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So many people want to quit they’re 9 to 5 job but do not know where to start. Hundreds of questions usually come up. Will I have enough money to sustain myself and my family? What will my partner think? What about job security, and the pension that I’ve been saving up for?

Should I quit my job? The way you can know if you can quit your job is by evaluating your social and economic circumstances and context. What is your current cost of life? Could you live more humbly? What is the cost of your aspirations and dreams? How motivated, dedicated and skilled are you?

If you are thinking about quitting your 9-5 job to build passive income streams there are some things to consider before going all in. We have added to color boxes to this article to provide more examples. The purple is a context of someone who is in a great space to leave their 9-5 job to go full time at making passive income. The red is someone who may not want to leave that 9-5 job at this point. Read on to learn more.

What are Your Circumstances & Context?

Your circumstances and context play a major part in your decision in leaving your 9-5 job, or not. A couple things coming to play with into play in this decision, notably with regard to your social and economic situations.

Social Circumstance

By social circumstance we would like to focus your attention on where are you in life at the present moment. Are you in your early twenties, living at home, with no overhead and a paying job? In that case, this may be a great time for you to dip your toes in building passive income sources. However if your 40, have a full-time job, and three young children, a mortgage and student debt, your ability to commit yourself to building passive income maybe a little more slow (but all the more important).

Mehdi is 22 and lives at home. He’s lucky enough to have started life out with no debt and currently has a well-paying job. He has set 6 months income aside, and is thinking about freeing his time by leaving His 9-5 job to make passive income.

Jennifer is 43. She has two kids, a mortgage and some student debt left over from a diploma that she wound up not using. She’s starting to think about her retirement, and is worried she will not be making enough income to sustain herself and her family in the future.

Family & Peer Context

Along the same lines as above, do you have a supportive family and peer group? Building passive income is extremely time demanding. Building a sustainable passive income source will require long days and long nights of work and dedication. Will your spouse or your life partner be supportive of your building passive income sources? If the answer is yes, that is great news 🙂

Not many people are fortunate to have a supportive partner when building passive income sources. However if you believe that your family or your spouse may not be supportive of your work, rest assured that there are ways to make compromises and also to find that support outside of your family and home.

One of the biggest drawbacks a life partner may talk to you about is “job security.” Although you can tell them over and over again, they may never understand that job security just does not exist. One way you can help reassure them while opening up more time for you to create your passive income, is by negotiating your terms at work. We talk about that more below.

It’s important to have a strong support system. One way you can find this is by subscribing to other YouTubers who talk about making passive income while providing inspiration and motivation. We highly recommend the following channels: Pat Flynn, Gary Vaynerchuk, Income School and our own channel Beginners Passive Income.

Subscribe to Beginners Passive Income on YouTube

Mehdi is currently single and has a very supportive family. His parents are immigrants and entrepreneurs who support him in building the life he wants, even if it involves taking some risk to achieve their dreams.

Jennifer’s partner is worried about job security. He believes that is better she stays in her accounting job that is very stable. He’s very comfortable in the current lifestyle although it is very demanding for Jennifer (job, kids, pets, house – the usual).

Employment Context

It’s really important to think about this before leaving your current job. What is it at your 9-5 that you do not like? Some things that usually keeps people from enjoying their job is a lack of:

  • Alignment with personal goals
  • Purpose
  • Flexibility
  • Free Time
  • Income
  • Encouragement

The main reason that people leave their 9-5 jobs is because it does not align with their personal goals. Therefore “know thyself.” No matter what you decide to do, create your own business, create passive income sources, or get a different job, make sure that what you chose aligns with your personal goals. We will have a closer look at that in the section on the cost of your dreams (below).

Before you decide to jump ship and leave your nine-to-five job, consider having a look at other options. Why not rearrange your schedule to free up your time? After testing things out, you may see some success and want to go part time. Being part-time will provide you more time in the week to build your own income sources.

Mehdi likes his current job but feels fairly unfulfilled, like he can do way more on his own. He catches himself looking at the clock every hour, excited to go home and continue working on his passive income sources.

Jennifer also feels unfulfilled at her current job. She would like to be able to spend more time with her family, have access to more income, and believes she has the skills that she needs to do so.

Personal Motivation

Working for yourself is very very different from working for someone else. Instead of having your task list dictated to you, you are responsible for creating your own schedule and providing yourself your own income. The best way to know if you’re cut out for this is to give it a try before you leave your 9-5 job. Another criteria that’s important with regards to personal motivation is your tolerance to stress and risk. If you are highly risk-averse, you may not be willing to leave your 9-5 right away, and that’s okay.

You can start out with a couple side hustles and see how much you enjoy them. These are income sources that can be fairly active initially, but can be made passive through delegation and automation. Starting out with a side hustle will allow you to better understand how you work for yourself, and if you actually like it. Not everyone is cut out to be an entrepreneur and that’s also okay 🙂 We have a full list of passive income ideas available in this guide. Some are more risky than others, some require more entrepreneurial skills than others. But each guide covers both criteria. Check them out.

See our Passive Income Ideas List

Mehdi knows what it’s like to be an entrepreneur since he has been working for his family’s business since his childhood. Putting in the hours does not scare him. He also knows how to prioritize this time, and be very productive. That’s one of the reasons why his employer does not want to lose him.

Jennifer is unsure that she can find the time to build a passive income sources the way she would like. She knows she has the skillset and the motivation to do so. Finding the time is a big issue.

Economic Circumstance

Your economic circumstance is also a key factor in evaluating if you’re ready to leave your 9-5 job. What is your current cost of life? Can you live more humbly? And what is the cost of your dreams?

What is Life Costing You?

We cannot tell you the number of people who do not know how much life costs them every month. Of course this number does vary month to month, however it is very easy to create your monthly average once you have calculated this over a year. The reason people do not calculate this is often because they do not have a tool to do so.

Download Our Cost of Life Excel Spreadsheet

Click on the button above for our budget planning Excel spreadsheet. If you do not have Excel on your computer you can open it in Google Drive (free for anyone with a Gmail account). Fill in that document to calculate your monthly average. And be honest with yourself. Now you have no excuses 🙂

Mehdi is currently setting money aside. He has six months income saved up, and feels confident that he can build his passive income sources fairly quickly if he went all in, full time.

Jennifer is in debt. She just about breaks even every month. The things costing her the most money are her mortgage and her commutes to work.

Can You Live More Humbly?

Now that you have an idea of your monthly expenses, it’s time to look at if you can live more humbly. Gary vaynerchuk often talks about moving in with your parents. This may sound absurd and socially unacceptable, but it is one way to save a lot of money.

After housing, Another thing that costs people a lot of money is there transportation. Is there a way that you could lower your transportation expenses, by taking public transit, commuting to work with others, walking, or using alternative means of transportation?

Also have a look at your monthly subscriptions. There are certainly things that you are currently paying for in a recurring manner that are not providing you that much value. If you can cut these things out of your budget you will save a lot of money in the long run.

Mehdi lives at his parents and uses an electric scooter to get around. He does not need a gym membership since he does a lot of walking and plays sports with friends for fun.

Jennifer spends a lot of time in her car. She knows it is not good for her budget or her health, and therefore wants better for herself and her family. She knows passive income would provide her exactly what she wants.

What do Your Dreams Cost?

This is so underestimated but so important. How much would it cost you to achieve your dreams? And it’s actually possible to calculate this! 

“What would you do if there was no way you could fail if you were ten times smarter than the rest of the world?”

Tim Ferriss, The 4-Hour Workweek

We are very grateful to have read the 4-Hour Work Week by Tim Ferriss (learn more about the book in our Passive Income Book Guide here). This book contains a PDF document that he calls a “Dreamline.” What dreamlining entails is calculating how much your dreams will cost you per month, in the following categories:

  • Own: Things you would like to have
  • Be: The person you would like to be
  • Do: The things you would like to do

Take the cost of all of these things and then divided over the time in which you would like to achieve your goals. Check out this PDF document to be able to calculate how much your dreams cost you.

Access The Dreamline PDF on Tim’s Site

Mehdi has fairly expensive dreams. His goal is to make enough passive income to live comfortably in a large city. He would also like to travel and give conferences all over the world. He wants to be able to speak multiple languages and one day give back to his parents by purchasing a house for them.

Jennifer would like a comfortable retirement. She would like to live in a warm place with her family close by. She does not need luxury or fancy things. She just wants quality time with her loved ones.

You May Not Need to Quit Your 9-5

“Jump when you can afford to drown.”

Gary Vee

After having evaluated all these things you may be wondering if you should leave your nine-to-five job. Gary Vee says “jump when you can afford to drown.” That’s excellent advice. Only you can decide once it’s time. But there is no reason not to get started right now.

See our Passive Income Ideas List

Mehdi knows he has everything he needs to leave his 9-5 job but decides to stay where he is. He knows he is young and has a lot to learn from his boss. However, he negotiates a part time salary instead of remaining full time. His boss accepts because he loves working with Mehdi and does not want to lose such an excellent employee. Mehdi is thankful and excited, as he can gain experience in a business working for his boss, while building up his own business on the side. Going part time allowed Mehdi to build passive income streams and comfortably leave his 9-5 job at age 25.

Jennifer can’t afford to leave her 9-5, but that will not keep her from achieving her dreams. She convinces her partner that job security does not exist, and that even if she stays in her current job, they will not have enough money to sustain themselves at retirement. They decide to sell their house, downsize, and move in with her parents for a year. Her parents are delighted to be able to spend more time with their grandchildren. Not only does Jennifer have more time for herself, she also starts making passive income right away. Her mortgage disappeared with the sale of their house and after placing ads on her car, downsizing their belongings by flipping them on Craigslist, and renting out things they no longer use, she also paid off her student debt. Now that they are in the clear, she is looking forward to getting started blogging over the next year to build enough passive income to sustain herself and her family for many years to come.

Check Out Our 12 Favourite Passive Income Ideas for Beginners in our Webinar!

Related Questions

How can I make enough money to quit my job? Some ways to make enough money to quit your job include lowering your expenses, saving money, living more humbly, and replacing your current income with passive income.

Should I quit my 9 5 job? Knowing if you should quit your 9-5 job can be based on factors such as social and economic circumstances and context. Evaluate your current cost of life, ability to cut expenses, and the cost of your aspirations and dreams. Also have a look at how motivated, dedicated and skilled you are.