The seven paradoxes of entrepreneurship

Entrepreneurship is a phenomenon driven by creativity and imagination and can be quite a tricky process for the uninitiated, due to a number of counterintuitive paradoxes that entrepreneurs have to contend with, in order to be successful. Let’s take a look at seven of these paradoxes.

The first paradox is you “lose money to make money”; so, what does that actually mean? Well, a startup enterprise is a blank canvas and a learning environment, and the founder has to try and figure it out, “experiment”, and collect data, much like a scientist. Naturally, these experiments don’t always work, and they can drain your resources completely, if not managed carefully. For example, you have just launched an online business, but you are not sure about your marketing tactics, so you start experimenting with different things, based on your customer personas. Things such as Facebook, Instagram, SEO, LinkedIn, etc. Some will work and some won’t work depending on how well the entrepreneur has identified their target market and the message they are sending out. Each experiment will cost money, and how much will depend on the entrepreneur’s budget and how they allocate and manage their budget.

The second paradox is you “relinquish wealth to create it”, (the entrepreneur’s or others). This is simply the capital investment required to start the business. Now, of course, some businesses don’t require a lot of capital to start, but as the business grows it will require some form of finance (such as debt) or investment (equity). For example, the entrepreneur could be required to second-mortgage their property in order to obtain finance from the bank, so all those years of paying off their mortgage are now handed back to the bank, and furthermore, all those years of wealth creation could actually be lost.

The third paradox is you “experience failure to experience success”. Every seasoned entrepreneur knows this is true. Success is not just a fork in the road; it’s not whether you either succeed, or not, but rather it’s a series of trial and error until that unique success formula is discovered. The problem with most entrepreneurs is they give up too early, either through disappointment, exhaustion, lack of capital, or marriage breakup. Something to consider here is that the average entrepreneur “fails” nine or ten times before they succeed. So, if you are wondering if you are a failure, then think again, you may still have a long way to go; there may still be lots of room for your success. As the famous US baseballer, Babe Ruth once said, “Every strike brings me closer to a home run”. Probability-wise, this is also correct, try something enough times and you will succeed, (provided one learns something from each failure, and they are able to correct it). So, the development of resilience and persistence is the key here, and a final thought, nothing great comes from doing something easy.

The fourth paradox is “planning the “unplannable”. Anyone that’s ever started a business will know that if you write a business plan, it is pretty much useless, after the first three months. In my experience of starting my own businesses and coaching and mentoring others over the last 28 years, I don’t think I have ever seen a business start and stay the same course over time. Businesses continually pivot, in order to survive, especially at the startup stage, when they are figuring out what to do. This is purely dictated by the market, (the customer’s needs and wants), the industry, and its competitive pressures.

In my first business in the early 90s, I set up a surf t-shirt manufacturing business, where I spent three months, full-time, writing a business plan, (which I was ever so proud of), and buying all the required equipment to print t-shirts. After, 3 months, one of my customers asked me if I could do snowboard wear. Now, in the early 90s, snowboarding was a “hot” and burgeoning industry, with very little local competition, so I said yes! I was able to completely transform my business into a snowboard garment manufacturing company, almost immediately. Within 2 years, I was already exporting to Switzerland, New Zealand, and Japan. My original business plan completely lost track.

Instead of a business plan, an entrepreneur must be guided by his/her vision, which includes their ideology and core purpose, as these rarely ever change. They should study the market carefully and listen to the customer, and then focus on creating their product/service. Then spend time figuring out strategies to build their market dominant position over time. Now, this will change as the market changes and competitive pressures increase, but will most likely take a lot longer. The tactics, which is what most business plans are built on, can change on a daily basis, hence the likelihood of it quickly being out of date.

Instead of writing a business plan, the entrepreneur should spend that time learning how to get a customer, then create a framework of how they will bring their resources together. Using, tools such as the Business Model Canvas can be very helpful and a time-saver. The key here is to be flexible and open to opportunities, as you are learning, but also turning to be focused on building one thing and doing it well, (again another paradox here).

The fifth paradox is “creating chaos to create order”. Now, this is very counterintuitive, however, creativity comes from our imagination, and this is where the “sparks of genius” lie. One also has to acknowledge that there is a fine line between genius and madness. It actually stems from the same point, and this point is often mired in chaos. However, the entrepreneur must be able to take that “chaos”, and bring “order” to it, to be able to execute it. Here is where the “genius” ability emerges; that ability to take that “madness” and put it into some form of “order” that can make sense to the “real” world.

The sixth paradox is “creative thinking “outside the box” for innovation but requiring discipline and focus to execute”. Now, this is linked to the previous paradox and goes without saying, entrepreneurs need to look at something from an imaginative perspective, or some kind of uncontrolled thought, which can often even tinge on “madness” (as this is where genius lies). However, to be successful in execution requires some form of order, including discipline and focus, otherwise, it ends up being chaotic and dysfunctional, which will lead to underperformance, and the worst case, failure.

Finally, the seventh paradox is “too much order and you lose creativity” the antithesis of the previous two paradoxes. When there is too much control, it often leads to bureaucracy, which completely kills creativity. In order to remain creative, an organisation must be flat, focused, and nimble, and encourage diversity and tolerance of failure.

So, as you can see there are many paradoxes to contend with, and the most successful entrepreneurs are able to have insight into these paradoxes. They are able to create strategies to overcome these paradoxes via fluid responses, built on flexibility and resilience, but also, they are able to be comfortable with ambiguity and uncertainty. They have a knack for being able to let things go and not get attached to them.

If you can think of any more paradoxes of entrepreneurship, please let me know.

By Tobi Nagy