Great questions break habitual thought patterns and allow you to discover new ways to get the results you’ve been looking for.

I’ve long collected powerful questions. Some questions have helped me discover new things about what makes me happy. Others have helped eliminate stress, sometimes instantly.

I’m a firm believer that asking yourself good questions is one of the easiest ways to upgrade your thinking.

Here’s a list of 17 powerful questions, which have helped at times personally, financially, and professionally.

# 1) Is there anything in my life, knowing what I now know, I would not start up again today, if I had to do it over?”

This question I first learned from Brian Tracy which he calls zero-based thinking. It can be applied to anything in life, whether a habit or a choice you’ve made. It’s power comes from limiting the inevitable mistakes we all make.

# 2) When is my financial independence day?

Net worth is fun to track. But what can be more powerful is knowing your financial independence day–the day you no longer have to earn income.

What’s so powerful is this number is an indicator of your entire financial picture (assets, liabilities, income, and expenses).

The simplest way to calculate the number is to use Personal Capital’s free retirement calculator.

# 3) If I had $10 million dollars in the bank, what would my ideal week be, and how much would that cost?

It’s easy to think more money is the solution. Yet, when it comes down to it, a lot of what makes us happy is cheap or free. An ideal life, which most of us assume we need large arbitrary number to sustain, is actually a lot closer then we realize.

# 4) If I lost my entire income tomorrow, what would I do to start earning money fast?

Sometimes you may need to take a risk in your career. To take a leap of faith in which you’re not sure will work out.

We often think these situations are make or break. That these risks are success or total bust.

But when it comes to it the “total bust situation” may not be that bad. By planning for these worse case scenarios, it allows us to see that the failures often are not “my life is over” but a small step back.

# 5) What do I own now that I wouldn’t buy again for its current value?

If you wouldn’t buy something you own today for how much you can sell for, then the answer is simple–sell it!

# 6) What big expenses are coming up in the next five years and how should I start planning for them now?

There are financial emergencies such as unexpected medical bills, a surprise job loss, or having to travel to attend a family funeral. It’s hard to plan for these things. This is why you have an emergency fund.

But a new car, when your current one has 200,000 miles on it. Or a wedding, when you’ve been in a committed relationship for two years–these expenses can and should be planned for.

# 7) What are my biggest concerns right now?

Sometimes we have a million thoughts going through our mind. Writing down your actual concerns can be a freeing exercise, that allows you to focus on what’s most important.

# 8) How do I wish things were currently different?

There’s nothing wrong with wanting a better life for yourself. But you have to know what it is you actually want. This is a great first step.

# 9) What could I accomplish this week that would make me really excited? 

With finances we often look 10+ years down the road. This often leads to inaction today. But there are things you can do this week which can improve your quality of life today. This is a powerful question to help uncover what exactly that is.

#10) What small things can I do in very little time, with no money at all, to have a big impact?

Time is limited. As is money. But that doesn’t mean results have to be. This question allows you to gather the 20% of activities that produce 80% of the results.

#11) What conditions or habits do I do I have to set, so that the outcome happens automatically?

Goal setting is the easy part. What’s difficult is the implementation. This question is a powerful strategy simplifier. It opens you up to new and easier ways to accomplish your goals.

#12) What would I do if I wasn’t afraid of failure?

Often we hold ourselves back from dreams and goals because we fear we will fail. We set goals inside of our circle of competence, which don’t stretch us. This question allows us to overcome this tendency.

To not limit yourself.

Pair this with planning for the worst-case scenario (question # 4)

#13) How can I multiply by subtraction?

It’s easy to want to add things to our lives. What’s many times more powerful though is taking away.

#14) If we were having this discussion three years in the future and you’re looking back over that three-year time span today, what has to have happened in your life, both personally and professionally, for you to feel happy with your progress?

This is a question I first learned from Dan Sullivan. I’ve found it powerful for identifying what I should be focusing on in business and life.

#15) What will I predict will happen if I continue with my current habits?

It’s easy to want to sugarcoat our current situation. But this question gives you a more accurate picture of the road you’re headed down.

#16) If you were looking at someone else’s life that shared the same qualities as yours and you had to place a wager on the outcome of their goals–how would you place your bet?

After you’ve placed a bet on yourself to accomplish your goal, try and identify how someone else would place a wager on you.

A unique twist to this question is to view your situation from an expert’s point of view. So, you could ask yourself, “If Financial Guru X” were to place a wager on the outcome of my goals, how would he/she place their bet?”

#17) If you successfully adopt these habits today, what will your life look like ten years from now?

Envisioning what your future life will look like is a powerful motivator. It allows you to make the small changes that lead to big results.


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