How to Inteligently Quit your Job

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You are now another step closer on your journey to your #ForeverVacation.

In this guide we will cover the following:


Misconceptions of quitting your job


How to overcome fear & social pressure


Opportunity cost of quitting your job


What you need before you quit


What’s the worst that can happen?

Quitting your job is the second step in the #ForeverVacation formula and if you have made it to this step, I’m assuming you have already launched your side business. If you have not, you should refer back to my free guide on “How to Start an Online Business.” I strongly believe everyone should have a business up and running before they quit their full-time job. I don’t want people just going into work tomorrow and giving their two weeks’ notice. You need to be intelligent in your timing on when to quit.

I truly feel the decision to quit your job ends up being more mental than anything. I have had multiple students who started a business on the side, and even when they were making the same amount of income as they were at their full time job, they still had a tough time quitting. A lot of this revolves around fear of the unknown, as well as social pressure from friends and family. Whenever something isn’t “normal” or “common” among others, people tend to shy away from it.

I quit my full-time job in 2010 to pursue my own company and start my #ForeverVacation. It was one of the scariest moments of my life, but turned out to be the best decision I have ever made. Let’s dive into the material so I can help you make the jump and get you closer to living your #ForeverVacation.


Misconceptions of Quitting your Job

I want to run quickly through a couple misconceptions of quitting your job in order to take your business full-time from someone who has experienced it first hand.

Here are two common misconceptions I hear about quitting your job:

● I need to keep my job for health insurance
● My current job is safe and stable

False: I need to keep my job for health insurance

This is something I hear constantly when I tell people that they should start to think about quitting their job full-time job. Sure, when you quit your job you will lose your health insurance through your employer, however, did you realize that you were already paying a portion of that insurance directly from your paycheck?

Yes, depending on your employer, insurance through the company can be really good, however, you can get monthly individual insurance for very cheap. For example, I pay $150/mo currently and that covers both dental and health insurance. To put it into perspective, at my full-time job back in 2010 I remember them taking out about $40 bi-weekly from my paycheck to pay for insurance. So basically it was a difference of $70 between staying with the company’s insurance or getting my own insurance. Just do a simple search online for individual health insurance plans and you will see the current rates available.

False: My current job is safe and stable

I always cringe when I hear people say this about their current job. The truth is, you are probably more safe operating your own business rather than working for someone else. If I were you, I would want to be in control of my own destiny rather than leave it in the hands of someone else.

At any time, your employer can let you go without notice. There is no safety at your current job. There may be a “perceived” safety net but if things start going downhill with the company, they will do what’s best for the company and not you. Just turn on the news. You are always hearing about people who worked for a company for 45 years and now they no longer have a pension, retirement benefits, etc. Don’t be foolish to think that the current job you have is safe and secure. I believe that the safest thing you can do is to be in control of your financial destiny. Don’t leave it up to someone else.

You will constantly hear people come up with reasons why you shouldn’t quit your job. This is due to the fact that, most likely, they have never tried to quit themselves. Take it from someone who has gone through this already. The scariest part is actually quitting your job. It only gets easier from there.


How to Overcome Fear and Social Pressure

When I first started telling people I was planning on quitting my job, people looked at me as if I was crazy. I actually had a lot of people tell me that I was making a mistake and pushing me not to do it. I found this very puzzling. I thought that when I started telling people, they would encourage me and support me, however, the majority of people did not. I later realized that people are afraid of what they don’t know. Also, I realized we live in a very jealous society. People want you to be happy and successful, but not more happy and successful than they are. Although that sounds a little negative that is what I realized over the last eight years.

So to prepare for this (if it happens to you), this is what you will need:

● Support system
● Clearly defined goals
● A firm “quit” date

Support System

As you begin this journey, be sure to find a handful of people who you can lean on for support. Generally, I like to have family members, close friends and people who have already achieved similar goals as me in my support system. The road to a #ForeverVacation can be lonely at times because it’s a road on which so few people ever travel. You will need help along the way to support and motivate you.

Clearly Defined Goals

In order to stay on track, it is important to set goals on the road to your “quit date.” You need to stay focused and if you already have a business that is up and running, you are 90% there. I want you to set weekly goals and consistently achieve them. That will help you stay in a positive state of mind and not let fear and doubt creep in. These goals should be simple and achievable to start. A few of my goals when I was in the process of quitting were finding an additional person to add into my support group, coming up with three new ways to promote my business and finding a new book to read on entrepreneurship. The point is to stay positive and focused on the end goal. These “little wins” will help keep fear from holding you back from your dreams.

Set a firm “quit date”

Lastly, to absolutely keep fear and social pressure out of the equation you need to set a “quit date.” This will be the date you actually resign from your full-time job. So the day you actually quit your job may be a couple weeks past this date but I want this date to be when you inform your company.

This date could be two months from now or eight months from now. I don’t care, as long as you set a date and stick to it. We all know how our minds can play tricks on us, so we are going to do three things to help us stick to our quit date.

Write down the date on five pieces of paper and stick them all around your house. I want this to be the first thing you see when you wake up and the last thing you see when you go to bed. You need to train yourself to know that this is the day your life will change for the best.

Tell everybody you see that you are going to quit your job to pursue your dream of making money as you travel. I want you to tell family, friends, people you meet at the bar and anyone else you come across. Tell them the date you are going to quit and what you are going to do after. This will help hold you accountable to your quit date because if you don’t quit, you will feel embarrassed for not sticking to your word.

One last safe guard will be to put your money where your mouth is. I want you to sign up for a free account on StickK ( StickK is a free site where you set a goal, set the stakes if you don’t achieve it, and then pick a referee and add friends for support. So basically you will set your goal as the date you will quit your job. Then I want you to add an amount of money that you will feel really bad about if you lose it. Next you will pick a friend to be your referee and add friends to encourage and support you. If your quit date comes up and you still have not quit your job, then you will lose all that money and will disappoint your support group. Utilizing the psychological power of loss aversion and accountability will help you stick to your goal of quitting your job.


The Opportunity cost of quitting your job

Opportunity cost is defined as, “the loss of potential gain from other alternatives when one alternative is chosen.”

Opportunity cost plays a big role in the decision to quit your job. This is mainly because you look at your current business and maybe it’s not exactly where you want it to be. Most likely this is due to the lack of time you have for your business. Think about it. You are working 40+ hour weeks at your current job and then you have other commitments, such as the gym, friends, hobbies, etc. It’s tough to really grow a business at first with so little time.

So how about if you looked at your business differently? Think about the potential of your business once you quit your job and had an extra 40+ hours a week to grow and expand your business. The potential would be limitless. If your company is already off to a great start with only a little time per week, just think about where it would be with so much more time.

So I want you to change your mindset and start thinking about where your company will be in the future with more time, rather than looking at the current state of your business. The possibilities are endless when you start factoring the opportunity cost into the equation. It’s still a leap into the unknown, however, you will be armed with more time and a more positive mindset.


What you need before you quit

When I was contemplating quitting my job back in 2010, there were a handful of things that really made it easier to quit my job and continue my transition to my #ForeverVacation. As I mentioned above, quitting your job is a scary moment so you need to have some things in order so you can lean back on them.

These are the things I feel like you should have before you quit your job:

● Support system
● A side business that is up and running
● Four to six months of financial runway
● A few clients/sales or at least some traction
● A loose plan on how you will operate your life after the office

Your business should be up and running

Since I have already discussed creating a support system, let’s jump right into the side business you created. Before you quit, I want your business to be fully operational. That means your website is live, you are starting to market your site, and maybe you even have a couple clients or sales (but not necessary). This way, once you quit, you will not be wasting any time building your business so you can focus solely on generating revenue.

Four to six months of financial runway

It’s important to have a financial cushion when you initially make the jump to running your business full time. Not only will it give you comfort knowing you have some money in the bank, but it will also help you if your business takes a little longer than expected to generate revenue.

I suggest that everyone has four to six months of financial runway. This means if your expenses every month are around $1,500, you should have between $6,000 - $9,000 saved in the bank before you quit. So take some time and calculate what the absolute necessary expenses are that you have every month (i.e. rent, car payment, etc.). Then, multiply that by four, five or six months (depending on your risk tolerance) and that will be the amount of savings you need to work up towards before your “quit date.”

A few clients/sales or at least some traction

As I mentioned above, I want to make sure your business is up and running before you quit your job. I would also like to see you have a couple clients or sales already in the business or at least be showing some traction. I want to see this in your business first, not just for the money, but to see if there is a market for your business. If you have been working at your business for a few months and are not getting any clients or nobody is visiting your site, it could very well be that there is not a demand for your business. At that point, it would be best to pivot and try something different if you’ve truly been trying hard but haven’t gotten any traction.

When I launched my first mobile app, Peekaboo Mobile, it started off slowly. I didn’t have much time to work on it since I had a full-time job that commanded most of my time. However, in June 2010 it started gaining some traction and we started seeing a spike in our user base. We were not making any money at that time, however, we knew the opportunity cost was huge if we could put more time into the business. That is when my business partner and I decided to quit our full-time jobs and pursue Peekaboo Mobile full time. I’m very happy we took the risk because a year later we sold for $1,200,000.

A “loose” plan for life after the office

An exercise I like to do with my students when a big change is in the near future is to have them envision what life will look like after they make the change. It helps them project a positive attitude towards the change and think about all the great things that will happen.

For this exercise, I want you to think about what you will do immediately after you quit your job. Will you stay where you are or will you move somewhere else? Will you work from home or would you like to work from a coffee shop? When would you like to work? In the mornings? Or do you work better at night?

Write some of these things down as you start to think through them. It doesn’t have to be a formal plan but I just want you to start training your mind to how life might be once you have this new-found freedom. It’s exciting to think about all the amazing things ahead and this exercise should train your brain to start preparing for the future.


What’s the worst that can happen?

Whenever I have a friend or student contemplating this kind of decision, I always ask them the question,
“What’s the worst that can happen?”

It’s a great question that really gets the mind thinking and more often than not you realize the worst isn’t so bad. Now if you applied this question to, “should I go skydiving or not?” than you might not like the end results. But let’s focus on quitting your job for the sake of this question.

I want you to take a piece of paper and split it into two columns. In the left column I want you to write, “The Worst” and in the right I want you to write, “The Best.” So you now have a piece of paper split into two sections and I want you to first write some potential negatives to quitting your job and than you want you write the potential positives to quitting your job.

I did the same exact exercise when I decided to quit my job and it looked something like this:

Worst that can happen

● My business does not perform as well as I thought and I need to find another job to pay the bills

Best that can happen

● My company goes great and I’m able to travel and work from wherever I want
● I meet new connections and entrepreneurs that I would have never met in my 9-5 job
● I learn a bunch about entrepreneurship and get the chance to be my own boss
● I have more time to do the things I actually want to do
● I make more money than I have ever made before
● People look up to me as a role model and I have more influence in society
● My life becomes more meaningful

Honestly, at the time, I could not think of more cons to add to the list. I wasn’t going to write, “become homeless” or anything like that because I knew I could always get another job to support me. Even if that job wasn’t my ideal job, I could still be a bartender or work in an office just to get me on my feet until I had the next business idea.

Please don’t forget to do this exercise. Nine times out of ten, the pros will outweigh the cons and you will feel more confident in your decision to quit your job.

My business partner and I with our company mascot “Peeks the Frog” after we quit our
full-time job

That’s a Wrap!

You don’t want to live a life of regret. One of the main things that pushed me to quit my job was hearing my co-workers say stuff like, “I wish I would have done this” or, “I wish I would have started my own business.” Don’t be like all the others that have big dreams but never chase after them.

One of my favorite quotes is, “People may doubt what you say but they will believe what you do.”

As always, if you have any questions please send me a message.

Best of luck on your journey towards your #ForeverVacation

Ben Dolgoff

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