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11 Things That Go Through Your Mind When You Quit Your Job to Freelance

by Alyssa James Sep 30, 2014

A few weeks ago, I went all ‘YOLO!’ and handed in my notice to the company I’ve been working for since last year. At the age of 25, this was my first “real” job — you know, the kind with paid vacation (four weeks!), a pension scheme, weekly Friday beers, and no fixed end date. Alas, the draw of location-independence and self-determination proved too strong, and I finally convinced myself getting out was the right thing for me.

Quitting your job to freelance is a big transition, a roller coaster of emotions and reactions. If I’ve thought these things, it’s likely they’ll cross your mind too. Enjoy the ride.

1. “Is it too late to take it back?”

I felt relieved after the conversation with my boss — for like, 10 minutes. Then shit got real. In one month you’ll no longer have a steady income, and those bills won’t pay themselves!

2. “I’ll never make any new friends.”

Before you actually quit, you have dreams of having the free time and energy to go to meetups and the gym or taking a language course, just because. Then you realize: You don’t spend all night watching Netflix because you’re overworked and oversocialized. It’s because you’re lazy and don’t really like people that much (fine, you’re “introverted”). Why else would you choose a job that involves spending most of your time by yourself? That probably won’t change when you’re freelancing. Besides, you’ll be too concerned with making rent next month to worry about who wants to go out for drinks.

3. “What am I going to tell my mom?”

Shit. And she was so darn proud of you for finally getting a steady job and growing out of that ‘find-yourself-while-traveling’ phase. Oops.

4. “I should accept that counteroffer.”

Against your better judgement (and most of the internet’s), you’re entertaining the possibility of a better role and a higher salary with your current company. Stop. Once you’ve decided that you want to work for yourself, working for someone else will never make you happy.

5. “I could be spending all of that money on an awesome trip.”

Most freelancers will tell you to save 3-6 months of living expenses before resigning. And you do it because it seems like pretty sound advice — right up until the moment you realize that six months’ living expenses (in London nonetheless!) could take you on an eight-month backpacking trip to Southeast Asia. Hmm…

6. “I wonder if my day job will take me back if I fail.”

It’s possible. They may even say they will. But don’t count on it.

7. “Wait, so I’m expecting people to take me seriously enough to pay me to help them?

When you start freelancing, you’re asking people to part with their money in order to get something in return. Until you do it a few times, you may have serious doubts about your ability to deliver.

8. “Maybe I should get in touch with clients at my job — they sort of already pay me to do work for them!”

There’s usually this thing called a non-compete clause in your job contract, and you don’t want to mess with it.

9. “There’s a good chance I’m going to regret this.”

If you’ve gone to the trouble of typing up a letter, giving it to your boss, and having that uncomfortable “How can we get you to stay?” conversation, then surely you’ve done enough research about what you plan to do. You’re ready, and the future is bright, my friends.

10. “Can I collect unemployment?”

Not if you quit your job, you can’t. Now suck it up, buckle down, and work your ass off for that almighty dollar!

11. “I have unwavering confidence in my talent, skills, and discipline. I can do this.”

Okay, so sometimes it wavers. But guess what? You’re free! And it took guts to follow your heart and leap into the unknown. If you can do that, you can do this, too.

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