Having a bad job is one of the most universal human experiences. Whether it’s unpleasant coworkers, insufferable managers, toxic environments or unsatisfying tasks, most people in the workforce have had to deal with negative situations that can either make or break their career.

But oftentimes, a bad job can be the beginning of something new. It can help people understand what to look for – and avoid – when searching for a new position, and even serve as the foundation of a complete career change. In other words, while “paying your dues” isn’t much fun, it can be motivational and lead to better opportunities. Many of us wouldn’t be in the positions we are today if we hadn’t suffered through some sort of work-related hardship.

And that is the topic of this month’s IT World Canada Twitter chat. On April 27 at 1pm ET, join us and several tech industry executives in openly discussing some of the worst – and best – jobs we’ve ever had and how this has helped develop our career paths. You can jump in by sharing your own experiences and deliberating on how the best and worst jobs have impacted you.

You’ll have the opportunity to interact with our guest expert panel, which includes:

jesse hirsh

Jesse Hirsh, broadcaster, columnist, public speaker, researcher and futurist

Jesse Hirsh is a researcher, analyst, and public speaker based in Toronto, Canada. His research interests focus largely on the intersection of technology and politics, and in particular, artificial intelligence and democracy. He recently completed an MA at Ryerson University on algorithmic media. He’s presently spending time at the IBM Canada Innovation Space, researching and writing about cognitive computing.


Anna Lambert, director of talent at Shopify

Anna Lambert is the Director of Talent Acquisition at Shopify. Anna embodies Shopify’s MO of Getting Shit Done. She joined Shopify as an intern in 2011, and has helped build the company from 150 employees to over 1900 today. Anna is also a passionate ally and advocate for inclusion in tech, and works tirelessly to make Shopify a company that moves the needle in this space. For example, as a way to give back to the community and provide a platform for voices often overlooked, Anna founded Beyond the Code three years ago. This conference is designed to empower individuals to make the tech industry a more inclusive space for everyone. Anna is also an avid snowboarder, runner, and the co-founder of her own Shopify store, Caged Collective.


Skye Smith, division director at Robert Half Technology 

Skye Smith is a Division Director with Robert Half Technology in Vancouver, where he matches businesses with talented tech professionals across B.C. Skye previously served as a technical consultant with the company, and helped to establish Robert Half Technology’s IT recruitment practice in the U.K. With a background in IT infrastructure and business analysis, his work keeps him on the forefront of ever-evolving consumer and enterprise technology, and where it merges with workplace trends and business needs.

Questions we’ll be discussing at the chat:

  1. Tell us about the worst job you’ve ever had. What was it, where was it, and why was it so bad?
  2. How did you deal with the experience?
  3. What did you learn about yourself going through the experience?
  4. If you hadn’t gone through this experience, do you think you would be where you are today? Why/why not?
  5. To what extent has this shaped your career moving forward?
  6. They say paying your dues at a bad job builds character. Do you agree or disagree? Why?
  7. What is the best job you’ve ever had? How did you get this position?
  8. What makes your best job so good? Was there a specific factor that really set it apart from the rest?
  9. What advice would you give to someone currently looking to leave a bad job situation?
  10. In general, what do you think the worst job ever is? (You don’t have to have personally experienced it, but just one that you could never imagine yourself doing).