There’s an old school eastcoast – westcoast rap battle that exists in the world of entrepreneurship that needs to be spoken to.
It’s not that all of the entrepreneurs are hitting the streets and duking it out in some kind of Mad Max style arena, although that would be interesting to watch….
What we’re actually doing is creating a mental barometer. We’re creating a tool for measurement, so we can see where we fall on the gradient as individuals.
Most people tend to have a through-line to their personality that ultimately leans in one direction or the other. On one end of the scale we find the pragmatists, on the other, the creatives.
Once we diagnose where we fall, we can start to unpack some possible remedies to get unstuck, and find the success we’re looking for.
Let’s first look at the Pragmatists.
These are the executors. These are the people who immediately say, “ya, but how” at the same time the idea is introduced.
These are the people who know all-too-well that there is a gap the size of the grand canyon between stating a good idea into the air, and getting it to actually happen in physical reality.
They develop and maintain important business infrastructure, and they eyeball potential exit strategies right from the start.
Personally, I probably could stand to be more practical… I lean more towards the creative side.
But it’s uncanny to me just how seductive it can be to think that an idea has any more merit to it, simply because it feels good on the inside when we think of it.
The pragmatist is definitely skeptical by right.
But… what should be an enthusiastic healthy skepticism, can devolve into a skittish dismissiveness, laced with hints and notes of negativity.
Pragmatists can be so focused on what’s “realistic” that they can miss, dismiss, or be afraid of unique breakthrough opportunities.
Also because they tend to downplay emotional energy, they can miss the emotional sale which investors, early customers, and team members often really need.
In addition, market opportunity windows can be very small, and analysis paralysis is a motherfucker. You can get stuck trying to perfect your execution plan, while very often “good enough for now” beats out “perfect later”.
Then there are the creatives. These people tend to be very entrepreneurial by nature.
They dream up interesting ideas and solutions that often cross the boundary of usual and normal. This is good, unless society wants to keep producing ideas and businesses that are carbon copies of one another… which obviously we don’t.
However there’s a dangerous line that gets crossed all too often, where the vision becomes stubbornness. Pivoting or abandoning an idea can feel like personal failure rather than plain ol’ practical.
Also, creatives can have a lot of trouble seeing past all of the possibilities in their mind. It’s harder for them to pick just one thing to stick to. And this creates a clarity problem, because you can’t get clear on all possibilities.
Clarity is a psychological bullseye we need in order to set up a direction to move in. And you can’t effectively market without being clear on who you’re creating for, and how it will help them.
As usual, the secret sauce is made with the perfect blend of ingredients.
Both qualities are needed in the right amount. Either an entrepreneur has just the right concoction to make it work, or more realistically, they need a good partner or team to balance them off.
The key is to do a deep dive on yourself – to admit the things that might make you a little uncomfortable, but that help you uncover your strengths and your weaknesses.
Then, you can either develop your weaknesses, or find a partner or pull together a team to support you where you need it most.
So now’s the time to ask yourself…. who are you really?




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