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!

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.


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

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 home that can help you toward making a decision.

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eBay Seller

If you have a good eye for value and a good sense of commerce, selling items on eBay could be the home business for you. But there are so many questions to answer before starting an eBay business. (What to sell? Where to get your inventory? Should you open an eBay store? How to price your items? How to write your listings?)

Mobile/Home Pet Grooming

Again, grooming will take skill and experience, but the beauty of a mobile pet grooming business is that you don't have to invest in the infrastructure of a storefront. And many customers


may prefer you come to their home. If you want to do it in your own home, be sure you know all the laws in your community about home businesses. 

9.Become A Tax Preparer

Did you know you can get trained online to become a Tax Preparer? This in-demand remote job can be done from anywhere in the world. A Tax Preparer prepares, files, and assists in general tax forms. 

To get started in this field, take a high-quality tax preparation course. Do your research to find the best one for you. After doing my research, I found that the TaxBiz Course is one of the best. You learn a step-by-step method to start and run a successful tax business. TaxBiz is a certified provider through the IRS, so you have the opportunity to indicate your authority as a Tax Preparer. 

I know you have so many questions about starting a digital tax business. You’re probably wondering if something like this is for you. That’s why there’s a free workshop to answer all of your questions. You can also read reviews from graduates and students on Better Business Bureau and Facebook.

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.

3.Pinterest Virtual Assistant

Pinterest has over 290 million active users. Over 24% of the United States uses Pinterest.

This is huge for businesses. Pinterest is a must for small and large business owners, which is why Pinterest Virtual Assistants are in high demand. 

A great Pinterest VA can take a business from being “okay” to being seen by thousands online. Pinterest Virtual Assistants can make businesses A LOT of money, which is why businesses hire Pinterest Virtual Assistants. 

You may be wondering how to get started as a Pinterest VA, where to find clients, how much to charge, and more. Become A Pinterest VA Today teaches you all of these things. You can live and work anywhere in the world to do this. In fact, you’ll see many Pinterest Virtual Assistant testimonials here of women who work and travel. 

You can even attend a free workshop here to learn more about how to become a Pinterest Virtual Assistant today.

P.S. Here’s an example of one student who is now a Pinterest VA after taking Become A Pinterest VA Today!

2. Identify the right business for you

Give yourself permission to explore. Be willing to look at different facets of yourself (your personality, social styles, age) and listen to your intuition. We tend to ignore intuition even though deep down we often know the truth. Ask yourself “What gives me energy even when I’m tired?”

How do you know what business is “right” for you? There are three common approaches to entrepreneurship:

Do what you know: Have you been laid off or want a change? Look at work you have done for others in the past and think about how you could package those skills and offer them as your own services or products.

Do what others do: Learn about other businesses that interest you. Once you have identified a business you like, emulate it.

Solve a common problem: Is there a gap in the market? Is there a service or product you would like to bring to market? (Note: This is the highest-risk of the three approaches.) If you choose to do this, make sure that you become a student and gain knowledge first before you spend any money.

7. Pick your business name

If you haven’t already, now is the time to start thinking about your business name.

The key here is making sure your business name is one you can live with long term. Once you begin the process of registering your business and establishing a brand, changing it will be highly inconvenient (and potentially expensive). Don’t forget to check that your business name is available on social media sites as well.

Resources to help you name your business and register your business name:

Traits You Need to Be Your Own Boss

It’s fluffy and sweet to say anyone can be their own boss, but that’s just not the case. Not everyone is made out for this kind of work, and that’s OK.

Just like there are special people in this world who love numbers (bless you, accountants) and others who love to code (developers, we’re talking about you), there are unique individuals who can be the boss.

Here are a few must-have traits you’ll need to be your own boss:


Overnight success stories are few and far between—expect to invest time and money before you see the fruits of your labors. At times, you’ll be tempted to quit and go back to the cushy, uninspired 9-to-5.

You’ll need to be patient and hold on. It’s always going to be challenging initially, but things start to smooth out as you learn the ropes and pick up the momentum.


You’re the boss. Nobody is going to tell you to get to work, stop watching YouTube, or pick up the slack. You’re going to need to have the self-discipline to notice (and look for) these things yourself and take action when you see something that needs doing.

You’ll also need the self-discipline to back off. You’ll do your business, your customers, and yourself no favors by hustling more than you can handle. Learn when to slow down and take a break to avoid burnout. There are always things to do, so it’ll be hard to ease up—but you’ll have to do it to succeed in the long run.


You’ll need a purpose. Being your own boss isn’t so much a purpose as a perk of being in the driver’s seat. Find what motivates you and gives you energy. Harness your drive and turn it into results.

From time to time, you’ll lose your drive. That’s OK—it’s all part of the journey. Learn to recognize when you’re losing steam and find ways to get your head back in the game. That might mean stepping back from the business for a long weekend, or it might be reading an email from a happy customer.

Find a drive that’ll keep you going, and tap into it when the going gets tough.


You’ll need to be able to ruthlessly prioritize. As the boss, you’ll have a million things you can do but only a handful of things you should do. Learn to avoid shiny object syndrome and stay focused.

That’s easier said than done, but it’s easy to lose yourself chasing the next idea or spending hours trying to find ways to save more time. Prioritize your to-do list, make a schedule, and stay on track.


This isn’t necessarily a must-have trait of a successful boss—plenty of less-than-pleasant people out there know how to run a business like a well-oiled machine.

However, don’t forget to be the boss you always wished you had. When you hire employees, remember to treat them with kindness and respect. Remember the reasons that made you want to quit your 9-to-5 and work to create a better environment for those you employ.

How to know it’s time to be your own boss

At some point, you may decide you’d like to be your own boss. 

Maybe you’ve had a great business idea for quite some time now but could never execute it. A contract ending or changes at a full-time role could be an opportunity to start your new business. Or maybe you’re eager for the potential benefits from being your own boss — more money, freedom, and flexibility. 

Whichever way you decide it’s time, you need to have one thing set: your business plan. If you’ll be selling products, how will you make them? What supplies do you need constant access to, and how will you keep up with production? Do you need employees or experts to consult, and if so, how many? Think about the small details you’ll need to sort out to start being your own boss. 

6. Build a support network

You’ve made the internal commitment to your business. Now you need to cultivate a network of supporters, advisors, partners, allies and vendors. If you believe in your business, others will too.

Network locally, nationally and via social networks. Join networks such as your local chamber of commerce or other relevant business groups. Here are some networking basics:

  • When attending networking events, ask others what they do and think about how you can help them. The key is to listen more than tout yourself.
  • No matter what group you join, be generous, help others and make introductions without charging them.
  • By becoming a generous leader, you will be the first person that comes to mind when someone you’ve helped needs your service or hears of someone else who needs your service.

Additional resources

If you’re serious about becoming your own boss, it’s a good idea to seek out as much information as you can about the process. There are several thought leaders in the field who have put out great resources on becoming your own boss; here are a few that are well worth checking out.

Briana is a content and digital marketing specialist, editor, and writer. She enjoys discussing business, marketing, and social media, and is a big fan of the Oxford comma. Bri is a resident of Portland, Oregon, and she can be found, infrequently, on Twitter.


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