Do You Want to Quit Your Job? Here Are 5 Critical Factors to Consider

I've heard this many times from friends. Quitting your job to pursue your passions could be the best thing you ever do. It could also totally screw up your life. Do you want to quit your job in the near future? Before you quit your job I want you to look at a few potential issues (along with solutions) so that you don't end up broke and begging for your old job back.“I want to quit my job. It’s time to become the CEO of my own life. I’m going to take control.”

I’ve heard this many times from friends. Quitting your job to pursue your passions could be the best thing you ever do. It could also totally screw up your life.

Do you want to quit your job in the near future? Before you quit your job I want you to look at a few potential issues (along with solutions) so that you don’t end up broke and begging for your old job back.

In movies or in motivational videos on YouTube, the story is usually the same.

The person quits their job with no safety net or any sort of backup plan. They tell their boss off and leave their job. They’re confused for a few days or possibly a few weeks before meeting a guru who changes their life. They usually end up starting some billion-dollar business or things just work out for them. Now they’re rich and married to a gorgeous partner.

This person then goes on to live a successful life where they share nonstop memes about how self-employment is the best thing ever.

In reality, it doesn’t work like this.

Quitting your job to work for yourself is very scary and intimidating. You’re going to experience many issues that won’t just go away. You’re going to be challenged like never before. You’re going to regret making the jump almost daily.

Let’s look at the issues (and solutions) associated with quitting your job to work for yourself…

What issues will you experience when you try to quit your job?

Before you quit your job, I want you to think about these issues. I’m not here to glorify working for yourself. You already know how much you hate your job and how badly you want to work for yourself.

I’m here to help you work self-employment on issues I had to figure out on my own.

What are the common problems that you’re going to experience when you start working for yourself?

Issue #1: You’re going to struggle to find a new schedule.

When you have a job, you have a set schedule. You’re told when you have to be there, when you can go for lunch, and when you can go home. You have to abide by the schedule or else you’re going to be fired. You never think about your start time or finish time.

When you work for yourself, you’re the boss. You get to decide when you start work, when you go for lunch, and when you’re done for the day. There’s a lot to think about.

You might be thinking that you’re going to be a productivity machine now that you have all of this free time.

I have some bad news for you. More time doesn’t equal more work done. I usually loiter around most of the day until it’s time to get some serious writing done at the worst times possible. I usually find myself working on the weekends when everyone wants to have fun since they don’t have to work.

Issue #2: Dealing with family and friends who want to interrupt you or give you unsolicited advice.

  • “Can you help me move since you’re free during the day?”
  • “I’m going to be in your area around noon, let’s do coffee!”
  • “Why would you quit your day job? That’s crazy!”

Those closest to you want what’s best for you. They also will think that you have all of the free time in the world now that you don’t have a traditional 9-5 gig.

You’ll have friends scold you, you’re going to have friends who think that they can just ask you for anything now since you don’t have a job, and you’re going to find that those around you may think that you’re not making the best move.

Dealing with close ones becomes even trickier when you have a family that you’re responsible for. It’s not exactly easy to give up a guaranteed income to chase the unknown.

Issue #3: Being in charge of everything is a lot to handle.

You’re in charge of everything from marketing to accounting. It may feel exciting to put “CEO” in your social media profile, but this means that everything falls on you now.

You have to deal with the following when you work for yourself:

  • Design work.
  • Accounting.
  • Sales.
  • Marketing.
  • Human Resources.
  • Technical support.
  • Customer service.

You can outsource most of this, but that won’t be free. You also have to decide what gets outsourced and what you’re going to do on your own based on costs and your skills.

Issue #4: Making money.

How are you going to make money on your own? How will you match your previous salary and everything that goes with that (retirement plan, health benefits, etc.)?

When you have a job, you know when you’re going to get paid and you know how much you’re going to get paid.

I have friends who are on salary who know exactly what they’re going to get paid and the exact moment that they’re going to be paid.

When you’re on your own, you have no idea when you’re going to get paid or how much you’ll be making. Sometimes, vendors will delay payment or people will try to get you to “work for exposure.”

You can also lose a major client due to no fault of your own. You can find yourself scrambling for money to just survive.

Issue #5: Your benefits and retirement planning.

I know many friends who stay at their jobs simply for the benefits and retirement planning. When you’re on your own, you have to figure out all of this.

How do you overcome these struggles of working for yourself?

Now that we looked at the most common issues with working for yourself, it’s time to overcome these struggles.

Solution #1: Trying to find a new schedule.

You have to tackle this first if you want any chance of surviving self-employment. You need a schedule because it’s far too easy to take a Monday off or to binge watch Netflix. You then end up catching up on the weekends and pissing off everyone around you.

How do you set a schedule now that you’re on your own?

  • Find an “office” space. This could be an extra room in your home or the local shop. You need to go somewhere to get in the zone.
  • Create work hours. You need clear working hours so that you’re not always on.
  • Focus on the work that brings in the money. It’s easy to get caught up in social media filters and things that don’t mean anything. You have to focus on what’s going to bring in the majority of your revenue.
  • Know when to stop working. You have to know when to stop for the day. You can’t always be working.

It won’t be easy at first, but hopefully, you can get into a decent routine.

Working for yourself doesn’t mean that you have free-time 24/7. You just have control over when you get to work and when you get to take some time off for yourself.

Solution #2: Dealing with friends and family.

It’s critical that you set expectations with your friends and family. There’s no other way around this. You have to sit those close to you down and explain what you’re doing.

On the flip side, you don’t have to explain yourself to every single friend or acquaintance from work. You don’t have to justify your decision to Steve from Accounting or some random dude from the gym.

Solution #3: Being in charge of everything.

The good news here is that your small business can stay small. There’s no rule that states you have to hire a whole team. Here’s how I deal with being in charge of everything.

Outsource everything that you can’t do easily and use tools to make your life easier.

Solution #4: Making money.

How do you handle this issue? This is where things get interesting. At your job you likely know that you’re going to get paid. You know when you’re going to get paid and how much you’re going to get paid. I have friends who know to the penny what their paycheck will be.

Here are a few financial rules that you should follow before quitting your job:

  1. You have to be making money with your business before you quit your job.
  2. To ensure that you can survive the lean times, it’s important that you save up six months’ worth of expenses in an account.
  3. I’ll say it again: prepare your finances before you quit.

Solution #5: Your benefits and retirement planning.

There’s no easy solution here. You’re going to want to take care of this paperwork before you quit your job. You’re going to have to reach out to other self-employed folks and you’re going to have to do your research.

You should absolutely take care of this before you quit your job. I just don’t want you to quit your job and then realize that you suddenly have no retirement plan.

Bonus section: A few other things to keep in mind before quitting your job…

As I finished writing this article on quitting your job, I realized that I missed out on a few factors that you should consider.

Here are 4 more bonus considerations before quitting your job:

  1. Job searching. Will you be looking for another job in the near future? Are you taking a career sabbatical to work on your own business?
  2. Updating your social media. Don’t forget to update your social media information to reflect your new situation.
  3. Interview skills. What will you do about your interview skills? The further removed that you are from the interview process, the more difficult that it will be to maintain your interview skills.
  4. Your social life. What will you do for your social life? Many folks only hang out with co-workers. Will you make new friends now? What will you do to combat the loneliness that comes with working from home?

That’s what you absolutely need to think about before quitting your job so that you don’t end up feeling overwhelmed. This may be a lot to think about but that’s because quitting your job isn’t a decision that you should take lightly.