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Why Money Can’t Be Your Barometer for Success
Entrepreneurs can't use money as a barometer of success

It’s funny how experience and age change context…

Remember when we were 23, fresh out of college, feeling enlightened, and loaded with an opinion on just about everything? How silly we were. We didn’t know shit about the real world, but you’d better not have told us that. The same goes for early entrepreneurial success.

Firstly, success and wealth can’t be measured by money made and portfolio balances. I know too many entrepreneurs who are wealthy beyond belief, and their kids see them on occasion. Or their second wife is on the outs etc. Money made is not success. For this entry though, let’s just delve into the money issue. Inevitably, I believe anyone reading this blog has a high chance of making a ton of money, if they apply themselves and make the necessary sacrifice entrepreneurship requires.


Wealth Context

A first reaction one might have when making their initial big chunk of change is a sense of accomplishment. But shortly afterward, when they start moving up the ranks, they are humbled. They realize that what they made (cash on a deal) was merely a step up, not a significant accomplishment, at least not on its own. They realize this because their circle of colleagues and the caliber of competitors begins to change. The biggest score of their life to date might be what others donate to charity every year, or it may be a rounding error for some ultra-successful entrepreneur. Context changes, so they pursue grander goals. That’s good. And there is an excellent  lesson in this…


Three Phases of Entrepreneurial Discovery After Making a lot of Money

It has been my observation that after making a lot of money many entrepreneurs become self-enamored. They think, albeit briefly, they’ve accomplished more than most. As human beings we compare ourselves to one another – setting benchmarks relating to the company we keep. At that moment of pride, they take their foot off the gas. 

The second phase is many get bored with their money because they quickly realize it isn’t what makes us (human beings) happy. They buy toys and develop an affinity for luxuries. The pleasure from this wears off quickly.  

Third, they recognize, no different than a 26-year-old three years out of college, they really haven’t done much and have a lot to learn. At this point, they reengage with the gas pedal, and ambitions, larger than ever before, creep into the psyche. This is the good part…

As we progress as entrepreneurs, our context on everything from scale, wealth and purpose changes. Our circle of acquaintances grows, inevitably including wealthier and hopefully more balanced people.

So what does this all mean? 

If you’re pursuing entrepreneurship for the money aspect, you will inevitably be let down, and probably be unhappy, no matter how much you make. However, if you’re committed to the entrepreneurial pursuit because of the challenge, growth potential and your passion for creating the best offering within an industry, you’ll be a happy camper, no matter how big the bottom line becomes.

You’re going to have to sacrifice a hell of a lot as an entrepreneur, so make sure you have a healthy barometer of success. Otherwise, the shallow measure of success (money) will leave you disappointed and bored.

Stay hungry,





PS – Entrepreneurship is about so much more than money. Learn how to play the game. Subscribe to my free newsletter below. Only my best content will land in your inbox.