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3 Realities of Being an Entrepreneur

Executive Summary

Approximately 25 million Americans own a business or are pursuing an entrepreneurial venture. One of the biggest motivators towards starting a business is eliminating authority. People want to be their own bosses.  

  • But, do they really? That’s the question Zack Friedman poses in an assertive expose of the current employment trend.
  • Friendman argues that being an entrepreneur is an arduous journey with an onslaught of rejection, uncertainty, and doubt.
  • He dispels the myth of serial entrepreneurship, and shows how digging deep into a business instead of skimming wide is the key to an entrepreneur’s success.

At some point, almost everyone thinks they want to be an entrepreneur. They like the glory of running their own company, not having a boss, being independent, setting their own schedule, and escaping the nine-to-five.

Do you really want to be an entrepreneur?

How many times have you been rejected repeatedly for one thing? And we’re not talking about the lottery for Hamilton tickets. We’re talking about something you worked really hard for, something you were passionate about, and no matter how hard you tried or how hard you hustled, you heard no over and over again. That’s what it’s like to be an entrepreneur.

Being an entrepreneur isn’t scripted. It’s not going to play out in a two-hour movie, with all the puzzle pieces fitting perfectly. There’s no get-rich-quick playbook. The reality is that to succeed in an entrepreneurial venture, there’s a lot of behind-the-scenes blood, sweat, and tears that people don’t talk about. You see the aftermath—the billionaires with private jets posing on magazine covers. But you don’t see them toiling away in the beginning. You don’t see their journey. There might be one photo somewhere on the internet that captures “the early days.” But you don’t get to feel what it was like for Jeff Bezos sitting at his first desk, which was literally a door, working in his garage in Seattle with a potbelly stove, trying to build the next big company to disrupt the world of e-commerce.

Entrepreneurship isn't All Sunshine and Roses

Reality #1: Being an entrepreneur is about repeated rejection.

Entrepreneurship is a lonely road to greatness. People think they can handle rejection. They think if they didn’t get into their first choice for college or if it took them six months to find a job, then they have the tenacity to make it as an entrepreneur. This is your passion, your life work. This is your pride, your baby. And you’re told over and over it’s not good enough. It’s not what they want. It’s not what they’re looking for…For an entrepreneur, seven rejections are the tip of the iceberg. Speak with any entrepreneur who has raised capital and scaled a business, and it’s not uncommon to hear stories of hundreds of rejections. Even the best entrepreneurs are told no. Even the biggest companies struggle in the beginning. Even the boldest ideas get ignored. Do you really know how rejection feels? Are you willing to take the hits over and over and keep going, even when people are telling you to give up? That’s what it feels like to be an entrepreneur. You have a vision that they don’t. There’s a disconnect. You know you’re right. You know they’re wrong. They don’t have the clarity that you do.

Reality #2: Being an entrepreneur is about wearing many hats.

You have a choice of what you do for a living. It may not be your dream job, be the job you want right now, or have the salary you think you deserve. But you have a choice to work for somebody else, or to work for yourself. The entrepreneurial path isn’t for everyone. There are a lot of reasons why. It may not be financially practical. You may not have that killer idea. You may not want the time commitment. Whatever you choose, own your career. Take responsibility for your actions and know that you do have a choice…It’s easy to want to be an entrepreneur. But what does it really mean to be an entrepreneur? What’s your niche? What’s your differentiation? What’s your competitive advantage? Your schedule as an entrepreneur won’t be easier than it is now. You’ll work harder and longer hours as an entrepreneur than you do in your current job. I guarantee you that you’ll work five times harder than you do now. When you’re an entrepreneur, you’re the boss, the employee, the supervisor, the board of directors, the secretary, the janitor. You’re everything because everything is dependent on you. You need to have that foundation to succeed as an entrepreneur.

Reality #3: Being an entrepreneur is about having the freedom to dream and executing on ideas.

Almost everyone says they want to be an entrepreneur. But it’s not for the reason you think. Too many people think that entrepreneurship, principally, is about getting rich. Entrepreneurship can be a pathway to substantial wealth, but that shouldn’t be the driving reason. The best part of entrepreneurship isn’t financial. Entrepreneurship is about a meritocracy of ideas. The best executable ideas win. You can beat people stronger than you, smarter than you, older than you, richer than you. The only thing that matters are your ideas coupled with your actions.

If you’re going to be an entrepreneur, do you think anyone cares where you come from? Do you think you’re going to sell more products because you went to a certain school? Do you think your company will get a higher valuation because you have “connections” on Wall Street? No one cares. None of it matters. Entrepreneurship is the ultimate playing-field leveler. It reduces hierarchy, seniority, and bureaucracy with the flip of a switch. It’s about the flexibility for anyone to chart their own course. Entrepreneurship is about building and creating something with your bare hands. It’s the freedom to develop an enterprise on your own terms, to leave the herd, and venture out on your own.

Beware of the Serial Entrepreneur Trap

Be wary, though, of the difference between an entrepreneur and a Change Chaser. It’s easy to call yourself an entrepreneur, or even a serial entrepreneur. The moniker sounds impressive: “serial” means this isn’t your first rodeo. You’re experienced and successful. A veteran entrepreneur. Many wear the label proudly on their LinkedIn profiles: Serial Entrepreneur. It sounds better. It looks better. It resonates. The problem is that too many serial entrepreneurs aren’t serial entrepreneurs—they’re Change Chasers. So, are you an entrepreneur or a Change Chaser?

Serial entrepreneurs do exist. Many are Daring Disruptors who continue to push the envelope. However, there are fewer genuine serial entrepreneurs than appear on LinkedIn. A serial entrepreneur isn’t someone who has founded multiple companies. A serial entrepreneur also has built, scaled, and often successfully exited multiple companies. A serial entrepreneur is a creator and an executor. Starting companies and then starting more companies doesn’t make you an entrepreneur. It may make you creative. You may be an effective idea generator.

You may be a trend follower. But you don’t get to wear the serial entrepreneurial badge because you’re a founder. There’s more you need to do to earn the title. Change Chasers jump from job to job, business to business. If opportunity knocks, Change Chasers answer. Unlike serial entrepreneurs, Change Chasers only scratch the surface. When things get difficult, Change Chasers are nowhere to be found. They’re onto the next adventure. However, that’s where serial entrepreneurs are different. It’s the period after turmoil strikes when serial entrepreneurs shine. They manage strife; they pivot; they rebuild. They fix the business model and weather the storm to ensure their business scales and succeeds.

It’s easy to confuse the two, but only one is the real entrepreneur. Make sure you know the difference. This way, you’re not stuck with the wrong label. Whether you’re an entrepreneur or an employee, when you lead a life with purpose and choose a meaningful career, you’ll create alpha at work and harness the power of the Lemonade Life.

Adapted with permission from The Lemonade Life by Zack Friedman, copyright Zack Friedman.

Bring It Home

I customized a Wordpress template to a color scheme that included shades of deep purple - my favorite color. With freshly contemplated copy conveying my unique voice in the marketing space, I launched my first website and started my freelance business. Clients came, I took on projects, and I kept taking them on until I realized that I couldn’t be all things to all people. Quickly, my entrepreneurial spirit diminished. This type of business wasn’t for me. And I had to come to terms with the failure. I had to accept that a change in direction was the best choice for me. Owning a business is hard. Chasing an idea is challenging. Entrepreneurship is about consistently choosing to build upon an idea that matters to you and provides a benefit to others despite resistance. Describe a time when you have conceived of an idea for a new business. What did you do with that idea? Why factored into your decision on being an entrepreneur or not? Share your story in the comments below! - HarperCollins Leadership Essentials

Zack Friedman

Zack Friedman is the founder and chief executive officer of Make Lemonade, a leading personal finance company that empowers you to live a better financial life. Previously, he was chief financial officer of an international energy company, a hedge fund investor, and worked at Blackstone, Morgan Stanley, and the White House.

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