The internet makes ditching your 9-5 look easy...then why isn't everyone doing it?

Scrolling through Instagram, you might think the entrepreneurial or remote employee life looks like a real-world version of utopia. Exotic locations, sleeping in, freedom, wealth…but all is not as it seems. If ditching your 9-5 was as easy as it looks on social media, then more people would be doing it. Let’s look at why they’re not.


The one good thing about your full-time office gig is that you know what to expect every day. You have a routine, you know when you get paid, you know your team and understand its quirks. Starting a business or working contract to contract is risky and requires you to be much more adaptable. Working from home as an employee is more reliable, and for some (like me) a lot more comfortable…but if you’re not used to it you’ll face an uncomfortable transition period while you get used to getting your shit together without a manager setting your daily agenda.

I get it. While I’ve worked from home part-time for nearly 10 years, it took eight of those years to get brave enough to go full-time. Since I hardly knew anyone else who did it, I had no idea what it was like and it seemed impossible. Who would pay me to work in my pajamas from home?

You also might really like your job. The thought of giving it up seems like a waste of the past few years or you’re concerned that if you don’t like your new remote job you won’t be able to go back to the good job you had. If this is the case, you need to decide what’s more important: the job you have currently or the lifestyle you want to live. Neither is certain, unfortunately.


Even if you rent a coworking space, you’re still working alone in your business. There is no next-door office neighbour to gripe to when you’re stressed out about a project. If you work from home, you’ll be alone for most of the day. I know a few people that admit they have a tough time being alone so much. Some people thrive in a busy office with in-person meetings.

When you work from home you have to make an extra effort to meet people outside of work. In the past 10 years, I made the majority of my new friends at work and living in a new city where I didn’t have a lot of friends hasn’t always been easy. Eventually, I made myself try Meetups and made an effort to go out and find new people. The result is that I’ve met a lot of really amazing people I would never have met otherwise.


Related to the other two points, some people believe they’re not suited to work from home. They’re not organized enough, they’re not technically skilled enough, their office isn’t good enough—all excuses, but legitimate ones if you aren’t willing to overcome them. You can learn how to get organized, you can learn digital skills (cheaply, I might add!), and you can remodel a corner of your home to make a suitable office space. My husband turned a bedroom closet into a beautiful little office for only about $50!

In the end, the only thing that stands in your way is you. You may not be suited to working from home, but you can also get used to it just like you got used to working in a regular 9-5 job. And you can always try it and then go back to an office job if you find out you don’t like it. Weigh the risks against the potential upside. What have you got to lose?

Probably less than you worry about.