The dubious promise of financial independence

Last week, we hung out with our man Sherman paralyzed by his $1.2 million salary and bereft of agency over his own life. He’d played his cards right – attending the right schools, developing unique skills and landing in a lucrative industry. Yet the path to financial independence was sealed off to him.

Well that’s an unwelcomed cold shower; if Sherman can’t pull it off, who the heck can? Well, there are a few outliers. On the right side of the distribution, there are the founders of unicorns (Lyft and Zoom) and the recipients of inter-generational wealth (Rothchilds, Pritzkers, and Rockefellers). On the left side of the distribution are the scorched-earth FIRE devotees, eating brown bananas, living in their trucks, and moving out of their beloved cities to save on rent.

And then there’s the 98% of us sandwiched between the two extremes. Should we just throw our hands up in the air and call it a day? Or is Financial Independence just a material (and dubious) solution to an emotional problem?

A $30 Billion industry

Just this week, the Annals of Internal Medicine published a study showing that “taking supplemental vitamins and minerals – either individually or in multivitamins – offers no discernible benefits in terms of reducing risks of death generally.” Whip out the tiny violin, this longitudinal study (which covered 30,000 people over a decade) revealed that while vitamins and minerals can extend your life, they need to come from basic foods and not pills.

Yet half of the US population regularly uses a supplement and 10% report using four supplements each day, bolstering a $30 billion industry. Why? Supplements promise one less pound, one more hour of energy, and a few more hairs on a balding head. In the words of a seasoned marketing executive, they’re “material solutions to an emotional problem.”

“Buy X, solve Y”

Hearing that phrase was quite the triggering experience. How many times had I bought something to solve an emotional problem? I bought a pricey Kindle Oasis because I wanted to read more. The emotional problem? Not feeling like had the right mix of skills as an entrepreneur. (And let’s not talk about the 50 unread books on my Kindle.)

I once bought a $2,000 road bike (which I never used). Emotional problem? The belief that a triathlon would be the challenge that shook me out of my corporate boredom.

Then there’s the numerous iPads I’ve bought in my lifetime (Who REALLY needs an iPad???), thinking that they’d make me more productive or more prolific as a writer. Emotional problem? The nagging anxiety that I was never doing enough and thus being outpaced by my peers.

Those new Nike Metcons for Crossfit? Because I wanted to squat heavier weights. As if squatting more could actually forestall the thing I feared most: my own mortality.

Was my relentless pursuit of Financial Independence yet another emotional problem looking for a solution?

Let’s take a test drive

I don’t know any Rothschilds nor the founders of Lyft. But I’ve been in Sherman’s shoes and have spoken with countless executives and entrepreneurs who have dipped their toes in the kiddie pool of Financial Independence. Some have created profitable side projects and others had some good years that provided the financial runway of stepping off the corporate treadmill. Some for months, others for a couple of years. What pearls of wisdom could they bring back to us? It turns out, they identified three prickly emotional problems.

Emotional problem #1: How can I feel financially secure?

“Protect the principal.” It’s a simple money aphorism that’s part and parcel with linear corporate trajectories. If you’ve saved more than you spend, dropped the leftovers into a Betterment account, and racked up those pay raises – chances are you’ve never seen that magical number in your bank account go down.

Regardless of whether you start with 10 thousand or 10 million dollars worth of savings, nothing can prepare you for the day you stop protecting the principal. And unless you’re a Rothschild or Lyft founder, during your path to financial independence, dipping into your principal will agitate your reptilian fight-or-flight reflex.

The inability to feel financially secure is one of the paradoxes of success. As the latter goes up, the former refuses to budge. Here are a handful of examples of successful professionals who are scared of being broke (emphasis mine):


  • In The Soul of Shame, psychiatrist Curt Thompson describes a successful marketing executive bracing for the day when his business would collapse and “he and his family would one day end up living in a box under a bridge.
  • ABC news anchor Dan Harris who worried that his receding hairline would impact his camera-facing career. In 10% Happier he described his irrational tendency to  “immediately project forward to an unpleasant future (e.g. Balding → Unemployment → Flophouse in Duluth).”
  • Andrew Taggart whose clients include Silicon Valley executives sent me the following note: “I, meanwhile, am beginning to count on my fingers the number of high-powered executives who have mentioned to me their fear of finding themselves in ‘the poorhouse’ someday. (I may have to rent some more fingers.)”


A hedge fund investor (and RadReader) described the importance of letting go of financial security as a key step towards financial independence. His advice for those contemplating a break and/or career switch is to answer the following question:

How much do you value security? This is critical. I’ve been able to have a life transformation because I don’t value security. I’m comfortable with the unknown of what’s next. I don’t need much to be happy. And I can figure things out on the fly.

Emotional problem #2: Why do I feel like there’s never enough?

Our days are book-ended by feeling like we haven’t done enough. And after internalizing this message for years, we internalize it with a simple shortcut: I’m not enough. This is the crux of the scarcity mindset:

The day starts with “I didn’t sleep enough.” Then the rush to get the kids fed and out the door is accompanied by the nagging feeling that as parents we’re “not present enough.” Next, a commute skimming articles on our phones and listening to podcasts at double speed. There’s too much to learn and “not enough time.” A coworker gets that coveted promotion implying there’s “not enough opportunity.” Therefore the new addition to the house will have to wait another year, because obvi, there’s “never enough house.” And as bed time approaches, it’s a race towards Inbox Zero. And what’s the last thought before your head hits the pillow? “I didn’t do enough.” 

This conundrum is a recurring obstacle in my money coaching practice and the simple graph below can diagnose the issue:

Consider an X-axis should without any numerical values, as this flat-lining curve will vary by individual. Most of my clients pursuing financial independence are somewhere between Point B and C. But here’s where the circularity gets a bit tricky. In What’s that next dollar worth to you (and what are you giving up to get it), I wrote about the move towards point D:

“[These clients] tend to have higher incomes, and are usually seeking more time (and more control over their time). For instance, a partner at a law firm could be close to point D but unable to tap into that potential happiness because she’s rarely free to have dinner with her family and is constantly on conference calls during the weekend.”

Which foreshadows the next emotional problem: Even if I had more time, I’m not sure I know what makes me happy…

Emotional problem #3: I’m not sure I know what makes me happy

If you aspire to become financially independent, I need you to stop right now and complete this three-minute exercise.

Close your eyes and imagine you won Powerball. The $764.8 Mega Million kind. You’ll enter the realm of the Rothschilds and have true financial independence. In There’s No Such Thing As the Number I asked you to answer the following question: Now that you’re a Rothschild, how will you spend the next five years of your life?

Five years is a long time, too long to pick one activity (family, travel, exercise, sleep) and do it for an extended period. The math here is simple: sleep 8 hours, spend 3 with your family, exercise and meditate for 2, and read for 1 hour. Even with these generous time allotments (eight hours of sleep?!?!), that leaves 10 hours each day (or 50 hours a week) of time to kill!!!! (Technically, weekends wouldn’t mean anything, so it’s actually 70 hours…)

I took the liberty of beginning this spreadsheet for you below:

And when I coach people busting their asses to achieve Financial Independence, most of them cannot answer the question. They fail to even allocate three of those ten hours. Jason Zweig, the Wall Street journal columnist and author of Your Money and Your Brain succinctly needled these folks with this tweet detailing his most unpopular opinion:

Filling the void

Tim Ferriss, the Maestro of Financial Independence describes “filling the void” of existential dread once you remove work. If you’r reading this, you’ve undoubtedly reached a professional milestone only to watch the accompanying feelings evaporate and morph into “the NEXT goal.” Harvard Professor Michael Norton conducted some dispiriting research on what makes millionaires happy and told The Atlantic’s Joe Pinsker how he interviewed 2,000 people with a net worth over $1 million and asked:

How happy they were on a scale of one to 10, and then how much more money they would need to get to 10. “All the way up the income-wealth spectrum,” Norton told me, “basically everyone says [they’d need] two or three times as much” to be perfectly happy.”

So if you’re seduced by the dubious promise of Financial Independence, first ask yourself: what emotional problem am I looking to solve? Remember, personal transformation is not delivered as a magical supplement. Not as a pay stub. And definitely not as a lottery ticket.

I’d love to take you on an alternative path a slower, deliberate and more Fulfilling Path to Financial Independence. Purchase our digital workshop which includes:


  • A two hour virtual workshop on Financial Independence
  • Two recorded Q&As with Khe Hy
  • activation templates to start planning your path to Fulfilled Financial Independence
  • Lifetime access to the curriculum and modules
  • Private invitation to the Financial Independence Slack Channel
  • Discounts on all upcoming courses and workshops


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