How to Quit Your Job and Achieve Entrepreneurial Freedom (6 Steps)

A massive shift in the U.S. workforce is happening right now.

U.S. workers are quitting their jobs at the fastest rate since the internet boom 20 years ago.

It’s not surprising.

Research shows a staggering 87% of employees worldwide report not being engaged at work. They’re not being utilized to their fullest potential.

Instead, these quitters are packing out coworking spaces and freelancing in exotic countries.

Solo traveler bookings shot up 42%over the past two years.

U.S. freelancers jumped by 8.1% over the last three years.

Fast Company reports freelancers will be the majority of the U.S. workforce by 2027.

What does all this mean?

Working for an employer is not fulfilling for a lot of people. People want more flexibility. They want to travel, let out their FOMO, and work from anywhere. The nine-to-five office job is dead.

But if you have one job at one company, you’re also putting all your income eggs in one basket, you could be let go at any time, it’s outside of your control, and it’s ultimately fragile.

There’s simply too much opportunity, too much to learn and experience, and too much life to be lived to stay in a job and wait until retirement to be free to do what you find fulfilling.

There is another way.

For some of us, not everyone, but for some, a better fitting career path is entrepreneurial freedom.

Entrepreneurial freedom is an untethered, independent way to build wealth doing what you love to do.

This post is a 6-step roadmap to achieve entrepreneurial freedom. It centers around answering this crucial question:

How do you build multiple income streams doing what you love to do from anywhere?

Let’s go 👇

1. Acquire a skill you love

This is the foundation of your career and will serve you for the rest of your life. A skill you love is the asset you will use to help others succeed, which is the foundation of business.

For me, it’s writing.

Ironically, I hated writing. I wasn’t good at it in school. My grades were, as Jordan Peterson would say, NOT GOOD. I didn’t enjoy it or see much purpose in it. Until my first job.

My first job out of school was as a marketing coordinator at a chamber of commerce. My first boss taught me a skill that changed my life.

She taught me how to write a press release. She was very hard on me and forced me to write with structure, clarity, brevity, and sticking only to the facts. Now, I know what you’re thinking.

A press release? How boring! I know.

But here’s what happened. After I wrote a press release and sent it to the chamber email list, it would be reprinted in the local newspaper. I would see an article I wrote in a newspaper that a ton of people read. It made me realize that a press release can have a massive impact on the business world and people’s lives. A press release can change how people make decisions, or alter events in the real world.

So in 2014, I started writing on Medium, publishing on other blogs, and growth started to happen. I was published in Inc. Magazine, Forbes, Business Insider, Axios, TNW, Smashing Magazine, and CNBC Make It. My Medium publication grew to over 91,000 followers. I learned if you don’t waste people’s time, stick to just the facts, and put the facts in the right order, writing is useful.

But it doesn’t have to be writing.

Your skill can be anything that adds value to someone or something else. So how do you find it? (Skip the following section if you already know).

Three questions that will help you acquire a skill you love

1. With what do you love to create? I believe everyone is innately drawn to create in some way. Whether it’s with words, wood, code, paint, or culinary arts. How do you express your creativity?
2. If you were given a billion dollars right now, what would you spend your time doing? A mentor took me out to lunch one day and sat across the table from me. He pushed the salt shaker towards me and asked me this question. He said, “Imagine if this was a billion dollars, how would you spend your time?” It’s an interesting question because it removes the need to make money. What would you do if all of your needs were met for the rest of your life?
3. How can you get really, really good at that one thing? This is a very pragmatic question. Nat Eliason said in an interview 90% of SEO expertise is writing the best answer on the internet to a specific question, the other 10% is the technical stuff like meta tags, alt tags, and keyword distribution. It’s incredibly hard, he said. So you have to be really good. Work hard and practice. Benjamin Franklin, one of the best writers in history, became legendary at writing by copying the famous columnists and authors in London when he was young and trying to recreate their arguments from memory and then comparing his own writing to theirs. Eventually, he found he could sometimes make the same point they were making, but in a clearer way with fewer words.

So, find something you love to do that helps others succeed and become really good at it.

2. Create things and fail (a lot)

When I told a friend about the importance of failure, he asked a clarifying question, “But the goal isn’t failure, right?” It’s true. It’s not. Nobody wants to fail, but failure means something completely different to an entrepreneur.

Failure means you took a risk and learned something.

Elon Musk said, “If you’re not failing, you’re not innovating enough.”

Jeff Bezos said, “Failure and invention are inseparable twins.”

Not only does failure teach you something useful, but it also develops in you a resilience that you will need as an entrepreneur.

I have half a dozen failures from my own life. Here’s one and the lessons I learned:5 Crucial Lessons for First-Time Founders
This is the story of my first startup, Efographic, and how I drove it into the ground. By writing this, I hope to save…entrepreneurshandbook.co

In the end, when a venture doesn’t go as well as you hope, try to remember this quote:

Teacher’s teach, coaches coach, entrepreneurs fail. It’s part of the job.

If you don’t learn from your failures, then you really are failing. But if you acquire strategies, insights, and relationships from each failure, next time, it should go better and better until you eventually gain traction.

3. Make big asks

Big asks accelerate your career.

A big ask is an audacious, bold proposal to do something that outsizes your current capacity to do it. A big ask could take the form of an email, a conversation, a phone call, a tweet, or a direct message over social. It could easily get rejected or ignored. But if it goes through, it could change the course of your career forever.

For example, I made a big ask for my second job ever. I had noticed a company that I really wanted to work at was missing a marketing lead. The firm didn’t have much of a brand presence online.

So I got to know the people in the firm, wrote the job description, title, and salary, and pitched it.

They accepted. I left my hourly job and became the new director of marketing at a commercial real estate company for the next two and a half years. After I left, they hired two people to fill my role. A big ask accelerates your career.

For entrepreneurs, big asks should be weekly if not daily occurrences. They are the secret to getting new clients, new partnerships, new sales, new press coverage, and great hires.

How to make a big ask in six steps

• Spend time with and study a brand/person with which you’d like to work.
• Recognize the person’s or the company’s need(s).
• Reach out / build relationships (HINT: see next step)
• Propose how you can fill that need. It should be aligned, specific, and helpful, so they feel silly not hearing you out.
• Negotiate the terms. Make sure it works for both you and them.
• Sign the dotted line.

Unfortunately, not everyone you meet is someone to make a big ask of. And not everyone has the decision-making power to give you an answer to your big ask. So how do you get in touch with the right people and reach the decision maker?

4. Network, network, network — but how

Networking creates opportunities to make big asks.

You meet new people through networking. These people have networks of their own — an exponential effect you can tap into — with access to new opportunities.

Through networking, I was able to build a portfolio of business that allowed me to quit my full-time job and strike out on my own.

For example, I was at an event in San Jose standing at my normal spot — by the food table — and shook hands with the editor of a well-recognized bank. We talked, joked, and bantered about the event. Did you try the cheese cubes? When the moment felt right, I made a big ask about writing for his team. We chatted and he gave me his card. I followed up a few days later. Soon, I signed a contract and got my first project writing at a rate of $1 per word.

I have more examples, but I’ll keep it short with this summary: Success in business comes from making big asks directed to big people at the opportune time. It starts with getting out to events and conferences and meeting new people, especially the speakers.

5. Always be selling

The fifth step in your roadmap is, as an entrepreneur, you must always be selling. For multi-income stream entrepreneurs like me, I am always “on.” In almost every conversation, at least one of the many things I do is relevant — my conversation starter app, novel, Medium publication, brand writing and editing services, writing courses, my client’s products — I could always be selling in every conversation.

But I don’t.

I don’t want to be smarmy, inauthentic, or annoying to people around me.

So how do you “always be selling” but always stay authentic?

The book “Integrity Selling” helped me answer this question.

In short, the message of the book is this simple lesson: Replace the word “selling” with “helping.”

It might sound simple at first, but anything you sell should provide genuine value to the buyer, even if it’s your own businesses. It has to be a win-win. No one is duped. Everyone benefits.

You have to be very careful and intentional in how you sell and who you sell to. Try to avoid these common mistakes:

1. You are selling to the wrong person — the thing doesn’t help them. It helps other people, just not them.
2. You shouldn’t be selling the thing — it’s a good thing and it helps people, but it’s not something you believe in. It’s really hard to sell what you don’t believe in.
3. The thing shouldn’t be sold — it’s not a helpful product or service.

If you can apply this thinking to your business, your sales conversions should dramatically increase (because they’ll be better targeted) or you will have the confidence to walk away from a bad job that you don’t believe in. Either way, it will help you always sell with authenticity — a critical trait of an entrepreneur.

6. Scale the right opportunities by splitting time between earning and investing

So at this point, you have a portfolio of work: You’re creating projects with the skill you love, getting out there and networking and selling, making big asks and suddenly, the good opportunities start pouring in. Huzzah!

But hold on. You’re only one person. Your time is limited. There’s only so much you can do. You have a ceiling. Listen to what Naval Ravikant, CEO of AngelList said about having limited time:

You’ll never get rich if you freelance for the rest of your life.

Freelancing is a brilliant way to establish a livelihood and enjoy your career. But freelancing is not entrepreneurial freedom. Freelancers are self-employed,— they have control of their time — but they are lacking a very important of entrepreneurial freedom: multiple sources of income.

Entrepreneurship involves creating a company/project that doesn’t need you to run. It allows for the possibility of passive income. A venture, once successful, can make money for you in your sleep. Freelancers can’t make money in their sleep.

An entrepreneur, on the other hand, can invest her time and money into building a product or business and create an independent cash flow independent of their time. This requires a significant upfront investment.

So, for someone striving for entrepreneurial freedom, their time should be split like this:

Earning is directly tied to income (freelancing). Your work earns income. It’s often in the form of an hourly rate or project rate.

Investing is work you don’t make income from directly, such as writing a book, creating an online course, writing articles, networking. These things don’t pay right away but they have the potential to pay off handsomely down the road.

You earn with your time to remain stable. Pay bills, support your family, eat and drink, travel, etc.

You invest your time to achieve the opportunity for asymmetric risk reward.

Asymmetric risk reward is a term Tony Robbins uses to describe an investment that has an exponentially greater upside than its downside. Could it really take off? And if it fails, can you afford to lose it?

The earn side of the diagram has a symmetrical risk reward — you put time in, you get money out.

But this is not passive or scaleable beyond you.

This is where the invest side is necessary — this is what drives you to write a book, or launch an online course, build an app, or invest in a risky OTC stock… they have the potential to make sales in your sleep.

The key to the Time Paradigm of Entrepreneurial Freedom is finding the right balance. If all you do is earn, you’ll never have multiple, passive, or scalable income streams. If all you do is invest, you could get caught in hot water between unsound or unlucky investments.

This healthy tension oscillates. But overall, when balanced, it leads to stable growth.

Stable growth is a sign that you’re scaling the right opportunities. If stable growth isn’t happening, you need to return to the beginning of this roadmap and find better opportunities.

All Rights Reserved for Dave Schools