How to Stop Being Rich and Happy

Entrepreneur Derek Sivers (who is full of deep thoughts and good advice) recently published a list of “directives” that draw from his personal philosophy and life experience.

For instance, his advice on how to get rich includes tidbits like: live where luck strikes, say yes to everything, pursue market value not personal value, shamelessly imitate success, benefit from human nature.

One section of the article includes Sivers' thoughts on “how to stop being rich and happy”. (Or, to put it another way, how to make yourself miserable.) His list seems especially relevant to folks who are financially independent — or hope to become so.

Here's what Sivers wrote (verbatim):

How to Stop Being Rich and Happy

1. Prioritize lifestyle design. You've made it, so it's all about you, now. Make your dreams come true. Shape your surroundings to please your every desire. Make your immediate gratification the most important thing.

2. Chase that comparison moment. You have the old thing. You want the new thing. Yes! Do it! Be happy for a week. Ignore the fact that the happiness only comes from the moment of comparison between the old and new. Once you’ve had your new thing for a week, and it becomes the new norm, seek happiness from another new thing.

3. Buy, not rent. Why rent a house, castle, boat, or car, when you can buy? It’s not about the thing, it’s about identity. This shows who you are now.

4. Internalize your new status. You worked hard to get here. Celebrate. Relax. Admit you are in a different class of people now, with different needs. Understand there is no going back.

5. Be a connoisseur. Learn what others say is the finest. Insist on only the finest. You will now be unhappy with anything but the finest.

6. Get to know your possessions. Now that you own the best, it’s time to focus on what you’ve got. Learn all about the features of your new possessions. Spend more time getting your surround sound and heated floor just right. Work out the solar panel charging of your Tesla car. This is important.

7. Acclimate to comfort. Eliminate every discomfort from your life. Blame others when the world seems hard, and is not living up to your standards.

Again, these are the things that Sivers says you shouldn't do if you want to be rich and happy. Do you agree with him? Disagree? Are there other warnings that you'd add to his list?

My Thoughts

Sivers' list is interesting. It makes me think. I agree with a lot of what he has to say, but also feel conflicted about a couple of points.

I wonder about the first item on the list, for example: prioritizing lifestyle design. As you know, I'm a vocal proponent of finding purpose and making meaning in your life. I believe it's vital for each of us to to build a life around our personal goals and values. Isn't that the essence of lifestyle design?

At the same time, I agree that it's dangerous to live a life built around immediate gratification, one in which you satisfy your every desire. That's a path to ruin — financial and otherwise. But is it truly lifestyle design?

Also, I'm not convinced it's a bad thing to know and appreciate your possessions (#6 on his list). In fact, it's often a good thing to understand how things work so that you can make the most of what you have. Perhaps this can be taken too far — to the point of obsession — but I'd rather people were familiar with the features of the things they own than they remained ignorant and had to rely on outside help to make things work.

My own personal weakness is #5, the dangers of becoming a connoisseur. If I don't police myself, I can fall into this trap. I'm fond of good whisky, nice electronics, and high-quality travel gear. Because I subscribe to the notion of conscious spending — the idea that you should actively spend on the things that matter most to you while cutting back on the things that don't — I can sometimes convince myself that it's reasonable to buy that bottle of 18-year Macallan single malt whisky.


In case it isn't clear, this video is meant to be funny.

Every time I make a purchase, I need to force myself to decide between “good enough” and “the best”. There are times that “the best” makes sense; most of the time, though, “good enough” is the correct option.

We are not perfect. I'm not perfect, and you aren't perfect either. What are some things that you've done with money that hindered your happiness instead of helping it? What other traps and pitfalls do people face along the road to financial success?

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PhysicianOnFIRE
PhysicianOnFIRE
4 years ago

I enjoyed Derek’s list and I think it could serve as a wake-up call to a lot of my big-spending colleagues. More likely though, they’d just be offended.

I do think it’s sometimes better to buy than rent, and better to take the time to know your expensive gadgets (what’s the point of an iPad if all you do is play solitaire on it?). I find nothing wrong with wanting to be comfortable, as long as you’re not afraid or unable to sometimes venture outside your comfort zone.

chacha1
chacha1
4 years ago

Yes, I think point 1 should be rendered as “prioritize immediate gratification.” It doesn’t really make sense otherwise. 🙂 Re: connoisseurship: I am not a habitual whiskey drinker, but the Glenlivet-Macallan 25 that I drank a couple of years ago was a completely different thing from any other whiskey I have tasted before or since! Since I don’t propose to spend that kind of money on something that is no good with food, it doesn’t pose a risk. If I had silly money, though, I suspect I would be tempted by the $125 bottle of wine a lot more often… Read more »

Sabbaticalia
Sabbaticalia
4 years ago

One big pitfall I face regularly is communications breakdowns with my spouse. I’m a planner and like to get things done. My wife in particular doesn’t know what she wants until after she sees it and speaks it, but makes no effort to actualize or verbalize. I get to guess at what matters, set balls rolling, and then claw them back (then send them on their ways again) as she changes her mind with no apparent trigger. On the whole we make progress because I manage to keep us aimed in the right general direction. I just feel like so… Read more »

CB
CB
4 years ago
Reply to  Sabbaticalia

Have you considered marriage counseling? That’s not really a healthy dynamic to have between two partners?

CalLadyQED
CalLadyQED
4 years ago

I also disagree with #6. It makes sense to learn all the cool things you can do with what you already have instead of buying new junk to do what your old junk may do better. Also, appreciating what you have makes you more grateful and content. This obviously combats unhappiness and poverty.

That said, I’m neither rich nor happy, so it’s not like I’m an authority.

Dividendsdownunder
Dividendsdownunder
4 years ago

Thanks for sharing J D. At first I thought the list was ironic which it sort of is I guess.

I think another theme is showing off your wealth. Show how you can’t afford the huge house or porsche. That’s just a quick trip to not being wealthy.

The main thing for everyone is not to not buy things you don’t actually want or need. It’s just wasting money.

Tristan

JKC
JKC
4 years ago

… reminds me of the weight loss metaphor to financial planning. You get down to your “fighting weight” so you can quit the diet, stop exercising and eat bon bons all day. It doesn’t work that way. Develop good habits for life. I would hope that most of your readers who have earned their way to solvency and beyond will continue to keep up the good habits that got them there. Unrelated to the above, I would love to hear your thoughts on an amazing article just published in The Atlantic: “The Secret Shame of Middle-Class Americans”. It resonates very… Read more »

stellamarina
stellamarina
4 years ago

Re. being a connoisseur: I see it with some gardeners who have to buy all the expensive equipment, hardscape and plants for their gardening. Check out the old eccentric gardener down the street or the new immigrant family near by and see how little they are spending on gardening but how much produce they now get for free.

Sam Smith
Sam Smith
4 years ago

Right now I’m stuck in a shame cycle of thinking I need a “new” house. Why do I need a new house, because all my friends are buying $700,000 to million dollar homes. Even the guy who reports to me at work has a new house that he paid $700,000 for. We are actually looking at a house tonight that is priced at $795,000. I don’t think the house is worth more than $650,000 so I doubt it will be a real temptation, its not bigger than our current home, in fact its smaller since we have a carriage house.… Read more »

chacha1
chacha1
4 years ago
Reply to  Sam Smith

If the “temptation” house in your neighborhood is almost $800K, there’s a fair bet you are already IN a $700K house. 🙂 It sounds to me like instead of looking at taking on a new half-million-dollar debt, you should invest in the house you have. Just as your friends how much mortgage interest they are paying every month, and that may help make the renovation budget look verrrry reasonable.

chacha1
chacha1
4 years ago
Reply to  chacha1

dang it … just ASK your friends. Monday morning typo.

Sam Smith
Sam Smith
4 years ago
Reply to  chacha1

No, I live in one of those quirky historic neighborhoods. Every house is different, size, style, niceness, etc. But your point is still fair. The house we live in is a $400,000 house. Its big enough for us, we also have a carriage house (garage and apt. above it) which is rare but not unheard of in our area. The house we looked at is on 2.5 lots, so much more land, plus a pool, and a water view (although its not on the water). The house was cool, I really liked the outdoor space, but we live in Florida… Read more »

chacha1
chacha1
4 years ago
Reply to  Sam Smith

Yeah, that $30K tax bill would scare me off for sure. 🙂 My parents moved to Florida for retirement, and one of the arguments they made (over just moving to the coast of Georgia) was that there is no state income tax. Well … yes, but they have no INCOME either! They are living off investments. So the much higher property tax rate they pay in Florida has been an education. And that’s forever.

Sam Smith
Sam Smith
4 years ago
Reply to  chacha1

florida doesn’t have an Estate tax either, another reason so many retirees live here. The no state income tax helps us a ton. Property tax rate can vary. We do have lots of housing protection laws, homestead, deductions for elderly, Save our Home, etc. We’ve gotten some very good protection since our property tax bill plummeted during the recession (along with the value of our home) and under Save our Home can only go up by 3% or inflation which ever is lower year over year. As a result, we are paying less in property taxes now vs. what we… Read more »

Mr. PIE
Mr. PIE
4 years ago

I’d add…

Try your darndest not to succumb to Cognitive Distortions on your path towards your goals. There are many of them and its hard to avoid them all….

CB
CB
4 years ago

I love the point about being a connoisseur – I don’t think I’ve heard that one before but it really resonates. Being picky and pretentious will not make you happy and it will not make you any friends.

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