Carelessness is very contagious, and if you’re around careless people, you too will likely catch the disease.

Being careless, or worry-free as many of the careless will call it, certainly is appealing at first glance, especially to those of us who obsess over the details and have busy minds and schedules. Sometimes it’d be nice to just turn it off… It’s what made the hippie movement so famous. A lack of stress. A pleasure-seeking life. But that doesn’t fly in the world of entrepreneurship. Carelessness ends in money lost, 9 times out of 10.

It’s Hard to See Your Own Carelessness

In the moment, it can be hard to identify when you’re being careless as an entrepreneur. So, here are some reminders as to when you may be vulnerable…

I’ve never been more vulnerable to making careless moves than right after a massive win/windfall. A sudden surge in capital creates a drive for entrepreneurs to deploy that capital quickly — put it back to work to expand one’s ‘empire’ and keep the momentum rolling. 

After one of my most significant returns on investment, I became more ‘liquid’ than I had ever been. So I put much of that capital into about half a dozen startups, all without meeting the CEOs (broke my cardinal rule). It was an attempted parlay. Long story short, all but one of those investments lost money (a lot of money). In hindsight, it’s pretty embarrassing to admit I was this careless. But in the fog of success, It didn’t seem so.

Carelessness can also come from wanting something too much. Whether closing a deal, forming a partnership, or launching a new business, pushing hard to wrap things up is when unwarranted concessions are made. When you’re hell-bent on getting a specific thing ‘done’ by a particular time, you often overlook challenges and ignore red flags.

When you’re trying to keep up with others’ success — otherwise known as FOMO — you’ll get careless, guaranteed. Chasing trends/fads can have many consequences. 

Being enticed by tales of overnight riches is an intoxicating drug. When facing a situation like this, remember you are an expert in a domain because you put in the years of work and effort to understand the nuances. That expertise was earned…

While it may seem like that crypto investor made her millions overnight, it took several years of studying, patience, and risk-taking. There is no such thing as overnight success.

Carelessness is a Quiet Killer of Businesses

The devil, and your success as an entrepreneur, are in the details. Prosperity depends on your ability to understand the facts and execute with precision based on that understanding. It’s the opposite of carelessness or care-free living. 

The difference between a successful restaurant and the one that fails next door to it is one entrepreneur understood the specific tastes of the community while the other didn’t. One understood the desired ambience of the patrons, while the other did not. One did the math on ways to minimize kitchen space to expand seating capacity, the other not so much. One did their homework, the other went with what they thought people wanted. One was careful, the other careless. 

Stay hungry,

Aaron