Success Could Be In The Way Of Your Fulfillment – Everyday Fulfillment
No Vacation Required
What if the version of success you’ve been chasing isn’t actually yours?
That’s where this week’s conversation begins.
In the first episode of this fulfillment series, we talked about the dream of the planet – the collection of cultural expectations that quietly tells us how life is supposed to work. In the second episode, we explored what happens when friends, family, and other people in our lives have their own dreams for us.
This week, we’re talking about success.
The challenge is that most of us inherit an idea of success long before we ever stop to ask whether it actually fits. Bigger titles, nicer houses, expensive cars – we’re surrounded by examples of what a successful life is supposed to look like.
But what if the things we’re chasing aren’t the things we actually want?
In this episode, we share a handful of personal stories that highlight just how deeply these ideas show up in everyday life. We talk about why alternative lifestyles can be so difficult for people to imagine, why freedom often looks strange from the outside, and how easy it is to confuse someone else’s definition of success with your own.
Onward and Inward,
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CHAPTERS:
(00:00) Mind Share: Why Beef Season 2 is worth your attention
(01:33) The third pillar of fulfillment: Success
(04:23) Story #1: The neighborhood where everyone is their job title
(07:23) Story #2: “We could never afford your lifestyle”
(10:47) The real problem: Success can limit imagination
(12:12) The retired traveler and the retirement script
(15:00) Lack of creativity and the inability to imagine alternatives
(17:07) The hidden costs of conventional success
(21:00) Choice, conformity, and the daily work of staying aligned
(24:22) Defining success on your own terms
(27:01) Nice things, personal values, and intentional tradeoffs
(28:07) Mailbag: Everyday examples of disappointing other people
(29:30) Freedom, flexibility, and the reactions they provoke
KEY TAKEAWAYS:
Success Is Often Borrowed: Many people spend years pursuing cultural definitions of success without ever asking whether those goals genuinely align with their values, priorities, and vision for life.
Every Version of Success Has Tradeoffs: A larger paycheck, prestigious title, or luxury lifestyle may provide benefits, but they also require sacrifices. Fulfillment comes from consciously choosing the tradeoffs that matter most to you.
You Need Self-Knowledge to Define Success for Yourself: The cultural script is loud. Without a strong understanding of who you are and what you value, it’s easy to mistake someone else’s definition of success for your own.
TRANSCRIPT:
(The following conversation is a consolidated, reader-friendly version of the episode. It is created using AI and may contain some errors.)
Kent
Okay, I’ve got something on my mind this week because I knew we were going to be recording about success as it relates to fulfillment and the world’s idea of success.
I can’t stop thinking about Beef Season 2. To be clear, I would have mentioned it even if it had nothing to do with today’s topic because it’s been on my mind, but it actually does connect to ideas of fulfillment, success, and striving.
So if you’re looking for something good to watch, check out Beef Season 2. And if you’re interested in fulfillment and the things we talk about on this podcast, put an extra star next to it. Great acting, great writing, and some really interesting themes.
Caanan
It was very good. We both kept saying it felt a little like The White Lotus, but maybe with a more direct plot running through it.
Kent
One storyline affecting multiple people. Honestly, we were kind of thinking it might even be better than The White Lotus.
So we’re in the third episode of our fulfillment series.
The first episode was about fulfillment as viewed through what we call the dream of the planet—the cultural script that tells us how life is supposed to work. The second episode was about the dream of everyone else, meaning the expectations that friends, family, and other people place on us.
When you combine those two things, it becomes nearly impossible to figure out what fulfillment means to you as an individual.
As we’ve said, this season is centered on the conversations we most want to have. Through our own experience and through working with thousands of clients over the last couple of decades, we’ve seen that people struggle with fulfillment. They struggle with change. They struggle with knowing themselves.
So we’re committed to sharing the best information we know from our lived experience and our work so people have something to think about when they’re asking themselves questions like:
What am I doing?
What does fulfillment mean to me?
Am I fulfilled?
This week we’re talking about success.
As we were preparing for this episode, we realized there were so many stories related to success that we couldn’t possibly choose just one. So we’re each sharing a shorter story.
I’ll go first.
We were heading to a new friend’s house for dinner. We pulled into this absolutely adorable neighborhood—beautiful homes, beautiful street, the kind of place where your first instinct is to compliment it.
So we walk in and say something like, “Wow, you live in such a cute neighborhood.”
Immediately, one of the hosts launches into a detailed explanation of what everyone on the block does for work.
“That guy is a VP at Amazon.”
“His wife works at Seattle Children’s.”
“The people in that house do this.”
“The people in that house do that.”
It went on for several minutes.
When it was over, everyone seemed to treat that as the completely normal response to our comment about the neighborhood.
And honestly, in our culture, it kind of is.
Now, before we go any further, I want to be clear about something. We like nice things. We have nice things. We appreciate beautiful neighborhoods, great jobs, nice homes, and successful careers.
After all, we spent years helping people build careers and helping organizations perform better.
This isn’t about being against success or material comfort.
What we’re talking about is the tendency to center those things so completely that they become the primary lens through which we understand ourselves and other people.
Caanan
That reminds me of another story.
We were downtown having drinks with friends. We’d taken the bus because Seattle is actually a wonderful city for walking and public transit.
Afterward, one of our friends offered us a ride home.
We hopped into their very nice car—a very, very nice car—and started talking.
As often happens, the conversation eventually turned toward our lifestyle and the way we’ve structured our lives.
At one point our friend said, “I wish my husband and I could do what you guys do, but I just don’t think we could ever afford it.”
And then there was this moment of silence.
Because the funny thing is that our lifestyle actually requires far less money than theirs does.
Now, I understand that appearances can be deceiving. Plenty of people have expensive things and financial stress at the same time.
But that wasn’t the situation here.
What struck me afterward was that I don’t think the issue was really affordability.
I think the issue was imagination.
This couple has successfully achieved what our culture tells them success looks like. They’re living inside the shared dream.
And because of that, it’s difficult to imagine a fundamentally different way of living.
Kent
That’s exactly why I love that story.
On paper, they could do almost anything they wanted.
But when you become attached to a particular version of success, it can be hard to imagine alternatives.
That actually reminds me of another experience we had recently while hiking.
We got to chatting with a woman on the trail who was talking about travel and retirement. Throughout the conversation, she kept framing things in terms of retirement.
“We get to do that because we’re retired.”
“That’s what retirement allows you to do.”
“We can finally travel.”
At one point she mentioned a three-week trip to Norway. Naturally, we said that sounded amazing.
Again, her response was, “Well, that’s what happens when you’re retired.”
The underlying assumption was that freedom and travel are rewards that come at the end of the process.
You work hard. You follow the script. You accumulate enough success. Then eventually you get to enjoy your life.
As the conversation continued, we started mentioning some of the places we’d visited over the years.
At first she seemed surprised.
Then increasingly confused.
And eventually maybe even a little irritated.
Because we didn’t fit the script.
We weren’t retired, yet we’d visited many of the same places she associated with retirement.
The whole framework stopped making sense.
Caanan
It’s funny because while you were telling that story I wrote down the phrase lack of creativity.
Not creativity in the artistic sense.
Creativity in the sense of being able to imagine that another way might be possible.
That’s what both of these stories have in common.
The retired hiker couldn’t imagine a different way of structuring life.
Our friends couldn’t imagine a different version of success.
They wanted aspects of our lifestyle—the freedom, the flexibility, the ability to own our time—but they couldn’t imagine getting there because they couldn’t imagine letting go of the version of success they were already pursuing.
They’re trying to figure out how to achieve a different outcome without changing the underlying assumptions that created their current reality.
Kent
Exactly.
The hiking conversation also included a discussion about this woman’s adult children.
She talked about them in terms of all the things they couldn’t do because of where they were in life.
One daughter couldn’t spend much time traveling because of her career.
Another had similar constraints.
And while all of those limitations were real, what struck me was how invisible the choices behind those limitations had become.
These were successful people by conventional standards.
But the very decisions that produced that success were also producing the constraints.
Again, it’s not that anyone was doing anything wrong.
It’s just that success comes with tradeoffs.
Caanan
And that’s where the word choice becomes so important.
We are all making choices.
Kent and I make choices every day.
The lifestyle we’ve built didn’t happen by accident.
There were sacrifices.
There were uncomfortable moments.
There were plenty of times when we questioned ourselves and wondered if we were the weird ones.
Even now, we regularly have to ask ourselves:
Does this actually matter to us?
Is this something we genuinely want?
Or is this something we’re being told we’re supposed to want?
Because the pressure to fall back into the cultural script never really goes away.
Kent
I think that’s exactly right.
Even after years of doing this work, there are moments when we’re surrounded by conventional definitions of success and we can feel the pull.
There’s a temptation to wonder whether we’re doing it wrong.
But ultimately, living according to our values feels far better than receiving temporary validation for playing a role that doesn’t fit.
Caanan
When you said “doing the right thing,” what I heard was living according to your values.
Knowing what matters to you.
Making decisions that align with that.
The challenge is that most people never get far enough beneath the surface to discover what those values actually are.
It’s not enough to ask whether something matters to you.
You have to keep digging.
Why does it matter?
Where did that belief come from?
Is it truly yours?
Or did you inherit it from the culture around you?
Kent
That brings us back to one of the core truths we’ve learned over the last twenty years.
You have to know yourself.
If you don’t know yourself, the dream of the planet will always be louder than your own voice.
The expectations of other people will always be louder than your own voice.
The conventional definition of success will always be louder than your own voice.
Only when you understand who you are and what matters to you do you gain the ability to create a different version of success.
Caanan
And to be clear, we’re not saying that everyone should reject traditional markers of success.
Maybe you genuinely want the title.
Maybe you genuinely want the luxury car.
Maybe you genuinely want the big house.
That’s fine.
The point is to understand the tradeoffs.
What are you giving up in order to have those things?
What becomes possible if you choose them?
What becomes impossible?
Once you’ve asked those questions honestly, you might still choose exactly the same path.
But if that path truly aligns with your values, you’ll be satisfied with your life rather than constantly wishing you had someone else’s.
Mailbag
Kent
We received a question related to our recent conversation about disappointing other people.
The listener wanted an example of how this shows up in everyday life.
A simple example happened recently.
We were talking with friends after a stretch of beautiful weather in Seattle.
Someone mentioned wishing they had more time to enjoy the sunshine.
We casually responded that we’d dropped everything and gone for a hike.
Immediately the reaction became, “Wait… how do you do that?”
And that’s the kind of thing we’re talking about.
For us, having control over our time is one of the highest priorities in our lives.
But when people hear that, the reaction is often less excitement and more confusion.
Sometimes even irritation.
We’re incredibly aware of how fortunate we are to have built a life with that level of flexibility.
We don’t take it for granted.
But it’s also an example of how living differently can create friction.
You say something that feels completely normal to you, and suddenly you’re reminded that you’re operating from a different definition of success than many of the people around you.