Several times each month, I find myself speaking with what Mark Cuban would call a "wantrepreneur." These entrepreneurs-in-the-making haven't yet made the leap, but have dreams of hanging their own shingles and being their own bosses.

Thanks to shows like Shark Tank and The Profit, entrepreneurship has become a staple of popular culture, making our noble profession a fulfilling one. However, while most entrepreneurs and wantrepreneurs alike choose to focus on the good times, most rarely consider the plethora of dark sides in the entrepreneurship game.

Like my entrepreneurial brothers and sisters, I'm definitely an optimist -- a glass-all-the-way-full kind of guy. But, I have friends, colleagues and acquaintances that have struggled to feed their families, had cars and homes ripped away to pay debts, and have even contemplated suicide (and sadly, I've heard of, but haven't personally known, a few entrepreneurs that have succumbed to this terrible fate).

That's why, when I meet wantrepreneurs, I typically pause to have a very serious conversation to gauge how well the person may or may not be prepared for what lies ahead. To that end, here are six questions to answer before starting a business, that will help you see if entrepreneurship is really the right path for you:

1. How do you take criticism?

When you're the boss, everyone's your personal critic. And, it does get personal. Everything you do will be on a stage both for your clients and your employees to see. Every meeting, every email and every phone call is a performance, and you'll have to always be "on," considering how your words and actions will affect both your short- and long-term goals.

If you don't take objective (and subjective) criticism well, you might become frustrated and mentally exhausted from all the work that your mind will undertake--work that absolutely no one will see or appreciate.

2. How much validation do you need?

You know who thanks an entrepreneur? No one. Meanwhile, you'll spend your days conveying lavish praise on everyone around you, to keep them happy and motivated. This may not be a big deal over a few months, but over many years you might start to feel bitter if you're someone who enjoys being praised for a hard day's work.

When you're the boss, most will see that as all the validation you need, so mentally prepare yourself accordingly.

3. How do you deal with conflict?

The best entrepreneurs must rise above conflict and play the impartial arbitrator--even when the conflict involves the entrepreneur herself. This can be very difficult, especially when the situation is unfair to you as the boss. You'll have to suppress any reactive behavior that shows defensiveness or emotion if you want to maintain the right image for your clients and/or employees. It's difficult to swallow pride and rise above, but it's a skill that has saved me a few times (and one that I learned the hard way, might I add).

4. What is your emotional IQ?

Can you read people? I mean, really read them? Can you set aside your own ego and pick up subtle cues about an unhappy client or a downtrodden employee?

I wasn't born with this talent, but I've learned a heck of a lot from my business partner who was gifted with an incredibly high emotional intelligence. As I've heard many an entrepreneur quip: business would be much easier if it weren't for all these people we have to consider! However, the truth is that business is only about people, which means you must have a strong command on behavioral psychology if you want to be an effective entrepreneur.

5. Do you think long-term?

Everything you do as an entrepreneur must be for a long-term benefit. For instance, it took me five years to get a paycheck out of my first company, but the company--like a growing child--needed the resources more than I did.

Decisions like this happen every day, where the long-term viability of the company must be put above absolutely everything else. Owners who reap short-term benefits almost always do so at the deficit of the company's future, which is a recipe for long-term mediocrity at best.

6. What are you willing to sacrifice?

If your answer isn't, "everything," then I would caution you against starting a business. A friend and fellow entrepreneur once told me that owning a business is like riding a tiger. Some days, the tiger acts like a horse. But other days, it acts like the tiger it is, and stands ready to tear you to pieces.

Being ready for the unexpected takes a certain mindset, one that prepares you as an entrepreneur to give up everything to make the dream happen. Fortunately, I've never had to give up cars, homes and retirement funds like some of my colleagues have; but, if it came down to it, I know that I would. And that makes all the difference.

Surely, if we only focused on the pitfalls of entrepreneurship, none of us would ever start a business. But, to go along with your presumably unhealthy dose of optimism, I encourage you to consider these six questions if you're thinking of striking out on your own.

That way, if the tiger does get angry, at least you'll be prepared to tame it.

Published on: Apr 5, 2017