10 Honest Reasons You Should Be Your Own Boss

working from home

You will never leave where you are until you decide where you’d rather be. – Dexter Yager

Tony Gaskins once said, “If you don’t build your dream someone will hire you to help build theirs.”

Tony, I couldn’t agree more.

It’s no secret that I strongly believe in building your dream and becoming your own boss. To drive that point home, here are 10 reasons why you should be working for yourself starting today!

10 Honest Reasons You Should Be Your Own Boss NOW

1. Create Your Own Schedule

The last time I worked in the office was about 10 years ago when I was interning for an entertainment news show in Toronto.

I vividly remember the agony of dragging my butt out of bed at 6:30 AM, trekking it 1km to the subway, to stand squished in the human cattle car that wreaked of burnt coffee and morning breath. This daily commute was then followed by 9 tortuously long hours of hating my life.

It took all of the two weeks for me to realize this outrageously constructive lifestyle was not for me.

What’s so great about solo entrepreneurship is that you get to be in charge of your schedule.

Are you a night owl? Sleep in and crush it till the sun goes down. More of a morning person? Rise and shine with the sun and then call it quits mid-afternoon.

The best part is, you can change it on a whim. You’re in charge, so do what you darn well, please!

2. Work Wherever You Want

Do you dig the hustle and bustle of loud, busy venues? Or are you drawn to the quiet, chill vibes of a library?

Maybe, what you’d really rather do is sit in your jammies from the comfort of your bed and work.

I must admit, I’m partial to the latter.

As long as you are actually getting work done, the freedom to choose where you work allows you to shake things up and consistently stay motivated.

3. Make As Much Money As You Want

Perhaps one of the best things about being an entrepreneur is that there is no salary cap; except for the one you impose on yourself.

Some people are happy banking a few thousand a month and others like to build multi-million dollar empires. Whatever your choice, the result is dependant on how hard you work, not some preconceived number created by upper management.

4. Establish Job Security

take risks

Long gone are the days when big corporations were synonymous with job security. Nowadays, nothing is safe.

Businesses see you as a means to an end, and when you are not fulfilling their bottom line, you are the first to go.

Working for yourself means there is no one to lay you off or fire you. You have to rely on yourself to stay afloat.

Some days this can feel harder than others, but having faith that you will succeed and make it, will lead you to a much happier life.

5. A Business That Benefits YOU

Like Tony said, you either build it yourself and help someone else and wouldn’t you much rather build your own dream?

Creating your own business gives you the opportunity to build something that benefits you directly. There’s nothing much more satisfying than that!

6. Build Your Own Dream Team

be your own boss

Do you need help growing your business? Now you get to be in charge of who comes along for the ride.

Having the power to build your own dream team allows you to suit up a team of Michael Jordan’s, rather than having to put up with a few bench warmers.

A great way to do this is by putting together SOP’s and SOD’s before hiring. Documents and procedures explicitly outline tasks ensures your team knows exactly how you want things done.

7. Goodbye Gossip

Having worked in an office and several bars back in the day, I couldn’t get over how much slanderous gossip there could be. It was like being in high school all over again – not a place I ever cared to revisit either!

When you run the show, there are no jealous colleagues trying to bring you down, and there’s no office Alpha to have pissing contests with.

8. Cash In On Your Own Success

Do you ever feel like you’re busting your buns at work, yet someone else is taking home the bacon?

Well, when you become your own boss you get to cash in on all that hard work.


When companies go through downsizing or mergers, someone higher up on the totem pole always seems to make out like a bandit, but if this were your business, you could sell it and be the bandit instead.

If you find something that works, duplicate it, flip it and enjoy the spoils. You earned ‘em after all.

9. Find Out What You’re Made Of

Running your own business is not for the faint of heart. Managing yourself, weathering the ups and downs, they can really show you what you’re made of.

You will gain insight into your personal strengths and weaknesses, what motivates you and what turns you off, whether you want to be in your business or run it, and so much more.

It’s incredibly enlightening and something you likely wouldn’t learn about yourself in a corporate -5 position.

10. See The World

Of course, this had to end of my list; it’s one of the best perks of being your own boss.

As you free yourself from the shackles of the 9-5 lifestyle, you open yourself up to the freedom of travel. You get to tour the world, encounter the uncomfortable and experience new countries and cultures.

In this respect, you will gain more wealth and perspective than any location dependent job could ever offer you.

So what are you waiting for? Throw caution to the wind, embrace your inner entrepreneur and unleash that special something that only you have. I promise you won’t regret it!

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Photo by Maria LaCosta

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