4 Questions You Should Stop Asking Yourself

#1 What would you do if money wasn’t an issue?

Maybe you’ve asked yourself a few of these questions before. As thought experiments, they can be pretty interesting.

But interesting isn’t always useful. Without answering how you can make things happen, it’s possible that these questions can become a misguided waste of time and a form of procrastination.

Perhaps, these questions help people put things into perspective. The issue I have is that the focus is often on the wrong things. Questions are only good if they lead to further examination and exploration.

So, let’s go through some of these and consider some better alternatives or follow ups.

“What would you do if money wasn’t an issue?”

This one is a classic but it’s a tremendous waste of time.

Money is either an issue or it isn’t. In either case, it’s a pretty redundant question.

Imagining that the problem doesn’t exist isn’t going to help you solve it.

The people asking this question are most likely worried about their finances. It’s probably their biggest issue.

If we rephrased this question, isn’t it basically asking what would you do if you won the lottery? And yet, people hate that idea.

Maybe there is a reliance on luck to change your circumstances. But asking yourself what you would do if money wasn’t an issue doesn’t quite explain how you get the financial freedom you are after.

I will be very honest with you when I say that I hated some of my old jobs. I was so tired of them that I often said my dream was to do “nothing”. My life was very similar to the movie “Office Space”.

When I finally got myself to a position where I could do whatever I wanted for a while, I decided to do nothing. After two long weeks, I felt like I was living such a pointless life. I realised that wasn’t what I wanted.

The majority of people are locked into work out of the necessity of finances.

Imagining a life where we don’t have to do that is great. Maybe it makes us feel better for a moment. Maybe it gets us to dream about what we would do or maybe even do nothing.

There is a reason why we aren’t all pursuing what makes us the happiest. It’s because some things are naturally more valued by society. Often we have to compromise.

By the time it takes you to attain financial freedom, what you want to do has most likely changed.

Better questions to ask:

• How much money do you need to live a decent life and how much for your dream lifestyle? How do you plan to make that happen?
• Is there something you would enjoy doing and be paid well to do it?
• What would you continue to do even if you weren’t paid to do it? Would you still do this even if you had to pay for it?

“What would you tell your younger self?”

Hindsight is 20/20 as they say and this question only serves to create a sense of regret and missed opportunities.

It can be a useful to think about if you are giving advice to people younger than you but it doesn’t do much for you now. When shared with others, it can sometimes misguide them if your advice focuses on results rather than process.

The advice you give your younger self is only useful if it helps shape your current and future behaviour.

The point isn’t to focus on changing the past, because that’s over.

The irony is that often, you probably heard the advice you needed from someone else when you were younger but just didn’t take it. Maybe it was a parent or a teacher.

But you know what? I can’t fault you for that and neither can you.

You don’t know what you don’t know.

You can only make the best decisions that you believe to be true at the time that you make them.

There is no chance to go back 10 or 20 years to change your mind because you learned something new later.

Questions worth asking:

• Are you making the best decisions based on what you currently know?
• Reflecting on the past, what lessons have you learned that can help improve your present and future situations?
• What lessons would you pass onto others and how can you deliver them in a way that will get people to listen?

“What would you do if you only had one day left to live?”

I’ll admit that I would be the first to cry and have a serious a breakdown. I’d spend my time with my family, telling them I love them and saying my goodbyes.

What I wouldn’t do is spend the day thinking about it.

The problem with this question is that it doesn’t cultivate a very healthy mindset. It wouldn’t be a very sustainable way of living to go through all of the above on a daily basis.

You can’t live your life always thinking that you will die tomorrow. You would be wrong everyday until the one time you are right. And even then, it wouldn’t matter.

The question is something you would ponder for a while and eventually ignore. You know it’s too focused on the short term. If you are going to die tomorrow, doing anything that requires a longer term perspective seems pretty irrational. You would stop delaying gratification.

I think to some degree we all buy into this fantasy of dying after living a full life (whatever that means). Knowing that we can die at any point can create a sense of urgency. But there should also be an certain level of acceptance that life won’t go exactly how you planned. If you are obsessing over the day to day, maybe you are trying to control too much.

Better questions to ask include:

• What do you value most in your life? Are you spending most of your time on this? If no, why not?
• What kind of legacy would you like to leave behind? How do you want to be remembered?
• What does a meaningful life mean to you? What makes you happy? What gives you a sense of purpose?
• What counts as having a good day?

“What do you want to be when you are older?”

It’s great to have dreams, ambitions and a sense of direction. It’s worth thinking about but it’s also possible you aren’t sure.

It’s very likely that what you want to become will change too.

Your journey isn’t linear, it isn’t defined by a single job or title.

Sure, I believe some people have an ambition of becoming something when they are younger and they see it through to the end. But I feel that is probably the exception and not the rule.

I imagine most of us succeed by making the most of the opportunities we have. We have a rough idea of what we enjoy and find things along the way that pique our interest.

The idea that we should fixate on one opportunity and ignore other possibilities doesn’t seem ideal. It can make us too stubborn to let go of things we no longer value. The truth is, there are multiple directions we can go that we would find satisfying.

What you want and value changes with your circumstances. Don’t ignore that.

Better questions:

• What do you find interesting that is worth exploring in the short, medium and long term?
• Does this meet the minimum criteria for your base level of needs and wants?

Conclusion

Focus on asking yourself the better questions and continue to explore what is important to you. The first question you ask is rarely the last. Hopefully, it leads to a series of questions that get more and more relevant and worthwhile.

Don’t dwell too much on what doesn’t serve you.

Once you figure out what you value and what you want, make a plan and focus on the how.

Life is a balancing act and you should prepare to compromise a little. Learning to accept that and being more adaptable is crucial to progress.