3 Reasons Not to Become an Entrepreneur, and How to Do it Anyway

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Can I share a concern with you? Too many people want to become entrepreneurs just because it seems cool.

Having gone through the sweaty, unglamorous, haven’t-showered-for-days slog that is starting a business, I can say with confidence this is a recipe for failure. That’s why it’s so crucial that you figure out right from the start whether this is what you truly want, and if you can muster what it takes to thrive.

Right now, an army of “wanterpreneurs” are being drawn into the world of startups. For them, entrepreneurship exists in the same sphere of activities as yoga (while covered head-to-toe in lululemon, of course), kombucha, kale, and Burning Man.

The cool kids of yesterday aspired to get MBAs from Ivy League schools and become VPs at Goldman Sachs. Today they want to drop out of school, learn Python, raise a few million dollars, and have a shot at becoming the next Zuckerberg.

And why not? Let’s face it—startups seem cool.

The idea of working from a funky coworking space or a remote tropical island seems way better than grinding out the 9-to-5 for some faceless corporation.

Meanwhile, computer programming—the exclusive domain of socially rejected nerds for over three decades—has rebranded as “coding,” and is now endorsed by supermodels.

The media also fans the flames of desire by announcing news of startup valuations that rival GDPs of some nations. Social media feeds of entrepreneurs, myself included, are often nothing more than showreels of #livingthelife.

Yes, I too, am guilty of hyping the entrepreneurial life.

For example, this is a shot from my Instagram feed, posted a few weeks ago:

Becoming an entrepreneur working on the beach

It’s real—I really was editing our company’s regular Sunday newsletter from a Caribbean island—but Instagram feeds like this one rarely tell the full story of what it means to be an entrepreneur. Rest assured, this is not what my life looks like all or even most of the time.

This is why I feel it’s important to distinguish between the “living-the-life” and “nose-to-the-grindstone” aspects of entrepreneurial life.

The good news is that, once you figure out how to not completely suck at becoming an entrepreneur, you’ll see plenty of both types of moments. But when you’re starting out, the latter tend to outweigh the former by a considerable margin.

Which means that if you’re drawn in by the sexy, Instagrammable elements of entrepreneurship, there just won’t be enough of them to sustain you through the journey.

For more context, this is also me—five years earlier, after a 40-day streak of working 16-hour days.

Becoming an entrepreneur can feel pretty lonely

My wife and I were house sitting a friend’s furniture-less apartment.

It was about six months after we co-founded Arielle Careers.

I was in debt, I hadn’t been to the gym in years, and right then I was probably taking a moment to decide where I could get some lunch in the fastest way possible, so that I could get right back to work (all while wondering about when the next sale will come).

It was gritty, stressful, uncool, isolating, and often infuriating.

But you know what?

I loved it.

It felt like I was on the adventure of a lifetime, figuring out how to do something I’ve always felt I needed to do. Every day was a step toward a vision I clearly saw in my mind.

Which brings me to the first of my 3 signs that entrepreneurship may be a terrible career choice for some people.

Before I begin, a caveat.

By no means is this an attempt to discourage you from becoming an entrepreneur.

Rather, it’s a heads-up about the personality traits and habits that can stop you from growing your business, as well as some advice on how you can overcome them.

Entrepreneurship is, in many ways, a battle.

Most people realize that it’s a battle against your competitors, however not many recognize that it’s also a battle against yourself, forcing you to confront your strengths and weaknesses.

There are numerous guides online that can show you how to win the former; in this piece, I want to explore how you can win the latter. Here are three reasons you might want to think again before starting a business, and some advice for working past them.

1. You Value Comfort Over Performance

There are two types of people in the work arena—those who derive satisfaction from the byproducts of success, and those who get satisfaction from the actual process of moving the needle.

In the context of entrepreneurship, it means some people get into the game because they dream of never having to work again; they dream of one day buying the boats, the cars, and the fancy dinners.

The benefits of becoming an entrepreneur- Man Relaxing in a Pool
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Others enjoy all those niceties just as much, but they also get a different—a more intense and fulfilling—sense of satisfaction when they get to will something into existence, when they connect dots in creative new ways and then they see a strategy they’ve been seeing in their mind start to take shape in the real world.

Furthermore, these people also tend to view entrepreneurship as a personal journey. For them, it’s a medium through which they can grow as human beings by feeling, and pushing past, their personal limits. In other words, for them it’s a way of stepping outside of their comfort zone.

In that sense, becoming a successful entrepreneur is no different than becoming a husband, wife, parent, martial artist, or traveler. Each one of these can be viewed as either a way to get more pleasure or a way to become a more complete, self-aware, and conscious person.

There’s nothing intrinsically wrong or right with either mindset.

However, when shit hits the fan (and it will) the more pleasure-seeking mindsets will serve you considerably less than others. Not only will the results that you produce be different, your experience while producing these results will be vastly different, too.

Fortunately, switching between these mindsets is a skill that can be cultivated.

For me, it’s simply a matter of becoming aware when I’m being driven by a mental state that does not allow me to reach my full potential and experience the moment in its most fulfilling form, and then taking action in a direction that better serves me.

Beyond that, I don’t see myself as someone who is in a position to provide advice on raising consciousness, and I don’t want to insult your intelligence by regurgitating commonly cited, obvious advice like “you should practice meditation.”

Thankfully, the topic of experiencing fulfilment through the process of recognizing and exploring your edge has been, and continues to be, explored by some of the most interesting people on the planet.

My key suggestion would be to seek out these people and add them to your roster of teachers.

Expect to find them in unexpected places and expect to experience difficulty when trying to pigeonhole them. They could be businesspeople, but they also could be dance teachers, yogis, philosophers, and martial artists. They could be all of the above or none of the above.

Mine currently are:

I find that the mere act of exploring the ideas of these people magnetizes me toward an inner place which feel more “right.”

The frequently mentioned “gods of entrepreneurship” like Gary Vaynerchuk and Tim Ferriss can teach us how to run faster and more efficiently toward a particular goal.

While their teachings are certainly valuable, I find that they become most powerful when they’re balanced with teachings of people I’ve mentioned above, i.e., those who challenge paradigms around our goals and invite us to solve problems in the most conscious way possible.

Need to talk to someone who has already mastered how to become a successful entrepreneur?

Click Here To Get Instant Access To Our Free Ebook, the “Ultimate Step-By-Step Guide On How To Find A Mentor”

2. You’re Goal Averse

It’s often said that, becoming an entrepreneur, you can work when you want, from wherever you want, and without anyone telling you what to do.

Ultimate freedom, right?

Well, not quite.

No business grows without a concrete, clearly defined strategy. And no strategy is effective without goals.

Man's hand and a watch showing the importance of entrepreneurial goals
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To become an entrepreneur and grow a successful business, you must hold a concrete, meaningful, and empirically centered vision in your mind at all times.

Everything you do inside the business (and, to a large extent, outside of it) needs to be subservient to that vision. Even when you do the most menial of tasks, and there’ll be plenty of those, you need to be aware of your big overarching goal, and how your current action serves it.

I still remember the first big entrepreneurial goal that I created and achieved. It was:

“I want to be able to make $50K/year of profit from my business. I don’t care how many hours per day I have to work.”

The figure of $50K was intensely meaningful to me, because I calculated that it’s how much I needed to quit my meaningless side jobs (I was still working part time in bars at the time) and yet live in reasonable comfort while doing what I loved.

It was a powerful goal, because it meant that I’d be able to support myself 100% through my business and not depend on employers for any income.

It also represented a graduation as an entrepreneur, which was an important milestone for me. In my opinion, when people ask you what you do, you can say that you’re an entrepreneur, but as long as an employer is paying your bills that’s not entirely true.

You need to find your own, overarching vision that will keep you hungry and focused.

It’s critical that you make your targets concrete and empirical. Many would-be entrepreneurs fall into the trap of creating vague and fluffy targets, such as:

“I want to work for myself.”

“I want to travel the world while running my company.”

“I want to realize my full potential.”

“I want to be successful.”

“I want to build the best business in the XYZ niche.”

You also need to ensure that these targets are outside of your current reach, but are realistic.

A target like, “I want to make $1 million in the next six months” is deliciously precise, however for most beginner entrepreneurs it’s too nebulous to act as a strong day-to-day motivator.

(One mistake I made, and often continue to make, was by not unpacking my one large goal into smaller milestones. I highly recommend that you follow Foundr’s excellent guide to goal-setting to create your own Goal Pyramid).

When you have targets that are tied to your “Grand Vision,” you suddenly have a larger context for evaluating all of the freedoms entrepreneurship ostensibly offers, and you realize that many of them are merely distractions.

For example, where to work today?

Sure, you could grab your laptop, drive into town, park your car and work from a hipster cafe while sipping a latte and eating a quinoa bowl. But is the money and time you spend on this activity bringing you closer to your goal?

If you were to stay at home, how much more closer to your larger goal would you be?

Sacrifice is an essential component of becoming an entrepreneur. And a goal-driven strategy is a mechanism for sacrificing little freedoms in order to achieve big ones.

Need to talk to someone who has already mastered how to become a successful entrepreneur?  

Click Here To Get Instant Access To Our Free Ebook, the “Ultimate Step-By-Step Guide On How To Find A Mentor”

3. You Don’t Deal Well With Stress

Entrepreneurship can create stressful situations in your life, and some people are less equipped to deal with stress than others.

There’s also a variety of people who create stress and drama in their lives because it provides them with attention from others. (If you’re one of these people, it’s probably best you stay away from entrepreneurship altogether.)

Thing is, stress can be significantly reduced or eliminated altogether. How?

Well, stress is a byproduct of being stuck in situations where you feel that you don’t have good options.

Being stuck in a dark alley with shady guys and your back against the wall? Stressful.

Same bunch of shady guys, but you’re armed to the teeth and have a number of planned escape routes up your sleeve? Not so stressful.

As you become an entrepreneur you grow your business by taking on calculated risk. The more risk, the more potential upside, but also more potential downside. If you get it badly wrong, your startup will tank.

The word “calculated” is instrumental here, because without calculation, the activity stops being entrepreneurship and becomes gambling.

People like Richard Branson create millions of dollars of value per day because they have become masters of risk calculation.

A person's shoes hanging over the side of the building showing that becoming an entrepreneur involves risk
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You must fully intend for the risk you take on to provide a return (in the form of growth, money, exposure, or something else you deem valuable). However, to stop yourself from being ridden with stress (and largely useless in your business), you need to get into a habit of having an acceptable Plan B (and preferably C and D) at all times.

The more palatable your alternative plans are, the less stress you’ll feel.

In fact, the art of entrepreneurship, to a large extent, involves learning to create, and be aware of “worst-case scenarios.”

Start practicing creating your worst-case scenarios now, with every business move you make. Let’s say some marketing hotshot comes along and tells you that he can build you an online strategy that will “attract hot leads and converts them like crazy.”

His fee? $20,000.

Should you go ahead with this?

Well, if his strategy tanks, but you have $100,000 in the bank and a few healthy revenue channels, your worst-case scenario is not that grim—you’d treat this mistake as a valuable learning experience.

But if all you have is $20,000 that you borrowed from your parents, zero cash flow, and happened to quit your job yesterday, your worst-case scenario would probably involve abandoning your business idea, scrambling to find a job, then spending the next few months repaying your debt while you lick your wounds.

While there are some exceptions to this, I generally recommend that if the idea of living out your worst-case scenario brings you a considerable amount of stress, you probably need to rethink the move you’re about to make.

Need to talk to someone who has already mastered how to become a successful entrepreneur?  

Click Here To Get Instant Access To Our Free Ebook, the “Ultimate Step-By-Step Guide On How To Find A Mentor”

Key Points to Remember

Becoming an entrepreneur and starting your own business is one of life’s most challenging and rewarding journeys.

It means different things to different people.

For some, like me, it’s a far superior alternative to the drudgery that’s offered by the typical corporate 9-to-5. I knew from quite an early age that following orders was not going to be my thing.

That being said, for all of the perks that the entrepreneurial path offers, it’s far from being all roses. Far from it. Being an entrepreneur means being a warrior. It means being a clever, hungry, often ruthless competitor.

From the first day you start your business, you’re in a battle for the top spot in your niche. To emerge victorious, you either have to invent the niche or dethrone the current kings.

When (or if) you do win this battle, and you’re bloodied, bruised, and scarred (but elated), you’re dealt a bittersweet surprise.

You now have to defend your title.

In that sense, I believe that entrepreneurs are not too different from UFC fighters, Spartans. Their fights are not meaningless brawls. They’re a result of being willing to stand for something, to risk everything for a chance of success and to grow in the process and maybe, just maybe, one day get to experience a fleeting, but deeply meaningful moment of glory.

In that spirit, I’ll leave you with one of my favorite quotes about entrepreneurship:

“The price of success is hard work, dedication to the job at hand, and the determination that whether we win or lose, we have applied the best of ourselves to the task at hand.” – Vince Lombardi, head coach of the Green Bay Packers (1959-1967).

By the way, I’m interested in your thoughts. Do you think that entrepreneurship is for everyone? As entrepreneurs, which personal traits and habits do we need to change to reach our goals, and experience fulfillment along the way?

  • kaos_theory

    Great article and great advice. The idea of “worst case scenario” is a great way to test your will…if as an individual you are able to honestly visualize what that is. I tend to find that many “wantrepreneurs” don’t have the perspective or the experience to understand what a crushing sense of desolation is. I do, however, feel that the stress and fear that occur from failure is part of what defines and shapes the personality of an entrepreneur. I would imagine that the fact that many entrepreneurs have failed a few times before reaching their bigger goals has something to do with their success and determination.

    There is a feeling that can only be experienced through the drive to be something greater, build something better, push the limits of your peers and see the results in real time – both up and down. It’s the journey, even more than the destination (as the destination often changes) that is what a true entrepreneur lives for. That is, if he/she can survive the of overwhelming self realization necessary to manifest their dream.

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