After 'Happily Ever After'
When what works in work, doesn’t work in life [The Other Side of Enough: Interview #6]
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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. Check out the last post: Waiting Decades to Finally Follow Your Dreams
Imagine you’re living in the middle of your favorite fairy tale. It’s the climax. You just beat the evil wizard, blew up the Death Star, or won the heart of the girl/guy of your dreams. You’ve returned home victorious, basking in your glory.
Okay, so now what?
No, really… what does life look like after the climax fades? When the story ends?
Because this time, there’s no sequel planned. All those skills that helped you beat the bad guys before? They don’t work anymore – in fact, they might make things worse. And who are the bad guys now anyways?
Your lightsaber doesn’t solve your midlife crisis. The love of your life has a weird psychological-tick that gets annoying after a while. And the evil empire you overthrew is replaced by a two-party system, in which neither party seems adequate at running the universe!
My next interviewee, Jeff1, faced a similar situation after returning home from the climax of his career. He won the game when he sold his company, earning more money than he’d ever need. He claimed all the prizes – two extra houses and a private plane, in fact! He rode off into the sunset, happily-ever-after.
Or so he thought.
Because you know that’s not how these stories go. There are no fairy tales here. You know by now that this hero’s story is complicated.
After “retiring” before the age of 50, Jeff realizes some things are off. Parts of his old life that he hated while working, he now misses. Skills that helped him become successful, now backfire. He’s gained unlimited freedom, but struggles with how to spend his time.
Jeff’s story invites us to think: what happens after the hero returns home?
The Hero’s Reinvention
Jeff sold his company in a life-changing deal, achieving the financial freedom most of us only dream about. If we stop there, it’s a fairy tale ending where everything is tied up neatly into a satisfying conclusion. But real life doesn’t end there. Jeff shows that after the glory ends, real life returns.
“I'm sure you're familiar with the hero's journey. The call to adventure and all the perils. And you develop these skills. And then you succeed and you return home, and then you live happily ever after…
But no one ever says: ‘what happened 5 years later on a Thursday?’
We slayed the dragon. The dragon's still dead. So then what happened?
Like, did you develop tennis elbow? Did you have to move your parents into an assisted living facility?”
The new part in Jeff’s journey, looks nothing like the first. In fact, so much from before now holds him back.
“When you get to where I am, in a way, it's time to embark on a second hero's journey. But the catch is all the things you learned before are gonna work against you now.
Because the dragon's already dead. So now it’s different. Your sword does you no good at all.”
Clarity of the Chase
Before his exit, Jeff’s life was clear: build, grow, succeed. The chase for money, however grueling, provided direction.
“There's a benefit I didn't realize while working and chasing money. The outcome was just so simple.
Bang! Bang the rocks together, monkey! Bang the rocks, and then get more rocks. Bang them together. Just keep doing the same thing.”
But when the chase ended, so did that clarity. Work can often feel meaningless, but the act of work can create meaning in itself. When that’s gone, it’s absence can become a source of anxiety.
“[People don’t think about] when the monkey finishes the job. When you don't have to bang rocks together anymore. There's a sense of loss about it.”
When Structure Holds Us Together
In retrospect, Jeff realized that the routines and obligations he used to resent, served a hidden purpose.
“One thing that was surprising to me in retirement was the negative aspect of the loss of structure. When you're in it, you’re like, ‘shit, it's Thursday. I gotta do the accounts receivable meeting.’
And then, when it's gone... I miss something about it. There was a rhythm or cadence to life.”
So many of us believe that freedom is the end goal. But have you ever talked to someone with total freedom?
We envy people like Jeff, who can do anything they want. But stripping away all the routines, habits and structure that are built up over decades comes with a catch.
“When I retired, I said, I'm not gonna use a calendar anymore. I'm just gonna roll with it, have this ultimate flexibility. But what ends up happening is I end up doing a lot of nothing.”
The question then becomes: how does he spend his days?
“People like me hate that question. Not because it's rude, but because sometimes the wheels start spinning about.
‘What do I actually do in a day? What am I doing? What am I?’
Oh yeah, I went and picked up those flanges at Home Depot that I needed for the shelf.
And then I think, ‘no, that was yesterday. That was not today. I did nothing today.’”
The structure that once seemed like a burden now reveals itself as something more.
“You lose all the scaffolding that feels like it was weighing on you. But in a lot of ways it was holding you up.”
Old Virtues, New Vices
Behind Jeff’s success as a founder and CEO were skills that helped him climb to the top—skills that are widely viewed as virtues. But as I’ve said before, every virtue, at some point, becomes a vice:
“One of the biggest reveals is how many of those things that were so effective before – running a company or doing whatever you were doing – are actively hurting you [now].
Not only are they not useful anymore, they're actively hurting you.”
Jeff lists previously valuable skills that now hold him back in his personal life:
accumulating (instead of decumulating),
optimizing (instead of leaving things as they are),
being in control (instead of letting go),
and his favorite: “the uncanny ability to find something that’s wrong and fix it!”
These qualities were essential for running a company, but now, “imagine going on vacation with this person!”
Getting Through Life
I spoke with Jeff on Halloween. His kids are much older now, but we talked about my kids who are still young and love the spirit of the holiday. He used Halloween as a metaphor for the difference between work and personal life.
“One of my great assets-turned-liability was my habit of finishing whatever I was doing as quickly as I could, so I could get to the next thing.
This is exactly the opposite of what you want to do on Halloween.”
He recalls how his business mindset bled into family life.
“I think back to when my kids were [young]. I bet I was trying to figure out how to get through Halloween.
Can we get this done so I can respond to that email or work on my spreadsheet? Or whatever it was.”
The metaphor deepens as Jeff imagines how a business-minded person might approach the holiday.
“Imagine optimizing Halloween. You're gonna have a schedule for when you get your costumes on. You're gonna have a quota for how many candy bars you give away. And you're gonna have a review of your goals and a system process review… [etc.]
Like, we just ruined Halloween, right?”
We laughed about what would happen if my son didn’t meet his candy-collecting quota. How would I hold him accountable for this failure?
“And when you're running a business, that's really helpful (if this was a Halloween business).
But it's not a Halloween business, man. It's just Halloween.”
Jeff uses another poignant example that will hit home for many parents:
“I used to take my kids on Sunday to eat breakfast, and it embarrasses me to say that I thought, ‘oh man, I'd rather just drink some coffee and sleep in.’
At that moment, 15-20 years ago, I would have given anything to have the Sunday [I have now], where I can do anything I want today. Nobody needs anything from me.
But man, I'd give anything now to have one of those back.”
But you can’t save up these moments like money. As Jeff sums it up, “life gives it to you all at once.”
Rebuilding with Energy
Today, Jeff’s chase has nothing to do with money. In fact, “money is forbidden” because he doesn't want to fall back into the familiar thirst for more. As he explains:
“Money and sex are the two addictions where everyone seems to envy the addict. And I have a money addiction.”
Instead of money, Jeff now chases what he calls “energy.” His first step was to move away from sources of bad energy:
“Negative energy is putting your time and resources into something that sucks and you don't want to be doing.”
It may be obvious to spot some negative energy, but the real challenge lies in the subtle ones. Jeff describes how he initially got caught up in chasing extrinsic goals, something that mirrors a conversation I had with Omar:
“So there's an extrinsic-should and intrinsic-should. And when I retired I certainly acted on the extrinsic-shoulds.
‘You should do nonprofit work. You should sit on boards. You should mentor startups. You should be an angel investor. You should, you should, you should.’
And I didn't like most of them. The shoulds, in my view, should be internal. Not what the world tells you.”
The True Limited Resource
Finding positive energy, on the other hand, can be elusive. Some of you might be thinking, "Just find a new dragon to slay." But it's not so simple! It’s no easy task to shift from an obvious source of motivation, like money or success, to something ambiguous like "energy."
“I don't know that you find it. I wish there was a way to find it. I wish there was a treasure map that you could wander and see what squares on the board raise your energy.
[My coach and the author] Rick Eigenbrod talks about inklings where you're drawn to something. You've had one of these ideas that keeps calling you. The very simple idea is just move toward it. So if you want to learn to play the drums, then, go take a lesson or go get some drumsticks and do something about it. And don't fall into the trap of [overthinking it]. Just take that 1st step toward the energy.”
That energy could come from anywhere and as Dr. Jordan Grumet shared before, it's about recognizing purpose in the small moments of life:
“Purpose could be health. It can be spending time with friends. Doing things you like, whatever it is.”
But while Jeff’s financial security might last him a lifetime, energy is a more finite resource.
“I have enough money. I don't know if I'll ever have enough energy.
Energy is draining. You're getting older. There will be a time where you can't lift your kids over your head anymore, or there'll be a time where I can't ski anymore. The bucket is draining.”
Eventually, it all empties.
“Yeah, the sweet embrace of the void.”
The 2nd Hero’s Journey
Jeff's fairy tale didn’t end when he hit “enough.” There’s another adventure after. But unlike the first journey, this one has no map, no treasure, and requires an entirely new set of skills.
His energy now comes from active pursuits – skiing, golf, or mountain biking – and also from helping other post-economic founders in his group: Beyond the Finish Line. Think of it as a gathering of folks like Aragorn, Harry, and other post-exit heroes who are trying to find their way in their new world. And this time, they’re exclusively focused on giving back, not taking any more.
“It's about having enough and being able to resist the temptation to go build more, more, more, more, more.”
Despite all the good fortune in Jeff’s life, he still does not feel settled. I asked him: “how long did it take you to feel comfortable in your new identity?”
“I'll let you know when I get there.
[For 4 years] I had bought, upgraded, and optimized all the things, and realized I'm just spinning here. I'm not going anywhere.
Then it's been 2 years where I'm still trying to figure it out. I can't say I've figured it all out, but at least I can talk intelligently about what happened to me. And I can help others who are going through the same [thing].
So I don't know that I'm comfortable with my new identity. I don't know if I have a new identity.”
So what keeps him going?
“The draw is more curiosity and a desire to be helpful to the next 100 people I talk to about this. And that's enough. That is the other side of enough.”
This interview was transcribed, then summarized and edited for clarity. Any emphasis is mine.
If you’re interested in learning more, check out Jeff’s group Beyond the Finish Line or connect with him on X (@RetiredFounder). He said he’s open to connecting with others in my audience.
Bonus Questions
What are resources that have helped you in your transition?
What Happens When You Get What You Want, by Rick Eigenbrod
What’s Next: The Entrepreneur’s Epilogue and the Paradox of Success
What has been your best purchase, since hitting enough?
Bicycle, golf club membership
What has been your worst purchase, since hitting enough?
Airplane 🤯, beach house
Before & After - on a scale of 1-10 (10 being best), how would you rate the following before and after enough:
Health: 6.5 → 9 (+25%)
Stress (10 is low stress): 1 → 9 (+80%)
Creativity: 8 → 4 (-40%)
Relationships: 8 → 5 (-30%)
Impact: 2 → 5 (+30%)
Meaning: 9 → 3 (-60%)
Work Hours/Week: 80 → 5 (-94%)
This is part of the series, The Other Side of Enough, exploring what life is like when you have enough to never work again. Check out the next part:
This Jeff is NOT Jeff Butler, the founder of Privia Health (the company I worked for)
The draw is more curiosity and a desire to be helpful to the next 100 people I talk to about this. And that's enough.
What a powerful way to end this interview. Thank you.
See this quote from Anne Herendeen "You think money can solve any problem, but all it s good for is buying the things it can, and leaving you free to pursue the things it can't." Hope there will be update of Jeff's story in the future weather he finds his calling which satisfy his soul and heart.