Are you a Post-Achievement Professional?

An Investment Banker takes a trip down to Mexico where he meets a local fisherman. The banker brings the fresh fish back to his villa and it’s the most delicious fish he’s ever tasted.

The banker comes back the next morning with a question.

“Why do you only fish 2 hours a day?” he asks.

“I only need to fish that much. Once I’m done, I go take a nap, play with my kids, jam on my guitar and have a glass of wine with my friends,” replies the fisherman.

The banker is besides himself. The fisherman was sitting on an untapped goldmine of fish (and profits).

He digs deep into his MBA experience and puts forth an idea:

“Hear me out. We’re gonna scale you. First we’ll raise a little bit of growth equity so that you can buy some additional boats and hire more fisherman. Then we’ll add a distribution center inland. After that, we’ll set up shipping routes to all the major cities in North America. And in two years we’ll be looking at an IPO and you’ll be rich!!!”

The fisherman gives him a befuddled look. “But what would I do with all that money,” he asks.

“You could fish for two hours, take a nap, jam on the guitar, play with your kids and have a glass of wine with your friends every single day!

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Hi, I’m Khe Hy. 14 years ago I quit my 7-figure job on Wall Street to become a writer. I explore topics like money, happiness, ambition, relationships, productivity and more.

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The deferred life plan

Now we know you’re definitely not the fisherman.

You’re probably more of the banker who’s pursuing the deferred life plan (and probably also beholden to the golden handcuffs).

And while the life of a banker is a cushy and cozy existence, you’re also left wondering “Is this It” and when do I actually get to start enjoying today?

And to be fair, the life of the fisherman doesn’t feel like a viable alternative. It’s missing drive, ambition, struggle and – of course – the giant payday that awaits on the other side.

But what if the fisherman-banker pairing is the wrong duality? I’m here to propose that there’s another path: The Post-Achievement Professional.

Post-Achievement Professionals: An origin story

The Post-Achievement professional is a special kind of professional.

But they enter the world Pre-Achievement.

At a very young age they enter into an unspoken contract with themselves. It’s a simple contract that says, “The key to happiness is to achieve.”

The conditions that surround this tacit contract can vary. For some, it’s inherited via their parents (and tiger parents) who themselves signed onto the deal when they were young. For others, it’s a ticket out of poverty and economic insecurity. All while Western culture and media narratives continue to propagate the capitalist dream of financial independence, a life of luxury and the bliss retiring before the ripe old age of 59 1/2.

Yet somewhere along the rat race for promotions, bonuses and liquidity events, the Post-Achievement Professional starts to question the playbook. They start to wonder why:

  • They can never stop thinking about work
  • They’re going through the motions in life
  • They don’t see any impact from their grueling hours
  • They worry about money (even though they have lots of it)
  • They’re constantly comparing themselves to others

They thought that all the achievements would look like a vertically instead step function:

But instead, it looks more like the constant dissatisfaction of addiction:

At some point, they realize start to realize that maybe the Achievement Playbook was a flawed one.

And maybe it’s time to throw it out.

To burn the motherfucker down.

Are you looking to become a Post-Achievement Professional? Join a likeminded group of ambitious and intentional professionals looking to rewrite their career journeys by enrolling in one of our coaching programs.

Post-Achievement sounds nice – but show me the money

Money plays a big role in this story. After all, the achievement is in service of some much larger spoils. The big payday on the other side of the rainbow.

And you’re absolutely right (but don’t forget the marginal utility of each additional dollar).

So let me introduce a trusty 2×2 matrix that captures the Post-Achievement Professional framework:

We’ll evaluate each quadrant.

The Eager Beavers (Pre-Financial, Pre-Achievement)

The bright-eyed and bushy-tailed college graduates who are just getting started on their Post-Achievement journey. They got the grades. And the degrees. And they are ready to watch the playbook work for them. They’re predominantly Gen Zs who don’t have the Do-What-You-Love call to arms of Millennials and the You-Gotta-Put-in-Your-Time cynicism of Gen X and Boomers. Let’s just say that the broader Achievement Narrative is already triggering their bullshit meter. They’re Pre-Financial because they haven’t made any money. And they’re Pre-Achievement because they haven’t done anything (besides be their High School Valedictorian).

The HENRYs (Pre-financial, Post-Achievement)

This group works at FAANG, on Wall Street, consulting and VC-backed start-ups. HENRY stands for High-Earners, Not Rich Yet. Here’s the Financial Samurai’s definition of the cohort:

These workers often attend good schools and join industries such as technology, management consulting, investment banking, law, and medicine. As a result, they end up making more money than the average person. However, given many of these high-paying jobs are located in expensive cities, they often don’t feel like they are getting ahead. HENRYs are usually under 40 years old, but can really be of any age. In terms of income, HENRYs are often defined as making at least $100,000 a year.

Now you’re probably saying to yourself, “These folks are still early in their careers, they can’t possibly have achieved everything that there is to achieve. How can they be Post-Achievement?

And while technically, you’re right this group is starting to feel the jadedness of the Achievement Hamster Wheel. They’re the ones starting to question if this playbook is worth dedicating the next 30 years of their lives.

In fact, when I was in NYC during the summer of 2023 (in the midst of the crazy Fed rate hikes) I met many professionals from Facebook and Google who had just gotten laid off (or had taken a buy-out). I’d put them in this Red Area as many of them decided not to re-enter the rat race.

They downsized, moved out of expensive cities, started working for themselves and generally retired from the big-money chase. Instead opting for a much simpler and lower-key existence.

Not a worry in the world aka “NAWITW” (Post-Financial, Post-Achievement)

These are the whales. The big dawgs. The ones who’ve “made it.”

Exited founders. Hedge fund (and VC and PE) managers livin’ off of that juicy 2/20.

They’re Post-Financial, because they objectively never need to work again. And they’re Post-Achievement because by societal and cultural norms, they’re business heroes. (In fact, many of these folks will then “pivot” and try to become famous on Twitter or by writing books.)

Now since 99% of us aren’t in this category (and probably will never be). But the promise of you’ll Never Have a Worry in the World might not materialize. You may have heard Jim Carrey’s words of wisdom:

I think everybody should get rich and famous and do everything they ever dreamed of so they can see that it’s not the answer.

Now, again. If you want to be rich and famous, Jim Carrey ain’t gonna stop you. But I work with countless folks (in my 1:1 coaching practice) in this bucket and I promise you that they’re just like you and I.

Sure, they have drivers, chefs and multiple homes. But they still worry about money. Their identity is on shaky ground. They struggle in their marriages. They struggle to be present with their kids. They’re lonely. They don’t feel alive and energized.

But again – telling someone this can only take you so far. They’ve got to experience it for themselves.

Trust Fund Kids (Pre-Achievement, Post-Financial)

I’m not going to give this quadrant any airtime.

They definitely are not RadReaders.

Post-Achievement ain’t the same for everyone

I think your graph is missing a Z-axis.

Paul Millerd author of The Pathless Path

Now that we’ve run through the matrix, you’re probably still scratching your head.

Let’s go back to The Banker, who is in the top-right quadrant – yet still plagued with angst and dissatisfaction.

Then there’s The Fisherman, a matrix-buster of sorts. What quadrant do they belong to?

Here’s where it gets tricky. Just like answering the question Is $5 Million Enough to Retire, the answer is a disheartening “it depends.”

I’ll use myself as an example. I work 30-40 hours a week purely on my own terms. I don’t have a boss. Don’t have meetings before 11:30 am (so that I can surf). I dedicate 2-3 hours a day to self-care (meditation, reading).

Yet we spend $200-300k a year (a big chunk on rent). I need to work to support my lifestyle. (Here’s a detailed breakdown of our finances.)

Oh, and I love my “work.”

So here’s the question? Am I Post-Financial?

I’d argue yes – since I have time freedom and the money to do whatever I want.

But since I can’t live off dividends or passive income, the textbook answer would say that I am pre-financial.

The same can be said about the non-stationary nature of being Post-Achievement. There are countless professionals in the world who derive their sense of identity, self-worth and community from not achieving things that can be measured by others.

You and I just aren’t one of these people 😉

How do you become a Post-Achievement Professional?

There’s another classic parable about becoming a partner at a law firm.

Yes, if you’re in corporate law at a white-shoe law firm in NYC you might clear $1,000/hour.

But the true prize of becoming a partner?

It’s like winning a pie eating contest… where the prize is more pie.

So far, we’ve discussed the Post-Achievement professional being someone who starts to realize on their own volition that achieving things doesn’t deliver the enduring peace and happiness that they thought it would. (Like the pie-eating contest winner.)

But there are other reasons that people become Post-Achievement professionals.

A brush with mortality

In my conversation with the former financial services executive Manisha Thakor we discuss how she nearly died – twice. In her pursuit of The Number, she had burnt herself to a crisp, gotten divorced and had two major health scares. The first health scare was when she contracted a severe case of dengue fever after a trip to Laos. The symptoms were gnarly: persistent vomiting, internal bleeding and organ failure. In Thakor’s book MoneyZen: The Secret to Finding your Enough she describes this inferno:

I developed a dangerously high 104 degree fever; chills so strong my teeth chattered with a force I never knew possible; bones that hurt so much to a degree that I was put on morphine; and oxygenation levels so low that I was quite literally grasping for air.

The doctors were unsure if she would make it, so her parents and brother flew to her to be by her bedside. Thakor adds:

I discovered the old cliche is absolutely spot-on: No one ever lies on their deathbed thinking, I wish I had worked more.

And while this should’ve marked a turning point in her relentless pursuit of achievement, the moment she realized she would survive, she was back at the grind. Immediately ordering her assistant to devise a game plan so that she could work from the hospital for her 3 months of doctor-ordered bedrest during her recovery.

Thankor had second brush with mortality that finally got her to step off the hamster wheel. This happened at age 49 when she was diagnosed with hyper-inflammation and an acute case of Epstein Barr – akin to a debilitating case of mono. Her doctor explained further that:

Years of stress-induced cortisol had not only made it impossible for her immune system to efficiently fend off the virus, but [her] body had also started to attack itself.

The only remedy was 6 months of bedrest, with absolutely no work. It was at this crossroads that she realized that she had strayed so far from her original life vision that she ultimately rebuilt her life around 3 core principles: small joys, simplicity and financial independence.

A major life event

It’s not just a major illness that can throw you into the quadrant of Post-Achievement – this can also arise from a major life event.

And a common life event that reshuffles the deck is having kids.

In my essay One Day your no Longer their Favorite person, I describe a special window of parenting:

“There’s a magical window – 8 to 12 years – during which you and your wife are their absolute favorite people in the world. They wait by the door for you to come home like a puppy. There’s no one on earth they’d rather be with. And then it’s gone. Now it doesn’t mean that they don’t love you as much. They still need you just as much. But the magical window is gone.”

Now while it ain’t easy, some Post-Achievement professionals will reorient their career (and desires) around being totally immersed in their kids’ lives. Admittedly, this isn’t always possible for a rash of reasons – financial pressures, job constraints, caretaking responsibilities and chronic health issues.

But with some creativity and the ingenuity of the human spirit, it is possible to reprioritize parenthood at the (perceived) expense of professional achievement. Financial Advisor (and RadReader) Jeremy Walter wrote about finding his Enough and the real trade-offs that ensued. Admittedly, as a small business owner he had some things working in his favor:

I have tremendous and loyal clients that span the spectrum from accumulators to retirees, we live in a relatively affordable area, I have no corporate ladder to climb, and my business model allows for recurring revenue.

But more importantly, he had reached his own version of Post-Achievement:

I don’t desire More. I don’t want to have the largest advisory firm, I don’t want to be in the top X% of income earners, I don’t want to be on the Forbes list. If I did want these things, I’d have to Do More to Get More. I’d have to hire employees. I’d need additional office space. I’d need to invest more time and more resources to get More clients/revenue/recognition.

And the trade-off was crystal clear to Walter:

“As a dad to small kids, I sometimes think that we all have it backwards: we spend our 30s and 40s working hard towards career goals, when in reality it’s this time that’s most valuable with our children! Perhaps we should all coast through our middle years then work hard when the kids start heading out on their own.”

(We’ll cover the loss of self-obsession a bit later in the essay.)

How did we get here?

How did we got to a place where achievement becomes the bedrock of our self-worth, identities and raison d’êtres?

Status games are everywhere (and unavoidable)

First, there’s status. Human beings are status-seeking machines. In my essay Status Games: Absurd or Necessary I explored how status originally involved questions of life or death within the tribe:

“Social status is a universal cue to the control of resources. Along with status comes better food, more abundant territory, superior health care.”

And since human beings are social beings – we’re always looking at our positioning relative to others. Yes, even if you decide to live in a cave, you’re making the status statement of “I don’t care about all the things y’all care about!” Here’s Stanford sociologist Cecilia Ridgeway on how Status Games are so intertwined in our lives:

[Status games] are part of the way we make our living or how we manage our lives. But status ends up being everywhere because it infects all these things. Because so many of the things require coordination with others to do properly. 

There’s no better example of status games than this social experiment of looking at someone for a job. They have two options:

Job offer A pays $100,000 per year but your similarly situated co-workers earn $200,000.

Job offer B pays $50,000, but your co-workers make $25,000 a year.

The chilling result: 50% of Americans would rather take B. Yup, they’d rather earn less but be better off relatively than their peers.

(Editor’s Note: I see this study quoted often, but have never seen the study itself.)

Should we blame Neo-Liberalism?

I did not have commenting about economic systems on my 2024 Bingo Card, but hear me out. The South Korean born German philosopher Byung-Chul Han has written extensively about Neo-Liberalism and Burnout Culture. I was first introduced to his work via a podcast on Achievement Society and the rise of narcissism, depression and anxiety (via Philosophize This!) and it absolutely blew my mind.

As a refresher (because I needed one too) Neo-Liberalism has nothing to do with progressive politics of the left – it spans red and blue. Neoliberalism is an economic and political ideology that emphasizes free-market capitalism, deregulation, and limited government intervention. It advocates for privatization of state-owned enterprises, liberalization of trade and investment, and a focus on individual entrepreneurship and competition. It’s the foundation of globalization.

In The Burnout Society Han argues Neo-Liberalism’s focus on removing constraints (i.e. de-regulation) flows downstream to the individual. We used to live in a society that was full of constraints. If you were born a peasant, you stayed a peasant. You married someone from the opposite sex. You couldn’t drink alcohol or gamble. This was a disciplinary society, one that made individuals “obedience subjects.”

Fast-forward to today and all these constraints have been removed. You can be anything. Anyone can be the CEO of Google (or so the story goes). You have unlimited potential.

Well, it requires further exploration. Han argues that we go from being obedience subjects to achievement subjects. We’re no longer workers, we’re “entrepreneurs of ourselves” – commodities (i.e. human capital) that also can be transacted upon using the mechanisms of the free-market. Therefore we give ourselves a “market value” which fluctuates based upon productivity, performance, success and achievement.

It gets even juicier.

This sets the stage for what Han calls Self-Exploitation where knowledge workers are constantly investing and improving themselves (um, hello podcasts at 2x speed). We internalize the pressure to perform and excel. And unlike the clear oppressor-oppressed relationship in traditional forms of exploitation (i.e. capital versus labor), self-exploitation makes it difficult for individuals to recognize the source of their stress and fatigue.

The “trance of unworthiness

Is there a relationship between the need to achieve and a deficiency of self-worth? If there was a relationship between the two, it could be the missing link in the transition towards becoming a Post-Achievement Professional.

In my essay examining the Enneagram “Achiever” archetype (Type 3) a common fear emerges:

They fear that they have no inherent value if they do not accomplish or succeed at external things.

I wrote that at their best, “achievers are ambitious, highly effective, self-assured and embody widely admired cultural standards.

But when pulled to their extreme, bad shit happens:

Their self-assuredness turns into a fear of failure.

Their charm metastasizes into narcissism.

Their ambition becomes exploitative and opportunistic.

What does the dark side of Achievers look like? Patrick Bateman.

In the book Radical Acceptance, the spiritual teacher Tara Brach describes the “trance of unworthiness” with a harrowing story about a daughter (Marilyn) tending to her mom in hospice.

Marilyn spent many hours sitting at her bedside – reading to her, meditating next to her, holding her hand and telling her over and over that she loved her. Most of the time Marilyn’s mother remained unconscious, her breath labored and erratic. One morning, she suddenly opened her eyes and looked clearly and intently at her daughter. “You, know,” she whispered, “all my life I thought something was wrong with me.” Shaking her head slightly as if to say, “What a waste,” she closed her eyes and drifted back into a coma. Several hours later she passed away.

How many of us are spending our careers filling up a bucket with “achievements – only to realize that the bucket has a hole in it.

How do you stay a Post-Achievement Professional?

Kudos for making it this far into the post. You’ve stepped into the path of the Post-Achievement Professional but there’s still an open question: What’s on the other side? Here’s my best attempt to distill the daily and lived experience of the handful of Post-Achievement Professionals in our community:

  1. You’re living in alignment
  2. Healthy source of motivation
  3. Desires are in check (and you’re clear on your enough)
  4. Ditch the myth of scale
  5. Stop viewing time as the enemy
  6. Lose the self-obsession

1. You’re living in alignment

For the first 20 years of my adult life, I was obsessed with productivity. GTD, $10K Work, Notion, you name it – I tried it.

Heck, I created an entire business around helping people squeeze more out of their days. However, I recently retired from the productivity genre after a simple realization. Chasing productivity is the wrong game, what really matters is if you’re living in alignment.

If how you spend your time and money aligns with what you value, by definition you’re productive.

Now, that’s easier said than done. You have to know what you value. You need some degree of control of your time. And while money helps, it can only take you so far.

2. Healthy source of motivation

Pre-Achievement professionals are often driven by an insecurity or unmet desire. Maybe you were the last person picked on the soccer team. The child who always got the hand-me-downs. Or were told you “walk like a girl.” (That last one is mine – and it was the ’80s.)

What the Pre-Achievement professional does is harness that criticism to turn it into gold. A “told ya so” moment of sorts.

But there’s countless research on the limits of being extrinsically motivated. Self-Determination Theory by (Edward Deci and Richard Ryan) highlights a few of these differences:

Intrinsically motivated people:

  • Show higher levels of creativity, cognitive flexibility, and overall engagement
  • Have more sustainable and of higher quality performance because they are self-driven and enjoyable
  • Are more resilient to setbacks
  • Have higher levels of personal well-being and satisfaction

Extrinsically motivated people:

  • Perform well on routine tasks, but performance diminishes when the rewards are removed
  • Are more prone to “surface learning,” where the primary goal is to meet the external requirements (rather than to understand the material deeply)
  • Are less likely to be fulfilled over long-periods of time since they always need a new reward

The podcaster-turned-VC Patrick O’Shaughnessy described how “great outcomes require an unusual fuel source:”

Great long term outcomes require an unusual fuel source. Chips on shoulders is one, but I tried that and it almost killed me. The best long term fuel source is some repeated act that energizes you in a way that then lets you become a generative person, who uses the energy to make things for others. A great question is “what is your renewable fuel source?” While its not perfect, I think the best answer is “do what you want.”

3. Desires are in check (and you’re clear on your enough)

The Pre-Achievement Professional often falls into a desire trap. These desires start from a healthy basis, looking to cover the bottom rungs of Maslowe’s Hierarchy – shelter, food and safety.

But over time, these desires metastisize. They engulf second homes, fancy cars, exclusive country club memberships – all under the umbrella of lifestyle creep. This behavior becomes even more problematic when you try to acquire things that money cannot buy.

Here’s where the Pre-Achievement Professional gets stuck on the hamster wheel. They are hypnotized by the belief that they’re one purchase – one achievement – away from enduring happiness and peace. But looking solely at what you have misses a key component of the equation.

In Arthur Brooks’ book From Strength to Strength, he lays out a simple formula:

Satisfaction = what you have ÷ what you want

Brooks continues with a powerful indictment of the hedonic treadmill:

The secret to satisfaction is not to increase our haves—that will never work (or at least, it will never last). That is the treadmill formula, not the satisfaction formula. The secret is to manage our wants. By managing what we want instead of what we have, we give ourselves a chance to lead more satisfied lives.

4. Ditch the myth of scale

Scale is seductive. A common refrain from Pre-Achievement professionals is “If you’re not growing, you’re shrinking.” Others have said, “Happiness is progress.”

And while I not against any measures to improve one’s self – the belief that everything must always be growing must be questioned. (Especially when it comes to bank balances and entrepreneurial pursuits.) Yet it’s still taboo to put the brakes on growth, or – god forbid – leave money on the table.

One of my favorite business philosophies is based on Paul Graham’s essay, Do Things That Don’t Scale. And while it applies predominantly to early-stage startups, it’s a lesson that I try to apply to all facets of my life.

Here are some things that don’t scale (but bring me tremendous joy):

  • I respond to many readers’ questions (often with a personalized Loom video)
  • I send handwritten cards to mentors and clients
  • I obsess about the design details across our various digital properties
  • I’ll meet up in person with someone who has shown a genuine interest in picking my brain
  • I speak on podcasts with very small audiences

It’s taken me a while to realize, but the activity that brings me true life satisfaction is having earnest conversations. If I do that, do it well, and do it often – I’m doing great.

5. Stop viewing time as the enemy

Time is not your enemy. Time is not a commodity. Time is not something that you bottle up so that it can be maximized.

Many of you reading this will disagree. You’ll listen to podcasts on productivity (whilst doing a productive activity like running on a treadmill). But we’ve got to ask ourselves, what’s all this productivity for? (And if you had a year to live, would productivity still matter?)

Why is this narrative on time so hard to refute? If we return to Byung-Chul Han’s concept of The Achievement Self and individuals keeping a “scoreboard” of their market values, time becomes a critical asset. More time boosts your value.

But I’d argue that there’s a deeper reason we view time as an enemy: our mortality. In my post deconstructing my fear of death, I wrote about the terrifying fact that we are finite beings living in infinite time:

During this [nightmare], all I saw were stars passing me by, like the opening credits of Star Wars. And centered amongst these stars was a rock, drifting away from me. As it disappeared, the rock turned into a pebble, then a speck of dust. Ultimately it disappeared as an indiscernible particle. As a child, I thought the rock was a metaphor for my brain; today (as an aspiring guru) I have the lexicon to call it my essence. My disappearing essence.

6. Lose the self-obsession

OK, time for some real-talk. Achievement-oriented professionals are borderline narcissists. At the end of the day, the pursuit of status and accolades is just a simple siren song that says:

Hey, pay attention to me!

Look at how talented I am.

Look at how smart I am.

Look at how rich I am.

Look at how powerful I am.

LOOK. AT. EVERYTHING. I’VE ACHIEVED.

The transition to becoming a Post-Achievement Professional involves realizing that the world doesn’t revolve around you. You know and feel in your bones what you’ve done and are capable of. It’s a quiet confidence. A surrender into a place that lets you step out of yourself (and your ego) to listen more intently, care more deeply and love others with an open heart.

Achievement pivots to service and love. Being there for others. Cheering on strangers. And doing something crazy.

Taking pride in their achievements for a change.

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