The Mental Shift from 9 to 5 to Entrepreneurship

from 9 to 5 to entrepreneurship

That’s the second part of The Leap from Employee to Entrepreneur: Quitting Your Job and Reclaiming Your Freedom. You may want to check it out.

The Scary Phase Between Breaking Free from The 9 to 5 and Entering The Entrepreneurial World

In How to Quit Your Day Job and Travel The World, Mark Manson reveals the truth no one wants to speak about:

“Chances are the thought of leaving your day job terrifies you. This is normal and expected… good even.
When I left the bank that day, I had only a vague idea of what I would do. I made a little bit of money here and there online. It wasn’t anything close to a full-time living, but I knew it was a new market that was growing quickly. And with some hard work combined with my savings, I (naively) believed I could have a full-time business up and running within a few months.

It turned out to take almost 18 months for me to earn a full-time steady income. I went broke a number of times, was supported by my ex-girlfriend for a time and then moved back home with my mother. For most of 2008-2009 I worked 10-16 hour days and the majority of my projects failed and made little or no money.

It was stressful to say the least.

People ask me what motivated me through this period. The answer is terror. Complete and unequivocal daily terror.

I was absolutely terrified to fail. Granted there was some love in there as well (I loved my job and still do). But that’s also where the terror came from: the idea that I would never make money doing what I love; the terror that I’d have to go back to living off a job I hated; the terror that I would have wasted two years with nothing to show for it; the terror that all of my friends and family who thought I was crazy would be proven right.”

Fear is the root of all of our problems one way or another.

I think overcoming it shouldn’t be an aggressive process. As this way we focus on it way too much and eventually end up having more of what we’re scared of.

The better way is to choose to let it be, and then let go of it with peace and acceptance. But there’s also another thing we can do – use it as our momentum, the driving force that will get us moving every single day, especially when we don’t feel like taking action.

Mark Manson continues:

“This fear kept me up at nights, and more importantly kept me up at nights working.”

That’s how you become a hustler. If you’re not naturally productive and haven’t found your motivator yet (which is a must as you’ll have to work more than you usually do so that you don’t have to live an average life), you can use your fear as a driving force.

Why You Still Haven’t Quit Your 9-to-5 Job?

There are a few common reasons:

• you haven’t figured out what you want to do with your life if you don’t work every day;
• you don’t feel ready (And you’ll never be. Truth is there’s no better time than right now.);
• it’s too risky – you feel safer at your job;
• you haven’t planned out your ideal lifestyle (which starts with outlining the perfect day);
• you aren’t in the right environment;
• you haven’t planned your escape.

It (the escape) should look something like that:
– sell everything you have that you don’t need;
calculate the amount of money you’ll need for your new lifestyle;
– figure out how you’re going to make money;
– if you can’t start earning right now, then save enough so that you can sustain yourself for at least 6 months – maybe in a cheap country – while working on your business.

Here’s what Sean Ogle says about making the mental shift from job security to uncertainty and from a paycheck to multiple income sources in this interview:

“When I left my job, my initial goal wasn’t even to start a business right away. It was to travel the world and then see what happened. So when I moved to Thailand and I was bringing in a little bit of income it was actually a nice surprise. I could live cheap, and I wasn’t expecting to have any income – so for that reason focusing on business as opposed to just adventure was a good move.

The secret to multiple sources of income, is not to try and have multiple streams of income when you’re just starting.
I worked on building one thing, and when that was stable, I’d consider starting something else. Otherwise you bounce around too much and don’t make enough progress on any one project for it to be sustainable.”

The Big Question: What to Do to Become a Location Independent Entrepreneur If You Haven’t Found Your Passion or Haven’t Yet Monetized It?

There are countless ways to start making money online, even if you have no knowledge or experience. Short term ones – which are fast and easy – and long term ones – which can sustain you for a lifetime, turn into passive income and can be scaled.

And you probably won’t believe that if you haven’t heard of any example or seen how many people have already succeeded.

I wasn’t sure if that was the case either before I did my research. Now one of my biggest sources of inspiration is reading at least 1-2 articles daily like the ones I link to in this post (plus a few others connected to my work).
And I think you should do the same.

Before you start, see what others have to say about the whole thing. They will encourage you, tell you what to do exactly, and – most importantly – they will tell you what not to do so that you don’t make their mistakes.

It’s a great thing to start making a little money in the beginning just to see that it actually works, and then give other things a try, come up with ideas, change your approach, and so on, until you find what works best for you.

It’s a process, remember that. You shouldn’t be waiting for a finishing line where you will just keep making money without doing anything.
In fact, you’ll probably enter new fields all the time, expand your expertise, partner with other entrepreneurs, try completely new things, etc.

Here’s Mark Manson’s answer when asked how he managed to travel the world without a ‘real’ job:

“The short answer is the internet. Before this blog, I ran a number of websites and projects that earned some money. Then I did some freelance work. Then I wrote a book. Then people started telling me to write more stuff and jump ahead five years and about 500,000 words and here I am.”

If you still don’t know what to start with to begin your new life, here are some things to check out:

79 Side Hustle Business Ideas You Can Start Today
There are many things you can do on the side that don’t require initial investment or special skills. You can also turn your hobbies into cash, be it for a start or with a long term goal in mind.

How to Make Money Online: The Basics

Building a niche site.
If you’re interested in that, read (a lot) more about it. The Internet is full of resources, most often it’s whole blogs on how to create successful niche sites and earn money without touching them after that.

It’s a subject worth exploring.

And some of the most helpful posts you can find are the ones by expert entrepreneurs who share everything you need to know to put things into practice right away. And we’re talking about creating a big business that can make you a lot of money if taken seriously.

Noah Kagan, for example, has published a post on the Tim Ferriss blog called How to Create a Million-Dollar Business This Weekend. And knowing what he’s achieved so far, I have no doubt his strategies are proven and can work for anyone if implemented correctly and with the right mindset.

“For some reason, people love to make excuses about why they haven’t created their dream business or even gotten started. This is the “wantrepreneur” epidemic, where people prevent themselves from ever actually doing the side-project they always talk about over beers. The truth of the matter is that you don’t have to spend a lot of time building the foundation for a successful business. In most cases, it shouldn’t take you more than a couple days.

We made the original product for Gambit in a weekend. “WTF?!” Yes, a weekend. In just 48 hours, some friends and I created a simple product that grew to a $1,000,000+ business within a year.”

Here’s more:

How To Start a Successful Business with $100
This is one of the most useful and motivational posts I’ve seen in a long time. The Start Up Bros have asked a big number of famous online entrepreneurs the following question:

“IF you had no idea, zero entrepreneurial experience and under $100 in your Paypal/bank account, what would you do in the next 90 days to launch a profitable Internet business?
What niche would you tap? What would you sell or promote? What would you avoid?”

And I can assure you that most of the answers are so detailed that you can take one and invest the necessary amount of work and time during the next few weeks. And if you do your research, do things right and are focused, you’ll actually make your first dollars outside your job.

It’s something the person has already succeeded in so you don’t need to question whether it works or not. And once you make that first sale, land your first client or see your site successfully monetized, you’ll make the most important step from an employee to entrepreneur.

You’ll see that earning money online is possible with the right strategy. That if you do the work first and offer value to people, they would gladly give money in return. And that it’s much more satisfying to work for yourself and create many side businesses in order to have multiple income streams – which is ten times more secure than any paycheck will ever be.


As I expected, this post turned out to be longer (again). It’s because I’m passionate about this topic, want to inspire people to explore the beautiful options I’m talking about here and have so many great sources of information I want to share.

So in conclusion, here are some podcasts to check out:
9 Tough Truths About Running a Business and Changing Your Life
Do We Need to Re-Train Ourselves to Enjoy Free Time?
Is a College Degree Useful For Entrepreneurs?
An Episode For Those Who Need a Business Idea

I’d love to hear your opinion on all this. It’s a big topic and there are many things to be discussed.

Are you an entrepreneur now? If not, do you want to become one and what step can you take first?

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How This Family Guy Makes $10,000/Month Online Teaching Others How to Make, Save and Invest Money

How This Family Guy Makes $10,000/Month Online Teaching Others How to Make, Save and Invest Money - Interview with R.J. Weiss from

This is an interview-style post with R.J. Weiss from The Ways to Wealth.

Hey R.J. What’s your background and what do you do?

I blog about all things personal finance at The Ways to Wealth.

Before I went full-time into blogging, I spent ten years in the financial services industry. Specifically, helping families buy the right type of life insurance.

During my time with a full-time job, I’ve always had different side hustles going on. From freelance writing, Amazon FBA, conversion rate optimization, to website design — there were many projects I pursued outside of work.

How did you start your career in finance?

I got started in finance straight out of college working for my the family insurance business. As I love the financial planning side of things, I choose to specialize in life insurance planning. This led me down the path to obtaining the CFP® Certification.

What made you start blogging?

The Ways to Wealth, which I started in 2016, has been my 5th blog.

The others mostly fizzled out most due to a lack of interest. But, in 2009 I started a personal finance blog called (no longer around) that had some success.

The idea was to write about what I was learning about studying to take the CFP®. The blog was, by all means, a success. I was able to gain valuable knowledge, pass the CFP® exam, earn some extra money and build up a good community.

I then took this knowledge and started a business blog, which allowed the insurance agency I was working for to generate leads.

I started The Ways to Wealth because my passion is personal finance–from investing to travel hacking, I love the challenge of optimizing my finances.

How was The Ways to Wealth born?

I didn’t have much of a plan for starting The Ways to Wealth when I purchased the domain name.

I was actually thinking it would be a niche site, which was inspired by Pat Flynn’s niche site duel. Then, I came across the income reports of Michelle Schroeder-Gardner and wisely changed direction to a more traditional blog.

This change came about 6-months after starting to blog.  I did a timeline of the site in one of my income reports.

What worked best when trying to grow the site?

I had a decent knowledge of SEO. So at first, I started growing the site with email outreach. One of the first posts I had about best investing books of all time, had about 15 links to it.

This was nice to start with but was quite slow to build up, as it can take a while to earn Google’s trust.

The big turning point came when I started to understand Pinterest. I spent a few frustrating weeks on the platform, then it finally started paying dividends.

I went from about 100 sessions a day to 1,000, which was huge for me at the time.

How did you get to 3 million monthly viewers on Pinterest?

the ways to wealth pinterest 3 million monthly views

I lay out my Pinterest strategy here. But at the core the idea is to:

1) Write high-quality content that Pinners want to click through, read, and share.

2) Pin to my own and high-quality group boards, with a keyword-rich description.

3) Continue to Pin my best pins across my own boards/group boards, ruthlessly eliminating Pins that don’t perform well.

One thing to keep in mind is impressions don’t mean much on Pinterest. What counts are clicks to your website. So, you want to design not for impressions but clicks.

What aspects of the online business are you outsourcing or automating and how?

The first thing I outsourced was Pinterest design. I’ll design about 30-40 pins a month, so this was big time saver for me.

Of course, it took some work to get going. At first, I hired 5 or so people on Fiverr. I found one decent designer but the work quality deteriorated over time.

I then went to Upwork and posted a job for a  graphic designer. I found a great team down in Argentina, who I’m very happy with.

I’m currently experimenting with working with a ghostwriter. A few of my latest posts have been transcribed from my recording, with the ghostwriter making sense of it all.

I can compile about 3 posts in 90 minutes, then take another 90 or so minutes to prepare them. Saving me around 3-4 hours per post this way.

What’s your main income stream and why do you think it works for you?

My main source of income for the blog is affiliate revenue. It works because the partners I do have are high-quality businesses, who deliver value and solve real problems. This makes it easy to naturally link to such a partner.

When did you start making more than $10K/month and what was the turning point?

My first month over $10K was in January of 2018. In December of 2017, income was around $3,000 and in July of 2017 around $500. So, it was definitely a jump.

What happened then in January?

First, personal finance is at its peak interest in January.

Second, I had multiple Pins go viral.

Third, in November I started driving traffic via Facebook to the site. So, in January I could take campaigns I’d been fine-tuning for a few weeks and scale them.

How do you balance work and family life?

I have a routine I stick to Monday through Friday.

When inside of my designated working hours, I work. When outside of these hours, I’m not.

This is a lot easier said than done. But the thing important for me is not to take work everywhere I go. This means I don’t have any apps on my phone that are work-related (email, analytics, etc..)

What are you 3 best finance tips for newbies?

  • Focus on your savings rate. How much you save is the most important decision you’ll make.
  • Small incremental improvements add up over time. My favorite example is increasing your savings rate 1% every quarter, means you’ll be saving 20% of your income in just 5 years.
  • Study happiness. Become a student on how to increase your level of happiness. The natural result is you’ll want less overtime, making the game of personal finance a lot easier to win.

What books, blogs or podcasts help you stay motivated along the way of growing an online business?

I read a fair amount to keep fresh ideas in my head.

My favorite podcast is The Tim Ferriss Show.

Two blogs I enjoy reading are:

Farnam Street
Barking up the Wrong Tree

And as far as books. I try to read one a week. A few books I would recommend to online entrepreneurs would be:

Deep Work by Cal Newport
The Compound Effect by Darren Hardy
The Four Hour Work Week by Tim Ferriss

Pin this post if you enjoyed the interview.

Check out my interview with R.J. from TheWaystoWealth to see how he entered the finance niche, started making money blogging, began bringing traffic from Pinterest and monetizing it with affiliate marketing, and is now making $10,000/month from his online business. #blogger #interview #blogtraffic #incomeideas #income