The Paradoxes of Entrepreneurialism

A portion of the definition for the word paradox at 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. A valued skill leading to success from the ground up is learning the paradoxes of being an entrepreneur. Consequently, navigating them is paramount. Experienced entrepreneurs are very well acquainted with them. You should be too.

An arrow pointing down made from arrows pointing up symbolizing paradoxesThree 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. You need to plan. But do not 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. But they are calculated risks.

#3 Especially in the beginning, everybody is going to doubt. There’s doubt everywhere in the field of business. You have your investors who 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.

Being cautious and well-planned is significant. So is being fluid in action and moving quickly. Movement is life. Speed of execution is what gets you past the competition. And remember all the resources that are at your fingertips as you move along on this journey. You might even consider reading the book The Entrepreneurs Paradox by Curtis Morley, which covers 16 pitfalls in the startup journey.

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 you. So, you feel 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 Entrepreneurialism

Rubics Cube nearly completed symbolizing entrepreneurismAnd 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. They have stockholders and may have analysts. Some have quarterly reports. Many have a reputable brand in the market, and they do not want to be stained by a misstep or your failure that they become associated with.

So, you better be able to show that you’ve got intellectual muscle and vital research and marketing muscle, with ample reserves to support executions. You have to offer that you can manage your supply, drive momentum, and thoroughly put forward your distribution.

The Paradoxes of Entrepreneurs’ Character Traits

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. There are also people that 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 common. 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 to want to and the ability to figure out how to make it right if you do.

Another Paradox of Entrepreneurialism; Talk and Listen

iron sign that says

Being a good listener is as significant as also being a fantastic storyteller. You must know when you hold your ground in your confidence for the vision and when you relent.

When do you take advice from others who have been there before? Which thought leader are you following? Think you know it all?

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 right into success. You will find genuine nuggets from their shared experiences.

And truthfully, sometimes, 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.” And you’re starved of cash, so you might 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. This falls under the scary category of growth expenses. And your entrepreneurial skills are necessary for this one, no doubt.

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 in small businesses, sometimes they are right. And sometimes they are wrong! This is your brainchild. It’s your baby. This is your vision. Therefore, your engineering and plotting how you will carry it forward and execute it is foremost. And, sometimes, you will have to take the risk of being right and them being wrong.

Business is Hard as an Entrepreneur

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 entrepreneurship 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 more 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.

A heap of old clocks symbolizing balancing the paradox of time as an entrepreneur

Balancing your time between personal and professional activity and rest can be the most 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 or, worse, lose your family. 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. This is all a part of entrepreneurship development.

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. The goal is to get that revenue up to cover those expenses and start applying revenue that can be used for growth. Done right, you are headed from being a startup company to financial independence. Walk strong, innovator; you got this!

And the revenue conversation for good business models in the United States? That’s a BLOG all in itself, so stay tuned.