How To Be Your Own Boss: 5 Steps to Break Free and Live without a Job

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Whether you’re looking for a side hustle or want to have a more enjoyable 9-5, there are several ways you can go about becoming your own boss.

Just imagine … no more clocking in, no more mean bosses, and no more incompetent coworkers to deal with.

Sounds like bliss, right?

But how exactly do you make it a reality? What do you need to do to be your own boss?

how to be your own boss


Sam Wilson contributed heavily to this post. Sam successfully became his own boss, and now runs Virtalent, a UK-based Virtual Assistant service.

1. Decide What You Want To Do

Nick’s Notes: Living without a job is awesome — I’ve been doing it for the last 10+ years.

But you’ll still need a way to earn income, and unless you’ve just inherited a giant sum of money, that’s probably going to come from a business.

Entrepreneurship isn’t an easy path, especially when we’ve been trained from an early age to be rule-following employees. But it is doable.

Here are some things to consider.

Which Type of Business Do You Want?

This is number one on the to-do list when figuring out how to be your own boss. There are literally unlimited options available when you’re deciding which type of new venture you’d like to try out.

The one that’s right for you will depend on:

  • the amount of time you have
  • how much start-up capital you have
  • your individual skillset
  • your goals

Two main choices are deciding between freelancing and starting your own business.

Freelancers are self-employed individuals who usually take on specific work in a particular niche and work 1-on-1 with their clients, while businesses are organizations of one or more people who provide a specific service or product.

Nick’s Notes: I consider there to be 3 basic business models:

  1. Selling a service (online or in-person)
  2. Selling a product (physical or digital products)
  3. Audience-based businesses (such as blogging or podcasting)

My latest book, The Side Hustle, explores each of these 3 business models in detail with lots of examples. And the Kindle edition is free!

Starting out, most side hustlers begin their business life as sole proprietors. Doing so, they avoid potential double-taxation on revenue, have simpler accounting requirements, and can started quickly.

Because there are expenses and red tape involved with setting up a corporate entity, I normally recommend postponing it until you’ve proven out your business and have real revenue. (Of course, certain businesses should register earlier for liability protection reasons.)

For more on this topic, be sure to check out:

Start with a Service

Still, ascertaining what you’d like to do is the first step in launching your business. Here’s a monster list of side hustle ideas to get your creative juices flowing.

A common side hustle path goes like this:

  1. Freelancing on the side (and keeping your day job)
  2. Freelancing full-time
  3. Building an agency (hiring subcontractors to do the work)
  4. Building a product (digital guide, software, etc.)

If you’re thinking this sounds like a viable plan, I encourage you to check out The Freelancing Mixtape, a collection of the best freelancing and service-business episodes from The Side Hustle Show:

The Freelancing Mixtape podcast

The biggest advantages of starting with a service-based business are:

  • Low to no startup costs
  • You may already have the skills you need
  • You can quickly and cheaply find out if there’s demand for your service

be your own boss

Photo by Brooke Lark on Unsplash

What Industry or Niche Will You Serve?

When you decide which one to go for, it’s best to think about the specific industry or niche you’d like to be in first.

Do you want to be a painter or decorator?

An accountant, writer, or artist?

Maybe you’re looking to sell a certain kind of product, or to provide advice and consultancy services?

Here are some general rules to think about.

  • Consider what you enjoy doing in your spare time.
  • What do people ask you for help with?
  • If money wasn’t an issue what would you do?
  • What do you never get tired of talking about?
  • What have you been paid to do in the past?

Don’t stress over aligning a business to a “passion” of yours if there’s not a natural fit. Research has shown that passion for a topic grows over time through practice.

Nick’s Notes: This is 100% true. I had zero passion for podcasting when I started–because I’d never done it before! Years later, it’s become a core part of my identity and I’m super passionate about creating a great show.

Think about what already exists in the market, what the potential revenue of that market is, and if there are any gaps you could fill.

2. Decide How You’re Going To Do It

Okay, so you already have a full-time job but now you’re also starting a business. How on earth do you juggle the two, and how do you even get started?

Get Clear on Your Financial Picture

Before you really start doing anything, you’ll need to take a realistic look at your finances.

The primary number you’re looking for is your total monthly expenses. This is what your new business needs to earn for you to be your own boss.

If your lifestyle costs $4000 a month, your business needs to earn $4000 a month (after taxes) for you to live without a job.

Based on what you’ve decided to sell, what’s it going to take to get there?

Set Aside Time to Hustle

There’s never enough time to do all the things you want to do, so you need to become a master of efficiency and productivity.

But here’s the truth: by definition, we make time for the things that are most important to us. Study where your 24 hours a day are going now, and find some space for your new business.

It’s not always easy, but if it’s a priority, you’ll find a way.

Create a Marketing Plan

When businesses fail, they most often do so because they aren’t reaching enough (or the right) customers.

Before you begin, it’s worthwhile to consider how customers will find you–or how you’ll find them.

For this, you might like Allan Dib’s 1-Page Marketing Plan:

1-page marketing plan

Remember, the #1 goal in marketing is to get in front of your customers where they’re already doing business. Go where the cash is already flowing.

Get your name out there and start pitching for jobs.

If you’ve joined a freelance website, you’ll probably need to bid on jobs against other freelancers. The key here is to bid on jobs that most closely match your previous experience and proven skillset, in order to increase your chances of being awarded the project.

Land Your First Customer

This is a major milestone toward becoming your own boss!

Nick’s Notes: One of my earliest businesses was painting houses, and I found customers by knocking on their doors. Not exactly an earth-shattering strategy, but it worked. And it was thrilling when I got that first “yes.”

Think About Pricing and Logistics

How much will you charge? Will you need to work for free or for a low rate to build a portfolio or testimonials for your business?

This is common in some industries like photography or design, but less common in other areas.

How will you actually deliver the work?

Make sure client expectations are aligned in reality in terms of your capacity and deadlines.

live without a job pricing and logistics

Photo by You X Ventures on Unsplash

Consider Creating a Simple Website

Nick put together this case study on the fastest, cheapest way to start a website for your service business. This may not be a priority based on your marketing plan or your target customers, but can be a helpful place to showcase a portfolio or begin to be found in Google.

3. Marketing Your New Business

Aside from a quality product or service, marketing is the key to business success.

Marketing isn’t a one-size-fits-all discipline, so you’ll need to think carefully about how you’re going to tackle it for your new venture.

Marketing on Social Media

Arguably the pinnacle of modern-day marketing, social media offers you the chance to engage with your potential customers while providing expert advice, insight and building your brand image.

You need to decide which social media platforms you’re going to use to market your new business and how you’re going to use them.

Let’s look at the four most popular social media platforms for business marketing and see if they’re right for you.

Instagram is a visual platform, allowing designers, artists and other visual-centric business to thrive. You can also display products, give insight into what’s important to your company and appeal to a younger, more dynamic audience.

Case Study: How April Whitney found a tribe of petite women for her online fitness business.

Twitter is a fast-paced platform where most content gets lost in a stream of never-ending tweets. However, it’s a fantastic customer service platform as it allows you to publicly address any concerns instantly. Twitter marketing does better with regular, daily content that people want to engage with–or direct outreach to prospects to start conversations.

Facebook is a pay-per-click haven. However, a lot of people dislike businesses on their Facebook stream, especially advertisements. It’s important to craft content that actually adds value to the user.

Nick’s Notes: A few colleagues of mine have used a particularly effective strategy to make money on Facebook. They joined (or were already a part of) existing Facebook groups or communities. When anyone had a question in their area of expertise — be it WordPress support, podcast editing, or Facebook ads — they were on it, offering useful advice and helping community members troubleshoot their issues. 

Before long, they’d become the go-to person for that subject and other members couldn’t race to tag them fast enough when a new question popped up. Word of mouth spread fast and these “resident experts” built thriving service businesses just by being helpful first.

YouTube is perfect for visual representations. From unboxing videos, walkthrough videos and much more, it’s a great choice for almost any business to present a video version of what they do, how they do it and who they are.

Nick’s Notes: My favorite recent YouTube marketing example comes from Paul Minors, who created a series of videos about Asana. That led him to people reaching out for Asana consulting, and Paul was able to quit his job to run his virtual consulting business and be his own boss full-time.

Pay Per Click

With a great return on investment when it’s done right, Pay Per Click advertising (PPC) gives you an instant way to increase the number of people who visit your website or social media pages and interact with you.

From Google AdWords, which allows you to target specific keywords and bid to be one of the top results for a given search, to social media advertising, which gives you the option of promoting posts to very narrow target audiences to increase engagement, there are a whole host of options out there.

Nick’s Notes: This is how I got my first customers for my original side hustle, a comparison shopping site for footwear. I’d bid on the keywords for specific models of shoes, point that traffic to a landing page where I showed visitors where to find the best price, and earned a commission on every sale.

Timika Downes used a similar strategy when she launched her brick-and-mortar lice clinic. She could target people typing in the exact problem her business solved.

pay per click ads

Photo by Launchpresso on Unsplash

Content Marketing

Content is, of course, king. So, how do you actually do content marketing and is it the right choice for you?

If you’re selling things on eBay or buying and flipping properties, probably not, but for many businesses and freelancers it’s an important piece of the puzzle.

Your content marketing strategy should include blog posts and social media. It should have a consistent tone and voice throughout every piece of content you create, and should include rich media content such as images and videos.

The simplest way to start is by creating content that answers questions your target customer might have.

Print Advertising

Despite what you may have heard, print advertising isn’t dead.

This can be an especially lucrative avenue for niche B2B businesses, who can place ads in trade magazines that go out to the industry they’re targeting. Even if you’re targeting the public, print advertising in the form of fliers, posters, and magazine advertisements may still work for you.

Again, think of who your ideal customer is and figure out where they might see your message. For instance, if you do clothing alterations, you might post a flyer at the local gym where people may have lost weight!

A Note on Branding

It’s important to keep in mind that strong branding is an essential ingredient if you’re going to create a successful marketing campaign.

Try to come up with a sentence or two that embodies what you want your new venture to represent and think of any Unique Selling Points (USPs) you can offer that would appeal to your target audience. This could be next day shipping or a US-based customer service team, for example.

4. Logistics: Delivering the Goods

Next, you’ll need a plan of action to be able to tackle the logistical aspects of your new venture.

Early on, you’re probably going to be wearing all the hats — marketing, sales, customer support, bookkeeping … maybe even janitor!

But as your business grows, one of the most important pillars of being your own boss is ensuring things run as smoothly as possible.

At its simplest level, your business is about matching supply and demand. Here’s what I mean.


If you’re selling a product, you’ll need to find a reputable, reliable supplier.

If you’re selling a service, that supplier might be you in the beginning! (Later it might be a subcontractor or a team of professionals.)

Keep in mind capacity constraints, delivery times, and skillsets.

Hiring a virtual assistant could also be a great way to lighten your admin workload, without needing to have a physical office, so you can focus on growing the “demand side” of your business.

how to live without a job

Photo via Unsplash


For physical products, it’s imperative to keep up with demand. This may take a little bit of trial and error at first, but you should quickly know how much stock you’ll need to keep up with purchases.

This is largely a function of how effective your marketing is, but you never know when you might get flooded with requests.

If you find yourself having to turn work away, that could be a sign it’s time to raise your prices.

5. Growth and Scale to Live without a Job Long-Term

Since you’re looking for ways to be your own boss for the long-term, it’s important to grow your business at least to the level of your monthly expenses–if not beyond.

Growth can include taking on more staff, outsourcing overflow work to freelancers, or simply providing more of something so you can make more money.

Once you start generating capital from your new venture, you can reinvest back into the business, allowing you to buy and sell more, outsource work, and increase your advertising and marketing spend.

Related: 7 Effective Ways to Scale a Service Business

All of these things contribute to the growth of your business, ultimately giving you more capital so you can start the process all over again and delivering exponential growth.

6. The Next Level: Reaching FIRE

Once your business is running well enough to support you without a job, the next level to think about is making work completely optional and leaving the rat race behind.

This is the goal for many in the “FIRE” community, that is, “financial independence, retire early.”

A standard way of thinking about this is to save 25x your annual expenditures in investment accounts–enough to theoretically live off that portfolio in perpetuity.

It may seem like a long way off, but it’s something to shoot for after you’ve become your own boss.

Common Paths to Be Your Own Boss

If you’re still looking for business ideas to become your own boss, don’t worry. Here are a few of the most popular ways to do it and the benefits of each.

Becoming Your Own Boss as a Freelancer

Becoming a freelancer is a great way to get started and can yield significant results. Freelancers are contracted by clients to deliver specific work on a case-by-case basis.

If you’re a freelancer, you’ll be able to work as much or as little as you want, choose which projects you wish to undertake and build yourself a reliable client base.

Later, you can expand (if you want) with other team members to help deliver the service.

Some popular freelance skills include:

Usually you need to start small to gain a reputation online or in your local area, which will then develop into multiple projects and eventually into your own agency or company.

Becoming Your Own Boss Through E-Commerce

With platforms such as eBay and Etsy available to anyone looking to start a small business, it’s easier than ever to start selling online and reach a global audience. You can set up your own eBay stores, or create an e-commerce website, and begin selling your products in a surprisingly short period of time.

You’ll need to remember, however, that if you’re a business there are certain rules and regulations you need to follow when selling online.

Some popular e-commerce business models include:

Becoming Your Own Boss Through Real Estate

Real estate investing is one of the oldest side hustles in the books, and for many investors, it’s a ticket to living without a job.

Perhaps the simplest model to understand is acquiring a portfolio of rental properties that bring in enough cash flow every month to pay for your lifestyle. One investor, Austin Miller, was even able to build his $1.2 million portfolio for free!

Other ways to get started in real estate investing:

  • Raw Land Flipping – “the best passive income model?”
  • Arrived – Arrived lets you buy fractional ownership of cash-flowing rentals for as little as $100. This allows you to add the benefits of tangible real estate to your portfolio — without the headaches of managing it yourself.
  • Fundrise – Fundrise offers a variety of commercial real estate REITs, targeting different investment goals and areas of the country. I like the quarterly cash flow, low minimums (just $10), and being automatically diversified in not having to pick-and-choose individual deals. Disclosure: I’ve been a Fundrise investor since 2015. When you join through my referral link, I receive compensation. Opinions are my own. 
  • Roofstock – Roofstock is a marketplace for “turnkey” rental properties. If the “no tenants” aspect is what attracted you to raw land, this one probably isn’t for you.

turnkey real estate investing

Photo by Tierra Mallorca on Unsplash

Becoming Your Own Boss Through Online Business

An ever-popular business model is that of starting an online business. One way to go about it is with an affiliate marketing model, as Sa El did with his website, which talks about different insurance products.

Sa had some expertise in the industry, having sold insurance door-to-door. He took that expertise online and is now earning $13-15k a month in affiliate commissions from his site.

If you’re looking into starting an online business of your own, be sure to check out Nick’s free video series here.

Nick’s Notes: I’m incredibly grateful to have been my own boss for more than a decade. I’ve dabbled in just about every business model mentioned in this post. Here are some of the ways I generate income today.

Your Turn

When you’re figuring out how to be your own boss, remember that the most important thing is to take it one step at a time.

Realize there will always be another hurdle and more to learn. Be excited about what you’re doing and keep going!

If you’d like to learn more about starting a side hustle, I think you’ll get a ton of value from my Start My Side Hustle Workbook.

It’s normally $49 but I thought I’d test offering it for just $19 for a limited time.

Not ready to buy yet? Make sure to fill in your name and email below. I’ll send you my free report, The 5 Fastest Ways to Make More Money, along with some of my best side hustle tips.


Big thanks to Sam Wilson from Virtalent, a UK-based Virtual Assistant service, for contributing heavily to this post!

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Nick Loper

About the Author

Nick Loper is a side hustle expert who loves helping people earn more money and start businesses they care about. He hosts the award-winning Side Hustle Show, where he's interviewed over 500 successful entrepreneurs, and is the bestselling author of Buy Buttons, The Side Hustle, and $1,000 100 Ways.

His work has been featured in The New York Times, Entrepreneur, Forbes, TIME, Newsweek, Business Insider, MSN, Yahoo Finance, The Los Angeles Times, The San Francisco Chronicle, The Financial Times, Bankrate, Hubspot, Ahrefs, Shopify, Investopedia, VICE, Vox, Mashable, ChooseFI, Bigger Pockets, The Penny Hoarder, GoBankingRates, and more.

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