I know…the title sounds a lot like click-bait, the kind that takes you down an internet rabbit hole.  I want to tell you about one (really hard) step you can take to live a better life.  I could write it in one sentence, but without some context, it’s probably not going to carry much meaning.  If you can stick with me as I weave my way through these pages, I promise to arm you with a real chance to get a handle on some financial stress.

I’m not qualified to speak to psychology, or what really makes the brain tick, but I have spent many hours talking with people about their individual definition of success.  I’ve seen how finance, emotion, and ambition mix in real life, and how it can affect decisions big and small.  Over a decade of conversations later, I can safely write this article, with most of the credit to the books I reference below for tying this up in a bow.

This is a personal finance blog, but let’s address money’s impact on your emotions and well-being.  As hard as one may try, it’s nearly impossible to separate money from emotions, the two are intertwined beyond our capabilities to extract one from the other.  As noted financial guru Tim Maurer likes to say, “personal finance is much more personal than it is finance.”  It’s not our fault; money is not just the tool by which we secure all goods and services, it’s also how we feed our families, put a roof over our head, move from place to place…It’s all but required for our modern existence.  According to the American Psychological Association, money is the number one source of stress in U.S. households, every. single. year.  Every day of our lives, dollars are mixed with a heavy dose of ambition, fear, greed, regret, shame, and so on…

So if we need money, and money is so intertwined with emotions, why is it so damn hard to talk about it?  I apologize ahead of time, we’re going to have to get a little messy…


“It’s my responsibility to be as happy as I can, right here, today” – June Driscoll, 30 Lessons for Living

Dr. Karl Pillemer is the founder and director of the Cornell Institute for Translational Research on Aging.  His title alone tells you he’s more than qualified to speak about ‘getting old.’  When Dr. Pillemer himself turned 50, he says he wondered “could we look at the oldest Americans as experts on how to live our lives?”

He then met June Driscoll, quoted above, and she gave him the final nudge to set out and research what would become the book 30 Lessons for Living.  To create it, he surveyed and interviewed thousands of people over 65, feeling that this group can rightly be considered experts because “they have the enormous advantage of life experience,” and they could assess accurately “what works and what doesn’t.”

The book is an excellent, all-encompassing look at life well-lived, I encourage anyone to read it to gain perspective on whatever challenge you’re facing.  One particular passage has continued to echo for me, and it’s relevant to my point here.  In the chapter that discusses work and career, Dr. Pillemer calls out one startling statistical finding from his work.  Remember, he interviewed over a thousand people:

“No one – not a single person out of a thousand – said that to be happy you should try to work as hard as you can to make money to buy the things that you want.

No one – not a single person – said it’s important to be at least as wealthy as the people around you, and it you have more than they do it’s real success

No one – not a single person – said you should choose your work based on your desired future earning power”

Those stats don’t need much commentary for effect, the 0-for-a-thousand metric slaps you right in the face.  Think how many people that have continued working in a role they hated, ‘just to make partner?’  How many times do you hear someone say ‘I’m miserable but I just want to stay until bonus time?’  

We’re all guilty of falling into this trap at times, but some people live their entire lives in a miserable job or situation by repeating ‘if I can just make it until _______.’

The evidence shows it’s not going to make us happy…but we do it anyway.


“Remembering that we are going to die is the best way I know to avoid the trap of thinking you have something to lose” – Steve Jobs

I use the work of George Kinder in my practice, he was really a pioneer in crossing over from financial planning to life planning.  The difference is subtle but huge.  Pure financial planning has always been rooted in numbers, quantitative, you work with people on dollars and cents.  Kinder’s Three Questions, as they’re known, is a way to force someone to examine their deepest values, with an extra context of finance.  He does this with somewhat unconventional means…to make someone picture their own death.  Here are the questions:

  • Imagine you are financially secure, that you have enough money to take care of your needs, now and in the future.  How would you live your life? Would you change anything?
  • Now imagine that you visit your doctor, who tells you that you have only 5-10 years to live.  You won’t ever feel sick, but you will have no notice of the moment of your death. What will you do in the time you have remaining?  Will you change your life and how will you do it?
  • Finally, imagine that your doctor shocks you with the news that you only have 24 hours to live.  Notice what feelings arise as you confront your very real mortality.  Ask yourself: What did you miss?  Who did you not get to be?  What did you not get to do?

I’ve seen hundreds of these responses, and without giving specific answers, here’s what I can tell you with certainty:  Nobody lists a great car.  Nobody says they would regret not joining the country club.  Nobody says they should have worked more hours.

The answers are usually some combination of:  spend more time with family and friends.  Volunteer more.  Pursue an art or talent, or work in a job that is more fulfilling.  Travel.  Experience more of the world…

You see where this is going.  Once again, we have data that say we’re prioritizing the wrong things, and this time it’s not some old person telling you their lessons of 80 years, it’s YOU!  You’re telling yourself what to prioritize, once you really examine what you value, yet the next day you wake up and go right back to focusing on that new car, or putting in more hours for a bigger bonus.  If a fancy car is really what people deeply value, why don’t think they think about it when they’re picturing their last moments?


“You cannot escape the responsibility of tomorrow by evading it today” – Abraham Lincoln

Dr. Sarah Newcomb is a behavioral economist with Morningstar.  In her new book LOADEDshe uncovered a fascinating little tidbit that I’ve tried to immediately incorporate into my conversations with clients.  In a survey of several hundred U.S residents, her work showed that a person’s perspective on time was far more influential than income, age, education, or gender when it came to personal finance.  The results said that the further someone thinks into the future, the higher their savings rate.  Simply put, if you picture your life in detail 20 years from now, you’re more likely to have a larger balance in your savings account.  

Sarah reports “people who think ahead are more likely to keep track of spending, pay bills on time, and carry zero balance on their credit cards.”  If we invert this concept, you quickly realize that only thinking about the present means you’re going to spend more money and not save.  What a powerful tool!

I’ve said a 10-year plan is laughable in hindsight, so many things will happen on the journey that you’ll change course many times.  If you’ve ever paddled a kayak across a big, busy body of water, you’ll understand the visual.  You’ll go slow, then fast, then turn sideways, hit some waves, probably go backwards at some point…all while still heading towards your original destination far away.  From a financial planning standpoint, this just tells us to make a plan, revisit it regularly, and stick to the process.  I’ve seen the very act of reviewing and reflecting on a broad financial plan with clients resets their daily behaviors to reflect their goals more accurately.


“There is a time in every man’s education when he arrives at the conviction that envy is ignorance; that imitation is suicide” – Ralph Waldo Emerson

Anyone who’s read Emerson knows he speaks broadly and passionately about forging your own path.  This particular quote, from his essay “Self-Reliance,” crystallized all of these concepts for me in a way that I felt comfortable getting all of this out of my head and onto a keyboard.  

When we talk about working a miserable job until that next promotion, waiting for just one more bonus, abandoning our core values so we can get the fancy car, refusing to save for the future so we can make just one more addition to the house…aren’t we really just talking about conformity?  A lack of independence from the herd?  Are we that terrified of being different?

I’ll often engage in a goals conversation with clients, and I’m fond of the phrase ‘remember, there are no rules.’  Ask someone for their goals off the top of their head and you’re likely to get a knee jerk response of ‘new car, bigger house, promotion, etc.’  But…, there are no rules.  No one gives you a life playbook, you don’t HAVE to have the new car, or the bigger house.  We just regurgitate the message of everyone else on our street because ‘that’s what we’re supposed to do.’

”Envy is ignorance…imitation is suicide”

As we saw above, no 80 year-old ever talks about the big promotion they got 40 years ago.  No person ponders their last year of life and reflects longingly on a new Mercedes.  To waste our time and money on these are learned behaviors;  we see what other people are doing and just follow along.  Our culture is saturated with messages of how great everyone is living.  A territory once reserved for and dominated by advertising agencies has now been taken over by that one girl from high school that seems impossibly happy, more so with each, hourly Instagram post.  Society tells us to ‘prove’ our success to others; show what you have!  Spending calls us, it beckons with marketing and the promise of a better lifestyle – if we just make that one, extra purchase.    

Why do we do this to ourselves!?!?  

Study after study tells us that happiness is only correlated with income up to a certain number, and depending on the study, it ends up being somewhere in the $75,000 – $80,000 range.  If you make $10,000/year, you’re going to be happier making $50,000.  If you make $100k and you’re working a miserable job just to get to $120k?  The data say your happiness isn’t going to budge, which is to say if you’re miserable before the money, you’ll be miserable after.

In his book Stumbling on Happiness, Dr. Daniel Gilbert (you probably know him from these Prudential ads) arrives at one conclusion relevant here (I’m paraphrasing for brevity):  if you want to be happy, figure out what makes you miserable…and then stop doing it.

Ask yourself:  are you living that way?


“There is only one success…to be able to spend your life in your own way” – Christopher Morley

There’s a small picture in the bedroom of my family’s cabin.  It’s such a dull frame with a dark background that you have to get really close and squint to see it.  It’s behind a small, ancient TV, you could probably tour the cabin right now and never notice its existence.  An inconspicuous picture in an inconspicuous spot in the Western Pennsylvania mountains.

I don’t know where it originally came from (dad?), I just know it’s been around the family for a long time, it used to hang in our basement.  The picture shows a solitary man in a small fishing boat with the Morley quote above.  It’s not pretty, it’s not very artistic,…yet for decades it has served as a compass in my life.

At the risk of being uncomfortably personal, I’ve been around a lot of tragedy throughout my life.  Death, disease, divorce…it started early and it’s been as constant for me as life itself.  This had an impact on how I lived, I was independent very early.  I’ve always had a little flair of non-conformity, I’m usually the last person to be peer pressured.   Despite that near constant reminder that our existence is fleeting, that we’re guaranteed nothing, that a new trinket will make you happy for about 5 seconds…I’ve often found myself in these situations too.  I knew I wasn’t happy, but I would talk myself into staying because it was easy.

It all changed for me the morning I woke up in the hospital with a cancer diagnosis.  They still didn’t know how bad it was, there were too many tests outstanding, but they knew I was in rough shape, enough that they wouldn’t let me go home until the chemo started.

Ask anyone who’s been in that moment…it’s very hard to articulate the flood of emotions.  I didn’t know if I had 2 years left or 50…I was living Kinder’s questions in real-time.  I flashed through my life, through the things I’d done, things I hadn’t;  you laugh at silly moments, you grieve for moments you’ve never experienced…and then you eventually land on your legacy.  What are you leaving behind?

That’s the moment I wish I could ‘teach.’  The moment of clarity that can only come from facing mortality.  It confirms your priorities, it sharpens your focus to a fine point.

I can also confirm for you every statistic and study I’ve quoted above.  You won’t think about money in the context of things, but you will think about how well you’ve saved for your family.  You won’t think about a job, but you will think about pursuing a passion.  You won’t think about buying another toy, but you will think about spending simple, invaluable time with your loved ones.

Why do we wait until we’re near death to make changes?  


Despite the heavy dose of emotion involved with this post, I want the practical application to be crystal clear.  It’s not meant to judge anyone’s spending habits.  If you can honestly say that you would be in your final moments on Earth, and your thoughts would dwell on a 7-series or a purse, then by all means, figure out how to purchase one.

But I bet that’s not true.

If most people took a hard look at their life, they would admit (sometimes begrudgingly) that they’re not living true to their values, at least when it comes to finances.  I’ve seen the majority of people living impulsively, in the moment, without regard for their future or values, and often above their means.  I can confirm the suspicions; a lot of the beautiful cars on the road are being driven by someone who can barely pay their bills each month.  Debt isn’t the disease, it’s a symptom.

So many people wish they could have more time to pursue a passion, or spend time with the kids, but cutting their spending even a little bit seems an impossible way to achieve it – What would the neighbors think if you downsized?!?!

What if we ignored what everyone else was doing?

What if we stopped caring about what other people thought?

What if we all stopped trying so hard to ‘fit in?’

What if we could apply all of this in a practical way?

Here are some ideas of how you can start this conversation, whether it’s with your spouse, your family, or yourself.  Remember, there are no rules:

  • Answer Kinder’s questions, or your own version of them.  Here’s an exhaustive list of core values I found.  What are yours?  Don’t wait for your ‘hospital’ moment of clarity, try to coax it out now.  Before it’s too late.
  • Before you make a large purchase or lifestyle upgrade, ask yourself honestly, am I doing this because it’s part of my values?  Will it really make me happier?…or is just because the Jones’ next door did it first?
  • Have the courage to admit that money causes stress, and money steers us towards bad, emotional decisions.  Talk this through with someone you trust (or a good financial advisor).
  • Try to align your values with your finances and budget.  If you value something, make it a priority.  I bet it won’t be a BMW.

I promised you One, Really Hard Step to live a better life.  I’ve given you the context behind it – what if you defined success as living your life in your own way?

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