13 Riotously Rad Reasons to Start Up a Freedom-Based Business

JillAffiliate Marketing, Lifestyle10 Comments

It's no secret around these parts that we are big believers in working for yourself. I mean, we wrote an entire freakin' book on how to work for yourself so that you could start working for yourself, like, yesterday!

And today is no different because I have 13 riotously rad reasons why working for yourself is the bees knees and these days, one of the most secure ways to make a living.

Have I said “working for yourself” enough yet? No? Well then allow me to continue….

13 Reasons to Start Working for Yourself

Okay, I'll stop now. I'm even annoying myself.

You Make Your Own Hours

I have to admit, the last time I worked in an office I was 22 (holy shit that's 10 years ago! Damnit! I'm old.) and interning at an entertainment news show for a TV station in Toronto.

I had to get up at 6:30 and walk my ass 1 kilometer just to get to the subway, resist the daily urge to get a drenched-in-cream-cheese-icing-and-sprinkled-with-raisins-and-pecans cinnamon bun only to sit on the train and stare at the floor, all cramped with people breathing their morning breath on me just to make it into the office by 7:30 and hate my life for the next 9 hours.

It became crystal clear to me within, oh, 2 weeks that abiding by silly corporate rules – not checking email, not taking longer than 30 minutes for lunch, not talking too loudly, not checking your phone, not eating at your desk, not being able to use the fridge, not asking the producers questions – was simply not my jam.

However, the beauty of doing the solopreneur thing is you can set your own hours and adjust them on a whim.

Prefer to get up with the sun? Rise and shine then pumpkin, smash out all your work before 4pm and have the rest of the night to yourself to do important things…like watch The Bachelorette *cough* Breaking Bad.

More of a night owl? Well then get up whenever the hell you feel like it and work throughout the night! You'll still get a lot done because chances are you will be one of the only ones awake!

It doesn't matter which you choose because the beauty of this lifestyle is it's solely up to you. You make the call. You're in charge. And you can do what you damn well please.

You Can Work Wherever You Want

Do you thrive surrounded by the chaos of a busy coffee shop? Do prefer the quiet of a library? Do you really just want to work from your besk (bed + desk)?

As long as you're getting your work done, you can do it wherever you feel your most productive.

I personally love to switch it up – I'm currently surrounded by gossiping Thai girls and the loudest espresso machine I've ever heard. But sometimes I prefer to work from home where it is nice and quiet. And sometimes, well, sometimes I don't leave my besk other than to eat.

It's the freedom of choice I really dig and ultimately, you just have to do what works for you.

Bonus: You don't even have to get out of your pyjamas…or wear pants if you don't want to. Just saying.

You Can Make as Much Money as You Want

This may just be our most favourite part of working for ourselves: we can make as much or as little as we want. Personally, we choose ‘as much' but some people may just want to make a few thousand a month and live a simple life; and that's cool, that's their choice!

The coolest thing about this lifestyle is the amount of money you make is directly related to how hard (or how smart) you want to work.

No longer are you bound by salary caps for a certain position or having to kiss management ass or suck up the verbal abuse all for 60k a year.

The power is officially in your hands and you are the only one you have to count on.

So go make that cash money and revel in the joy of not having to make someone else happy just to do so.

You Create Your Own Job Security

I think we all know that these days, nothing is safe. Your job isn't safe. That big company you work for isn't safe. Hell, your pension may not even be safe.

The only thing that is safe and secure is relying on yourself to make things happen and build an asset for yourself and your future.

Believe in yourself enough to know that you won't let yourself down, that you won't let yourself go broke, that you will adjust to the changing landscape and thrive because of it.

You Get to Build Your Own Company, Not Someone Else'sย 

When you go into the office and punch the clock you are making money to fund your life, but you are also making hoards of money for someone else. You are growing their business and if they want to be done with you, they will cut you loose.

When you start up your own gig your efforts are solely going towards something that benefits you, not a bunch of board members that don't even know your name.

Your Creativity Pays Off

Regardless of your niche if you can come up with creative promotions, products, posts or marketing tactics you can increase your revenue drastically within even 30 days.

The creative strategies you put into play can change the game for yourself, your business and your revenue with nothing more than a few unique ideas and the dedication to see them through.

Tell me the last time one of your creative ideas resulted in extra money for yourself in your day job.

You Can Build Your Own Dream Team

Another aspect we love about running our own business is hiring the people we truly believe in and the ones who bring us the biggest results.

Byย creating SODs and SOPs you can leverage your time, create a team you trust and grow your business without having to kill yourself over the smallest of details.

Bonus: You can hire people who are far better than you at different elements of your business and ultimately learn from them.

Another bonus: You can surprise your team with an end-of-the-year bonus, a company retreat, a gift certificate or a cute little pressie welcoming them to the team. You can go the extra mile to lock in that loyalty and build morale without having to clear it with anyone because you call the shots!

Water Cooler Gossip is Non-Existantย 

You run the show which means there are no bitchy colleagues trying to bring you down, undermine your work or sabotage your career and you don't have to play nice, make nice or be nice if you're having a bad day.

All you have to do is keep to yourself, get your work done and start fresh tomorrow.

Best of all you will never have another stare down with the office Alpha or fein interest in that boozey faux-paux from the office party the other night.

You Can Cash In

Instead of clocking in the hours at a thankless job only to have to go through the motions of a merger, a restructuring or a downsizing you could have the chance to cash in on your efforts and sell your business.

It happens all the time and some make ridiculous coin in the process!

Then all you have to do is roll the dice and repeat the process again. The good news is you won't be working for years just to sell your business, you will also be making money in the process. Win!

You Will Learn More About Yourself than Ever Before

One thing you will realize after starting up a business is how much you will learn about yourself.

You will gain insight on what you can handle, what you can't, what gets you jacked, what sets you off, what inspires you, motivates you, defeats you and angers you, the kind of business owner you are, the kind of boss you want to be and where you want to take your business.

You simply would not have the opportunity to develop into the type of person you could be without the trials and triumphs, the tears and the laughs, the setbacks and the progress that come with managing and growing your own business.

You Have the Opportunity to Make a Difference

No matter what business you choose to start up, you have the chance to better someone's life through the words you write, the products you create or promote, the services you offer or the customer service you provide. Don't squander that chance.

Nothing feels better than hearing from a reader/viewer/customer/fan that you made a difference in their life, solved their problem or gave them hope. Nothing.

You Can See the World

You had to know this was going to make the list since it is one of the biggest reasons Josh and I do what we do: You have the ability to traipse this glorious globe of ours.

When you free yourself from the constraints of a typical 9-5 you create opportunities for yourself that you wouldn't have had otherwise and nothing accelerates this process more than travelling.

Travelling and experiencing new countries and cultures not only gets you out of the familiar but it introduces you to people with unique perspectives, a wealth of information and a different way of looking at things.

Most importantly, it rips you out of your comfort zone – forcing you to take action and create the life you want.

I can truthfully say that travelling changed my life for the better and without it I wholeheartedly believe I wouldn't be where I am today…literally and figuratively.

You Learn to Embrace Failure

One thing you need to wrap your head around before you step out on your own is that you are going to fail. Often.

The good news is you want to be failing often!


Because without failure you wouldn't know what resonates and what doesn't. You would be stuck in limbo assuming that everything you are doing is correct, yet not understanding why you aren't moving forward or making more money.

Whether these are niches you enter, posts that didn't do well, marketing strategies that tanked, backlinking practices that got you slapped, products that didn't sell or relationships that didn't pan out the way you wanted them to – all of these tiny setbacks are crucial lessons you need to learn if you want to grow your business and fund your ideal lifestyle.

Though it may sting a little, you need to see them for what they are: stepping stones to your future success.

And for God's sake, have a little fun while doing it, will ya?

After all, “Fortune sides with him who dares.”*

So throw caution to the wind and be daring. Be bold. Be brazen. Be dauntless, fearless, audacious and a little cheeky.

Indulge that little whisper within you, begging you to take that chance and be courageous. You will only regret it if you don't do it.

Screw the nine to five. It's bullshit anyway.

* uttered by Roman poet, Virgil.


  • Amen! It’s not for everyone, but those are some good reasons to consider it!

    • Jill

      Oh I agree it’s definitely not for everyone…but we’re kinda hooked on it ๐Ÿ˜‰

  • After starting out the day a bit slow, reading this reminded me of what I’m striving for. Thanks for the motivation!

    • Jill

      And thank you Jamie for that message ๐Ÿ™‚

      Just what I needed to hear!

  • Sara

    Read it. Love it. Now getting my crap together and starting it. Thanks for the #inspo ( too much Instagram, not enough willpower) Thanks for the swift kick to the bott bott!

    • Jill

      Holla! Thanks so much Sara and happy to provide any kicks to the ass when necessary ๐Ÿ˜‰

  • Ahh LOVE this! I worked at an office one summer when I was 19. Vowed to never do that again. Finally building a business that does more than pay the bills, and the freedom is beautiful! It’s so true… you learn TONS about yourself, and while the rest of the world seems to think I’m never growing up, I feel a hell of a lot more responsible and grown up because I make all my own decisions and I trust myself completely. And I get to take spontaneous trips to Costa Rica. It’s brilliant ๐Ÿ™‚ Great post- thank you for the reminders!

    • Jill

      Ah Kate I love this! Thank YOU for such a sweet comment and for driving home the fact that for people like us, this is the ONLY way to live! Yes, it’s full of ups and downs but that’s what makes you even stronger in the long run.

      And I heart Costa Rica! We got married there and it will always hold a special place in my heart ๐Ÿ™‚

  • Tracey

    Hi Jill,
    I am reading your Art of Authority. I am a single homeschooling mom and I want to travel with my daughter and give us a better life. I have tried affiliate marketing and have not been very successful.
    I have to make this work. I am determined to make this work. I have to find the right system for me. I am hoping that your eBook will give me some guidance.
    Thank you for your site.
    Respectfully in kindness,

    • Jill

      Hey Tracey!

      I love your motivation to create a great life for you and your daughter ๐Ÿ™‚

      I have faith you will make it all work! Remember, there is definitely a trial and error process but you should be able to figure it all out with relative ease.

      Hope you like the book and it helps you out!