What If?

by Krantcents · 26 comments

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Many years ago, I used to do “what if” scenarios. As I get older, I find I reflect on my decisions much more and often do “what if” scenarios as a way to plan for the future. I think my ability to plan well helped me achieve or accomplish much more than others. After all, how do you improve your decision making or judgment if you do not reflect on your decisions? Do you reflect on your decisions? 

Why the ending matters?

I often see my wife turn to the end of a book to see ho w it ends. When I ask her why she would want to know the ending before you start reading the book, she responds that it make a difference!  I never understood that thinking until I got much older. I have roughly thirty (30) years left and I am in no hurry to get there, but I want to know how I will be remembered? Will it my life’s work with children, personal accomplishments, sense of humor or family? I have often thought about writing my eulogy, but it seems too vane!

Turning this exercise into something less vane and more positive, I thought about what I can do in my life that was worthy of remembering. As I think about where I am in my life, I think about changes and if they proved out to be good or bad. Usually, it is neither! It falls into the gray area of maybe it would have made certain things better, but I will never know. That is one of the problems of doing “what if” scenarios. You can only guess if it would turn out better. Could I have made a better decision?

Question everything?

What if I were a better student? What if I would have waited longer to get married? What if I would have done this or that? I sometimes think it is a worthless exercise because I cannot change the outcome! It is not worthless because I will make better decisions next time. It is part of learning from your mistakes and improving your decision making abilities. I know there are a lot of great scientists and business people who use their imagination with what if scenarios to create great things. You can too!

Steve Jobs who is thought of one of the greatest innovators will be remembered for his accomplishments and much more! He is often quoted for his 2005 Stanford commencement speech where he says, “Stay hungry, stay foolish.” He followed his own advice by changing our daily lives in many ways thanks to his products. He kept asking questions and it helped him develop more innovative solutions. It also allowed him to fail and ultimately succeed. A lesser known part of the same speech was something I embraced much earlier.

Death and Taxes is guaranteed!

In the same 2005 Stanford speech, he said “if you live each day as if it were your last, someday you’ll most certainly be right.” It reminds me of the broken clock quote of “a broken clock is right twice a day.” Time is something we never have enough of and yet we squander it so easily. We squander it when we are young and when we realize how important tit I s, we are generally much older. Then we regret it! I often told me children to make every day count by applying your best effort. I often give the same advice to my students too.

I still question everything

After a lifetime of parenting, teaching and consulting, I realize I can only give advice! It is still up to the other party to take the advice. Advice such as investing in yourself by getting a good education, saving and investing for the future or staying out of debt is still up to the individual. Yes, I am reflecting on giving advice, teaching and my future. I look back on my decisions to learn how to make better decisions. I evaluate my mistakes and accomplishments to improve my decisions.

I wrote an article called Doing Your Resume Backwards! which addresses planning your future so you can include it on your resume. I am planning my eulogy so I can plan my future. It may be vane or just a way to motivate better results! Either way, I want to do more and “stay hungry, stay foolish.” How do you think about your future or legacy? Do you do “what if” scenarios to reflect on your accomplishments or failures? Perhaps, the better question is do you think about your future? Not five (5) or ten (10) years out, but much longer such as your lifetime or time left?

Final thoughts

“What if” questions make me reflect on my decisions! I sometimes think about what if I did things differently, but more often think about how to make better decisions. It all starts with making goo well thought decisions and a lot of planning. When my students make bad choices I ask them why they did that. They often say, “I don’t know.” I realize that is a typical teenage response, but it does describe how a lot of people do not think before they act. “What if” scenarios are a great way to plan and reflect on your decisions?

Photo by:  Flickr

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Snarkfinance December 3, 2013 at 3:29 am

I am constantly performing “what if” scenarios in my head, often to the point where I forget to live in the moment. Then I try to live in the moment and realize the moment sucks, and go back to dreaming. I think this is what most people would call a quandary.

Krantcents December 3, 2013 at 6:56 am

“What if” scenarios are intended to help you set goals and plan. It is also another way to reflect on your decisions.

Holly@ClubThrifty December 3, 2013 at 5:09 am

I think that “what if” is a great question to ask in many situations. It can be motivating to consider the possibilities and I need all of the motivation I can get.

Krantcents December 3, 2013 at 6:56 am

I think it also makes you focus on what you think is important.

SuburbanFinance December 3, 2013 at 5:48 am

There is a lot of power in reflection, but there is also a lot of power in acceptance and moving forward. Sometimes it’s fun to play “what if”, but more often than not, it can be a bit of a waste.

Krantcents December 3, 2013 at 6:57 am

Everything depends on what you do with it!

Financial Samurai December 3, 2013 at 5:58 am

What if + One more year = ?

I haven’t asked myself what if much this year.
Rather, it’s more ” I know I will regret if I don’t so let’s go for it!!”

Krantcents December 3, 2013 at 6:58 am

Don’t lose sight of the bigger picture. Where do you want to be in 1, 3 or 5 years?

Money Beagle December 3, 2013 at 12:14 pm

I think the ‘How will people remember me?’ is something that definitely gets more recognizable as you age and especially when you have circumstances where the answer is more important, such as looking at how my young children will grow and how they’ll see and remember the times they have with me now and the years we have left.

Krantcents December 3, 2013 at 12:21 pm

Funny, I never thought much about a legacy when I was much younger!As I get old(er), it becomes more important. I already know that I influenced some of their good habits! Hopefully, they will remember many of the experiences that made me happy.

The First Million is the Hardest December 3, 2013 at 5:03 pm

I always reflect on the “what if’s” but rarely get too hung up on whatever they may be. I’m pretty good at making a decision and moving on.

Krantcents December 3, 2013 at 5:24 pm

I agree, but I try to learn from every decision.

Levi @ Wealthnote December 3, 2013 at 6:21 pm

My wife does the same thing. She likes to know the end of everything before she starts. Books, TV shows, movies, and it drives me crazy. When it comes to entertainment I must be surprised.

When it comes to my life though knowing how it ends is a must. My master plan has a very specific ending!

Krantcents December 3, 2013 at 7:43 pm

I agree! One of the things I like abuts sports is the outcome is less predictable. It makes it more interesting. Life is more interesting when you can affect the outcome.

Money Saving December 4, 2013 at 5:35 am


This is a great post that really spoke to me. I very much fancy looking back at things and wondering – what if I had done things differently. I think it’s a healthy exercise to help you understand that there are no right answers in life. Choices come with consequences, and those can be good or bad depending on your perspective and how you wield the results.

Krantcents December 4, 2013 at 6:58 am

There are some choices, I wish I could run in parallel! Unfortunately, I cannot.

Little House December 4, 2013 at 6:56 am

I like the idea of using the “what if’s” for the future. Making a goal, visualizing what you want your life to look like, then making a step-by-step plan to get there. I’m no where near perfect in this process, but I’m working on it. And yes, when I try and give students advice about working hard and how that will impact their future, sometimes I feel like I’m talking to a wall – only they can decide to take the advice to heart. (But, hey, middle school kids know it all, so what the heck am I talking about?! ;) )

Krantcents December 4, 2013 at 7:00 am

I usually start with their goal of “rich and successful”. I back into my point of how education helps you get there. I usually can get their attention using where they want to end up, but they have no idea what it takes to get there.

maria@moneyprinciple December 4, 2013 at 1:23 pm

I like ‘what if’. There are danger in it though. Sometime it can paralyse you and you stop acting because you just build this horror as the single scenario. This needs to be controlled: the ‘what if’ works best as a strategy tool if a whole range of scenarios and possibilities is developed.
Oh, and tell your wife I used to do the same: I always read the end of the book. It may be my impatience or the fear I’ll die and won’t know the ending. Don’t do it any longer: hard to do with e-books.

Krantcents December 4, 2013 at 2:11 pm

The “what if” scenarios comes from my planning background. I tend to rely on my strength of planning to make better decisions. It has worked very well for me! I also use it as another way to reflect on my decisions. I think it improves my judgment over time. BTW, my wife says that she reads the ending to determine if the book is worth reading. Planning has some of the same characteristics. You start with the outcome and work backwards.

Untemplater December 4, 2013 at 11:21 pm

I used to drive myself crazy with what if questions. I almost got paralyzed from trying anything new because I was too afraid of what could happen. What ifs don’t all have to be bad thoughts though, there are tons of positive what ifs to think about and use as motivation.

Krantcents December 5, 2013 at 6:51 am

I use it in my planning and reflection on decisions. It helps in the analysis and learning from mistakes.

Alexis Marlons December 8, 2013 at 2:42 pm

I guess as we get older, we tend to be more responsible with our actions and decisions and think a lot of “what ifs” unlike during younger years when we were so impulsive.

Krantcents December 8, 2013 at 2:46 pm

I do not think I was ever impulsive, but age and experience does help make better decisions.

Bobby @ Making Money Fast and Slow December 9, 2013 at 8:08 pm

What if I had studied harder in high school instead of making websites (in turn going to a better college)? I don’t think I’d be as happy as I am now

Krantcents December 9, 2013 at 8:57 pm

It would be really nice, if you could go back and do it over. My “what if” is more of a reflection on your decisions vs, a do over!

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