Are You Really Cut Out To Be the Boss?

One afternoon you’re  sitting on the freeway, driving home from work, and then it happens—the trumpets sound, the clouds part, and the answer appears in a shining blaze of insight:

I should be working for myself!

Sounds good, right? But before you turn in your resignation and order new business cards, you need to think long and hard about your motives and learn the truth about striking out on your own.



One afternoon you’re sitting on the freeway, driving home from work, and then it happens—the trumpets sound, the clouds part, and the answer appears in a shining blaze of insight:

I should be working for myself!

Sounds good, right? But before you turn in your resignation and order new business cards, you need to think long and hard about your motives. Yes, entrepreneurship can—about fifty percent of the time—produce rewards for those willing to take the risk, but constant euphoria is not one of the typical rewards.

Hey, welcome back. This is Roger Reid with another episode of success point 360.

Regardless of your particular goal — for example, to create the next best-selling phone app, buy a fast-food franchise, or grow your fledgling used car business into the number one automobile dealership in the state — it probably started with great ambitions and dreams of financial independence.

But if, after several years of hard work, you’re still struggling to keep your business afloat, or worse, your efforts ended in failure, debt, and disappointment, you may be asking . . .

What happened?

Why did your competitor’s plan blossom into financial success while yours ended in failure?

Granted, you may have faced problems with municipal zoning, financing, or bad timing. But there’s another reason for failure. And it’s one very few of us like to talk about . . .

Not everyone is cut out to be the boss.

Your venture may have been unsuccessful because you weren’t aware of the necessary changes in mindset, attitude, and life priorities. Maybe you underestimated the time, the commitment, or the discipline it would take to get your new business off the ground.

Or maybe you didn’t consider the sacrifices —giving up time spent with family, recreational pursuits, or social activities — and you decided to give it a shot because you wanted to join the fashionable trend of starting your own business.

For many, the final decision to become an entrepreneur came after asking themselves the question, “Why not?”

And now, they know the truth.

They jumped into self-employment on a lark, maybe even calling it an experiment, and then a year later, they’re looking at themselves in the mirror, wondering how they’re going to make the next house payment.

What’s the takeaway from all this?

Running your own show is no cakewalk.

It takes long hours, it’s financially risky, and it’s filled with the stress of living a life completely out of balance. So why is it such a popular concept? Why do so many people dream of owning their own business?

One reason, is because the media promotes the notion of being an entrepreneur as universally appealing. It implies that the independence, potentially unlimited compensation, and freedom of self-direction are common aspirations coveted by all workers.

Based on this kind of poster-child logic, we should see a steady and ever-increasing number of new business start-ups annually.

The facts tell us otherwise.

Historically, the number of full-time workers starting or running their own business is a consistent 13 percent (based on the Global Entrepreneurship Monitor).

This may jump a point or two in the short term, but after factoring in the number of new businesses still operating after five years, the number doesn’t change much.

Yes, other sources (the Freelancers Union and Entrepreneur for example) claim much higher percentages, often alleging as much as a third of the workforce is engaging in some kind of self-employment. But this refers to the so-called “gig” economy, made up of part-time workers or those wanting to generate a second or side income, and does not reflect the actual number of full-time entrepreneurs.

And before I go any further, I know that some of you may be thinking that the purpose of this episode is to talk you out of becoming an entrepreneur. And if that’s the case, you’re missing the point.

Working for yourself is not only possible, it can be exactly what you need to find financial freedom and a sense of satisfaction with your career, and ultimately, with your life.

But it’s not a magic placebo for those who are unhappy with their job, or their boss, or the kind of work they do. Those are things that push employees away from toxic work situations; they are not realistic motivations to start your own business.

That comes from the need to be in charge of how you spend your time, how you allocate your resources, and how you feel about your own self-worth.

There are plenty of reasons why some people would and should continue to work as an employee. And there are other reasons why they shouldn’t.  And it’s important to do some self-assessment, to look at not only your circumstances, but your personality, your mindset, your ability to manage your time and recourses to your advantage –and then determine if you’ve got what it takes to strike out on your own.

I’ve put together a list of the most common characteristics of successful entrepreneurs. There are ten in total, but in the interest of time, I’m going to concentrate on the top five, the ones that can make the difference between success and failure in starting your own business. If you’d like to see the entire list, it’s available in the show notes for this episode. I encourage you to read it, and compare your own skillset to those who have been there and done it successfully.

So what does it take?  What’s the mindset of the successful self-employed?

  1. They have perseverance. When you own your own business, you take the failures—big and small—personally, but you process them with perspective. Giving up is not an option. If every little hiccup sends you into a tailspin, you probably don’t have the tenacity to be your own boss. Entrepreneurs are willing to work until they get it done. Whether it’s a website, a presentation, or preparing a complex estimate for a potential client, entrepreneurs understand the necessity of meeting a deadline, and they often work nights and weekends to make sure nothing falls through the cracks. And no, you don’t necessarily have to be a workaholic to become a successful entrepreneur, but it doesn’t hurt. Keep in mind that in spite of having intentions of maintaining a balanced life, most entrepreneurs sacrifice their health and personal relationships to ensure the success of their business— especially in the beginning stages, when they typically start their venture as a one-person show.
  2. They have a grasp of the big picture. They understand their industry inside-out. They know the motivations and buying criteria of their customers. They know how much it costs to manufacture the product or provide the service they sell, right down to the penny. And they know how that compares to the competition. In other words, they know the numbers.
  3. They are goal-oriented and use time-management skills religiously. They know how to separate the important from the trivial and they make sure they accomplish the highest priority tasks first. And they also know that nothing is cast in stone.
  4. They enjoy what they do. They like the people as well as the products or services associated with the industry. They know that doing it only for the money is a fast route to burnout. They also know that building a successful company takes time and dedication, not to mention the investment and re-investment of personal capital. Unless you believe in what you’re doing, the problems, setbacks, and outright failures will send you running for the nearest job-placement service.
  5. They’re not afraid to break the rules. They know that circumventing traditional procedures and processes is often the key to finding success, especially when it comes to beating the competition. Many times this means thinking way outside the box. I’ll give you an example: About thirty years ago, my wife and I started a commercial photography and video production business from our home. To give our clients the assurance that they were in the right place, we mounted an expensive laser-etched sign displaying our company name and logo next to the front door. And while we lacked the first-impression credibility of our store-front competition, the sign helped convey the idea that we were every bit as professional. However, within two weeks, we received a complaint from city zoning—we were in violation of the signage regulations. Specifically, we were advertising a business within a residential community, which was strictly against city ordinances. Not wanting to give up the positive impression our signage conveyed to clients, we needed an alternative. The following week, we bought a white Chevy Astro cargo van and hired a graphics artist to paint the name of our business, our logo, and phone number on both sides. The result was a high quality mobile billboard that made a far larger impression than our original sign ever could have. We left the van parked in our driveway so it was the first thing our clients saw as they approached from the street. And the best part? It was legal.

As I mentioned, this list contains only five of the ten points, but it’s representative of the mindset and typical skills most people need to make a successful transition from employee to business owner. Yes, I’m aware of the few brilliant eccentrics that “seed” a new enterprise solely with their research or original design, and then use others to perform the marketing, networking, and sales. But for every introverted, anti-social, digital game designer, there are hundreds of well-rounded, socially-active, business-savvy individuals who built their operation from the ground up, doing whatever was necessary to move toward eventual—and more probable—success.

Let’s get back to those numbers, the ones that indicate new business startups tend to remain consistent at about 13 percent annually. What does that say about the workforce?

Those numbers tell us that not everyone wants to be an entrepreneur.

And there’s something else, and it’s even more important: The overwhelming majority of people are satisfied — even happy — with a conventional eight-to-five job, even when they say they are not.

Although they may complain or argue they would much rather be in charge of their own professional destiny, their complaints usually reflect temporary disappointments and dissatisfaction inherent in ANY occupation. And seldom do they consider their grievances bad enough to leave the illusion of security provided by an employer.

In short, they’re comfortable with the subservient relationship they have with the boss, and consider the inherent company bureaucracy a necessary and inescapable evil.

So why does entrepreneurship and the idea of working for yourself continue to be such a hot topic?

Because the idea of achieving financial freedom is a powerful aphrodisiac, used to sell everything from business manuals to how-to courses.

The experiences of the few who managed to find their way to the top of the financial pyramid are often touted as everyday success stories, written to entertain, sell a book, a training course, or to gain product recognition by exploiting an individual’s notoriety or celebrity through product endorsements.

Companies involved in multi-level sales or those using independent sales reps often use the “millionaire next door” pitch, citing the examples of a very few outstanding achievers as a recruitment tool. In spite of the fine print disclaimer at the bottom of the page, the implication is clear: They did it, and so can you!

But In reality, over-the-top success is rare.

For example, after the success of Fifty Shades of Grey, the previously unknown author was touted as a less-than-average writer who found fame and fortune by relentlessly pursuing her passion.

But when long-time industry pros were asked to estimate the chances of another unknown author being able to garner the same level of success, the answer was a bubble-popping but realistic zero.

In other words, the success of Fifty Shades was an anomaly — an extremely rare happenstance of luck, competitive timing, market receptivity, and social media marketing.

If we take a close look at all the folks out there who tried kick-starting their own business, or jumped into multi-level sales, or tried to write a book, or offer their photography, paintings, or sculpture for sale, you’re going to find a large percentage of them that were financially forced to give up when success, money, or recognition didn’t come within the first year. Or the second. Or the third.

And while motivational speakers, success bloggers, and life coaches are quick to dismiss them as the complacent majority who live in a world of excuses, the reality is often just the opposite.

They worked extremely hard, giving it everything they had. But the market, the economy, the circumstances surrounding the timing of their business launch just wasn’t ideal for their product or service. Maybe they couldn’t compete with the competition. Whatever the reason, they failed to make their dream a reality.

So where does that put them now?

Many who’ve experienced an unsuccessful business venture look back on their failure as a learning experience — a real-world evaluation of their talent, marketing, and sales ability, and most important, their entrepreneurial mindset . . . or the lack of it.

This very personal feedback has allowed them to make better choices in their financial and career goals, with many returning to conventional employment.

And they don’t return as failures. Far from it.

They’re more confident and sure about their life-plan. And most are quick to point out that, without having tried to make it on their own, they wouldn’t have developed an appreciation for a traditional career path — nor would they be as happy.

So if you’re one of the many who tried and failed to make it on your own, you have two choices:

First, keep trying. Learn from what happened, and start again. If this makes sense to you, and you can’t consider any other way of achieving personal success and satisfaction in life, then go for it. Give it everything you’ve got. Commit yourself 100% to the task and be prepared to make whatever sacrifices are necessary along the way.

Your most powerful resources are determination and persistence — long after reason and logic are exhausted.

The second choice?

Take satisfaction in having learned who you are and what makes you happy. Don’t let the stories of the few who inhabit the mansions of the rich and famous lead to frustration and dissatisfaction with your own life.

The mainstream media’s latest version of the perfect career, with its astronomical level of financial success, is often nothing more than conjecture mixed with a touch of fantasy. Don’t let it adversely influence you with unrealistic expectations.

Discovering your personal strengths and weaknesses is an important part of finding fulfillment in life — even though as a result, your true identity may not mirror the current trend describing the media’s latest avatar for success.

If you’re truly dissatisfied with some aspect of your life, take steps to change it. Otherwise, accept it, and make it a point to stop comparing yourself to those whose circumstances led them down a different path.

Hey, that’s it for this episode, but wait! Don’t hit the stop button just yet. This episode marks the end of season one of Success Point 360. I’ll going to be taking a break for about thirty days, to work on season two, and to finish recording the audio version of my new book, Navigating the Corporate Maze. It’s scheduled for release on October one, and I’ll have more information about it as we get closer to the release date.

So what’s up for season two? I’m promising some surprises, as well as a lot of new content designed to help you become more financially independent and to promote a greater sense of satisfaction with how you make your livelihood. So please join me again on July 14, when I’ll return with a brand new season of Success Point 360. My name is Roger Reid, and I want to thank you for your comments, questions, and for supporting the first season of this podcast.

Thanks for listening, and I’ll see in season two.

© 2020, Roger A. Reid