The Right Beginning Always Starts at the End

Over the next several weeks, you’ll hear how my friends and colleagues – across multiple and diverse industries – responded to one awkwardly open-ended question…

Let’s start at the beginning, by talking about the end.


Isn’t that what we’re all really after? Think about it. Here’s the common thread I hear when I speak to entrepreneurs and business leaders.

I want to be successful.
So I can be happy.
And being happy is being comfortable.

Of course, those three statements are always packaged in a variety of exciting and interesting stories, but the central theme is the same. The next three statements typically come a little bit later:

I’m finally comfortable.
But I’m not very happy.
And I don’t feel very successful.

And there we are, right back at the beginning.

If you were to ask me what I do, I’d tell you that I help entrepreneurs and business leaders solve unique (and sometimes) complex challenges using technology development and intelligent workflow.

If you were to ask me what that actually means, I’d tell you that I spend the majority of my time helping them discover and define two comprehensively relative words:


Because, of course, we all already know exactly what those two words mean, right?

Only we don’t know at all – even worse, we spend almost no time to discover and define them for ourselves. Imagine if we universally accepted the definition of other words that are equally relative?

Like, expensive.
Or, fun.
Even, interesting.

(Just ask my wife how fun and interesting the NFL is.)

You can’t truly define success until you can define happiness. And you can’t begin to discover happiness until you shake off the fabricated notion that being comfortable is the one, indispensable quality that matters most.

It’s not.

Most of us have been conditioned to believe that success is measured by money, and money leads to happiness, because happiness is being comfortable. If you cut through the clutter and scripted responses, you’ll almost exclusively hear people say:

If my company/business/product can be successful, that success can make me a lot of money. And when I have a lot of money, I’ll be happy because my life will be comfortable.

Boiled down:

“I want to be successful so I can be comfortable.”


“I want to be successful because I’m uncomfortable.”

If you make comfort the ultimate achievement of your entrepreneurial journey, you will never be truly happy because happiness has very little to do with being comfortable.

And if you can’t find personal happiness in what you’re setting out to accomplish, then what’s the point of being successful?

So often, smart, talented people with fantastic ideas spend some of their best years chasing after success and happiness without ever considering how they’re individually expressed, understood or realized in their own lives. They blindly and sometimes unknowingly accept the lie that comfort is the ultimate destination of all achievement in life.

Then one day, when all the bills (and future bills) are paid, big picture goals are realized, execution tasks are delegated, and everything about life feels pretty comfortable, they wonder…

Why don’t I feel very happy?

Don’t make the costly mistake of ambitiously driving towards success and happiness without an examination of what those two words actually mean.

And most importantly, don’t believe the lie that being comfortable is the same thing as being happy.

If you start your entrepreneurial journey with a true consideration of the end, you’ll always find your way back to the right beginning.

Follow the #WiseUp Campaign

Over the next several weeks, you’ll hear how my friends and colleagues – across multiple and diverse industries – responded to one awkwardly open-ended question…

Showing 3 comments
  • Jesse

    Well said! Glad you found success and happiness!!!!

  • James Riley

    We’re always interested in your articles! I really felt what you wrote was well stated. For many happiness & comfort is the meaning & purpose of life & true happiness is an inner quality of the mind that brings peace & that quality comes from (The Prince Of Peace) & if your mind is at peace you are happy. For you can have everything the world can offer, pleasure, possessions, power but lack peace of mind you can never be happy.

    Keep writing man, you have a gift!! Love dad❤️.

  • Justin

    Great post.

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Hey, I’m Jason. I solve digital problems for brands with purpose. Ready to go? Text, call or email.

(760) 284-0732