The only rule that matters for Wealth Freedom and Happiness

by Peter Shallard

Wealth Freedom & Happiness - the only rule you need

Every now and then, I get set on fire with a burning desire to figure it out. You know… Life, The Universe and Everything.

This is one of those posts. Don’t worry though, I’m not going to throw you into the philosophical deep end. I’m simply going to reveal the simple psychological formula shared by some of the most successful entrepreneurs I’ve ever met.

It’s the philosophy I try to incorporate into my daily behavior. Despite being “deep”, it’s also the most practical decision making strategy I’ve ever stumbled across.

Get this one thing, really get it, and you’ll rapidly transform your world. Indecision will vanish. Wealth, freedom and happiness will be yours. Really. 

I was at dinner in Manhattan. My friends, seated around the table from left to right, were  an MD redefining “empowerment” through charity, the CEO of a private jet company, an entrepreneur hellbent on revolutionizing the food industry, New York’s premiere General Contractor (renovator of insane apartment spaces) and the CEO of a trapeze school.

Sometimes, I have to pinch myself. Having friends like this is something I’m phenomenally grateful for and it makes last year’s journey to get to New York 110% worth it.

Inevitably, the conversation went deep.

We shared “the best advice”, trying to distill the ultimate, greatest and most profoundly useful suggestion.

Jonathan, the trapeze guy, talked about the secret to becoming the ultimate romantic. Nick, our jetset pal, talked Freedom. I mentioned “Perception is Projection”.

Then, James, our General Contractor extraordinaire (who, incidentally, destroys any pre-conceived perception anyone might have about a GC) threw down a thought-bomb of such magnitude… well, I had to write about it:

“If it feels good, do it. If it doesn’t feel good, don’t do it.” 

Jonathan chimed in: “…. and if you fear it, confront it.” 

That’s it.

It may have been the plantain crusted sea bass, but this sounded (and still does sound) like the most profound principle for mindful living I had ever heard.

If it feels good, do it. If it doesn’t, don’t. If you fear it, confront it. 

My hypothesis is that the majority of pain in people’s lives is caused by not following this principle. Assuming a baseline of internal integrity (that “doing good” feels good etc), this is the ultimate life principle.

It busts through every notion that distorts people’s view of the world and the decisions they make. It destroys the notion of “should”.

You should get a good steady and secure job.

You shouldn’t take so many vacations.

You should work harder.

Does it feel good? Because if not, the only should is this: You shouldn’t do it.

Now, this principle comes with a pretty major caveat or two. You need a built-in sense of ethics (hurting people shouldn’t feel good) and you need to be sufficiently psychologically “healed” – you need to be free of most baggage.

The obvious examples, like teenagers (who are a mess) and victims of sexual abuse (who tend to have baggage), should play with this principle carefully. Or, invest time and energy in healing, before embracing it.

But for those of us (most of us) who are in a pretty good place, following this rule can create wealth, freedom and more happiness than we ever thought possible.

Take a good look at your life and think about the things you do that don’t feel good. When did you decide that you have to do those things. Why? What motivated you?

One of the best examples at the dinner was the whole notion of parenting. So many happy young couples transition into Miserable-Parent-Mode the moment they see the blue strip on the test. Suddenly, by feeling trapped, they do things because they have to. They deny themselves permission to ask “What would feel good?”

What’s worse, is that in this example and many others, we forget to ask “How can I make this feel good?” about the things that we clearly need to do. Caring for an infant fits into that category.

Applied to business, this principle of applied hedonism becomes really interesting. Instead of looking at other people’s business models, trying to build the business people tell you that you “should”… you can ask yourself “What would feel good?”

Instead of building some kind of venture-of-misery, you might be able to create a business where the journey is just as much fun as the destination. Another strike against the Four Hour Work Week principle.

This principle, when applied as a decision-making mantra (“Does it feel good?”) will awaken you to the frequency with which you make decisions that, simply put, make you feel like crap. It will show you that the criteria you normally decide on are fairly bogus in the context of your overall happiness.

How many entrepreneurs are driven only by trying to impress others? Or to satisfy their inner voice (parent driven – let’s be honest) that whispers “Should, should, should”?

This new principle actively encourages a form of enlightened hedonism. Should that be a crime? Does reading this article make you angry?

Curious. For some people, even contemplating acting so “selfishly” raises a cacophony of “should-nots” – it’s scary! When did we become so committed to suffering in the service of our goals and responsibilities?

When did we decide we can’t do the things we need to do, without suffering? We like to think that martyrdom is a concept leveraged only by suicide bombers, but most entrepreneurs are crucifying themselves to their business goals, or the commitments thrust upon them.

Yet we chose to be where we are today. We’ve arrived at this spot as a result of the sum total of decisions (both conscious and unconscious) we’ve made in our lives. It’s not an accident. We chose.

Which means we’re free to start choosing to do what feels good. If you have a life filled with commitments that feel miserable, it might take some time and energy to shift those. But it can be done.

My experience is the longer someone has been making decisions that don’t feel good, the longer it takes to reverse the process. It’s never impossible though. And it always happens faster than you think it will.

Does it feel good? Do it. If it doesn’t, don’t. If you fear it, confront it. 

Apply this rule to your business interactions and you will win. Every time. You’ll crush sales opportunities, while pushing yourself into all sorts of new dis-comfort zones. The kind that feel fantastic to conquer.

You’ll also avoid interacting with your business commitments (taxes) from a place of suffering, martyrdom and misery. By not doing what feels bad, you’ll procrastinate on important things (taxes) until you force yourself to find a good, pleasurable way to do it.

You’d think it’d be impossible in the context of your health – except one of the weight loss coaches I know has built a business that revolves around this principle. And, applying this principle to exercise is the way that all the pros do it.

Relationships? Please.

This applies to every sphere of life, but it’s the most important for entrepreneurs.

Entrepreneurs have this terrible habit of starting businesses in pursuit of wealth, freedom and happiness then rapidly painting themselves into a corner where they have access to none of those three.

It’s not okay. And it’s completely unnecessary.

Happiness is just a state. It isn’t a goal to be pursued. You can have it whenever you want. You can lose it just as quickly. Yet entrepreneurs with established businesses can be some of the most miserable people around. They sometimes joke (har-har!) about wishing they could just go get a job!

This happens to entrepreneurs who are consistently making decisions to do things that don’t feel good. Who aren’t confronting their fears and who refuse to find the goodness, the pleasure and joy, available in their lives.

If you ever feel like you might be one of these people, you can perform a full one-eighty. It’s simple. Ask yourself:

Does it feel good? (you know the rest)

{ 53 comments… read them below or add one }

Nick Reese April 16, 2012 at 10:06 am

Bummed I missed this dinner!


Peter Shallard April 16, 2012 at 10:27 am

Yeah man. We missed you that night also. 🙂


Cory Annis, MD April 16, 2012 at 10:43 am

Peter, I’d like to hear you talk a bit more about “feeling”

For most people, many things that are good and lead to feeling good, don’t “feel” good initially. Confronting fear, for example. Once one has made a practice of confronting fear for a while, it can become it’s own reward. You look forward to squaring off with it and screaming “bring it!”… but only once you know that the feeling of terror can be lived through.

Similar is taking a stand that is not popular but IS in integrity with your highest self (that is a tough one to separate from “should”). It might give you a warm feeling when you’re on the other side but risk everything, including your life, by living in integrity with it. Look at civilians in the streets of Syria, or perhaps the last remaining provider of safe abortion in America.

“Feeling” can be so ephemeral….procrastination “feels” good. Accomplishing something “feels” better but not necessarily at its initiation.

It’s a very fine point…because martyrs are usually born of the “If it feels good, I must be doing it wrong” school. And yet those who are willing to bear the discomfort, “feel bad”, try the untried, take a stand, risk the wrath, risk it all … are the ones who move us forward.

How do *you* make the distinction between the superficial meaning of “feels good” and a meaning that actually has value, transformative depth and staying power to it?

Thoughtful, provocative subject. Well done.


Peter Shallard April 16, 2012 at 1:20 pm

I make the distinction intuitively… by being able to introspect deeply, and rapidly. That’s why the healing part is so damn important.

Most of the disconnects with this principle you mention are examples of broken people making decisions based on a whole different set of criteria. Lots of “shoulds”… shoulding all over people.


e.n. April 16, 2012 at 3:15 pm

excellent points re: the value of confronting your fears.


Bob Gower April 16, 2012 at 10:50 am

Great stuff Peter. Lately my prime directive has been to use what I’ve got to create the experiences I want. Life is too short not to enjoy the ride.


Peter Shallard April 16, 2012 at 1:21 pm

It’s true. If it feels good, do it!

The subtle reference to death is important. Lots of those articles floating around the net right now about “Top 10 things dying people say they regret” confirm this precise principal… folks regret living based on external (and imagined) “should-do” criteria… instead of doing what feels the best.

Thanks for commenting! See you tonight btw 🙂


James Chartrand - Men with Pens April 16, 2012 at 10:52 am

I love this post. Your best ever.

It has huge caveats, too, which makes me grin – “Use this technique only if you’re a mature, serious adult with the ability to introspect and make wise choices”. A lesser person, given ‘if it feels good, do it!’ can end up in a lot of hot water.

So I like that this post speaks to the higher mind… and in such a simple way.


Cory Annis, MD April 16, 2012 at 11:10 am


The “Performed by a professional on a closed course. Do not try this at home” disclaimer. This is like a Zen Koan…If you think you got it right off the bat, you probably missed the point.


Peter Shallard April 16, 2012 at 1:24 pm

I actually think people SHOULD try this at home. Having a friend on the psychological belay ropes might be a smart move though …


Peter Shallard April 16, 2012 at 1:23 pm

Aw *warm fuzzies*

Yeah. This is totally an elitist form of self-development material now that I think about it.. LOL


Cory Annis, MD April 16, 2012 at 1:55 pm

*putting finger on nose with a wink and an enigmatic smile*


Wendie Kause April 16, 2012 at 1:35 pm

All I can say is YES, YES, YES!!! This is exactly why I started my company. My J.O.B. was absolutely no longer fun any more. It did not feel good anymore. I am finally in a space that I had the right state of mind to realize that life is too short. Face the Fear and take the Leap! I have promised myself no 12 -14 hour days because that is what I “should” do to be successful. I am successful with short days, doing what I love for people! Spending the remainder of my day doing the things privately that I enjoy! Thanks Peter for the Confirmation that I am on the right Track!!!!


Peter Shallard April 16, 2012 at 10:34 pm

Hey Wendie,

Glad I could be of service. You seem to be doing this right… and I’m sure you’re already reaping the rewards 🙂


Saskia April 16, 2012 at 1:48 pm

Thank you Peter, for another great article.
The should, should, should/ parent driven part resonates most with me.
I never realised how big of a rol this played in my life, untill I’d lost both my parents over the last couple


Saskia April 16, 2012 at 1:57 pm

.. Sorry, submitted to soon by accident..

So, when I my mum died last, apart from all te grieving an stuff (or along with it, I’m not sure), this sense of freedom came over me.
It suddenly became very obvious and clear to me, that I was quitting my well payed, government employed, building project manager job, and that I was quitting it soon.
Since then I’ve been doing what I love, helping engineers growing professionally, by learning managent and reflecting skills and such.
I deceided I was going to do this, out of live and enthusiasm, as opposed to Not dining this because of fear.

This is a year ago now, and I’m loving my life and job so much, I can’t even explain it.

I’m definetly not saying I wouldn’t want my parents here to see it, and I miss them loads. But I’m also not so sure h


Saskia April 16, 2012 at 2:01 pm

hm, it happened again, damn these iPhones, sorry folks.
I’m nearly finished, bear with me..

So, I’m not sure how long it would have taken me to build up the confidence to go against there ‘shoulds’ had they still been here..

Thanks again Peter!


Peter Shallard April 16, 2012 at 10:36 pm

Hey Saskia,

It’s a mixed blessing that you’ve experienced. Sometimes the death of a source of “shoulds” has to happen in order for you to really be able to start doing what feels best… and sometimes, for some people, even the death doesn’t make a difference.

While I’m sorry for your lost, I think it’s grate that your mom’s parting gift was giving you the ability to give YOURSELF permission… to do what feels right.

Way to go Mom! 🙂


Saskia April 16, 2012 at 2:04 pm

And sorry for the typos, def not doing this on my (autocorrecting) iPhone again..


Martin Stellar April 16, 2012 at 2:45 pm

Rocking post, Peter. So very true – been experimenting with this for the last few months (or maybe years, I can’t really tell) and it’s bringing me more and better every day.

@Cory: Inasmuch as my experiences matter: ‘Feeling’ good or bad is pretty simple: If something is not a good idea, there’s a little knot in the pit of my stomach, a tiny tension. It’s tricky though, since the ‘feeling’ of fear is very similar. It takes time to learn the difference, but once you do the difference is very easy to spot.

Over time I’ve come to recognize that ‘little tension’ as the giveaway for things that I really shouldn’t do. Now it’s just a matter of learning to trust it blindly. Every time I have trusted it so far, it’s been dead on right. And every time I’ve ignored it, things turned out bad. The body is a great thing to listen to!


Peter Shallard April 16, 2012 at 10:37 pm

Hey Martin, right on. Great input around the “gut” instinct – that’s exactly how it’s done.


Martin Stellar April 17, 2012 at 3:19 am

Heh cool. Thanks Peter


Lynn Hess April 17, 2012 at 4:22 pm

Martin, I love how you described the little knot, the “tiny tension.” That’s about as good a description as I’ve ever heard, I think! I’m still not great at discerning it from fear a lot of the time, but this conversation (short as it was!) really helped!


Martin Stellar April 18, 2012 at 4:42 am

Thanks Lynn. It’s really tricky, because the ‘fear’ and the ‘nope, don’t’ are so similar. With me, both give me a slight flustered feeling and a slightly faster heartbeat. The difference for me is that when it’s fear, it lacks a type of anxiety, which the ‘don’t do it’ situations always have.

Whenever I’m not sure, I hold off on decision, three times. Always works for me. By the third time contemplating or considering, I always know what.

When in doubt? Don’t.

Kate Northrup April 16, 2012 at 4:59 pm

LOVE this article. This is exactly how I organize my life and I love the validation of hearing a group of badass entrepreneurs discussing it over dinner. Have shared it to remind my folks that something feeling good is enough of a reason 🙂


Peter Shallard April 16, 2012 at 10:37 pm

Yes! We need you at one of these meals soon Kate 🙂


Siita Rivas April 16, 2012 at 7:29 pm

God! I love your thinking Peter!
You express thoughts that resonate so perfectly that they leave is a sweet hum in my head as it nods in agreement.
I’ve also observed the ‘money can’y buy happiness’ thinking to be pretty accurate.
That’s the observation that across socio-economic classes once a certain level of our basic needs are met, experiences of happiness don’t really vary greatly on a scale.
No activity has exclusivity to happiness.
To me this goes hand in glove with your ‘if it feels good do it’ because the happiness we get doing things we love are all fairly similar – Like the plunge into the sea after a week of hard work will pretty much on a par with the level of happiness Mr 61 in his hot red Porche has as he drives past you afterwards.
There’s solace in that.

This article’s a keeper.
Thank you Peter.


Peter Shallard April 16, 2012 at 10:39 pm

You’re welcome Siita! Glad this one it the spot. Thanks for the observations on happiness – I think you’re spot on. “No activity has exclusivity to happiness” <- spot on 🙂


Siita Rivas April 16, 2012 at 8:31 pm

P.S – I need a post edit button – sorry about the typos above –
NTS. Breathe – there’s always time to check words before hitting submit!


Dean April 16, 2012 at 8:42 pm

Hi Peter,

When I think about things in the past that have happened to me for one reason or another, the great positive ones that stand out have been where I have taken that approach.
I will apply this thinking & attitude more often from now on..


Peter Shallard April 16, 2012 at 10:40 pm

Hey Dean, I know right? It’s weird how long it takes us to connect up the dots and finally *get* that … yes, in fact… doing what feels right is the right thing to do !


Joanna April 16, 2012 at 11:04 pm

Thank you. Thank you. Thank you.
It felt good to read this article, like a little part of me opening and smiling. I guess that is the way with inner truth. The call to not compare yourself to others or try to emulate others’ methods for finding their happiness was particularly poignant. I am not sure where I fall on the ‘maturity’ or ‘ready’ spectrum but I have often felt like I (ahem) “should” have to apologize for pursuing ideas, paths, choices that make me happy. Or I have spooked myself into jumping back onto a safer road even when I know it leads to less happy places. This was a much needed reminder to listen to and amplify that inner voice that urges towards intentional enjoyment especially when it means confronting a fear (or 7). I’ve never regretted those choices once they have played out but regretted often not taking those leaps.
Thank you (and your friends)


Peter Shallard April 16, 2012 at 11:09 pm

Hi Joanna! You’re welcome x3 also 🙂

Comparing yourself to others is definitely a major source of “should-dos” that can disconnect from what feels good.. thanks for pointing it out. Great example to supplement the article with.


Juliane Gardner April 17, 2012 at 7:31 am

This article (shared with me by my best girlfriend, Mary, who just returned from “I can do it” in Atlanta) has reminded me to approach my latest idea of printing my “heart rock” nature photos in a way that feels good. Wanting to pass along that feeling when they are purchased by using a percentage of each sale to help an organization to help persons less fortunate then myself. Hearing that you had this discussion over a “think-tank” lunch also made me want to create my own weekly- bi-weekly time with a group of likeminded friends to discuss ideas on these types of subjects of empowerment and peace of mind, helping each other achieve both. Thank you! I’ll leave you with 2 of my favorite quotes… “thoughts become things, choose the good ones” & ” if you’re always 2 inches off the ground, no one can pull the rug out from under you”- peace – Julie


Peter Shallard April 17, 2012 at 10:03 am

Hey Juliane! Thanks for stopping by and for sharing your quotes… great to have you here.

The dinner we had wasn’t a planned think-tank… just serendipitous awesomeness 🙂


Will Bontrager April 17, 2012 at 9:21 am

Years ago, a concept was expressed to me this way: Follow your feelings with integrity. It was also pointed out that the feeling of excitement (again, with integrity) is a reliable guide for most rewarding life direction.

But no mention of confronting fears, that I recall. So I didn’t have that. Thanks for filling in the blank spot for me.



Peter Shallard April 17, 2012 at 10:08 am

Hi Will, welcome back… great, eloquent expression there. I like it a lot. “Follow you feelings with integrity” really gets to the heart of the matter…. and the people who struggle with integrity have a clear way of identifying what they need to work on, i guess.

The fear is important too… so I’m glad we could give you one more piece of the puzzle 🙂


CL Midroe April 17, 2012 at 11:15 am

I received this from my wife this morning. It obviously struck a note in her. After I read it, I thought … hhhm it seems a really basic principle for decision making, one that I use without ever giving it thought as to its universal application. There are a number of catch phrases that could be attached to “If it feels good …” like “Just Do It”, “Analysis Paralysis”, “What if I’m wrong”. I have been working in an industry that requires various levels of business decisions every day, most timely, by workers on the shop floor and managers in the office. My assistance to both comes in the form of experience and encouragement not to be afraid of making a decision but what did we learn from it and then onto making a correction if required… even though it felt good on the first go it feels just as good when it’s on course.


Peter Shallard April 17, 2012 at 7:33 pm

Hi “CL”, I think in that example, the person making the initial decision probably isn’t taking the time or energy to do that mental inner check to see what really *feels* good…. and is instead acting out some kind of “should’ (and not the one you’re telling em to!)

Just saying 🙂


Lynn Hess April 17, 2012 at 4:34 pm

Great article! We all know life’s too short to spend it doing things we hate and that make us feel bad — yet millions and millions of people spend their entire lives doing them anyway. Crazy!

I loved when you asked “Does reading this article make you angry?” I can absolutely see how it could make some people furious. People who’ve spent years and decades doing all the stuff they “should” might get a little ticked off to hear that all the suffering wasn’t necessary and (even worse) probably held them back!

Your mention of doing what we can to make the less-pleasant experiences feel good reminded me of Martha Beck’s suggestion to “Bag it, Barter it, or Better it” when faced with stuff we don’t really feel like doing but that we want to do because it serves our greater purpose (taxes, for instance :)). I’d love to hear some of your suggestions for how you “better” your not-so-feel-good tasks.


Peter Shallard April 17, 2012 at 7:37 pm

Hey Lynn!

What you’re describing is what therapists (and particularly NLPers) call “reframing” – when the picture inside the frame has to stay the same (i.e. because it’s an inescapable reality – like taxes!) but where putting a different frame on it can change the way we *view* and experience it.

The entrepreneurs I know who enjoy their tax management are those who know that to truly be financially powerful, they need to cultivate AWARENESS about their financial realities, month by month. When people have that frame, they never hate doing their taxes (because they’ve kinda been doing them month-by-month the whole year).

Just one example. But an important one.


Mike Hrostoski April 18, 2012 at 12:40 am


Great post. This is basically how I’ve been living my life for the last four months. Some may call it hedonistic, but when someone asks me what I’m doing with my life I can honestly respond, “I’m making every day the best day of my life.”



Peter Shallard April 18, 2012 at 11:24 am

Rock it Mike. Awesome philosophy 🙂


leroy snow April 18, 2012 at 8:46 am

It’s “principle”.


Peter Shallard April 18, 2012 at 11:22 am

Thanks for the contribution leroy


Saskia April 18, 2012 at 12:20 pm

Thank you Peter for replying.
I really love the way you put it in to words; the permisson to do what feels right.
I’m not sure who gave it to who, but it’s here now. At least most of the time..
And yay Mom indeed!
Bless her and Dad, their shoulds and the good intentions behind them 😉


Jennifer Carson April 23, 2012 at 11:04 am

Thank you – love this post. Several years ago, I woke up miserable in a life I had built on “shoulds.” Can’t point to a specific moment that woke me up, but I knew I needed to change just about everything about how I was living or I was going to be on that misery bus until the day I died. Without realizing it consciously at first, this is the exact question I used to create a new way of living. Dread is gone. Replaced with excitement, peace and relaxed shoulders. Everyone’s inner knowing knows. Once you can access that, things flow way easier.


Peter Shallard April 24, 2012 at 2:32 pm

Hey Jennifer! So pleased to hear you’re living this principal. Keep conquering those fears!


Gill April 27, 2012 at 10:48 am

You are so right, Jennifer: everyone’s inner knowing knows. If only we could all stop ignoring ourselves, we could all be in such a fabulous place. 🙂
Glad to hear you’re living your dreams.


Gill April 27, 2012 at 10:46 am

I loved this post!
The only thing that bothers me is that some people may read the third part, and apply it to the second … ie, confront your fears, but if it doesn’t feel good, don’t do it. I fear that some people will never confront their fears for fear of it not feeling good … ack! 🙂

Great article. Principles to live by. Love it!


_Jon April 27, 2012 at 11:18 am

I recently wrote a note on Happiness for my sister.


There are a lot of parallels.


Joe A. May 21, 2012 at 8:07 pm

Hey Peter, thank you for sharing your wisdom and your friends’ thoughts. I rarely reread blog posts, but I will be rereading this often.


Peter Shallard May 22, 2012 at 10:20 pm

What up Joe! Glad this one hit the spot 🙂


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