Kevin O’Leary Goes to Work in Pajama Bottoms — These 5 High-Income Jobs Allow You To Do the Same

Kevin O'Leary talks with his hands outstretched
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Tell anyone that you’re a remote worker, and one of the most common responses you’ll get is something along the lines of, “lucky you, I’d love to work in my pajamas all day.” While these quips are often sparked by envy, they also carry an assumption that working from home means you’re not working hard enough. 

Tell that to Kevin O’Leary. The powerhouse Canadian entrepreneur, investor, and “Shark Tank” star is a proponent of remote work. So much so that he poked fun at the stereotype by appearing on Instagram clad in a suit jacket and tie to deliver some election analysis — while wearing pajama bottoms and flip-flops. 

O’Leary is far from alone in his belief. Many high-paying jobs are shifting to telework or hybrid models to attract top talent. If you’re looking for a role that lets you apply your skills while sporting fuzzy slippers, here are five fields worth considering. 

1. Web Developer 

When Indeed compiled a list of high-paying roles with ample remote opportunities, web developers came out on top. These professionals are the backbone of many enterprises, using coding languages like HTML, JavaScript, and CSS to create websites and web apps

If you have these skills and love collaborating with copywriters, graphic designers and user experience teams — while sipping coffee from your favorite mug, fresh from the dishwasher — might have just found your dream role. 

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According to Indeed, web developers earn an average annual salary of $80,498. 

2. Freelance Marketing Consultant 

Going freelance can be risky, but if you have the skills and connections to land well-paying corporate clients, the freedom to work from home and set your own schedule might be worth it. With a background as a marketing consultant, you can partner with companies and organizations to help them boost brand awareness and optimize advertising strategies.

You’ll play an integral part in shaping marketing campaigns and building relationships with high-level marketing managers and executives — all from the coziness of your couch. Indeed reports that freelance marketing consultants earn an average national salary of $91,255 annually. 

3. Project Manager 

A good project manager is the linchpin that keeps all the moving parts of a project on track. This role involves creating strategies, road maps, and workflows, as well as defining product features and ensuring deadlines are met — all tasks you can tackle in your pajamas or with your beloved pet by your side.

Project management is in high demand, which is why FlexJobs lists an impressive salary range: $73,000 to $143,000 annually. 

4. Cybersecurity Analyst

In today’s digital age, when everything from national secrets to family photos live online, cybersecurity analysts are worth their weight in gold. Or, per FlexJobs, anywhere between $56,000 to $120,000. 

What does the job entail? These professionals monitor security systems for breaches, stay up-to-date on IT trends, and develop plans to address outages or data compromises — all tasks that can be performed remotely. 

5. Psychologist

Mental health work is intimate by nature, and practicing remotely can offer psychologists the ability to better serve clients while maintaining their own work-life balance. Virtual appointments allow professionals to reach a broader range of clients, including those in underserved or remote areas, while working from a familiar, calming environment. 

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FlexJobs estimates psychologists earn between $56,000 and $128,000 annually, depending on their level of experience and field of practice. 

Conclusion

The next time someone jokes that working remotely is just an excuse to stay in your pajamas, you can nod along and have a good laugh — because you know better. You know that many high-paying jobs across a range of industries are available to people willing to work hard and think big — all while wearing their favorite PJs. 

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