Why You Shouldn’t Quit Your Job and Work For Yourself

Why You Shouldn't Quit Your Job and Work For Yourself

Should you quit your job and work for yourself? It sounds kinda cool. Sleep in. No stupid meetings. Lunch when you want. Decide your salary. Sounds like a dream, huh?

And, yes, you probably know someone who’s left their day job and is now happily working for themselves—or posting on Facebook as if they’re perfectly happy. If you don’t know anyone personally who’s done this, you’ve heard of some success story of someone storming out of their corporate office and hopping on the first flight to Tahiti!

These stories might even have you thinking about trying this. As a person who has quit their day job, and hit a few countries afterwards, I want to point out some reasons this may not be for you.

Reasons Why You Shouldn’t Quit Your Job and Work For Yourself

The obvious reason is money. If you don’t have enough money to live without an income, you want to think hard about this. However, if you have a side hustle that can generate income for you, and are willing to shrink your cost of living, you might be OK.

But when we think beyond money, there are some other reasons that the decision to quit your job and work for yourself might be too radical.


Why You Shouldn't Quit Your Job and Work For Yourself

You believe in the work you’re doing in the daytime

You’re annoyed with the company you work for, but you actually like your job. Unless your job has really broken your spirit, you probably don’t need to grab your passport and jet-set for the rest of your life. You might just need to work for a different company.

Sometimes your current situation makes you feel so defeated that you think you’re “over it”, when you really just need a break. A little time to think about what makes you happy, and how you can spend more time doing that, might really be all you need.

You might enjoy enjoy working set hours

Some people need routine and don’t even realize it. Having to work at set hours might actually be really helpful to your productivity. If this is the case, becoming a full-time entrepreneur could be really overwhelming for you. As a part-time entrepreneur with a full-time day job, you can only work on your own business for a limited amount of time, which forces you to work only during set hours. And, for you, that might be a good thing.

You like your job

If you really enjoy your job and you’re thinking about leaving to work for yourself, ask yourself a few questions first:

  • Are you willing to do all of the things your company does (not just your job) by yourself?
  • Are you bored at work and looking for a bigger challenge?
  • Are you only thinking this because you’d really like to travel more?
  • Would you do your job if you weren’t being paid to do it?

You see, many things can contribute to a desire to be down with team #DigitalNomad or #OvernightCEO (is that last one a thing…? It is now). But leaving your job to work for yourself full-time might not make you happy the way it makes other people happy—especially if you haven’t worked part-time for yourself first.

Try building a side hustle

Whether you’re thinking you want to quit your job and work for yourself in a totally different career field or work in the exact same area you’re already working, a great test to see if you can hack it on your own is to develop a side hustle. Before you quit your job and work for yourself, see how much you like yourself as a boss. Learn how much you like what you’re working on when no one is looking. Find out how much you still need to learn about your craft, or about business, while you still have access to daily guidance and experience on someone else’s dime.

This summer, you can learn how to build your side hustle while staying on top of your day job in Side Hustle Summer School. It’s absolutely free (and may even win you a few prizes). It will help you structure your side hustle in a way that keeps you productive, without spending excessive hours on your side hustle, and will help you decide if the entrepreneur life is for you.

(Side Hustle Summer School 2016 has closed, but if you’re still looking for some guidance, check out Side Hustle Business School or,  for 1-on-1 guidance, check out Side Hustle Commitment Therapy)

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