The reason why you started your business may determine your failure or success

Your answer as to why you went out on your own to start a business might just be the most important factor deciding the fate of your venture. Two years after founding his video production company, Tom would find out if his answer to this question was the kind that led to success or failure.

An offer to bankroll

I first met Tom a few years ago when his father, Walter, hired me to coach his son. Tom, who was 27 at the time, had been struggling for the last few months with his business, which he’d started over two years earlier. Back then, after being recently laid off, Tom asked his dad’s advice on job hunting. Walter, a wealthy entrepreneur, instead encouraged Tom to start his own video production company. He even offered to bankroll Tom till he got in the swing of things.

Birth of a business

Tom agreed and within a few weeks he had a company name, a business bank account, a website, state of the art equipment and an office in the second bedroom of his apartment. All he needed were some clients, but his father helped there too. Walter tapped into his network, which led to a couple of gravy-train contracts for Tom, including one with a software company that needed someone to produce training videos.

No fishes bite

Soon enough, Tom’s business was hum hum humming along. A couple of years whizzed by like this, then the software company ditched its video training program and another client closed up shop. Suddenly Tom was only billing a few hours a week. His father put out some new feelers, but no fishes bit. That’s when I got called in.

Red flag

Because business had come on a silver platter in the first two years, Tom had done little planning or marketing. As I began to help Tom in these areas, I noticed a big, fire-engine red flag—his lack of passion for his business. When I asked him why he went into business, he told me about the conversation he’d had with his dad the night he’d sought his job-hunting advice. After I probed on what the business meant to him personally, he said he liked the idea of being a businessman like his father.

A business dies

I asked him whether there would be a huge hole in his life if he didn’t become a businessman like his dad. When he answered “Not huge, I guess” I knew that Tom had a problem. I continued to probe, trying to help Tom find some deeper purpose for being in business, maybe something he hadn’t considered before, but he had nothing more to offer. That’s when I knew his business wouldn’t survive—unless, of course, his father came to the rescue. Within a few months, even though Tom had a solid business plan and great strategies for growing his company, he went looking for a fulltime gig. He found one, folded up his business and has been at his new job ever since, where he is actually pretty happy.


The reason his business bit the dust was because Tom didn’t have a good enough answer to the question of why he started it up in the first place. In a sec we’ll go into why the answer’s so important, but first take a look at these answers from three other business owners I know that measure up:

John—a dog’s business

A few years ago, John was walking Jasper, a dog he’d rescued, when he had a life changing inspiration. In the previous 12 months he’d lost his life savings in an investment that went belly up, he’d broken up with his girlfriend and his father had passed away. He was struggling to find hope and meaning in his life. He looked down at Jasper, a creature whose love had sustained him during this trying time, and thought that if he could somehow earn a living doing something with dogs, his life would mean something. As that thought bloomed into a fiery passion it hit him that he’d never actually done what he loved in his life. Now here was his chance.

Couldn’t be happier

Later that night he came up with a plan to open a dog kennel. Right away he jumped on his new path, finding a job at a kennel, learning everything he could about dogs, working odd jobs to save up money. A couple of years later he was ready to open up his business. He got a small government-sponsored loan and founded his kennel. He scraped by as paying customers trickled in, but eventually his business began to grow, then thrive. Today he couldn’t be happier.

Marie—cut off from the family

Marie used to work in the family catering business with her mother and older sister. She worked there during high school and through college, where she studied culinary arts, before joining fulltime as a junior partner. She was particularly passionate about sustainable food and frequently urged her mother and sister to move the business in that direction. Neither of them supported the idea, believing it would cut their profits drastically. But Marie kept urging them, until the day her mother and sister called her into a meeting and forced her out of the business. It was a devastating blow that threw Marie into an emotional tailspin.

An even more profitable business

When she began to pull herself together many weeks later Marie decided to open up the business she had long argued in favor of. Today, a few years later, along with a partner, she runs a successful—and yes, profitable—sustainable-food catering company. In fact her business is more successful than the family business ever was.

Steve—heart attack to art attack

Four years ago, Steve went to hospital and gave birth. Yes, a man can give birth—but for Steve it was a business, not a baby. Giving birth was not the reason he was admitted; Steve was there because he’d had a heart attack. Shortly after waking up from surgery he thought long and hard about his life, primarily about the last fifteen years he’d spent working for a tyrannical boss as a senior manager at a marketing firm. Despite the anguish his boss caused him he had stayed at the company all those years for the decent salary. But that was no longer a good enough reason, especially considering he knew his health problems stemmed largely from work stress. So he made two decisions that day. One: that he’d worked his last day at that company. Two: that he would turn his hobby—illustration—into a business.

Back to the drawing board

Steve loved illustration, had studied it at school and had kept it up, mostly as a hobby, but occasionally for money. He had also worked on and off over the years on a graphic novel. He had always dreamed that one day he would finish that novel and do illustration fulltime. That day had just arrived. He quit his office job, opened up an illustration and graphic design company and dove back into his novel. Finding enough paying clients was challenging for a long while, but he plowed on. Today he works out of his house, has a handful of steady clients who love him and is shopping his graphic novel around. He’s living his dream and his health is great.

What makes an answer good

Why are John, Marie and Steve’s answers for why they went into business good ones? Because their answers were powerful enough to drive them through the tough times. As John faced the long challenge to get his business off the ground, as he endured hardship and worry, he clung to the memory of that day in the park with his dog and what he learned about himself. He drew on that to keep going. Just like John, Marie drew on the emotional pain of what had happened with her mom and sister to fuel her through the early years of her company. She believed in her heart that her ideas about sustainable-food catering would rock and she was going to do whatever it took to prove that she was right. Steve too would frequently recall the promises he made to himself in the hospital to push on.


Unless your answer is a good one, one that you truly believe in, you won’t do what it takes, you won’t muscle through the stress, the anxiety, the sleepless nights, the financial burden. You won’t charge into battle and fight your way to victory, because victory doesn’t mean much to you. For Tom, the idea of being like his father wasn’t enough. But if he absolutely had to be like his father, if he lost sleep over the idea that he’d never measure up—he would have walked over whatever hot coals stood in his way to success.

The emotional engine

Successful business owners don’t limp into a business the way Tom did. They drive headlong into it. Urging them forward is some emotional engine—some pain they need to heal, a dream they must fulfill. Sometimes the inspiration for a business comes from an event, as it did for Marie and Steve. These events can be anything—a health crisis, a layoff, the birth of a child. But it’s never just the event, or even an event at all—it’s that you’re inspired to get closer to your true self, to recognize some pain you harbor, a dream you’ve forgotten about. Suddenly you see that being alive, truly alive, means pursuing something meaningful. You turn the painful event into something positive—into a personal manifesto, a mission. A business.

What drives you may come from a good place, or a bad place. It may be love, meaning, purpose, fear, pain. The truth is, in business it doesn’t matter. The only thing that matters is that it’s powerful enough to keep you moving.

Losing our way

Sometimes on our journey we lose touch with that power, that emotional engine, and we need to reignite it to pass through the dark days. I remember talking to Steve one afternoon as he was going through a dry spell. While we reviewed some strategies he could use to find more clients, I noticed he was down and having trouble focusing. So we changed the conversation and talked about life, about everything he’d been through. Eventually we got around to that day in the hospital and he began to feel the fire again. The despair disappeared. Within a few weeks he’d managed to pull his business back on track.

How to pass the tough tests

As the different results of Tom and Steve show, you can map out a business plan and put together strategies, but unless there’s an emotional driver, those plans and strategies won’t come to life. Tom didn’t have the necessary deep connection to his business to turn ideas into reality. That’s no judgment on Tom. He’s a fantastic guy—bright and talented and passionate about lots of things in life, just not about running his own video production company. If you’re like Tom, you will find your commitment to your business tested the moment things get tough. If the test is hard, you might not pass. But if you’re more like John, Marie or Steve, you’ll meet your challenges with courage. You’ll find the strength, because you have to. And you’ll stand the best chance possible of achieving your business goals—whether that’s to replace a lost income, build a business you can sell later, or run your own practice for a few years before you take on another challenge.

The big takeaway: As you lead your business through this new year, maybe a business you just launched or one you’ve been at for a few years, you may encounter challenges. If you do, explore why you started your business. What it means to you. Dig deep into your emotional well and draw strength from it. And when you do, when you find it forcing you out of bed each morning and fueling you through your workday, you will move ever closer to the success you’re after. You will find yourself like Marie with her thriving food business or John with his booming dog kennel or Steve with his stress-free illustration practice. You will find yourself living your dream.

If you want to share your own story about why you started your business or how digging deep emotionally has pulled you through challenges, please let us know in the comments section below, or shoot me an email at donald (@) freshbooks (dot) com.

Author’s note: this post is based on business owners I know or have coached. I’ve changed all their names and some telling details.

about the author

Former Staff Contributor Donald Cowper is a best-selling author and head of content at .