently at in your career and the areas of your job that you like and those that you don’t like. “Use this to optimize your learning to strengthen your strengths and outsource your weaknesses,” says Ibiyemi. She adds that it’s also important to consider other, more practical factors like program duration and entry requirements as well as costs.
- Speak to your boss: No, we’re not talking about your significant other (although this is important too and we’ll get to that in the next point). Ask your line manager or HR about tuition reimbursement programs, projects you can take on during upskilling and apply at work almost immediately, and accommodations you might need while upskilling.
- Speak to your family members and friends: Your continuous learning affects people in your personal life as well as you’ll have less availability for them.
Okay, so now you’re ready to sign up for a course or certificate but in order for it to be a success, Ibiyemi offers some practical tips for time management, communication, networking, and applying it to the real world.
Tips on How to Upskill
- Use your calendar religiously: Ibiyemi advises to consolidate your calendars (i.e. work, school, and personal all on one calendar and colour-code if possible so you can clearly see which of those aspects of your life are taking up the most time). Also, she says it’s important to put all the assignment dates into your calendar as soon as you receive your course outline or syllabus and turn on reminders two weeks and one week in advance so you don’t miss anything.
- Talk to your employer: As mentioned above, it’s important to communicate with your boss before you start and ask for accommodations as necessary like time off to study or do group projects.
- Get connected with people in your class: Don’t be shy - get out of your comfort zone and talk to people in your class - especially those who aren’t necessarily in your career field as you’ll learn more from someone who is approaching learning the same subject but from a completely different role - as will they! Ibiyemi says to be proactive and “form study groups and share resources in case you’re not able to make class based on last minute work deadlines.”
- Apply it to the real world: Don’t just be a sponge and take in the learnings, do the work, and go home. “Take what you’ve learned and apply it within your workplace to solidify your learnings,” says Ibiyemi, adding that you can ask to demonstrate what you’ve learned by taking on a new project or perhaps coming up with an idea that you’d like to try at work.
Support Your Goals
If you’re feeling overwhelmed with how to get closer to your goals, Toronto Metropolitan University and The Chang School offer academic advising to prospective and current learners to help you choose the course or program that’s right for you, improving your chances of admission, and navigating the general enrolment and registration process.
Furthermore, all current learners with The Chang School have access to a career education specialist who can help you change or choose your career path, develop a job search strategy, or improve your resumé., cover letter, networking and interviewing skills, or LinkedIn profile.

Ibiyemi Balogun, Founder and Lead Career Coach at Foot in the Door Consulting.
Need More Help?
Ibiyemi offers career transition coaching programs to help mid-career professionals with six to 10 years experience pivot into new industries without starting from scratch. She also offers services through one-on-one & group coaching programs. If you’d like to learn more, you can reach out to her directly.