What No One Tells You About Quitting Your Day Job
Career Growth

What No One Tells You About Quitting Your Day Job

by Jessie Hunter
Photos Ana Raab | February 26, 2016

EVERYONE HAS ADVICE FOR YOU WHEN YOU'RE CONSIDERING QUITTING YOUR DAY JOB AND GOING IT ALONE, BUT THERE ARE FIVE VERY REAL THINGS THEY SOMEHOW ALWAYS FORGET TO MENTION. 

After weeks, months, or years of contemplation, you think you're finally ready to leave your 9-to-5 and strike out on your own. Congratulations. Simply making it to this headspace is an achievement in and of itself, and we commend your bravery and willingness to take a risk. That being said, breaking out as an entrepreneur comes with a set of facts that no one seems to warn you about. Ever.

I discovered these things myself when, after several years at a kushy corporate job, I left to pursue the writing and travel that made my heart sing. Here’s what I wish I'd known then and what you should know now: 

1. YOUR FREE TIME WILL BE YOUR WORST ENEMY 

The first week out of the office will feel like a breath of fresh air. Literally. You'll get outside more and breathe at a slower pace. You have no schedule to militantly abide by, and chances are you will take this week or so to decompress and build out your game plan for what the next week, month, or year will look like. Maybe you'll even let yourself sleep in until noon once or twice.

By week two, though, you will feel a quiet voice inside you start to mumble. If you don't have a rock solid schedule for how to spend your days, this voice will begin to grow louder until you hear it as a shout from this spot in your rib cage directly under your heart. I can't make this up. Do whatever it takes to have a schedule in place by week two, even if that means adding "Get coffee and work from 9 to noon" to your calendar or booking morning workouts twice per week. It'll help.

2. IMPOSTOR SYNDROME IS REAL AND YOU WILL EXPERIENCE IT 

I have yet to meet an entrepreneur who, once they quit their day job and began dedicating time to their own pursuits, did not experience an overwhelming fear that they'd be exposed as a fraud. The feeling is not so much rooted in self-doubt as it is a certainty that you've fooled everyone else you know. They're supporting you and letting you do this thing, but eventually someone is going to realize that you have no idea what you’re doing and you’re faking it in the hopes of making it. This all-consuming set of feelings is called Impostor Syndrome, and it will eat away at you for a while.

The first step in dealing with Impostor Syndrome is recognizing it. You're not a fraud. Tell yourself that this feeling is not reality because you’re not pretending to leave your job and work on your passion, you are actually doing it. The second step after acknowledging these facts is to simply keep moving forward in your new pursuits. Every time those feelings creep back into your head, politely remind yourself where they belong, then continue doing you.

3. ALL THAT FREEDOM MEANS YOU'LL LOSE FOCUS

While this may seem like a throwback to point number one, there's a distinction. When you have all the time in the world, it can be overwhelming to choose exactly how you’re going to spend it. But what you'll also find is that when you are no longer subject to someone else’s instructions on how to move the company forward, there are an infinite number of directions you can take. You can focus on profitability, revenue generation, partnerships, or attracting investors. What you cannot do, however, is focus on all of these aspects of your business. Playing Jack of All Trades, Master of None means you'll build a business that's without focus and, frankly, unlikely to succeed. The only way to avoid this trap is to have not only a business plan, but also a company focus prior to leaving your day job.

4. YOU WILL MAKE A TERRIBLE MISTAKE (OR TWENTY)

One of the most difficult things to foresee is also one of the most inevitable—at some point you will fail. Maybe (hopefully!) not your business entirely, but you will make a mistake at some point that will feel insurmountable. You'll run late with an important project. You'll lose your biggest client. You'll burn through cash reserves too quickly. Something will go wrong, and you'll ache sorely from the embarrassment of having been so foolish. And right about then, you'll likely wonder what on earth made you think it was a good idea to leave the comfort of your previously stable job.

This is the moment that will decide if you will become someone who tried or someone who succeeded. Those that "tried" a new venture will slink away at this point and chalk the whole experience up to back luck and/or oversized ambitions. Those who succeed will study their mistakes, tearing the situation down to the bare bones of lessons learned, and then they will try again.

5. YOU WILL FEEL MORE PRIDE IN YOUR WORK THAN EVER BEFORE

When you leave your day job and risk it all for a venture you truly believe in, at the end of the day your nervousness, stress, and exhaustion will be matched only by the overwhelming pride that you have created something new. You'll pay for your morning coffee one day and think: Wow, I earned this $3 on my own terms, off of my own work. This is my coffee. Taking ownership of your income, career path, and professional self is life-changing and it's worth holding your head up high. It's an indescribable feeling.

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What did you learn that you weren't expecting when you quit your day job? 

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