Why Chasing Success Will Never Make You Happy

How will you know when you’ve made it?

What is the metric of success that will inform you that you’ve done it?


If the metric of success is outside yourself, for example, the answer to,


“What’s Your Number?” (The idea that there’s a monetary amount that will make you happy.)


I can tell you what has the highest probability of happening:


You’ll strive, you’ll chase, you’ll work your ass off to get there, and maybe one day, you’ll reach this magical destination.


And you’ll expect a switch to flip, and suddenly, everything in your life will be exactly how it’s meant to be — because you hit “it.”


All the tumblers will align, and you’ll be “happy.”


Sure, you’ll most likely experience happiness that hit your goal, but that happiness will always fade, and you’ll be left feeling empty, confused, and determined that the number wasn’t “right” and that maybe you did something wrong.


To comfort yourself, you’ll expand your lifestyle to meet your new income level.


Hell, you deserve it, right? For all the crap you had to put up with to get there.


Net net, you’re right back where you were before you hit the number.


Your spending is commensurate with your new income (you’re on the golden treadmill), and the magic number that will make you happy has increased.


Back to the chase, you’ll go, believing that if you sprint fast enough, you’ll catch the carrot on a string.


You can see it; it’s so close that your fingers can almost grab it…but it’s always just out of reach.


But the vision of it keeps you going.


You’re constantly chasing without ever feeling arrived. It’s emotionally, mentally and physically exhausting.


You put tremendous effort into catching the carrot, but what is that carrot anyway?


Have you defined it for yourself?


Is it strictly monetary, with the expectation that how you want to feel will come after you grab it?


Do you know where the carrot came from? Is it a product of your upbringing, shoulds, expectations, and what society has told you need to do to be happy?


If capturing the carrot worked, why are you still chasing it? You didn’t catch the “wrong” carrot; you captured an inauthentic carrot.


If you’re ready to get off the golden treadmill, here’s one of the first things you must understand.


You’re the one holding the stick. You can bring the carrot to you.


You can do this when you redefine what success means to you outside of external markers, shoulds, expectations, and other’s opinions.


When you realize you don’t want the carrot you’ve been chasing, you want how you believe it will make you feel when you catch it; you can create a definition of success that brings you authentically to those emotions.


If you believe the carrot will make you happy, what activities can you do right now that make you happy? Do you schedule time for them, or not, because you’re too busy chasing something else?


If you believe the carrot will bring you financial security, but, like me back in my corporate days, you’re the walking definition of lifestyle creep, no amount of carrots will ever make you feel secure.


Cut back on the bullshit you think you think you deserve because the work you do to catch the carrot sucks, so you need to make up for it with materialism. Less spending on things you can’t take with you equals more financial security.


If you believe the carrot will bring you acceptance from others, understand this: they’re not accepting you; they’re accepting your lifestyle.


When you fully, deeply, and implicitly accept yourself, you no longer need anyone to accept you. You’re comfortable in your own skin, and I can’t think of a better place to be.


Try this: slow the treadmill down just enough to catch your breath so you can examine your life.


If the work you do to catch the carrot is without meaning, purpose, and fulfillment, and you have a success-sized hole in the middle of your life, the faster you run, the more you’re handcuffing yourself to the very thing that’s making you suffer.


Ask yourself questions,


“Is this how I envisioned my life?”


“Can I be happy now, in this moment?”


“Who am I really, beyond my professional and financial success?”


“What does success look like beyond professional and financial metrics?”


“If I continue on my path, will it take me to where I authentically want to go or where I believe I should go?”


“If someone were to wave a magic wand, and you could be doing anything you desired to earn money, would you keep doing what you’re doing right now?”


It’s never too late to redefine success for yourself, and the sooner you do, the sooner you realize you’re holding the stick.


The carrot isn’t “out there”; it’s within.


I’m Craig Stanland, a speaker who transforms the hard-won lessons from my journey through federal prison into actionable insights. I empower audiences to unlock their authentic potential, redefine success, and thrive personally and professionally.


Let’s chat if you’re interested in having me speak at your next event. Contact me here.