How To Become Your Own Boss - 8 Ways to Make Money Without a 9 to 5 Job | Pickled Plum (2024)

The last time I ever held a 9 to 5 job was in Toronto, Canada, back in 2004. I was working for a newspaper selling ad space and attending morning meetings that seemed completely pointless. After months of sitting in a cubicle and sounding like a broken record – “Hi, my name is Caroline and I’m calling from XYZ newspaper. I saw that you were advertising in another newspaper and thought you might be interested to know that we can double your exposure! XYZnewspaper can boost your sales and I can show you how, if you have a couple minutes to spare.”

Ugh.

You know when you read something off a page but don’t believe a word of it? That was me. I couldn’t have cared less about ad space. But it was a fairly easy job and my coworkers were sweet as pie. So I stayed on for a few months and thought I could hack it until I found something better.

Then one morning during a meeting, the newspaper’s business manager stormed into the room and expressed his disappointment in all of us.

And you know what he did? He gave each one of us a quarter.

“That quarter,” he said, “is for calling yourself a cab when you get fired. Because that’s what’s going to happen if your numbers don’t start improving soon.”Remember, this happened in 2004, before everyone owned a cell phone 😉

While most people in the room were shaking in their boots, I on the other hand was disgusted by the manager’s behavior. I thought it was completely out of line. “No one is going to treat me like that,” I clearly remember thinking. But instead of walking out right then and there, I took a deep breath and returned to my cubicle feeling both angry and deflated.

That’s when I realized I had two options: either I quit my job and take a chance at starting a brand new life with the possibility of great happiness and satisfaction – or I stay here for an undetermined amount of time feeling unaccomplished and resentful.

And then I thought about my dad who passed away when I was only seven years old. I’m sure he would tell me to live the life I envisioned for myself because I deserve it.

The next morning I walked into my manager’s office and gave him a week’s notice.

I quit my job and it felt good, really good!

I promised myself to never take another 9 to 5 job for the sake of money or to give my life the illusion that it could be more stable. Sure, the steady paychecks made it easier to manage my bills, but that was about it. I felt more unstable emotionally than I ever had, and my happiness level was dangerously low.

I realized that, by following the self employed path, I might give up on a safe retirement. But that didn’t matter to me. I just wanted to be happy again! And if that meant having to work a string of jobs, hopping from one career to another to find what I’m passionate about, well it was worth the risk because -> HAPPINESS.

And hop I did. A lot!

But at least I had fun doing it!

For the next six years I worked as a waiter, bartender, lifestyle model, I was an actor (for TV commercials), did extra work (background), was a tour guide for new developments (condos), worked in retail, did online technical support, was a sous-chef for a catering company, was an executive assistant, a makeup artist and dabbled a little in graphic design.

Phew!

And believe me, every time I started something new it was with the hopes that I would love it enough to turn it into a career. And although none of them turned into a full time job, I learned something incredibly valuable: I’m resilient and always take good care of myself. So no matter what happens in my life, I’m going to be okay – because I will never let myself down.

That’s powerful.

That conviction gave me the courage to start a blog and the strength to keep going whenever it looked as though I wasn’t going to be able to make it succeed.

Wearing different hats is also good if you are trying to figure out what career to pursue, because it’s the only way to find the right fit.

For me, I noticed that I was at my happiest whenever I cooked, tended bar and took pictures. What made me most miserable was interacting with strangers (customer service) on a daily basis – and being away from home for long periods at a time (acting).

I’ve created this post to help those of you who feel stuck at work and dream of becoming your own boss. A lot of people ask me how I manage to stay so busy and constantly have different streams of income coming in. They also want to know if I make enough to live a comfortable life – and the answer is yes. In fact, I made $212,161 last year which is more than I ever made working in a office!

Plus, I give myself 2-3 months vacation time so I can travel and enjoy life to the fullest!

Before we get started, it’s important for me to mention that I don’t have any children. This post is written from the perspective person without the huge responsibility of providing for kids. And because of that, I prefer not to give specific tips for mothers on how to quit their job. However, Single Moms Income has a great post about single mothers working from homethat can help you toward making a decision.

Before quitting your job, ask yourself these questions

So you want to quit your job because you find it unfulfilling, or your boss or coworkers are driving you nuts.

Is it time to give your two weeks notice?

Yes!

But before you do so it’s important to find out if the timing is right. When I quit my job at the newspaper, I was able to do it quickly because I had money in savings and no one to support financially. It wasn’t a lot but enough to create a safety cushion in case I wouldn’t be able to find work right off the bat.

Here are a few questions to help you find out if you are a good fit for freelance work.

1. Do I financially support anyone other than myself?
2. Do I have money in savings? If so, enough to pay my bills for 3 months?
3. Am I comfortable moving from one job to another, working in different environments?
4. Am I comfortable working with different people on a regular basis?
5. Am I willing to work on call and sometimes put in long hours?
6. Am I good at motivating myself?

If you answered yes to all the questions except #1, go and give your two weeks notice – you are the perfect candidate for freelance work!

How to Successfully Work From Home

You may be surprised by this, but the hardest part about not having a job isn’t finding work.

The hardest part is to stay disciplined enough to maintain a steady and productive work schedule. This means waking up at the same time every morning to either look for work or focus on creating something that will become your next full time job.

The first few weeks are all about getting used to a new life and setting yourself up for happiness. Don’t be afraid to try new things or apply for jobs you think you have zero chance of getting. You are free and this is the time to explore new avenues and possibilities. Besides, what’s the worst thing that could happen? Either you don’t get a reply or one that says, “no thank you.”

By being unafraid and opening yourself up to new opportunities, your world will suddenly expand. Only then will you be able to see how easy it is to find work and how exciting being your own boss can be!

Also, the more digging you do – the better. Find out about what it takes to start a business, sell your creations on Etsy, become a freelance writer. The world is your oyster! Want to become a blogger like me? Read my posts on How To Start A WordPress Blog On BluehostandHow To Write Your First Blog Post.

The Ultimate Work Bundle

Obviously you can find all the information you need online for free, but there’s another way to go about it that takes less time and effort. TheUltimate Work Bundleis a collection of e-books, courses, and resources created by people who successfully work from home. And because you are buying the material as a bundle, it’s sold at a discounted price. It’s great because you have all the tools you need to launch your new career all in one spot – written/recorded by people who have gone through the process.

With the bundle you can learn how to:

• Create simple work routines to fit your family’s schedule.
• Find work-from-home clients or companies who will appreciate your skills.
• Identify your marketable skills and differentiate yourself from the competition.
• Turn your business & entrepreneurial dreams into a reality.
• Learn to avoid scams and identify legitimate work-at-home opportunities (plus discover 150 real companies that hire from-home-workers).
• Ditch the guilt and balance work + family life more gracefully.
• Learn legal and accounting best practices to keep you worry-free.
• Market your business with easy-to-implement strategies for social media.

Click here to learn more about the Ultimate Work Bundle.

8 Ways to Make Money Without a 9 to 5 Job

Below are different ways you can make money working from home or anywhere. My recommendation is to go for all of them if you want to be busy. I have done it and sometimes was so busy I had to turn down work! Working from Home

1. Start a Blog

I had to bring this up since I am making a good living from blogging 🙂

I have been blogging full time for the past 4 years and am more successful than I ever could have ever been as a 9 to 5 employee. Yes, blogging has its challenges – it takes patience and resilience in the beginning – but the advantages quickly outweigh the negatives.

1. Everything I create belongs to me 100%. When I was working for a company, the effort I put in ended up benefitting someone else in the end. That’s something I’ve always been bothered by.
2. I can pack my bags and move to Spain tomorrow if I want to, and still have a high paying job. There’s something incredibly liberating about knowing that I can move anywhere I want to and not worry about finding work. That’s what I call freedom!
3. I make up my own schedule. This means I can cram a 40-hour workweek into 4 days and take 3 days off if I want to. It also means I can start working at 6am and finish at 3pm during the summer, so I can enjoy the beautiful weather outside.

There are plenty of ways to make money blogging – you can review products, make commission from third party affiliates, banner advertisem*nts, open your own Etsy shop, sell your own product or class, sell an ebook, write sponsored posts… The longer I blog, the more I realize that the possibilities to make money online are endless!

If you are interested in starting a blog, I have created a post that details step by step how to start a blog for cheap. You can start a blog at just $2.95/month (this price is only available through my link) for blog hosting, including a free domain name.

2. Become a Freelance Writer

Freelance writers are very much in need these days.

Because websites are constantly pushing out new content, they need the help of freelance writers to get the job done quickly. You can also write technical content for catalogues, write about music, lifestyle, politics, etc. The list is endless!

Click here to download a free list of 200 Freelance Writing Niches To Choose Fromto spark some ideas on what to write about.

How to become a freelance writer

Sign up for freelance accounts like Odesk, Upwork, Toptal and Freelancer. The more accounts you have, the better your chances of getting hired are!

Reach out to blogs and websites you like to see if they need a freelance writer.

Increase your exposure on Linkedin. A lot of companies use Linkedin to find future employees.

3. Participate in Online Surveys

This is more of a side job, something to do while you are watching television or sitting in the subway.

It’s an easy way to make a few extra bucks, anywhere between $100-$300 per month on average.

I recommend joining as many survey companies as you can to raise your chances of qualifying for surveys. But beware of sites that are not legitimate.

• If a site asks you for money upfront, do not sign up with them. All legitimate survey sites are free to join.
• If a site claims you can make a living from just answering surveys, they are probably fake.
• If a site pitches you other products or services (unless it’s pointback or cashback scenarios), they are not a real survey site.
• Look for a Privacy Policy page. Legitimate sites always have one.

This is a list of legitimate survey sites you can safely join. There might be more out there but I only feel comfortable listing ones I know are 100% real.

1. American Consumer Opinion. The company started in early 1986 as a small mail survey panel and went online in 1996. Since then, memberships were opened up to all countries across the globe. The panel currently includes over eight million men, women, and children throughout the United States, Canada, Europe, Latin America, and Asia.
2. Pinecone Research. With Pinecone research you can get paid for doing online research, playing games, shopping online and answering surveys.
3. Harris Poll Online.Most surveys pay between $3 and $4 each for about 20 minutes of your time. They also have lengthier ones that pay up to $75.
4. Swagbucks. Swagbucks if pretty well known in the survey world because of its various ways to make money. You can get free reward points and can redeem cash via Paypal or gifts cards from big retailers like Amazon.
5. Inbox Dollars. Earn cash for taking surveys, playing games and watching videos. The downside is they pay comparatively low (some people like to call them Inbox Pennies).

4. Become a Virtual Assistant

Many of us bloggers will hire a virtual assistant to help lighten the work load.

That’s because our schedule is so busy we need to outsource certain tasks in order to better focus on what’s important – our content.

So what does a virtual assistant do?

A virtual assistant is a self-employed person who usually works from home and provides technical, administrative or creative assistance. It can be for a singular project or ongoing, like answering emails and sharing posts on social media.

You can become a virtual assistant for websites, bookkeeping, online research, database entries, scheduling, etc.

How to become a virtual assistant

Take a course

There are a few courses you can take online but the one I recommend is by Gina Horkey who is a successful virtual assistant. Gina created her business in 2014 and was able to book her first virtual assistant job within a month. Within six months she was earning $4,000 a month!

The upside of taking a course is that virtual assistants are more and more in demand. To be more informed about the industry means you are raising your chances for success.

Just these past three years, the demand has gone up by 95%. This means you are investing in your future and in a career that allows you to work from home or anywhere you want.

A virtual assistant makes between $25-$100 an hour and can work part-time or full-time.

Click here to learn more about Gina’s 30 Day Virtual Assistant Class.

Advertise your services

Sites like Upwork allows you to connect with businesses looking for freelance workers. You create a profile, upload a resume and add some of your work samples (for example: websites you’ve conceptualized, if you are a web designer). You can also apply for jobs and projects through the job board.

Problogger is another site you can use to advertise your services.

Networking

You know I’m big on networking!

That’s because I was able to find most of my work through connections I made throughout the years.

Let everyone know – through social media, emails, text messages – that you are a virtual assistant looking to help on short term and long term projects. You never know, there could be a huge job opportunity waiting for you!

Working Outside

5. Become an Extra or a lifestyle model

Most people think you have to live in a major city or be really pretty to do this type of work, but it turns out that’s not entirely true. I may have agencies in New York and Toronto, but I also have one in Philadelphia and another one in Des Moines, Iowa.

Okay, for sure you will be busier with this type of work if you live in a bigger city, but I can vouch for this – the smaller markets are also good to keep in mind because there is less competition. I have gone to Philadelphia for an NBA catalogue shoot, and had to turn down a jewelry TV commercial in Des Moines because my schedule conflicted with the shoot dates.

Doing extra work and lifestyle modeling is great if you want to make a few extra dollars every month. And who knows, you might end up booking a big job that pays five or six figures!

How to become an extra

An extra, or background actor, is someone who appears infilm and television in a non speaking role. The pay isn’t great if you are not part of the union (SAG-AFTRA), but it’s a fun job if you love movies and TV shows. You could end up on the set of your favorite show and maybe meet some of the cast.

You don’t need to sign with an agency to become an extra. Anyone can do it as there are no requirements.

You can sign up with a few online casting companies such as Central Casting,Casting Networks or Actors Access(the more the better if you want to get booked often) and upload a few pictures of yourself.

Another way to do extra work is to find a local agency that focuses on that. Or, if you live in a smaller city, contact talent/lifestyle agencies and ask if they also book people for background work.

How to become a lifestyle model

Lifestyle modeling is different than extra work because you are the main subject. You can do:

• Print – catalogue, posters, flyers, magazine ads.
• Online – advertisem*nts on social media and for websites.
• Video – TV commercials, online commercials, industrial video and tutorials.

It’s harder to book this type of work because you have to fit the profile of the hero, which is the main character. In big cities like New York, you will have to attend auditions to book this type of work. In smaller cities like Des Moines, they skip that and book you based on pictures, which is why it’s important to have good headshots done professionally.

Online casting companies like Casting Networks and Actors Access post lots of auditions – all legit – you can submit yourself to.

I would also encourage you to look for local representation by doing some quick Google searches for Talent Agencies + name of the city you live in, and Lifestyle Modeling Agency + name of the city you live in.

6. Catering

Catering work is easy and can pay quite well! I did quite a bit of catering when I lived in Toronto and sometimes got paid up to $25/hour + tips.

Catering is basically passing trays of food around at events – or putting dishes together in the back kitchen. You need a good pair of shoes because you will be standing and walking around for 4-8 hours at a time.

I personally enjoyed catering because I like food and going to fancy parties! It was fun to cater an event for the Toronto Film Festival where celebrities like Marilyn Manson and Michael Douglas were part of the crowd. It was also fun trying new dishes (you do get to eat and take home leftovers) and going out for a beer with the crew after a long shift.

What’s also great is the fact that most people who are in catering do this as a side job. If you ask them for help finding other work, they will usually provide you with tons of information and contact numbers!

To find catering companies, do a quick Google search by typing Catering Agencies + the name of the city you live in, and either send an email or call them directly.

7. Join a temp agency

Joining a temp agency is great because you have someone representing you and helping you find work.

I was with a temp agency both in Toronto and New York and was able to find decent work that way. I was a bilingual receptionist (my native language is French) and also worked in retail for a high end fashion brand.

The interview process is straight forward and you can tell them exactly what type of work you are looking for.

You might also find a job you love and get hired as a full time employee. This happens all the time!

To find catering companies, do a quick Google search by typing Temp Agencies + the name of the city you live in, and either send an email or call them directly.

8. Become a dog walker or pet sitter

I live in an area of Brooklyn where people make a TON of money walking dogs and pet sitting! If you enjoy being active and love animals, this may just be the dream job you’ve been waiting for.

I have never dabbled in this type of work so I can’t say much about it. However I do know someone who walks dogs as a career and she loves every minute of it. In fact, she used to be our cat sitter but had to stop because her schedule was too busy. She was so overbooked that she rarely had any time to spend with her own cats at home.

If you are someone who is attentive and caring – remember that pets are just as important to their owners as children are – you may want to give dog walking and/or pet sitting a try.

To become a dog walker/pet sitter:

• Post an ad on Craiglist offering your services.
• Word of mouth. Let your friends and family know you would like to walk dogs and pet sit for a living.
• Contact your local pet sitting service and let them know you would like to work with them.

Want to Start Your Own Project/ Sell Your Own Product?

Then read Will It Fly? by Pat Flynn.

This a great book for self-starters. I bought this book last summer and ate it up in three days! Will it fly? combines action-based exercises and real-world case studies on how to find what you are good at – and then make money from it.

Part of the book is about categorizing your likes and dislikes, writing down jobs you’ve enjoyed vs ones you didn’t. Then you sort through all the skills you’ve gathered throughout the years. It’s truly a wonderful book that can help anyone who is feeling a little lost in finding their true calling. I read it a couple of years ago and, because of the book, I was able to zero in on the type of content I really wanted to create for the blog.

Ben and I also decided to start our own production company after doing some of the exercises. Those exercises quickly made us see how much we love video and photography and was just the push we needed to turn an idea into reality.