Quit Job To Start A Business? A Practical Guide From Someone Who Did It

Quitting your job to travel the world, do what you want when you want, and not have to ask anyone for permission.. this is the dream of many.

Every year countless people quit their job to start a business
with hopes of being able to make it.

Eventually most of those people ask themselves “should i quit my job to focus on my business?”

I know because I am one of those people and I spend most of my time with people like that both as a friend and also as a teacher & coach.

I have started an online business, built it up to the point where it can finance my lifestyle, and successfully quit a soul crushing insurance job.

It wasn’t pretty.

I didn’t do many things right, and especially not in the right order.

If I could do it all over again, I would have done it completely differently.

And as I coach hundreds of people every year on their own journey to free themselves from a traditional job, I see my mistakes repeated, and my advice ignored time after time.

As someone who eventually quit their job and built a business to finance their lifestyle, I wanted to give you a practical guide of how to actually quit your job in the shortest, least painful time possible.

My advice is not what you want to hear, I know because I wouldn’t want to hear it, and I know because I tell it to people all the time and they ignore me, only to come back 6 months later with something along the lines of “soooo, I should have listened to what you said.”

Evidently a lot rides on the success of your business to be able to pull this off, and even though this article is not necessarily focused on how to grow a business (check out this article for that), there are key things you can do in your business that will facilitate growth much faster, and on the contrary, not doing them slows down your ability to quit your job tremendously.

Before you quit your job to start a business, or to transition from your existing business, let’s look at some common mistakes.

the 5 most common mistakes when trying to quit your job

First and foremost let’s look into the 5 most common mistakes people do when trying to quit their job & live off their business, then I’ll give you the perfect plan of how to do it in the fastest time possible.

Mistake #1 – Quit too soon

I quit my job 2 weeks after starting my online business as someone with zero experience, no clients (or even remotely close to getting any), simply because I couldn’t stand staying in my job anymore.

And as I came to learn..

The faster you prematurely quit your job, the longer it’ll take you to quit working for someone else.

Now if you can’t stand your current job that’s ok, I’ll tell you later on what to do about it, for now just cool down.

Think of your business as a car.

When you quit your job you stop getting income.

Income is effectively gas for your car, and what happens when you run out of gas?

You can push your car sure, but how much faster would you progress if you had gas in the tank and could drive? Even when you made a wrong turn you could just get back in the car and go back.

And by the way, you’re going to make A LOT of wrong turns, that’s why you need a lot of gas.

If you’re able to constantly fill up your tank with gas you’ll be able to reach your destination so much faster than if you have to push your car. You’re still going to make wrong turns even when you’re pushing the car, so just imagine how much longer everything takes.

And to put the metaphors aside for a second, when I write “gas for your car” what I’m really saying is advertising budget, hiring freelancers, coaches, courses to get educated, etc.

Just imagine how much better off your business would be exposure-wise if you spent $1000 on Facebook compared to not advertising at all.

It’s the difference of tens of thousands of people knowing that you exist, versus no one knowing.

This is why quitting your job too soon prolongs your journey.

The difference between being able to put $500 into your business every month versus not being able to, is staggering.

Mistake #2 – Focusing on profits instead of momentum

The second biggest mistake I see, and also made myself, is focusing on making as much profit as possible, instead of building momentum.

Let me explain.

But before I do let me just clarify something: I’m writing this article with the idea of creating a “real” freedom business where large parts of it can be automated and delegated.

This is not about starting an award winning traditional creative agency, or a one man band (freelancer) but rather a business that can get new clients using the internet, and deliver to them without being there doing all the work yourself.

So why focus on momentum instead of profit?

Well at first no one wants to work with you.

You have no results to share, your offer is probably not as clear as it should be, your internal processes are nonexistent, etc.

If you get out there and manually close 1 client @ $10,000 by cold calling, that’s great, but I’d much prefer to do the same amount of work building my sales funnel, adwords campaign, and getting 10 clients @ $1,000 each.

Same revenue, one option has the potential of 10 new testimonials to add to your website, you learned a lot more about your own processes and delivering to clients, but most importantly, the way we acquired the client was done using the internet, and it can be automated and scaled.

1 client @ $10,000 sounds great but in my experience was less favorable. If you only have 1 new client every few months you never get to build up any processes in your business, you don’t automate anything because tasks are done so infrequently there’s no need to automate them, and so you end up running a one man band that entirely relies on you.

If you have a lot of clients you’re forced to build a real business with internal procedures, and even a team of people that can help you run it.

If you get too focused on profit you’ll say no to projects that you definitely shouldn’t in the beginning. Every new client is more experience, a testimonial, a referral opportunity, and more pressure on you to build a real business instead of your one man band. This is something I screwed up big time.

I had decided on an arbitrary price for our services, and lost a lot of business because of our price. If I’d started with lower prices we would have made less profit per customer, but we would have had a lot more clients, meaning more experience, more momentum, and more of a real business with procedures and staff, not just me.

The less tangible but crucial point to make here as well is the confidence you’ll get from consistently getting new business. It adds up quickly and puts you on a path to win.

Mistake #3 – Siphoning profits from business

This is simply a combination of mistake #1 and #2 in some ways.

We’ve talked about being able to fill up your car (business) with gas in order to reach your destination.

We’ve talked about the importance of momentum.

What’s the fastest way to lose your gas money, and lose your momentum? By not having money to pay for gas.

If you make $1,000 profit from your business and you withdraw it to go travel (I’m not judging, this is what I did), you’re also NOT putting that $1,000 into your business, and in the long run that will hurt your business.

What if you spent that $1,000 on advertising in order to make $2,000?

What if you got $1,000 worth of freelance help that would allow you spend more time on growing your business, instead of delivering to clients?

Ultimately many of us start a business in order to go travel and have fun, which is fine, just realize that you could probably travel more in the future if you reinvested the money.

$1 invested in your business today is $5 tomorrow.

Mistake #4 – Being impatient

I’m a master at impatience. I’m one of those people who execute before my brain has finished a thought (my SEO guy told me to write this blog post less than 12 hours ago, and I’m already doing it). This can be a great asset, and it can be devastating for your business.

The execution side of impatience is great, it’s the frustration of lack of results that can be dangerous.

When you get frustrated what tends to happen is that you make short term decisions because you can’t deal with the discomfort of executing on the long term strategy.

I just wrote about it in the mistake above. If your goal is to go travel as soon as possible, then you’ll take the first profits from your business, pack your bag, and head out into the world.

When you’re on the road it’s impossible to grow your business at the same level as when you’re in a solid routine, so naturally your business suffers on that front, and of course, you’re spending the money on your travels, as opposed to investing into your business.

Your impatience got the best of you, and the instant gratification of traveling NOW hurt your business in the long term.

The 4 weeks in Thailand where you spent $2,000 could have been spent working on making $4,000.

So your trip was great, but now your frustration is double as you come back to your routine and realize that you have no new leads, the money you made has been spent, and you’re back to ground zero.

There’s a balance at play here. If you started your business in order to get yourself the freedom of being able to travel and have fun then that’s exactly what you should do, the question is WHEN?

If I could go back and do it again, I’d postpone my travels and get my business to a better place before spending all those profits.

Mistake #5 – Quitting too late

On the flip side of all the mistakes I’ve covered so far is the person who is actually doing everything right in their business, but don’t have the stones to cut the umbilical cord.

You’ve got a solid online business with semi consistent sales, you know your business could really use your attention to get to the next level, but you’ve got a job that you don’t mind.

You don’t love your job, but you don’t hate it either, and on top of that it brings in a nice check every single month.

This is a VERY dangerous place to be.

If this is you I believe you have to take a moment and write down some goals you need to hit, and once you do, you have to pull the plug, otherwise you’ll get stuck forever.


Now that we’ve looked at the most common mistakes I thought I’d offer a practical game plan for how you can quit your job while minimizing the risks.

A practical game plan for quitting your job to live off your business

This roadmap is the result of making tons of mistakes myself, and coaching hundreds of people since 2014 on how to successfully quit their job and live off their business.

Here’s the way to do it, and the sequence is extremely important.

  1. Figure out your monthly expenses
  2. Add $3-500 to put into your business monthly
  3. Only work enough for someone else to make that much, put the rest of your time into your business
  4. Once you have some stability and a few months’ worth of savings, cut the cord and go for it

Let’s go through them one by one.

Step 1 – Figure out your monthly expenses

How much money do i need to quit my job and start a business?

Well let’s figure that out.

This is simple in theory, just make sure you are honest with yourself.

Make a spreadsheet of all your monthly costs.

This includes your rent, food, car, insurance, any business expenses like website hosting, etc. And by the way, the less fancy you live now, the faster you’ll get there.

Every $1 NOT invested in your business adds another day to reach your destination.

Let’s say for example that your monthly expenses are:

Rent             $600
Food            $400
Insurance   $20
Car               $0
Business     $200

Total           $1,220

This is totally realistic for some, and way under budget for others. It depends on your life situation, and where you live mostly, but like I mentioned above, the less fancy you live now, the quicker you’ll get there though, keep that in mind.

Step 2 – Not required but highly recommended – Add $3-500 to put into your business monthly

Here’s your gas money. Fill up your business tank with 3-500 dollars a month and you will expedite your journey to freedom.

Let’s add $300, making my total $1,520, this number is pretty close to what I would have needed when I was starting out.

Step 3 – Only work enough for someone else to make that much, put the rest of your time into your business

Since I need to make $1,520, that pretty much equates to a half time job, which is great. It means I can work 20 hours a week for someone else, and spend the rest of the time on my own business.

If you already have a job you have 2 options:

  1. Stay in your current job but go down to part time
  2. Get a new part time gig, ideally in something that helps your business (like sales or marketing)

Since I couldn’t stand my job I ended up quitting, and eventually got another job as a phone salesman. This was perfect because a) it was part time, b) on weekends I could bring my laptop and work on my business at work (don’t tell), and c) I was learning how to sell which also benefited me in my own business

If you have the option to stay in your current job but go down to part time that’s probably the easiest. If you don’t think that’ll sit well with your employer you may need to switch jobs.

And of course if you don’t have a job at all I’d recommend actually getting one.

When it comes to choosing a job there are a few things to keep in mind.

If you can get a remote job, you’ve already won. Assuming your ambition is simply to make money while you travel the world and have some fun, you can accomplish this without starting a business of your own, by simply getting a remote job.

So whether the remote job is actually going to satisfy your end goal directly, or it’s a stepping stone, I’d highly recommend looking into it.

Check out https://weworkremotely.comhttps://remote.co/remote-jobs and https://remoteok.io – also check out this article on actually landing a remote job

The second thing I wanted to add to the conversation of choosing a job is to, if possible, choose something that adds to your business in some way.

For example I was learning sales in my job, obviously a crucial part of any business which was beneficial for me.

Think about what others could pay you to do, which would actually benefit you and your own business as well, and see if you can find a job in that space.

Once you’ve got your part time gig, or in the worst case a full time job, then just continue building your business, making sure to add gas money every month.

Focus on your sales funnel so you can acquire new clients consistently and predictably, as well as the delivery side of your business. Build out procedures, and start hiring part time freelancers (you can start with as little as 3 hours per week!) so that they can free up your day allowing you to focus more and more of your efforts on actually growing the business.

It is very important to get yourself to the point of being able to focus mostly on working on your business and have others work in your business.

And finally..

Step 4 – Once you have some stability and a few months’ worth of savings, cut the cord and go for it

No explanation necessary. I’d recommend 6 months savings but saying that I also know I’m the type of person to bet on myself being able to pull it off way sooner than that.

Bonus step 5 – get a part time location independent side gig

This is something I highly recommend. You don’t have to do it right away as you’re focused on growing your business right now, but having a second source of income will give you some peace of mind, especially since your business is bound to go through ups and downs like everyone else’s.

Let’s say you run a Facebook ads agency, and have a good understanding of digital marketing as a whole.

Finding a long term gig as a content writer for another company is an example of a job you can do anywhere that will bring in a consistent stream of some extra dollars.

This will only take up a few hours of your time.

Another example would be to take on 1 or 2 coaching clients within an area you’re confident you can help people with.

Jay Leno said he always had two jobs. One job was to pay his bills, and the other job was for money he could do whatever he wanted with.

I suggest the same. If possible, pay your bills with your part time gig, and reinvest/have fun with the profits from your business.


Please let me know in the comments below, what was your biggest takeaway from this article?

Thanks for reading!
Robert