Chasing Success vs. Creating Meaning: The Truth About Fulfillment

I remember the day the executed contract was delivered.


Nine months of work paid off, and I landed the massive deal.


I’d busted my ass for it, and when the deal came through, I was nothing short of ecstatic.


I was happy my hard work paid off, but I was mostly happy about the 75k commission check I earned.


That money was spent before it ever hit my bank account because the money would make up for the fact that the work to create it sucked.


But a couple of things happened that derailed my win.


My company changed course on the fly and determined they would pay the 75k over 3 years, so I’d be getting 25k instead of 75k.


I understand 25k is a tremendous amount of money, but this change wrecked me.  


I was banking on that 75k; like I said, it was already spent, and it would make it all “worth it.”


It would give meaning to the meaningless, and my happiness and self-image depended on it.


Secondly, when years 2 and 3 came around, the 25k I was owed for each year magically disappeared, and no one “remembered” the arrangement.


Oh, and the client tried backing out of a significant part of the deal through a series of blatant lies equal to them saying something along the lines of,


“I know I emailed you that 2+2=4, but that could mean a lot of different things.”


So I was left with 25k, but that’s not what this story is about.


I was left with the fact that I hated working on this deal.


It was nine months of hell of dealing with a terrible client, kissing their collective asses, and dealing with my own company consistently asking where the deal was but offering no real support.


We want the deal for the bottom line, but we won’t invest ourselves too deeply to get it in case it goes belly-up. That way, we don’t have to accept responsibility for it.



Every day I worked on this deal was filled with stress and anxiety.


It was a terrible process that, to this day, 15 years later, when I recall it, I cringe that I thought this was the way to live.


I was chasing an outcome; I was living from the Outside->In.


My happiness and self-image were in the hands of externals, many of which were out of my control.


I didn’t realize it then, but I was relinquishing agency over my life.


I hated the work to create the outcome, and when the outcome changed, I lost what would give the hate for the work meaning.


When I look back on this achievement, that I was convinced (at the time) would be the greatest thing since sliced bread; all I see is a hellish experience and a whole lot of inauthenticity.


I have no idea what I bought with the 25k to give the work meaning, but I definitely know this: I don’t have any of it now.


Let’s juxtapose landing the big “life-changing” deal with writing my first book, “Blank Canvas: How I Reinvented My Life After Prison” and delivering my TedX.


In the beginning stages of creating both achievements, I set lofty external goals like book sales and views. I don’t get in a car without knowing where I’m going, so the goals provided a direction.


I missed, for both my achievements, those lofty goals by a country mile.


For context, I missed my view goal by about 2.88 million.


But when I reflect on the memories of creating both achievements, I’m filled with a deep sense of satisfaction, meaning, fulfillment, and joy.


I feel it as I write these words.


When I see Blank Canvas on my bookshelf at home, in the library, in our town’s independent bookstores, or out in the wild when people share pictures on social media, I smile the relaxed smile of pure contentment.


Writing Blank Canvas and delivering my TedX are two of my greatest successes, regardless of external metrics.


Why? I totally failed to achieve my goals.


The goals were merely a destination; the journey, however, was an act of becoming the person who works toward those goals.


And I loved that journey.


I loved the work of creating the book and the TedX.


The time I invested daily in their creation filled my life with direction, meaning, purpose, and fulfillment.


When I closed my laptop at the end of every work session, I was victorious, no matter the work product I’d created.


My biggest fear pre-prison, and still lingering to this day, is to be seen, heard and understood as my authentic self.


The book and the TedX required that I face that fear every single day I worked on them.


They required me to face the version of myself that made the decisions that landed me in prison, and for a long time, I wanted that version dead.


They required me to unpack my suicide ideation and not only accept that version of myself but also love him fully, deeply, and implicitly.


Both of these achievements were acts of becoming; they were transformational.


They required me to discard the Outside->In model of living and instead embrace an Inside->Out model.


When I live from the Inside->Out, I seize agency over my life.


My decisions are no longer inextricably interwoven and pushed and pulled by externals; they’re driven by what will create the feelings and experience of life I say I want.


They’re driven by authentic expression.


When I operate from the Inside->Out, I love the process, which is all I ever have, because the outcome was never mine to begin with.


Because here’s the thing:


The next minute of life isn’t guaranteed.


I may never reach the outcome I’m working toward. But the journey that’s mine, and I want to enjoy it as much as possible.


If I’m fortunate enough to reach my destination, that’s merely icing on an already delicious cake.