Freedom Lifestyle

Transition from Employee to Entrepreneur: 4 Steps to a Freedom Lifestyle

Earn more, work less, and live on your own terms.

The universal truth about happiness is that we all want control of our lives. My dad spent 30 gruelling years screwing parts into cars. He hateeeeeed factory work. So, he blacked it out and never spoke about it, focusing instead on his pride and joy – his family.

I graduated from university with options. Unlike my father, I could design a life where I loved my work.

And if I acted with that intention, I could take it a step further. I could find the perfect harmony between work and play, with a job that gives me the freedom lifestyle.

If you want to work less, earn more, and enjoy complete autonomy over how you spend your time, keep reading.

Most of you will read this and do nothing.

We’re programmed to choose the safest path. The ‘freedom thieves’ inside our heads prevent us from taking the risk required to achieve the freedom lifestyle, to make that terrifying transition from employee to entrepreneur. 

The Procrastinator Thief says, “I’ll do it later.”

I’m too busy. I’ll think about it later. I’ll do it when I have savings.

The Perfectionist Thief says, “I don’t know how.”

I don’t have the skills, tools, or knowledge to be an entrepreneur. I’d rather not start at all than suck initially.

The Failure Thief says, “I’m scared to try.”

I’ll go broke. I’ll embarrass myself. I’ll let myself down. It will all just be a waste of time.

Three hand cuffs describing pitfalls preventing transition from employee to entrepreneur.
The freedom thieves preventing you from taking the actions required to achieve the freedom lifestyle.

It’s easy for freedom thieves to control you when you don’t have a plan. Without a concrete goal to work towards, you’ll prioritize fun or chilling over your ambitions.

Those who truly want the freedom lifestyle have a vision for their lives. They make small strides towards a big goal until they have enough momentum to achieve it. It’s called the snowball effect.

So, let’s slap these thieves in the face and do the thing: sell yourself.

Is the freedom lifestyle for you, anyway?

There are SoOo many ways to make money, and transitioning from employee to entrepreneur is just one of them. But the freedom lifestyle does not align with every entrepreneurial endeavour.... or person, at that.

The average person living the ‘freedom lifestyle’ ...

Has a marketable skill or product people will buy

Will take risks

Has a good relationship with money

And doesn’t care to build a scalable company

I learned this lesson the hard way. My first business required “more” to be successful.

“More” employees. “More” projects. “More” partners. “More” expectations.

But more didn’t mean better.

The more I gave, the less time I had. It defeated the whole purpose of pursuing entrepreneurship in the first place.

If you want a freedom lifestyle, I recommend these types of businesses:
  • A 1-person business with extremely tight processes and minimal overhead costs (no employees, no office, low cost of doing business)
  • A passive income stream that makes you money while you sleep (think real estate)

I’ve optimized my 1-person service business to work 30 hours a week. So, I’ll speak to what I know – single-person service businesses.

How To Transition From Employee To Entrepreneur In 4 Steps

1. Give people a reason to give you money.

Just because you can sell anything, doesn’t mean you should.

People who succeed in going from employee to entrepreneur must channel their strengths into a marketable skill – the ability to do something people will buy.

Most people are too generic. And when you’re too generic, you end up competing with everyone.

If you target an industry, have a unique process, or can package your service as a product, you’ll instantly stand out.

To say it bluntly, you need a niche.

Now, you might be thinking, ‘Reagan, I don’t want to exclude anyone.’

Let me ease your doubts.

If you want to become known, you need to differentiate yourself and cut through the noise.

If you want to charge premium prices, you need to be really good at what you do (Hint: That doesn’t happen when you spread yourself too thin).

If you want to have more time to enjoy life, you need to develop processes to save time on projects. If all of your clients look different, it’s impossible to do that.

Getting super specific on what you want to do and sell is step one. But to successfully transition from employee to entrepreneur and achieve the freedom lifestyle, you have to have a money mindset and get hella comfortable asking for it.

2. Build a relationship with money.

Social media glamourizes solopreneurship.

It's true. You can work from anywhere sipping margaritas on the beach.

Reagan Bradley enjoying the freedom lifestyle from Mexico.
Enjoying the freedom lifestyle from a beach in Mexico!

But this isn't possible if you're not in a "comfortable” financial position.

I put “comfortable” in quotations because what's comfortable is subjective when it comes to money.

Financial comfort means having...

Savings or investments

No debt

A good income

When I was learning how to transition from employee to entrepreneur, I had savings to support me for a solid six months and was lucky to have no debt to worry about.

I also never had a salary high enough to subject me to lifestyle inflation – the bad habit of spending more because you make more money.

I was used to living off of a $50K salary and still saving, so my financial benchmark for my first year in business was low.

Luckily, I’ve long surpassed that. And as a reward, I booked a trip without asking for permission, living the true freedom lifestyle.

If your goal is to start a business, take a hard look at your finances and figure out the bare minimum you need to survive.

Set the expectation you may have to temporarily decrease your spending or dip into your treasured savings account until your business turns a profit.

Short term pain equals long term gain. But don’t worry, the ride on the financial struggle bus should only be temporary!

Graphic illustrating the negative effects lifestyle inflation has on your savings goals.
Lifestyle inflation is the the bad habit of spending more because you make more money.

3. Know your worth. Don’t cut deals.

People who want to achieve the freedom lifestyle don’t cut deals. They know their worth, set profitable prices, and only work with clients who can afford them.

I had a full-time job when I started my business, and having the salary to fall back on meant I didn’t have a problem selling my services for low prices.

But in order to transition from employee to entrepreneur, I had to raise my rates. After all, my goal wasn’t to merely survive. It was to thrive. 

To achieve the freedom lifestyle, you need to know how to set profitable prices that cover your taxes, business expenses, and a healthy salary for yourself.

Most entrepreneurs forget to factor their time into the pricing equation.

They calculate their expenses and work themselves to death in order to hit that number.

For example, if you bring in $100K but work 80 hours a week, you’re not profitable.

You’re technically making $13 an hour after you account for the costs of doing business.

Let me show you.

Bad: Time not factored into pricing
Revenue Minus Business Expenses Minus Income Taxes Equals Income Divided by Hours Worked Equals Hourly Rate
$100,000 $20,000 $22,400 $57,600 4,160 hrs - 80/wk, no vaca $13/hr

The last time I made $13 an hour, I was in high school.

Service providers need to measure their profitability against their time.

For example, I want to work 30 hours per week and take three weeks of paid vacation. I also know that a $70K income after taxes is enough to reach my savings goals, pay all my business expenses, go on a few trips, and not stress about money.

So, let's see how much I need to charge hourly.

Good: Time factored into pricing
Goal hours worked Goal income Plus Income Taxes Plus Expenses Revenue Goal Equals Hourly Rate
1,470 hrs - 30/wk, 3 wks vaca $70,000 $19,600 $20,000 109,600 $75/hr

When you flip the equation to start with the number of hours you WANT to work in a week, you can calculate a profitable hourly rate.

Do this equation and ask yourself, “Am I charging enough?”

This exercise will give you permission to hold your ground in negotiations or chase bigger and better opportunities.

4. Get clients.

Sadly, the phrase "if you build it they will come" is simply not true.

Making the transition from employee to entrepreneur does not guarantee success. You have to confidently sell yourself. 

In the beginning, the most effective use of your time is to have direct, one-to-one conversations with people in your network. 

These people already know, like, and trust you. 

They’re more likely to think of you when an opportunity comes to mind than some stranger who interacted with your post on social media.

My first order of business as an entrepreneur was to reach out to every mentor, old colleague from my agency days, and people in my network who offered services mine could complement. 

I had a catch-up call with everyone in my network, even people I hadn’t spoken to for years, to find out what they were doing and give specific examples of how I could help them. 

I was prepared to do anything to get clients because I needed the business. I offered to white label my services (do work on behalf of another company) and even work on projects that didn’t align with my niche or core offering.

Building your referral network as an entrepreneur is one of the most powerful and important things you can do when transitioning from employment. When you do good work for people who know you, you’ll strengthen your relationship, and they’ll have positive things to say about you as a result.

And let me tell you – Word-of-mouth is the single most influential form of marketing. 

So use this template to start the conversation:

Hi [NAME]!
How's everything going with [Business Name]? I saw you recently [achievement]. Congrats!

I'm touching base to share I've launched my freelance business. I help service providers develop their brand, communications and website.

I know business is booming for you, so I wanted to offer my services to support you on projects.

My capabilities include:
- Brand Strategy
- Copywriting
- Website Strategy
- Web Project Management

Here's some of my recent work:
- Professional Service: AutoAgents
- Coaching Service: Nicole Dauz
- SaaS Service: Snappy
I hope things are going well for you. Keep up the content on [insert topic], it's super inspiring! :)

Your next steps

I believe everyone has the power to learn how to transition from employee to entrepreneur. Find the sweet spot between your passions and what people need, then sell it. Be smart with money, know your worth, and make a plan to achieve your version of the freedom lifestyle.

Here are the next steps you can take to achieve the freedom lifestyle: 
  1. Become aware of freedom thieves preventing you from reaching your goals 
  2. Create a business that fits into the freedom lifestyle 
  3. Be specific about what you sell and why people should care
  4. Avoid lifestyle inflation so you can budget for entrepreneurship  
  5. Set profitable prices so you don’t have to worry about money  
  6. Build your referral network before you start posting on social media 

Achieve a freedom lifestyle - steps to transition from employee to entrepreneur

I run marketing experiments and share my insights with my network. 

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