What if your current definition of success is backward?
The commonly accepted definition of success is rooted in the idea that achieving specific milestones will make you happy.
Some of those milestones look like, but certainly not limited to:
- The right school.
- A promising corporate career.
- A lifestyle that effectively communicates to others you’ve “made it.”
It’s a model of external achievements to create inner happiness that’s been passed through generations, leading us to chase the idea of what we believe success means.
It creates a life where we live from the outside -> in.
But what if it was backward?
What if, instead of living from the outside -> in, we learned to live from the inside -> out?
What if our sense of happiness, and its deeper cousin joy, came from within and wasn’t dependent on externals?
What if we choose to feel how we want to feel now, not if we achieve a particular milestone?
What if we redefined success as a connection, creation, and contribution model, not a chase?
It creates a life where we experience life from the inside out.
Pre-prison, I was the poster child of outside -> in living.
I hit many of the prescribed milestones, yet something was missing.
The commonly accepted definition is a highly transactional formula that’s wickedly incomplete.
Success is spelled with a “U,” but it makes no allowance for “You.”
More often than not, the prescribed metrics of success require us to shelf our innermost desires:
Our dreams, our passions, the most profound expression of our authentic selves.
We foolishly believe that one day, when the time is right, we’ll pursue those dreams.
99/100, that time never comes, and the part of ourselves that longed to come alive slowly dies.
The number 1 regret of the dying, according to palliative care nurse Bronnie Ware, is:
“I wish I’d had the courage to live a life true to myself, not the life others expected of me.”
Everyone who expressed this regret chased a definition of success that wasn’t their own. They knew deep down that they weren’t living a life true to themselves.
They never stepped outside the commonly accepted definition of success and experienced profound regret when it was too late to do anything about it.
Here are 3 simple steps to avoid that regret:
Define What Success Feels Like—Not Just What It Looks Like
Instead of listing achievements, ask yourself: “How do I want to feel in my life?”
Fulfilled? Free? Inspired?
Write down the emotions you crave, then identify what activities, relationships, or environments actually cultivate those feelings.
Reconnect with an Abandoned Dream
Think of one passion, hobby, or dream you’ve shelved in pursuit of “success.” It could be as simple as painting, writing, or learning a new skill.
Schedule just one hour this week to engage with it.
There is no pressure to be perfect—just reconnect.
Audit Your Definition of Success
Take 10 minutes to list the current markers you’ve been chasing—titles, income goals, status symbols. Now, beside each one, write: “
Is this truly mine, or was it prescribed by someone else?”
Reflect on what you’d keep if no one were watching.
—
If you’ve checked all the prescribed boxes of “success” and yet you’re woefully unfulfilled, it’s time to redefine success for yourself, not others.
You’ll never find what’s missing when you look outside yourself.
It’s time to put the “You” in success.
—
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.