Paradoxes of Entrepreneurialism

One of the definitions for the word paradox at Merriam-Webster.com is “one (such as a person, situation, or action) having seemingly contradictory qualities or phases.” One of the jobs that may showcase this definition more than most is that of being an entrepreneur. There are seemingly two sides to every step, every choice, and nearly all the actions in entrepreneurialism. One of the best skills leading to success from the ground up is learning the paradoxes of being an entrepreneur. Consequently, navigating them is paramount.

Three Paradoxes Right From the Start

#1: You got to be a bit old school; measure twice, cut once. But you’ve got to know when perfect is the other side of doing. There’s a time to act.

#2. Another paradox is caution. Planning is integral. You cannot over-prepare, or you’ll never get into action. This means you will be at specific times and points in the growth cycle where you must take risks. Most are calculated risks.

Being cautious is significant. So is being fluid in action and moving quickly. Movement is life. Speed of execution is what gets you past the competition.

#3 Especially in the beginning, everybody is going to doubt. There’s doubt everywhere in the field of business. Your investors are worried about losing their money. They’re not getting the ROI from you that they feel comfortable or confident they can get elsewhere. So here you are selling them on taking a risk.

But in the Meantime, On the Inside

And inside, you’re dealing with your self-esteem and doubt. You don’t want to fail. Everybody is afraid of failure. No one wants to disappoint the people who trust them. So, there’s this intense tension. You are in a constant pressure cooker. While facing and dealing with your doubt, you must simultaneously inspire, encourage and overcome the suspicion of those around you.

Sometimes that doubt comes from your investors, a manufacturer, a publisher, an executive, or a software developer. It could be someone that you want to support you instead of the job or career path, or business they are currently serving.

As I said before, in an early-stage business, you’ll be dealing with the paradox of planning versus risk-taking, managing your self-doubt with the doubt of those you need backing and support from.

The Capital Paradoxes in Entrepreneurship

And then the next master skill nobody wants to discuss is raising capital. Because, in the early stages of a new venture, many people you’ll have to do business with want you to eliminate their risks and protect their brands. Most have stockholders. Some may have analysts. Many have quarterly reports. They have a reputable brand in the market. None of them want to be stained by a misstep or your failure that they become associated with.

So, you better show that you have intellectual and vital research and marketing muscles, with ample reserves to support executions. You have to offer to manage your supply, drive momentum, and thoroughly put for your distribution. In 2017, SSRN posted an abstract paper titled Paradoxes of Entrepreneurial Thinking: Why Entrepreneurship Can Hardly Be Taught. This paper includes uncertainty, strategy, opportunity, risk-taking, and more. It’s worth the read.

The Paradoxes of Entrepreneurs’ Character Traits

A not so kind man thinking in the dark

Now, there are specific underlining character traits in entrepreneurs. Sadly, some people with the courage and the fearlessness to convince people to back their ideas and objectives while steering them away from other agendas and alternative ambitions often have no conscientiousness.

You’ll find sociopaths. Some just don’t care. Everyone around them is a pawn to get used to their means to resolve a situation or produce an outcome. And what happens is being that kind of particular entrepreneur leads to all sorts of disasters in business. Failed businesses, fraud, misrepresentation, and torn partnerships are typical. People are let down because the expectations set weren’t met.

So now you got to have all this other stuff. In addition, you also must have good character and give trustworthy, lasting persistent, and honest interaction. You have to do what you say. And that doesn’t mean you won’t fail, but you better have the want to and the ability to figure out how to make it right if you do.

Another Paradox of Entrepreneurship; Talk and Listen

You should be a good listener as much as you must be a fantastic storyteller. There must be the strength to know when to hold your ground in your confidence for the vision and when to relent.

When do you take advice from others who have been there before? Realize you must sometimes set your pride aside and redirect or pivot. It would help if you were willing to listen to experienced mentors, professionals who have been around the block. Listen to those that have ridden this rodeo before. There are genuine nuggets to be found in their shared experiences.

Although sometimes, truthfully, their feedback is the last thing you want to hear. Sometimes that exclamation is, “Hey, we got to ask this to professional focus groups before we can put it to market.” You’re starved of cash, so you protest but finally relent and do it.

The next thing you know, you’re pushing your launch back a year, spending extra money you have to raise to rearchitect, redesign, repackage, and relaunch your product as though the entire business is starting from scratch.

It’s deep the amount of convention and grit, the pure strength required to look partners in the eyes and tell people the bad news that we must shift. You have to be able to give bad news to good people.

The Paradox of Confidence and Intimidation

The paradox here is you always really must know your business. It’s easy to be intimated by people with Ivy pedigrees who have been parked in Fortune companies. These people advise on how it should go, how it should be, and how they think it should be done, and their advice can be intimidating and cause you to doubt yourself.

Here’s the problem, sometimes they are right. Sometimes they are wrong! This is your brainchild. It is your baby. You clearly see your vision. It contains your engineering and plotting how you will carry it forward and execute it. On some days you will have to take the risk of being right while they are wrong.

Business is Hard

In my blog “Business is Hard,” I talk about how to meet the challenges head-on and the significance of understanding from the start that being a successful entrepreneur is not easy. Some of the evergreen advice in that blog included: do more than you’re paid for, show your intention, find a mentor, and don’t quit.

There are always ways to do pilots and tests and crunch data. More tools are at your fingertips, and more simulations and affordable market testing are available now than ever. Sometimes it’s not ability; it’s time. Time is crucial. You’ve got to make the time, and you make the time by prioritizing the work. Sometimes that can feel like a vast paradox in entrepreneurship.

Balancing your time between personal, professional activity, and rest can be challenging. Choosing a solid balance here may be the first and foremost settling of a paradox you will prioritize. If not, you will eventually give up one for the other and may lose your business. Don’t do that. Remember the paradoxes you will come against, balance them well, and step by step, you’ll find yourself one day closer to those goals and dreams you set out before you.

 You Got This!

Once you get the people, the infrastructure, the phones, and the utilities on the books, if you’re not driving growth, you’ve got operating losses. You don’t want to carry those any longer than you must. You want to get your revenue up to cover those expenses and start applying revenue that can be used for growth. That’s a BLOG all in itself, so stay tuned.

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