How To Ditch Your 9-5 Grind And Join The Ranks Of Solopreneurs

Become A Solopreneur

The alarm on your phone goes off.

Time to get up, shower, grab a bagel and coffee for the road, and drive to work.

It seems every day you’re on autopilot. There’s no need to think – just do.

For many people, having a traditional 9-5 job, while being somewhat secure, is not what they envisioned it would be when they signed up for it.

You may only get two weeks for vacation; the pay is lousy, the people are a bunch of gossipers and the work – well, let’s just say you don’t really need your degree to do what you’re doing.

More and more people are starting to move away from a full-time job, especially Millennials. Climbing to the top in a company isn’t an expected career path anymore.

Instead, Millennials often see freelancing, starting your own company, or growing your own business as the new norm.

And the data shows it; freelancing is on the rise. Over 50 million Americans are choosing to freelance, which equals nearly 34% of the entire workforce.

Seven years ago, they made up only 15% of the workforce. And it’s only going to keep rising as more people realize the freedom being a solopreneur allows.

You’re stuck

As every day rolls by, you can’t wait until the weekend so you don’t have to think about work. No more having a boss breathe down your neck, no more pre-arranged breaks and definitely no more long commutes.

You live for the weekends. You know you don’t want this job anymore, but you’re stuck.

Whether you want to quit your job to travel more, to try something new, or if you’re just bored or unhappy with what you’re doing, you want out, but just don’t know how.

What do you do?

How do you quit your stable and secure job for a life of hustling for work? And can you even make a living from freelancing?

Let’s look at how Colin Newcomer, a copywriter and freelance writer, quit his job and made the leap into solopreneurship:

I don’t think I have a typical journey to freelancing. From ages 17 to 24, I was self-employed thanks to a graphic t-shirt blog that I launched in high school. Then, around 25, I made the decision to get a “real job” at the Vietnamese version of Google (sounded like fun!).

You know how most people wish they could have the freedom of self-employment? Yeah – I was the opposite. I wanted to try what it was like to work the standard 9-5. Don’t mock me too much – I was curious.

Satisfaction at my job lasted…9 months. Then, I realized I was crazy! And so I began plotting my journey back to self-employment. But this time, instead of Internet marketing, I was going to go into freelance writing. And given that WordPress and digital marketing were where my experience lay, those writing niches seemed like the obvious choice.

I told myself that as soon as I made as much from freelance writing as I did from my job, I could quit (I admit that this is more easily done when you live in Vietnam and make an equivalent salary).

That sucked. I would work 10 am to 7 pm, come home, eat, and work on freelance writing until 11 pm. But I was determined not to ever feel desperate for freelance work. And I figured that the best way to achieve that was to wait to quit my job until I could sustain myself from freelancing.

Thankfully, that only lasted less than 2 months. By the time I finished out my 30 days’ notice at my job, I was already making triple my salary from freelancing alone. That was September 2016. Since then, business has only been getting better. I hit a personal milestone for income in March 2017 and have a steady stream of work without needing to pitch clients anymore.

His story is similar to many other freelancers who left their job and decided to have that financial independence they’d been craving.

If your worry is not being able to replace your day job income from freelancing, you shouldn’t let that stop you. It’s possible and Brent Jones is not the exception.

According to a survey by the Freelancers Union and Elance-oDesk, 77% of freelancers are making the same amount of money as they did in their previous job and 42% say they are even earning more money.


While this post is mainly focused around leaving your 9-5, let’s quickly explore another scenario.

Can you avoid the 9-5 grind altogether? The short answer is yes!

Here’s how Jason Quey from The Storyteller Marketer made his leap into solopreneurship:

Some people go to college, get a degree, find a nice salary job, then try to escape the 9-to-5.

Others go to college, dropout, and start a million dollar business.

I did everything wrong.

I went to Bible college in the winter of 2009. Like most my age, I only had a faint inkling what I wanted to do. And after graduation, I wasn’t much closer to knowing what God wanted me to do.

After years of occasionally selling goods on eBay, I stumbled on a steal-of-a-deal: A pair of top-selling Nike shoes at 25% off.

But rather than buying them, shipping to my house, listing the shoes, then risking whether or not they would sell, I decided to do something a little different. I listed the item on eBay, waited for the shoes to sell, then promptly shipped the shoes to the buyer. 5 days later, it worked like a charm.

As sales started coming in, I realized I knew nothing about running a business. After all, I went to Bible school.

So I poured over every marketing article I could find. What I did not learn until later is that there’s a big gap between what you read online, and what you learn in the trenches. Armchair marketers can only go so far.

I launched The Storyteller Marketer, after seven failed blogs before it.

How did I know it would become a go-to blog on influencer marketing? I didn’t. In fact, most of my blog has changed drastically over time by doing, rather than just reading.

The biggest difference was I had a half-baked promotion plan. Unlike, you know, just posting onto the void of Facebook and blindly hoping something would work.

Later on, I pitched to work for Sujan Patel. That connection with Sujan later allowed new opportunities to connect and work with many other marketers. I would not be where I am today without working for him.

There’s a lot of things I wish I could go back and do over again. Then again, those painful lessons are what made me who I am today.

If you learn nothing else from my ramblings, remember this: action beats perfection.

As I write this, I have the ability to pick up a few clients.

Rather than coming up with a perfect sales system right away, I decided to pitch potential clients a system to get them from 0 to 50,000 visitors a month, in a year.

There are plenty of sales blogs to read to improve my prospecting skills.
There are plenty of Youtube videos I could watch to improve my presentation skills.
There are plenty of books, podcasts, and courses to tell you everything you need.

But you don’t need more information. What you need is to act on that information.

Whatever position you’re in right now, here’s a guide to making that switch as seamless as possible:

1. Set a timetable

Making the jump from a full-time worker to a full-time freelancer is a big move. To make it more tangible, set a timeframe of when you plan on making the transition. This can help you stay accountable and motivated for when times are a bit rough.

It’s a good idea to set an actual date so you can let your boss know your future plans.

This is what Jeffery Trull, a copywriter and content strategist, did before making the leap into freelancing,

I left completely on my own terms. My boss actually knew way in advance that I’d be leaving May 2012, and I gave her official notice of my last day about a month ahead of time.

On May 25th, I walked out the door for the last time and never looked back.

When deciding on your timetable, you need to consider not only your financial picture but also how you’re going to leave your job. Are you going to make a clean break or – if it’s an option – transition gradually?

A couple of things to take into account are:

  • How will your expenses change once you quit your job? For example, you may save on gas and commuting, but you may spend more for health insurance.
  • Is your company interested in retaining you as a part-time consultant? This can help the company transition and provide you with some guaranteed income while you navigate the solopreneur lifestyle.

2. Have a goal in mind

Everyone chooses to quit their job and go freelance for different reasons. After making a timetable of when you plan on leaving your job, figure out the big goal you want to achieve in that time frame.

Carrie Smith, a freelance expert, did this before leaving her bookkeeping/business account job.

I wanted to replace my day job income while having the freedom and flexibility of taking time off work whenever I wanted. No more asking for permission!

And in three months’ time, she was able to achieve her big goal!

Carrie Smith Earnings

Having a big goal not only helps you keep focused, but it also increases your motivation and achievement.

When you start working for yourself, you’re not going to have someone else tell you what to do. So, by making a big goal and sticking to it early on, it’ll only help give you the skill set you need to succeed once you make the leap into solopreneurship.

3. Plan it out

By figuring out what your goal is and how long you think it will take to achieve, the next part is laying out the steps you’re going to take to actually reach your end goal.

Let’s look at three steps soon-to-be freelancers should incorporate into their plan:

Research what you want to do

The fastest way to achieve your goal – if it’s an income goal – is to leverage your previous work experience.

Alexa Mason, a freelance writer, used her past work history to quickly land quality writing gigs when she first made the transition to solopreneurship.

The first few decent paying freelance blogging jobs I got were insurance related. Not because I loved writing about insurance, but because I was an insurance agent at the time and understood the terminology.

While many freelancers use knowledge acquired from their trained profession to make a smoother transition to freelancing, still others might use their passion to kickstart their freelance journey.

Ashlea Wheeler, a travel blogger and creative, was sick and tired of her receptionist job. She bounced around from one job to the other until she had enough.

She decided to take the reigns and start an Etsy shop selling DIY printables.

This idea took off very quickly – I had my first sale within a month or two, so from then on I’d get inspiration from Pinterest, magazines, and wedding blogs to create new DIY printable stationery designs to add my shop.

Once you figure out what you want to offer, start researching the industry and looking at other businesses in the space to make sure it’s a viable option and that you can make a living from it.

Set your rate

The whole point of being a solopreneur is to have the freedom to travel or quit working at 2pm. It doesn’t mean slaving away 18+ hours a day trying to make ends meet.

In saying this, setting your rate so that you can live comfortably comes in stages.

Earlier we learned about Brent Jones’ story. He mentioned he worked for very little money when he first started his own business. For him, he knew he had to prove himself online by taking any job that came his way.

You might have to do this too. Performing small amounts of work in exchange for a testimonial or referral – especially when you’re just starting out – can help you build that all-important track record and client base.

You’re not working for free; you’re just working for something other than cold hard cash.

Having those first few projects under your belt and the social proof that comes with it will only help you establish your credibility as an expert in your field, driving your rate up.

As you progress in your business, don’t be scared to charge what you’re worth – definitely charge more than you would make if you were doing the same job as an employee.

Let’s say you were earning $40/hour to perform a certain task at your old job. Do you really think your employer was charging the client that same rate? No way. They were probably charging them three times that!

You’re both the employer and the employee now, so you’ve got to act the part.

Fail fast

What if you take the leap into freelancing, and three months down the road you find out there is no market for your service?

Or, you find out the industry you are in – maybe it’s writing, design, coaching or blog management – just isn’t paying the bills?

If you end up failing, fail fast. Accept that you need to change what you’re doing and move on to the next thing.

If plan A doesn’t work, go to plan B or even plan C. This might mean going back to work. It’s not ideal, especially if you hated the demanding work schedule at your previous job, but it doesn’t have to be forever.

Or it might mean you end up pivoting to something else more profitable.

You could enroll in a course or hire a coach or mentor to help take your business to the next level. This may give you more skills you can add to your list of services, diversifying your portfolio and ensuring more consistent work.

This is what Kristen Larsen over at Believe In a Budget did. She started her budget blog to document getting out of debt in 2014.

It wasn’t until early 2015 that she got serious and enrolled in a blogging course. This led to her creating a product and kickstarting her Pinterest management and image services.

I do have to give credit to Elite Blog Academy for lighting a fire under me. I took this 12 week course last spring and it helped my blog go from around 1,000 page views a month to 160,000 page views by the end of the year.

Let’s say your website design business isn’t bringing you consistent income. Switch it up and offer graphic design services to include social media banners, blog post images, infographics or eBook covers.

4. Do it as a side hustle first

To minimize the risk of failure, most people break into solopreneurship by moonlighting on the side while still employed at their full-time job. This allows you to try your hand at hustling and landing clients, while not having to totally commit.

By freelancing or working on your Etsy shop products during your downtime, it will help you see if you can actually do this full-time.

Be warned, though, this doesn’t always give you a true picture. If you have the luxury of guaranteed income from your job to fall back on, are you really going to give it your all to be successful with freelancing? Laziness and procrastination can kill your drive even before it gets started.

Also, as a side hustler, you’re still responsible for administrative tasks, paperwork, billing and invoicing, as well as managing sales or projects – something that may be new to you. This can be a huge time suck when you only have limited time.

With these new roles, you may end up learning this is exactly what you want to do, or you may learn it’s too overwhelming to be responsible for every aspect of running a business.

For many people, however, side hustling helps them get started with branding, networking and earning side income. This makes the leap into full-time freelancer easier.

This is what Kali Hawk, a freelance writer and content marketer, did before she went full-time with her digital business.

In November of 2013, I casually applied to a few writing gigs that I found on sites like Problogger… By December of the same year, I was getting nibbles from almost every line I cast… In January 2014, I started dropping lower-paying gigs to make room for better opportunities and higher-paying offers… I’m still a little bemused that everything happened so quickly, and in three months I went from making $0 off my writing skills to making over $2,000 (my side income total from January).

Related Reading: 50+ Side Hustle Ideas You Can Use To Earn Extra Money.

5. Start Saving

With the extra income you receive from moonlighting, use this to build a cushion for when you quit your job to pursue this full-time.

How much should you save?

According to experts, the standard is to save three to six months’ worth of your income to account for any emergencies, slow periods of work and client attrition. For freelancers with obligations like a family or a mortgage, however, the recommendation is to save six to twelve months’ worth of expenses.

So, for any money you earn from your new business, put it in a separate savings account.

Jessica Hanna, a freelance writer, is currently working full-time and writing on the side. She has a plan to save up enough money before she makes the leap.

My goal is to have 6 months’ salary saved up before I do, so that I don’t put unnecessary stress and risk on my partner or myself. It has become my #1 determining factor of when I will leave my full-time job for freelancing.

6. Make the jump

You’re now juggling your full-time work and your side hustle. The time you originally set to achieve your big goal is fast approaching.

Before you hand in your resignation, here are a few things to make sure you have in order before cutting ties with your employer and taking your side hustle to full-time status.

Secure enough clients beforehand

How many gigs or projects do you need to feel safe enough to quit your job for good? You’ve saved enough income for slow periods, so now you need to look at whether or not the clients you have will allow you to cover your expenses – and then some – every month.

Have a plan to land more clients

Being a solopreneur also means being a hustler. Just because you have steady gigs or are making regular sales from your products or services, it doesn’t mean everything can’t change next month.

It’s important to have a strategy in place for when a client cuts down your work or they end the collaboration.

Typically, you want to work on reducing or eliminating lower-paying clients as you start to replace them with higher-paying clients. This will free up some time and move you up the pay scale.

Similarly, you also want to get your name out there so that prospects start approaching you. This may be done by having a website for your services.

This is what Grayson Bell, financial blogger and WordPress pro did when he opened up his WordPress maintenance and support service.

iMark Interactive

Note: An easy way to find your first clients is by using one of the many freelance job websites. Check out our list of top freelance job websites to get started.

Structure your day

Without a boss to delegate tasks to you, the onus is on you to create a productive schedule every day.

The idea of just stopping work and going for coffee with a friend is tempting, but if you aren’t working, then you aren’t making money.

On the flipside, many solopreneurs understand the pressure of doing everything themselves and end up spending 50-60 hours per week building their business.

That’s why it’s important to structure your day. A great tool to use is the Pomodoro technique.

This is a time management hack whereby you split up your day into 25-minute hyper-focused work sessions with five minute breaks in-between. Each 25-minute work block is called a Pomodoro and after completing four blocks, you can take up to a 20-minute break.

You might also end up needing some productivity tools to streamline your day and maximize your effort.

And for others, being in a quiet room, meditating or doing yoga before work is enough structure for them.

Either way, decide how you will structure your day so that distractions are low and productivity is high.

Wrapping it up

You’ve finally made the decision to quit your job and take control of your life and finances.

With your plan in place, you’ll soon join the ranks of other freelancing solopreneurs like Brent Jones, Carrie Smith or Grayson Bell.

It’ll be an exciting and rewarding day when you finally say goodbye to your 9-5 and welcome in the new life of complete freedom from an employer.

Related Reading: