Should You Quit Your Job? I Think So – Here's Why...

Should You Quit Your Job? I Think So – Here’s Why…

This was a guest post I wrote for Carol Amato last year. It was originally published on her blog October 19, 2015. Within a couple weeks, it had accumulated hundreds of shares and comments.

Unfortunately, on November 11, 2015, Carol announced that she would be taking her blog offline.

I have since decided to republish this post here on my own blog.

With any luck, maybe we can get that share count back up. Comments are also open below for those of you who may wish to comment again, as well as for those of you checking out this post for the first time.

I’ll never forget September 6, 2014.

It was the day I handed my written resignation to my boss… the conversation that followed was brief, and it went something like this:

The Boss: I had no idea you were thinking of leaving.

Me: Don’t take it personally. I just don’t want to have a job anymore — not this one, or any other.

The Boss: You know you’ll be giving up your equity in the company, right? You could lose out on millions should we go public.

Me: I know. And I already earn more than anyone else in this office… it isn’t about the money.

The Boss: Is there something I could do to make your job easier? Maybe we could hire an assistant for you.

Me: Nope. I like the challenge my position offers me, and my hours have never been unreasonable.

The Boss: Is this about one of your coworkers?

Me: Not at all. I love the team. I simply don’t want to have a job anymore.

The Boss: So what will you do?

Me: Freelancing. I want to build my own business — one that will allow me to work from anywhere in the world.

The Boss: Yeah, but doing what…?

Me: I’m not sure yet.

And with that, I put my jacket on and went home.

The countdown began the next day. In one month, I’d be unemployed… with no work, no prospective clients, and very little digital marketing experience…

Heck, I didn’t even have a Twitter account, other than the one use I used to follow funny accounts…

But I felt on top of the world.

I arrived home that day to find Andréa — my wife — holding the keys to our new house.

Well, new is probably a bit of a stretch…

Fort Erie, Canada

We had just purchased our first home — a very old house in the rather remote town of Fort Erie, Ontario, which sits directly across the American / Canadian border from Buffalo, New York.

June 25, 2014

Andréa had moved to Canada from Atlanta, Georgia just six months prior and we were newly married. At the time, we were living in a 500 square foot one-bedroom apartment in Toronto with two active dogs… needless to say, we had outgrown our living space.

Gibson & Stirling

We needed a home — preferably a large house with a fenced-in backyard for our dogs.

So we chose to purchase a home in a more remote — affordable — area… after all, so long as Fort Erie had high speed internet, I could freelance.

The moment we had the keys in hand, I quit my job.

And even though I could always fall back on finding a new job, professional employment opportunities were few and far between where we were going.

At that moment, it was essentially sink or swim for me.

Freelancing had to work.

Because if it didn’t, I had no other cards to play.

Put another way, I voluntarily chose to put myself in a position that most people would rather avoid…

This, my friends, is the true story of how I started freelancing…

I’ve never told this story before — not even on my own blog.

And I sincerely hope that through telling it, it will inspire some of you to take action… particularly those of you 40 and up.

In the final quarter of 2015, I had four different guest posts publish on four different blogs. The topics included:

  1. What Is It That Makes Your Blog Special?
  2. The Ultimate Guide to Creating a Video Interview Series
  3. The 7 Best Ways to Include Influencers in Your Content
  4. 5 Super Simple Strategies to Capture the Attention of Influencers (Without Being a Jerk!)

(Apparently, I love writing about creating content and influencer marketing…!)

But when Carol invited me to guest post for her — knowing what I do about the demographics she serves — I knew this was the topic I had to write about:


Starting your own online, service-based business.


To fully appreciate this post, I recommend you download a free copy of my checklist, Everything You Need to Start Freelancing.

What I intend to do today is to help some of you understand a little better why I took the path that I did… and why I think some of you ought to do the same.

The economy needs employees, too…!

As the saying goes,

There are two types of people in this world — entrepreneurs and everyone else.

And I don’t refer to everyone else condescendingly. The economy needs employees, too. We can’t all be self-employed.

The question is, which are you?

  • Do you enjoy the security and stability of paid employment? Or,
  • Would you prefer the challenges and autonomy of employing yourself?

Me? I would prefer the latter. And maybe you would, too.

Let me offer some context.

When I was 11 or 12, my father was downsized out of a job after serving his employer for more than two decades.

Then a factory worker, he returned to school in his forties. He acquired the training to work in geriatric care.

Later into his fifties, he returned to college and graduated from a business program with a specialization in human resources.


I was always proud of my father for that — he was never afraid to work hard, and he did whatever he had to do to support his family… even if it meant totally changing career paths midway through life multiple times.

Now, contrast that with me…

  • I dropped out of both university and college
  • I declared bankruptcy when I was 20 after a failed business venture
  • I spent the remainder of my twenties pursuing sales and business development opportunities

Eventually, I gained enough skills and experience to acquire a director role that paid well into six figures, which was the role I resigned from prior to freelancing.

Yet, I can still hear my dad trying to tell me throughout my twenties that it wasn’t too late to return to school. That I could still get an education and land myself a really good job.

And it wasn’t because I wasn’t capable of it — I always had good grades. I’m a huge nerd. I love learning, reading, and documentaries… my favorite game show is Jeopardy! for crying out loud.

It just never appealed to me. I couldn’t understand pursuing an education I didn’t want to land a job I didn’t care about.

Some people are better suited to paid employment opportunities — like my father. They value…

  • Regular work hours
  • Routine pay periods
  • Paid benefits and vacation time

And even some of the smaller luxuries, like the option to call in sick and miss a day of work.

But the way I saw it, I would rather go all-in and take a chance on building something I was truly excited about… a business that would allow me:

  • The flexibility to work where and when I chose
  • The freedom to be in complete control of my business
  • The financial independence of a recurring income that I could grow exponentially

And that’s exactly how I saw freelancing.

It was a low-risk and high-reward business opportunity that I could eventually scale into a full-blown digital marketing agency, if I chose to.

Is this starting to resonate with you?

Because I’m not suggesting that the entire world should quit their jobs and start a business. Just as the example I illustrated with my dad, there are some people who are always going to be wired to pursue paid employment.

And there is nothing wrong with that…

…so long as it fulfills you.

But if you’re working a job strictly because you fear the unknown, you are setting yourself up for disappointment and regret.

The question ultimately becomes — if you’re valuable enough to make money for someone else, why would you ever doubt that you’re valuable enough to make money for yourself?

It isn’t too late for you… I promise!

Now, I know what some of you are thinking…

Brent, it’s all well and good that you quit your job to work for yourself. But I have three kids to support, two car payments to make, and a monthly mortgage payment much greater than yours. And I don’t know a darn thing about Twitter or Snapchat or Hootsuite or anything else… plus, I’ve got 17 years of seniority at my current job. I couldn’t possibly give that up!

Hey, I get it. I really do.

You’re like my dad — and I respect my dad. There’s nothing wrong with sticking with what you know.

But think of it this way… if you could work for yourself, and you could earn what you do now (or more) while enjoying more time with your family, would you do it?

If the answer to that question is yes, I want you to consider this…

I recently watched a video from Gary Vaynerchuk entitled 6 MINS FOR THE NEXT 60 YEARS OF YOUR LIFE:

Have you seen it?

It’s fantastic — and it speaks to Boomers… folks in their fifties, sixties, seventies, and even older.

Early into the video, Gary says,

It’s not over. If you want it so bad, if it’s in you, maybe it’s not time to take up golf or pack it in. Maybe it’s time to triple down and really focus on your 7 pm to 2 am.


There’s so many people that truly are good entrepreneurs or have entrepreneurial DNA but they just weren’t lucky enough to be born during an era [when] that seemed practical.

What seems practical to most grownups is the idea of getting an education, getting a good job, and then working in that chosen career path until retirement.

In other words, to collect that steady and stable pay check…

But let me ask you this… is there really such thing as a steady, stable pay check? I’m not so sure.

There’s an old adage in sales that goes,

You’re only as good as your last sale.

It seems to me, however, that the same can be said of just about any profession.

I don’t care who you are or what job you do — there are no guarantees. The world will change in ways we can’t imagine, and we either need to evolve with market trends or get left behind.

For instance… try going back in time and telling the mailman of the 1960s that — one day — machines will make it possible to electronically transmit letters. And almost every household in America will have one of these machines.

And the world will change further — many times — in both your lifetime and mine.

In fact, studies suggest that 40 percent of Americans will be freelancing by 2020.

So if the only reason you’re clinging to paid employment is because you believe it is more secure than entrepreneurship, consider this…

You’re essentially saying you would rather gamble on the system than gamble on yourself.

You’re talking about the same system that…

  • Downsized my father out of a job, and
  • Laid off some of your friends and family, too.

And it might just be coming for you next…

That same system could take your job, your savings, your 401k, your house, and worse…

Of course, I’m painting a rather dramatic worst case scenario here, aren’t I?

All I’m trying to illustrate is that there are no guarantees — none.

But I would hazard a guess that you are — even the tiniest bit — curious about working for yourself… am I right?

Well, let me finish this post by sharing with you…

A look at my first year of freelancing:

It’s been over a year since my final day of paid employment and since I completed my first paid freelance gig.

In that time, my wife and I have traveled to…

Vancouver, BC

…Vancouver, British Columbia // December, 2014

Punta Cana

…Punta Cana, Dominican Republic // April, 2015

Las Vegas, NV

…Las Vegas, Nevada // June, 2015

Atlanta, GA

…Atlanta, Georgia // July, 2015

And by the time this post published last October, Andréa and I were already three days into our United States road trip, with stops including Milwaukee, Chicago, Seattle, San Francisco, Reno, Salt Lake City, and others…

(We even took our dogs with us…!)

Road Trip 2015

Best of all, Andréa and I both freelancers, which means that we can take full advantage of our “work anywhere” business model any time we choose.


Grab a free copy of my checklist, Everything You Need to Start Freelancing. It might be the best decision you ever make.

The reality is that within six months of leaving my job, I built a freelancing business that replaced my earnings. Because as it turns out, there is an abundance of work available online for freelancers who are willing to shed some blood, sweat and tears to make it happen.

So much so that:

(a) We hired help to reduce our workload, and

(b) The direction of my blog and video interview series will be entirely focused in 2016 on helping new freelancers.

I don’t share any of this to brag or boast; rather, I want to underscore the possibilities.

I am not the most talented copywriter and social media manager to ever enter the digital marketing space, nor am I well-educated, a seasoned entrepreneur, well-connected, or a savvy businessperson…

But I was willing to learn, to work hard, and to take risks.

Are you?

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