How to Be Happier by Asking Yourself Better Questions

On being happier… Courtney Carver, author of Be More with Less, said, “The reason I didn’t stop drinking 10 years ago is because I thought, ‘If I don’t have a problem, I can keep drinking. If I’m not an alcoholic, I’m good.’ But maybe I was asking the wrong question. Maybe instead of comparing my drinking and asking, ‘Am I an alcoholic?’ I should have been asking, ‘Is alcohol adding value to my life?’ or ‘Does alcohol make me the best version of me?’

Carver’s comment got me thinking about success in general. Maybe making the best choices in life is about asking ourselves the best questions. If we aren’t asking the right questions, we could be creating a less than fabulous life for ourselves.

Is there a better question to help with clearing clutter?

This makes perfect sense from a clutter-clearing perspective. I know from personal experience that my natural tendency is to ask the wrong question. If I hold an object in my hand my natural instinct is to ask, ‘Could this be useful some day?’ Wrong question! The answer will invariably be “yes” which doesn’t facilitate the clutter-clearing process. Now, if I ask, ‘Have I used this in the last six months?’ that is a much better question. Both appeal to my utilitarian, practical nature, but the second is the better question because it forces me to consider whether I am currently using an object or not. And, if not, then I have a hard time justifying keeping it given it might prove truly useful to another person. Into the donation box it goes!

This past week I’ve been taking inventory of duplicates and realize that I have duplicates all over the house. For starters, I have five sets of measuring spoons, six different spatulas, multiple sets of bed linens and towels…all useful items and often aesthetically pleasing, but how many duplicates does a body actually need? One spare is perfectly reasonable, two spares may border on excess. Three spares is probably clutter!

For maintaining a clutter-free space, it helps to ask yourself, ‘Is this an upgrade?’ If it isn’t, you’ll have a hard time maintaining the one-in-one-out rule for staying clutter-free.  And, there is Marie Kondo’s wonderful question, ‘Does it spark joy?’ Obviously, why buy it if it doesn’t make you happy?


What about money? Is there a better question to make the shift from being a spender to a saver?

If you catch yourself asking, ‘Do I have room on my credit card to buy this?’ instead ask, ‘Is this worth making my future-self poorer?’  Or, ‘Will my future-self thank me later for buying this?’ Or, ‘Could I make do without this?’

To think and act like the truly wealthy, Robert Kiyosaki suggests a really great question, ‘Will this put money in my pocket or take money out of my pocket?’ This question encourages you to focus on buying income-producing assets instead of buying “doodads” at least until your assets generate enough income to buy the stuff you want. It is all about delaying gratification, which research has shown actually increases one’s experience of happiness in life. Don’t indulge now; put it off a bit longer and you’ll be happier.

Try postponing the impulse to buy an item by telling yourself, “I’ll add it to my list of wants and wishes and if I still want it in 30 days, then I’ll buy it.”  This has the wonderful effect of dramatically reducing your spending without making you feel deprived. You aren’t ever saying you can’t have it. It’s more of an, “I’ll see if I really want it by waiting 30 days.” Even better if you say, “I’ll buy that luxury item when I have an income-producing asset to pay for it.” For example, “I’ll rent that Ferrari when the income from my rental property covers the cost of the car.”

Being a natural spender, I found making a budget restrictive and unfun. However, I loved the idea of creating a spending plan because my husband and I would sit down together to do it. We’d see what money was left over after our expenses, and then decide how to best spend that money, whether on home improvements, travel, clothes or dining out or anything else we might need or want. This was fun and ensured that we were thinking about and asking, ‘What would maximize our enjoyment of life?’ as opposed to just spending on a whim and realizing after the fact that a different choice would have led to greater joy.


How about questions for making better use of your time?

Ask, “If I had one more year left to live, would I be spending my precious time on [watching this TV series or box set, social media, surfing the web…]?’ Or, ‘Does doing x add value to my life?’ And, I’d ask, ‘Is this in alignment with my top core values and passions?’


A better question for achieving happiness and success?

Shaun Achor, author of The Happiness Advantage has a TED talk on the topic of happiness and success. He points out that being successful isn’t the key to being happy (e.g., I’ll be happy when I get that raise/promotion). It actually works in reverse; you are much more likely to be successful by being happier first.  Try asking yourself, ‘Will this choice make me happier?’ And, you may want to add, when eyeing those lovely new shoes, ‘Will this make my future-self happier, too?’

You can’t go too far wrong if you are happier both now and in the future. As Derek Sivers, the super successful founder of CD Baby says, “If it isn’t a ‘Hell, yeah!’ it’s a no.” He made all his business decisions based on what made him happiest. This goes right back to: focus on happiness to be more successful. Then, even if you never become successful, at least you’ll have been happy along the way.

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