Expectations Never End: Finding freedom after enough

Former CEO retires to a life of health, family, and… expectations [The Other Side of Enough: Interview #2]

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The Way of Work explores stories of where we fit in the world of work. This is part of the new series, The Other Side of Enough, exploring what life is like when you have enough to never work again.

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You can become free from money concerns. But can you ever be free from expectations?

Avon is a former high-performing CEO. Having reached his “enough number,” he now spends his time working on his health and his household, as a stay at home dad. He has some small work projects in between, but that’s not where he’s “playing offense,” as he describes.

Avon (not his real name) is in his 40s and has lived most of his life as many high achievers do: with high expectations.

“[Growing up,] I had all these people who really believed in me. Like a lot of people… teachers, family, friends.

I was like the superstar where I grew up. I had a public reputation. I felt like there was a lot attached to my brand.”

Expectations came up a lot in Avon’s story. How he grew up with them, then defied them, and then how those expectations now seem to linger, only in another form (more on that later).

Avon is clearly philosophical, having thought deeply about existential questions more than most. But you may not agree with his thoughts on meaning. And you may not feel sympathy for his troubles, given his envious position.

Is Avon better off after achieving enough? He says, “yes,” but his unique struggles suggest that getting to the other side of enough doesn’t mean the end of expectations.

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Social isolation

“I feel a little bit like Tom Hanks on that island, [talking to the volleyball] Wilson. And I’m tired of Wilson, because there's no one else to talk to!”

My conversation with Avon started with a jolt. It seemed like I had offered him an opportunity to unload a great weight of thoughts that had been floating around his head, and he felt alone in carrying their burden.

While many of us believe “success” brings social approval, extreme achievement can paradoxically deepen feelings of isolation, by distancing the achiever from others who can no longer relate.

Yeah, that sounds like one of those “nice-to-have-problems,” right?

But whoever we are, we want to feel understood. We want to feel heard.

“I don't know that many people that are in my position or who are living this life. And it's a little awkward.

I'm used to being an outlier. I've been an outlier my whole life. I’ve built a career around being an outlier. But this is probably the most-weird-outlier I've ever been.

[Before I was] within people’s framework, on one side of the bell curve in terms of a point of view. But now I feel like I'm not even within the framework anymore.”

Because of this outlier status, Avon avoids certain social gatherings, especially with old colleagues:

“Yeah, I don't really want to go. I wouldn't know what to tell people.

I wouldn't want to go in there and deflate everybody's bubbles.

And I don't want them to think ‘what's wrong with you,’ either. So forget it.”

These moments of isolation weren’t new to Avon—they were a familiar reminder of the detachment he felt early in his career.

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A journey of self-discovery

After excelling in the structure of childhood and school, Avon’s career started out with an impressive position at a prestigious company. But he quickly realized it wasn’t for him:

“Career-wise, everything is going great. [I realized] I can make lots of money. I can have a Porsche. I can have this. I can have that.

But I'm pretty miserable. This sucks.”

His career takes a sharp turn as he quits his job, letting go of all the prestige, to go on a personal journey of sorts. There he went through a “midlife crisis” in his 20s, asking and answering serious questions about life:

“What is our role? Why are we here? What is the point?

And my conclusion is that we humans have made a mountain out of a molehill. We're just another set of sentient beings on this earth. There were others before us. There will be others after us.

When you just get really quiet, you zoom out, and you look at Earth from the perspective of the Moon, or another planet, or another galaxy… life as we know it is so small.

So if you're not smiling, if you're not enjoying the time you have on Earth…

Because you're lucky to have this time and it is not consequential.

Basically enjoy life to its maximum because you're here, and then you're dead, and that's it. There's nothing bigger than that.”

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Work as a means to an end

While to others, that perspective may sound depressing, it seemed for Avon to offer a refreshing clarity to life. He knew what he had to do now, and the purpose of work became more clear:

“I'll get back on the treadmill. And the goal of the treadmill is to be able to create the freedom.”

And after years of hard work, culminating in his time as a CEO, he accomplished that goal. A fact that he needed to be reminded of when he got there:

“When I [left work] initially, I was pretty depressed.

But then my friend reminded me: ‘Don't you remember? You said that this was your goal. You've arrived.’

And I thought, ‘well, actually, you're right.’ I guess I did arrive.”

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Rediscovering joy in what’s next

When I asked Avon about whether he’d go back to work in some form, while he was less clear about what exactly he’d want to do, he was clear about having the right intentions around it:

“I got to do what I wanted to do. And I was successful. And I was really happy about it. I was really proud of it.

I just couldn't see, ‘what else is there for me to do?’

Just do this again because I can make more money? That's not meaningful. That's not fun. In my mind, I had felt like I had reached the apex.”

But he can’t just do nothing. He has a longing—not for more accolades, but for a renewed sense of purpose. This desire for meaning over monetary gain reveals the complexities of identity after success. It challenges the notion that once you’ve achieved enough, clarity about your next steps will naturally follow.

“I still need things. I'm too much of a problem solver. This is my core skill, right? And I need to put it somewhere. I can't just put it in hibernation.

[I could] go do something that would be for fun. Not for money. Not for impact. Not to build my resume. Not so that I could say something at a social event.

I would just do it because… dare I say it? The word: joy.”

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Something for himself

Avon has a vision for activities he could do just for himself, pursuing these things purely for their own sake, unattached to external measures or expectations.

For Avon, he’s found that achieving enough offers an opportunity to return to the childhood joy he found in sports:

“[One activity that is] deeply personal, not for anybody else, is fitness and sports. This is the most important thing that I do for myself.

This goes back to something deep within me, when I was in high school, I wanted to be an athlete. So I had this hole there of some kind. I had this very neglected itch.

And then, as I was working through the grind years, I was just getting less healthy. I worked out, but I would describe that as the bare minimum.”

He plays sports and trains most weekdays, then seeks out a competitive partner on weekends to hone his skills. He’s also become more involved in his kids’ sports:

“I got to be a kid again.

The best thing as a dad… there can be nothing better than this, to have [an athlete for a kid].”

I believe this engagement in physical activity isn’t just about fitness; it’s part of his quest to rediscover joy inside himself. Reclaiming it, after having been overshadowed by the demands and expectations of his former career.

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Playing offense at home

In his new life, Avon has become the manager of the household. His wife still works, looking to build a career of her own, despite the lack of need to do so for monetary reasons. This imbalance - her working, him not - will be something that comes up again in a minute.

But being a stay-at-home-dad is a lot more than he expected:

“…everything from like, what are we having for dinner? How do we make sure everybody's laundry gets done? What are we watching for movie night? 

In the end it ends up, taking up a lot of time! I can't explain why, but it does.”

Beyond the daily household upkeep, Avon says he is “playing offense” at home with his family, looking for ways to be a “value-add.”

I found this to be a refreshing way of looking at being a parent. Parenting can feel like a game of catch-up that you never really win. You’re playing defense all the time, just trying to get through the day. After hitting enough, Avon has felt the difference:

“I don't think I'm necessarily spending that much more time with them than I was before. But I do think that I'm able to have the mental capacity to help them solve problems.

There's a kind of a qualitative difference in the way I'm engaged with them, that's very hard to describe or articulate.

Without having a job, I feel like I'm basically their coach or mentor, or something like that.

There are ways in which I'm really engaged now in their lives, that really bring me joy.”

Avon has also realized that the time of being an involved father, may be ending soon:

“It's dawned upon me that I only have my kids in my house for another [few] years. Then they'll be gone.

So we're having so much fun together [now].

It's really very, very different than when I was a teenager. My approach to my parents was something like, ‘get the fuck out. I don't wanna be here. Stay out of my life. You don't understand. You don't get it.’

And so I want to really maximize that time with them for the next [few] years. And then, who knows what that leads to. I don't know what that means once they’re adults.

But while I have them and they're mine, I'm gonna squeeze every drop of juice out of this thing.”

But even as Avon has carved out a new role at home, he still wrestles with the pressures he’s carried throughout his life—expectations that really never faded after reaching enough.

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The chains of expectation

Avon enjoys the freedom to structure his life exactly as he chooses, yet this freedom has come with a strange, paradoxical weight. He feels he “should” be taking advantage of this unstructured time - relaxing, reading, enjoying life. But even in the comfort of his success, old expectations persist, holding him to an invisible standard he can’t shake.

The freedom that once felt like a reward has, in some ways, become another expectation in itself:

“I thought I would sleep better, but I don't sleep that much better.

I still don't have answers to [questions I’m] struggling with.

‘Why don't you just enjoy your house for a whole day? Go watch a movie? Watch some TV? Take a nap? Read a book? Just like, do whatever?’

I haven't had one day that looks like that.

I've just been like: go, go, go! I'm still running at a thousand miles per hour, just on a different set of things than I was before.

‘What is going on? Why am I like this as a person?’

It's just a really deeply disconcerting thing. I guess I do feel the need to be socially accepted. Despite being an outlier in my perspective. I don't want to be so much of an outlier that I'm out.”

You might think that, if you were in his situation, you would feel at peace.

But what if everyone around you - your spouse, your kids, your friends - weren’t able to be like you? What if your spouse still worked, trying to build their own career? What if your kids were still building their own lives?

Might you feel held back a bit? Might your freedom feel tainted by the lingering expectations that still remain?

I’ll end with Avon:

“If all I'm doing is playing, and there's no working, then I'm a bit worried about what message that sends [to my family].

‘Why is it that you can't hangout at your house or even for a day on your birthday?’

I think it's because… my family is in it. If I get rid of them, and it's my house for the day, ‘Hell, yeah, I'll have a really damn good day!’

But while I've got them in the house, I can't just be who I want to be.

It should be easy. ‘You have the money, you have the resources, you have the time.’

It's like, ‘What? Why can't you just take a fucking break?’

And I just can't. I can't.”

Thank you to Avon, who chose to be anonymous for this interview, for the deeply personal discussion. This interview was transcribed, then summarized and edited for clarity.

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Bonus Questions

What are resources that have helped you in your transition?

• Siddhartha, by Hermann Hesse

• Zen & The Art of Motorcycle Maintenance, by Robert Pirsig

• Guns, Germs, and Steel, by Jared Diamond

What has been your best purchase, since hitting enough?

• Coach to work with me on my sports

Before & After - on a scale of 1-10 (10 being best), how would you rate the following before and after enough:

• Health: 5 → 8 (+30%)

• Stress (10 is low stress): 6 → 7 (+10%)

• Creativity: 7 → 7 (0%)

• Relationships: 7 → 7 (0%)

• Impact: 6 → 6 (0%)

• Meaning: 7 → 7 (0%)

• Work Hours/Week: 50 → 10 (-80%)

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This is part of the series, The Other Side of Enough, exploring what life is like when you have enough to never work again.

Intro: The Other Side of Enough

Part 1: Everywhere But Home: The search for belonging after reaching financial freedom at 32

Part 2: Expectations Never End: Finding freedom after enough

Part 3: Breaking free from a life that doesn’t fit

Part 4: Will you get what you want, after reaching financial independence?

Part 5: Waiting Decades to Finally Follow Your Dreams

Part 6: After ‘Happily Ever After’