before i quit my job

7 Things I Wish I Knew Before Quitting My Job

Quitting your job is a huge leap of faith.

After jumping off that cliff, you either spread your wings and fly… or you go splat!

Or more aptly, you:

Sink or Swim…

sink or swim business success

Many people are scared to quit their jobs, grab life by the horns and take control of their destiny.

Instead, they sit in their cubicles waiting until they can clock out, only to come home too tired to do anything else with their lives, let alone start living their dreams. 

Except you have the tools to do it. You have the energy and the will to do it.

But don’t hand in your resignation notice just yet!

This is not a decision to be made hastily. Assuming you are relatively young with a few business ideas, read this article first!

Note: If you are older and retiring, or you are lucky enough to have ten million dollars in the bank, this may not apply to you.

What you would do after you quit your job depends on your business plans, how well your investments are doing and how much cash you have in your savings accounts.

Assuming you leave your boss and team in good graces without burning any bridges, here are seven things I wish I knew before quitting my job and striking it out on my own. This way you will avoid the major pitfalls or costly mistakes that can affect the rest of your life.

1. Make Sure Your Business Idea Is Viable

best business idea

Before staking your entire financial future and livelihood on a business idea, you ought to test it first.

There’s nothing worse than quitting your job and going all-in on your business, only to find that no one wants your product or service.

I made that mistake.

I quit my job before testing my business ideas to see if people would actually buy my products and services.

Take it from me:

It is not a good feeling when you finally launch and… nothing happens. After those panicky “what the hell have I done with my LIFE?!” moments, I had to scramble to come up with a business idea that would actually work.

There are ways to test a business idea to make sure it is viable. Fortunately, you can do this without quitting your job first.

For a service-based business, just throw up a cheap website and put in a few Facebook ads to see if anyone bites.

Talk to people, friends, family members, and pitch your business idea to them. Don’t worry about them stealing your idea. Most people are too busy with their own shit to even consider snaking your business idea out from under you.

For selling a product, don’t go out and buy thousands of items or get in a contract with a supplier. First, set up a website with a nice landing page with a pre-order call to action. You’d basically ask people to give you their email address if they are interested in buying your product. If this quickly generates some interest, you might be onto something.

Some business ideas just don’t work, though. If your idea falls flat and doesn’t generate the interest you hoped for when you put it to the test, you’ll be happy you didn’t stake your future on it!

Let’s say you had a business idea and already put it to the test. People are interested. You have some email signups. Congratulations! You have a viable business idea.

Now, you need a marketing plan.

2. Have a Legit Plan to Get Customers or Clients

marketing plan for your business

How will you scale your idea to earn enough income to support yourself?

You will need to get your name and domain out there. Spread the word about your business. Blast some social media ads or write content to gain traffic.

More importantly, you will need to convert the traffic you gain into actual buyers.

For example, your business may have a marketing strategy using a sales funnel. Starting with the first-time website visitors, you’ll need to convert these to your email list subscribers. Engage your subscribers with a drip email campaign getting them to buy your product, while using social media ads in a remarketing campaign to bring back previous website visitors who hadn’t already opted into your email list. And so on…

Whatever marketing plan you come up with, you should at least have a plan to acquire customers or clients. Do this plan for a month or two, and then assess whether or not this plan is working. If it isn’t working, change your plan.

Some things, like SEO and brand building, take time. Obviously this would need to be factored into your sales and marketing plan.

If you’ve never started a business before, it’s easy to have high expectations that depend on factors beyond your control. For example, market interest and conversion rates often don’t turn out as half as good as we hope.

Assuming you have a viable business idea and a workable marketing plan in place, the next things you need are focus and discipline. This addresses the next two points.

3. Stay Off Freelancer Sites Like Upwork or Freelancer

expat freelancers

This applies particularly if you are doing service-based work for clients.

I’ll tell you right now: they are a waste of time.

Massive global freelance sites are not the places to find well-paying clients. They are dominated by cheap nit-picky clients who don’t pay more than peanuts to low quality freelancers from third-world countries who are all too happy to work for peanuts.

You can find good clients on these sites, but they as rare as a needle in a haystack. You’re more likely to find good clients on smaller niche freelance sites, but even that is still not ideal.

Spending the whole day spamming shit-paying clients with shit-value bids is neither a real business nor a sustainable location independent plan.

You’d be doing yourself a huge favor by skipping these sites and going straight to your niche market. You just have to know how to find quality clients, which is a different post altogether.

4. Don’t Read 50 Books, Listen to 100 Podcasts or Sign Up For Every Newsletter Relevant To Your Business

stop reading and take action

When was the last time reading a book or a newsletter actually earned you money?

It never has for me.

Only taking action has earned me money.

It’s fine to read a just a couple books to educate yourself on how to start a business, but that’s it. The more time you spend building your business (or making mistakes and learning from them, adapting as you go along), the faster you will make money.

You can only learn so much about business just by reading.

And I hate to break it to you, but listening to podcasts won’t help you build a business either.

Sure, podcasts will give you a fleeting moment of extra motivation, but that’s about it. Nothing more than a little hot air. Think about it — when was the last time you listened to a podcast and cha-ching! — you earned $800 the next day?

Probably never.

The bottom line:

You won’t get rich by reading Rich Dad Poor Dad or listening to Tropical MBA podcasts.

You get rich by starting a successful business and/or making smart investments that earn you money over time.

It’s easy to browse the Internet looking for the best ways or how-to’s for growing your business, and signing up for one newsletter after another, ad nauseam.

Before you know it, your inbox is getting flooded with emails using shady marketing tactics (I’m looking at you, Clickbank) that use a false sense of urgency and pull you in different directions:

  • I made $100,000 dollars with this new SEO method! Join my webinar NOW!
  • Buy a set of 5 Udemy courses at only $19.99! Come get it now before it’s gone forever!
  • Hurry, learn about this new drop-shipping opportunity before the market saturates!
  • Listen to my podcast LOADED with $10,000 worth of information!
  • Only three seats left!!! Sign up NOW! Unless you don’t want to succeed…

And you wonder why you don’t get anything done.

If I could just take back all the time I wasted even just deleting all these marketing emails, I would be much further along in my journey to location independence.

This is all about focusing on what’s really important, not just busy work. Busy work will make you feel busy, but it will not make you money.

If you must, just pick one newsletter most relevant to you — and only one. Otherwise you’ll waste a lot of time. Better yet, unsubscribe from everything, cut off all the noise and just focus on your business.

5. Network More

networking for expats

A real life connection is worth far more than ten online connections with people you’ve never met.

When I worked my job, I just kept my head down, did my work and went home. As any good obedient worker bee would do.

In retrospect, I wish I had networked more with other employees outside of my own team.

Maybe Linda in Communications has a connection with the head of product marketing at Google.

Or maybe Paul in Engineering has a friend who is an executive at Lockheed Martin.

You never really know who knows who, and you’d be surprised how small this world is. Whatever business you grow, you probably know a few people who knows other people who can take your business to the next level.

If I were to go back, I would have done the following:

  • Look up from my computer and scan the room
  • Talk to more people
  • Make more connections
  • Engage with them
  • Nurture these relationships

Perhaps I might have connected with someone within the same niche who would steer buyers to my business. By not networking, I left future money on the table. Potentially lots of it. So I have to start from ground zero and work my way up.

Don’t make that mistake. Network more!

6. Lack of Structure Is Harder On You Than You Think

setting a good routine as an expat

When you’re striking it out on your own, you will no longer have the 9-5 structure your corporate job affords you. If you’ve worked a corporate job all your life, taking that structure away will surely be jarring and disconcerting.

It’s easy to get carried away partying and traveling while blowing off work. I’ve done that.

To be productive and work effectively, you have to create your own structure. 

Not your old corporate structure.

Not your entrepreneur friend’s structure.

Not a party-till-5am-sleep-until-3pm-and-nurse-a-skull-shattering-hangover structure.

Your own.

It will probably take you a while to find out what works best for you. Some people are most productive in the mornings. Others do better in the afternoons or early evenings. Yet others may have clients 10 time zones away, so they might need to work at night.

Try working at different times of the day to see when you are at your best performance. Once you settle on your preferred time of day, try to work during the same time window each day. Working at the same location each time helps establish a routine that feeds into your productivity.

It’s also best to not travel every week or change cities every month, because a lot of your time will be spent traveling, resettling and reorienting to each new place. Doing this too much will destroy your productivity.

Personally I go to the gym in the mornings, work at a quiet cafe between lunch and dinner, and either practice language learning or go out at night with friends or on a date. Apart from the occasional weekend trip, I travel once every 2-3 months.

In short, find your best productivity window during the day, work during the same times each day and have a go-to work location closest or most convenient to you.

7. You Are Now Responsible For Your Own Taxes and Health Insurance 

expat taxes and insurance

When you work for a company, they take care of your health insurance for you. They take care of your taxes by withholding a portion of your paycheck to save you from a big tax bill.

If you are an U.S. citizen, your employer pays half of your Social Security, Medicare and Medicaid taxes, and they deduct your half from your gross pay. That’s all taken care of before you take your paycheck home.

All you need to do is show up and work. You don’t worry about these things.

Not so if you run your own show.

After you quit your job and start your own business, some things will become more complicated for you:

  • You will be paying both halves of your Social Security, Medicare and Medicaid taxes.
  • You will have to buy your own health insurance.
  • You will have to manage both your personal finances and business operating budget.
  • You will have to run your own payroll if you incorporate your business.
  • You will have to track revenue and expenses for tax reasons.
  • You will either do your own taxes or hire a tax accountant to do them for you.


That might be enough to discourage you from starting a business, and if it does, you really shouldn’t quit your job.

But if you want it badly enough, you will find a way to do all of the above AND to run your business that eventually makes money and allows you all the freedom you want in your life.

Putting It All Together

With a solid rolodex of contacts, you’ll be as ready as you would ever be to strike it out on your own.

With a solid business idea you tested before you quit your job, you know you have a viable business and a marketing plan to boot. You are prepared and disciplined enough to create your own routine. You are ready to take on the extra work dealing with taxes and insurance.

With those factors in place, you’ll be on your way to growing a successful business as long as you stay disciplined and not waste time reading other people’s marketing emails or catering to the wrong market for your business.

Email Consultation

email consultIf at anytime you need a little help in getting something going, or get some business advice, feel free to reach me at any time for an email consultation.

4 comments On 7 Things I Wish I Knew Before Quitting My Job

  • Thank you so much! Great post! Very interested article! My takeaways: find your best productivity window during the day, work during the same times each day and have a go-to work location closest or most convenient to you. Thank you for remembering me this important point! Continue to share your amazing tips!

    • Exactly, Sara. Those tips alone helped my business grow 10x this month over the past six months. It’s a fantastic feeling to have months where you can actually save money — because you earn more than you spend. I’ll share more tips along the way. Thanks!

  • Did none of the above and as you said I wish I did when I left but what gives. In the end I am glad I just winged it otherwise I wouldn’t have the experiences that made me who I am today. Good read!

  • I see you don’t monetize your blog, don’t waste your traffic, you
    can earn extra bucks every month because you’ve got high quality content.
    If you want to know how to make extra $$$, search
    for: Boorfe’s tips best adsense alternative

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