How to Quit Your Day Job: Un-Talked About Concerns

How to Quit Your Day Job: Un-Talked About Concerns

The purpose of this article is to guide you through the steps necessary to go from: a) working at a job that turns you into a zombie you’re not happy with to b) beginning self-employment.

What this guide is not: The following is not meant to teach you how to create a successful business. That is beyond the scope of this article.

So, if this isn’t meant to teach you how to create a business, how can it help you to quit your job?

Well, it turns out there is a lot more that goes into quitting your job than just creating a self sustaining income.

You’ll have to figure out how to talk to your family and partner about it, set and stick to a firm date, go through the uncomfortable transition to being reliant on your self employed income (surprisingly difficult if you like a feeling of safety and security) and create a savings fund to cushion your transition (unless you prefer no safety net when you jump - upon which I would say you're crazy).

This guide intends to address these often un-talked about concerns.

Being dissatisfied isn’t enough

A lot of people know that they would rather not be stuck in their current work situation.

But knowing what you don’t want and being dissatisfied isn’t enough. And while dreaming about what you’d rather do is great (it keeps your hope alive), it’s not enough either.

At some point you’re going to have to address the gritty, practical and tactical side of how you’re actually going to change your situation.

Below, I’ll address each of these topics related to taking the plunge (actually quitting your job and doing what you want):

  1. Is self employment right for me? Or am I just jumping on a bandwagon?
  2. Finding your thing and establishing yourself.
  3. Setting your date for your final day of work.
  4. Approaching the topic of quitting with your partner and loved ones.
  5. Safety nets, savings accounts, and preparing for the transition.
  6. Saying “I quit” and reclaiming your time.
  7. Acclimating to freedom and the schedule-free life.

Let’s get started, shall we?

Is self employment right for me? Or am I just jumping on a bandwagon?

There are a lot of blogs out there (this one included) that tout the benefits of self employment: more freedom, greater control of your work, and choosing the people you want to work with, to name a few.

All of this is awesome, trust me, but are you also willing to accept the responsibility?

When you’re self employed you are the one responsible for making sure enough money comes in each month to pay the bills.

When you work for someone else, you don’t have to think about that. You just wake up and do your job.

Are you also okay with running the details of overseeing administrative work, scheduling, taxes and operations in your business?

Most people talk about the rosy and alluring side of working for yourself, but they don’t mention some of the very real changes you have to make that you might not have known about.

I’m not saying that it’s not worth it, it is. But it’s not right for everyone.

So, the first step is to ask yourself… Do I really want this? 

If the answer is yes, then proceed. And if it’s not, that’s okay too. You’re not any less cool than the “lifestyle design digital nomads.”

Finding your thing and establishing yourself

I mentioned earlier that this isn't intended to teach you how to start or run a business (impossible in a blog post).

But we should at least cover the two most important steps:

  1. Selecting a market
  2. Opening up for business.

A lot of people email me telling me how they’d like to start a business. But they’re paralyzed. They’re unable to make a decision about the market they’ll get into and continually second guess themselves.

There’s a place for exploration and discovery, but at some point you have to saddle up.

There are a lot of resources out there that can help you with this.

But if you don’t firmly choose a market you’re not even in the game yet. You’re just sitting on the sidelines. And it’s hard to build a business that way (obviously).

Finding your thing is a means of trial and error. The biggest hint that you're onto something is engagement.

If after 6 months of genuinely trying, are people reaching out to you? Complimenting you on your work, thanking you. Companies wanting to work with you.

Once you find your thing, it's then time focus. Stop f'ing around doing multiple things. Focus in on serving your audience.

Shiny Object Syndrome - The Secret to Success is FOCUS
As an expat with an online business, I’ve learned the hard way that the secret to success is focus. Singular focus on one business model and to stop getting distracted by shiny object syndrome. You need a singular focus because you can’t build and scale anything without it as you’re

By that I mean actually putting up a website and making an offer. If you have a “blog” that you want to eventually “monetize,” then you don’t have a business.

You don’t have a business until you actually have something for sale. Until you then, you only have a hobby.

That’s fine if that’s what you want.

But then why are you reading this article?

Obviously you don’t just want a blog, you want a business. So don’t put off creating an offer until you have X amount of subscribers or “1,000 true fans” or whatever you think you need to start.

Go through the trial and error process of finding your thing, then focus and get to work.

If you wait to put out an offer, you have no idea if people are willing to buy something from you.

And that really sucks.

You might spend a lot of time building an audience that is just there to hang out. Great if you want a hobby or community, bad if you want a business.

Setting the date

People that are engaged know this. If you haven’t set a date, then your getting married may or may not happen.

Who knows, right?

Same thing goes with quitting your job. Without an actual date it’s just a nice idea.

So if you haven’t already, what I want you to do right now is set an actual date. Write it down. Put it in your calendar. And if you’d like type it out in big 48pt. type, print it, frame it, and put it on your nightstand.

Now it’s going to happen.


Because now your mind has shifted from “Nice idea” to “Damn, I’ve gotta figure out how to do this by this actual date.” It makes a huge difference.

For me, I was doing VIPKID which replaced my "rent money" from my cushy University teaching job.

Quitting this easy job and going it independently made me sick to my stomach to be honest. It really is a transition from perceived safety (in reality safe is not safe) to being dependent on my own work.

Talking about quitting with your partner and loved ones

If you want to quit your job, at some point you’re going to have to tell your partner (or whomever is close to you) about it.

The best approach, particularly if you're talking to a woman is to have a plan and make her feel safe with your decision.

So actually come up with a plan that details at the very least:

  1. How you’re going to become self employed.
  2. How much money you’ll need in savings.
  3. How much you expect to be making at the time you quit.

He or she may not believe you at first, but when the money started to come in, they may start to believe that this might actually be possible.

And guess what? It is possible.

How to Make a Small Amount of Money Online (and Grow It)
Without a doubt, every single person I’ve met who has a command of the ability to make their own money is more charismatic. The reason for this is simple: if you have mastery of the ability to provide value in order to generate income it boosts your self-confidence. Then

Some people will respond and be more supportive when you show them results. But either way, talking to your loved ones about it and showing them you consider them in your decision (because it most likely affects them, too) goes a long way.

It’s scary to know that you may be met with skepticism and disbelief, but the more you show them with your actions the more they will begin to take you seriously.

It should also be noted here that if you want the best support on your path to work freedom, it’s best to look for that from people that are already self employed or currently on the same path as you.

They will be the most sympathetic and are more likely to cheer you on. It’s not fair to ask the same of people living in a completely different reality.

Safety nets, savings accounts, and preparing for your transition

Should you have a cushion when you jump or are you confident that you’ll land on your feet? This is something you’ll really need to consider.

When I quit my English teaching job to work on my YouTube channel, websites, freelance and to do VIPKID, I was almost $7000 in debt.

It's a weird thing, like being overweight and not wanting to step on the scale. But when you're in debt you also tend to put your head in the proverbial sand.

In retrospect what I did was quite risky. But I had it a breaking point in my life. Sign my contract for another year at a University located in the country side of Thailand in Ratchaburi province.

Another year as a handsome, strong man stuck in the middle of nowhere...

...or quit and move to Bangkok.

I chose to quit and move to Bangkok and get on with my life. It was stressful, but I did start to make double what I was making as an English teacher and then triple.

Soon, paying down my debt became an easy and realistic possibility.

So, you’ll need to ask yourself a few questions:

  1. How much money do I need in savings to feel comfortable quitting my day job?
  2. When do I need to save this money by? (Hint: it should be your quit date that you defined a few minutes ago. You did do that, right?)
  3. Do I expect to be making the same amount of money from my business (job replacement income) as I’m currently making from my job when I quit? Or am I okay with quitting without making any money (or only some) from another source?

I know a lot of people that are okay with only having a giant savings and no money coming in yet from alternative means.

I wasn’t one of those people.

I wanted proof that I could consistently make the same amount of money I was making at my job before I felt safe quitting.

You’ll need to decide what you’re most comfortable with and plan accordingly.

Saying “I quit” and reclaiming your time

When it finally comes time for you to give notice to your employer, you must follow through.

You will likely second-guess your decision at this point. This is perfectly natural. But now is not the time to back out. You’ve been working diligently for months (or perhaps years), and you’ve done all you can.

Nothing else at this point will prepare you anymore. You have to get in the water to learn how to swim.

A month or so before your quitting date, it’s a good idea to take some time to think about what you’ll say to your employer. Writing it out helps. You can have fun with this too. In my resignation letter I told my boss “I will no longer be requiring your employment services.”

Obviously you don’t want to burn any bridges (or do you?), but feel free to be creative. This is something you’ll remember for the rest of your life; why not make it fun?

You may even want to write your resignation letter now. Doing this helps make it more real and in turn will help you follow through.

Dear sir/madam,
As of month/day/year, I will no longer be requiring your employment services.
While mind-renting has had its perks (I’ve always had a thing for fluorescent lighting), it’s time for me to move on.
I wish you the best, and pray to God I will never return.
Yours truly,
The newly self-employed

Acclimating to freedom and the schedule-free life

It would be a bit dramatic to say that reclaiming your time is the same as being released from a long sentence in the state penitentiary.

But it does have a parallel in that you will need to take some time to adjust. Things will feel funny at first.

You’ll feel weird not having to ask for permission to take a long lunch or go for a hike in the middle of the day.

One day you might wake up late and start automatically thinking about the excuse you’ll tell your boss. Rest easy, you’re the only one you need to answer to now.

But the schedule-free life also comes with its own set of challenges.

Now that you have the reigns on your time, you’ll need to develop your own methods to ensure things get done.

You could have worse problems, right?

The last thing to do once you’ve finally quit is celebrate. Do something special for yourself and savor the rite of passage you’ve just undergone.

When I quit I took off on a trip to Chiang Mai and Chiang Rai. Heading up to Pu Chi Fa in northern Thailand. During the semester when I would have been stuck in a classroom.

Just like writing your resignation letter in advance helps to make things more real, so does deciding what you’ll do to celebrate on the final day.

Freedom is created

You have to create your own freedom. If you don’t, no one else will do it for you.

If you don’t have a plan for yourself, it’s likely that someone else does. Or you’ll just end up living by default, by a template you certainly didn’t design.

If you want to be your own master, you’ll have to reclaim ownership of your mind.

So… over to you.

What do you find to be the most challenging or daunting thing when it comes to quitting your job? Or if you are already self employed, what was it when you were preparing to quit?

More? More!

26 Reasons Why You Should Never Have a JOB
I used to watch this show called The Big Idea with Donny Deutsch while at University (I’m dating myself now!). I loved the stories of people doing something creative to make more money than they ever did before. This show was a source of hope and inspiration for me