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The Today You Versus Yesterday You
competing against yourself

After ‘making it’ as an entrepreneur (becoming financially free), my routine changed. My schedule got busier, and my focus expanded to, ironically, the point where I was constantly distracted… I spent little time building (which is what led to my success) and more time investing and meeting people. I thought that was a clever play: leverage my time and money and hire people to do almost all the jobs I once had to do when building my company. That was so wrong.

During this period, there were about five years when I didn’t learn a new entrepreneurial skill other than schmoozing and delegating (if those are even skills). My routine didn’t allow for anything else. And I was getting left behind from a skillset standpoint compared to younger entrepreneurs in my field. They were innovating, and I wasn’t. Eventually, I felt empty in my professional life. It was because I wanted to build and create something once again. I think all entrepreneurs wish to do that more than anything else.

Don’t Lose The Early Entrepreneurial Version of Yourself

Entrepreneurship may be one of the only careers where you are encouraged to leave the trenches when you become a leader in your field.

But why?

Artists never stop painting. Elite athletes don’t stop improving on the same fundamentals they learned early on.

Remember launching your first business? The early days? When you had minimal means and a whole lot of enthusiasm… you were learning as you went — drinking from a firehose and loving every second.

Remember how scrappy you had to be, given your lack of resources and need to succeed? You probably didn’t have a fallback plan. Those were the days you proved, not only to those around you but to yourself, that you had something special. And when you finally realized that your venture would work very well, what a feeling!

The Trenches Are Where Entrepreneurs Must Live

Getting an idea off the ground and to a thriving state based on sheer will and determination is an incredible confidence booster. It’ll change your life forever. And it does beautiful things for your psyche. Yet when we become successful, we avoid the bootstrapping attitude and scrappiness that launched us to where we are today.

Any new project we launch now probably has a team involved. You certainly oversee, but do you get your hands dirty?

Most successful entrepreneurs make excuses for not returning to their early days’ mentality and routine. “I have too many things to do now.” “It’s not the best use of my time.” “Too many people to manage.” The list goes on…

From my experiences, there’s nothing more important than getting back in the trenches, no matter how wealthy and successful you may be.

I have a friend who built an incredibly successful CPG company. But his company hasn’t grown much in the last two years from a revenue standpoint. One of the things that propelled his company from the onset was he produced enthralling content. It was clever and engaging. His copy was the best I’ve ever seen. I fully believe the content he crafted was what sold tens of millions in products. But after his brand took off and the revenue came in fast and furious, he stopped writing the copy… he outsourced. And to be frank, his company’s content now comes off as ‘corporate-like’ and sterile. It’s boring compared to what he used to create. So I’m not surprised revenue growth has pretty much stalled. I’m convinced his business would be doing huge numbers if he was still writing the content.

Oftentimes, when entrepreneurs become successful, they go on autopilot. They have a jam-packed schedule that leaves little time to create, learn, and test themselves. If this sounds like you, be honest… are you getting better these days? Are you future-proofing yourself as an entrepreneur?

Those days of bootstrapping your first venture may seem long behind you and, dare I say, beneath you. The company you built by being scrappy and resourceful all those years ago may have a 1,000-person headcount today, but that doesn’t mean you shouldn’t push yourself to once again make something out of very little. Test your ingenuity once again.

This Is More Than Just An Entrepreneurial Exercise

When you get down in the dirt and fight with a lack of resources to build something economically viable, you learn new skills that will serve you for years. You future-proof yourself as an entrepreneur and your business. You test your competitiveness against the new class in your industry, those that want to take your market share as you did all those years ago to another entrepreneur/company. And you realize your customers’ wants and needs have changed.

Take a small sum of capital, say, $5,000… that’s your budget to start a new project or initiative within your company. Within 90 days, it must garner a positive return on investment (pick a critical KPI and use that as a marker). Test yourself. Get in the trenches again.

Stay hungry,


PS – If you’re a successful realtor with a team under you, when was the last time you sat for an open house and listened to what prospective buyers were saying to one another? Or, you run a successful software company. When was the last time you coded a new program? Own a massive plumbing company… when did you last do a service call?