Is There Anything You Would Have Done Differently?

by Robb Sutton

I was asked a question the other day that many of us are presented with on a regular basis. It’s an interesting one to say the least as it requires you to step outside and look in with hindsight awareness and knowledge on your life both professionally and personally.

Before we jump into it…hindsight knowledge is a funny animal. When you go into situations throughout your life, you try to make the best decisions you can given the facts presented to you at the time. With hindsight, you are able to know all of the facts and an outcome given certain actions. In essence, it is cheating and that is why I typically do not like looking at situations in hindsight.

So onto the question…

Looking back at your professional life up until this point, is there anything you would have done differently?

The short answer…no. But let me explain.

Given that this is a yes or no answer, there are two types of people that answer a certain way.

  1. If you are happy with your life and your current situation, you typically answer no.
  2. If you are unhappy with your life and current situation, you typically answer yes.

Makes sense…but let’s look into it a little bit deeper and then I’ll give you my angle.

I Wouldn’t Change A Thing

The person that is happy with their spot in life wouldn’t change a thing. Why is that? Each of the experiences in our lives brings us to where we are today. It affects the people we meet, the decisions we make and the path we eventually walk. By changing any one of these decisions and actions, we are derailing the path and we end up at a different destination.

If you are happy with your life, why would you want to change anything? Yes…there are decisions that you could have made in the past that you could have done better, but the person that answers no to this question uses this as fuel to make better decisions in the future instead of focusing on the bad decisions of the past. It isn’t regret or depression. It is motivation to become better.

I Would Have Done Things Differently

For the person that answers that they would have done things differently, this normally stems from a dissatisfaction in their current state. Instead of trying harder for the future, this person looks to the past and what they could have done differently to be in a different situation today…instead of looking where they want to be in the future. By focusing on what they can not change (the past), they can separate themselves from the responsibility and ownership of making things better.

Let’s put it this way…if you are running into people that are always complaining about how they could have done it better, they are always performing sub par to their abilities because one day they will be complaining about today. Instead of using the time an energy it takes to make a true difference, they are wasting that time worrying about thoughts and actions they can not change.

Would I Change Anything?

Absolutely not. My life has not been perfect by any stretch and I am not alone in that fact. But the experiences I have had through the course of my life has made me who I am today. My life time line has given me a beautiful wife, two great dogs, a great family and a house I can call my own. Could I have more? Sure. Are there more things I want? Absolutely, but the fact that I do want more makes me strive to be better…not worry about how I could have gotten those things in the past.

As we look back on our lives with hindsight knowledge, use those experiences for what they are…fuel for the future. That is your ammo to take on the world with the knowledge that you can be bigger and better. While others will let the past cripple their growth, you are going to use it to allow you to fly even higher…

Image by DimitryB

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Elie April 12, 2010 - 7:15 am

Robb, I get your point about not focusing on the unchanging past, but I still think there are those who could answer yes to your question, and yet not be avoiding their responsibility.

As an example, take my own professional story. I had a hard time finding my first job, so I took the first one that presented itself, working for a large corporation. Within the first 6 months, I knew that this type of career was not for me. However, 3 years later, I’m still working at the same company.

I now have a daughter and am the sole provider for the family. Today I can’t just quit my job, which is why I spend so much time building up my network on the side, so that I can reach the point where I can become my own boss. My network is fairly solid, and I’m confident that if I keep working on it, I will get to the point where it’s sustainable.

The one decision I would change, though, is to have quit 2 and a half years ago. At that time, with no child and another source of income (my wife was still working then), there would have been more flexibility to build my own business, and I could have done it during the day and night instead of only after hours.

Does this mean I’m shirking my responsibility to improve? No, because I don’t focus on that decision, and I’ve learned a lot about business in the 3+ years at my employer’s company. But when asked if there’s something I would have changed, the answer is certainly yes.

Robb Sutton April 12, 2010 - 7:22 am

But my point is that if you would have changed that decision back then…then you would not have your daughter today. Would you give up what you have today to change that decision in the past?

Elie April 12, 2010 - 9:24 am

Perhaps, perhaps not.

I don’t regret my daughter by any means, but it’s another path I would have taken in hindsight. However, I’m happy that I do have my daughter today, and my focus is no longer on whether or not I would change that decision, but how I can bring myself to have the opportunity to make a similar decision in the near future.

K9 Coach April 12, 2010 - 10:41 am

I hear where you are coming from here…

Another view that comes to mind when reading your story is that as a person who has been self employed all my life, in a few different areas and know others in the same situation… the thought that you would have succeeded wildly at the time is just a hypothesis.

Even the most successful people in the world have failed in the most opportune times. Granted, those who really want it get back up and get successful for the most part… but the path you are on could be one that happened for the destiny of success on your own in the long run.

Just a thought 🙂

Elie April 12, 2010 - 10:46 am

Thanks for the support!

As you say, success along another path is just a hypothesis, but being on my own is the path I want to be on. At that time, I had more flexibility from a time perspective to be successful – if it took longer to reach a certain level of stability, that was okay.

Today, that’s no longer true for me. The length of time I have to reach stability is until yesterday. As such, while I focus on reach success on my current path, I recognize that certain aspects to that might have been easier if I made a different decision in the past.

If you ask me the same question a few years from now, my answer might be different. Perhaps, as you say, my path to success lies through years of working in what, at the time, seems to be a suppressive environment for me. Maybe that’s what will define my own success, by experiencing the exact environment that I don’t want to live in for long.

John Paul Aguiar April 12, 2010 - 8:03 am

Man, I have made some mistakes and made some smart choices.

All In All I wouldn’t change anything, I believe I have learned and benefited from the mistakes as much as I have from the success.

No one is perfect and looking back at what you coulda shoulda woulda did is a big mistake.

Just keep working, keep learning and keep making mistakes,, only way to succeed.

Robb Sutton April 12, 2010 - 9:15 am

I’m with you. I have learned far more from my mistakes than my successes.

K9 Coach April 12, 2010 - 10:36 am

Woulda, coulda, shoulda’s. Many people spend a lot of time there. The fact is no matter what you wish you could have done or would have done, you chose to do what you did. And it leaves all of us with what we have today.

Now, I like being able to take all of my experiences and use them to choose exactly how I deliberately want to move forward in the future.

It’s an interesting thought process and one that makes me very thankful for all that I have now. There is nothing more or nothing less, but what I have now.

Robb Sutton April 13, 2010 - 6:28 am

“Woulda, coulda, shoulda’s. Many people spend a lot of time there. The fact is no matter what you wish you could have done or would have done, you chose to do what you did. And it leaves all of us with what we have today.”


I really like your point about being thankful as well…key part to living a happy life in my book.

Drezz April 12, 2010 - 10:59 am

You can’t rewrite the past, and you can’t predict the future. So why waste the present thinking about either.

I prefer to just learn from the mistakes or the opportunities missed and keep moving forwards. Eventually you’ll get good results. That’s your future coming true.

Robb Sutton April 13, 2010 - 6:27 am

You can’t predict the future, but you can take certain actions that affect the outcome. I am a strong believer in long term planning so I will differ with you on this one a little bit.

I plan my result and then take the steps to achieve it when I can. Things always come up…and plans almost always change…but that plan is still there.

Jewelry Secrets April 12, 2010 - 11:09 am

Very good points. Very true as well. If we didn’t go through those experiences we wouldn’t be in the position to learn what we do today. Well said. Keep focused on the future. That we can still change! 🙂

Robb Sutton April 13, 2010 - 6:26 am

You have some control on the future and zero on the past. Keep rockin’ it!

Jewelry Secrets April 12, 2010 - 12:43 pm

Hey I wanted to let you know, that I came here earlier today and saw the top 4 articles and thought that you didn’t post a new article. I didn’t realize that the top 4 were not the most recent posts. I didn’t know until I saw you tweet it. Now I know I have to scroll down to see it. 🙂

Robb Sutton April 12, 2010 - 1:11 pm

This article shows up on the left in those top articles. They are the latest from each category.

Karen April 12, 2010 - 7:24 pm

Hi Robb,

Count me as someone who wouldn’t change a thing. I don’t believe in having regrets and believe that all of our experiences (good or bad) go into the life-experience pot. We can’t know sometimes when we’re living in the moment whether our decisions are good or not. It all comes with hindsight and hopefully, we will learn from our mistakes and make better choices in the future. As someone who spent years of her education in a field that I never ever worked in, I don’t regret the education or the sunk cost of that education. My life took a different turn as did my profession. That’s okay though. My new profession has enabled me to live a pretty good life. Who knows if I had stayed with the other profession where I would be?

Interesting topic and discussion.


Robb Sutton April 13, 2010 - 6:25 am

I’m with you Karen. If you take away my bad experiences…you also take away the lessons I learned from them that have helped me in my good ones.

Tony Grogan April 14, 2010 - 7:57 am

There is very little I would have done differently in hind site. My biggy is not getting my four year degree. I stopped at an associates degree, and went to work. I have had a good life but now suddenly after 30 years in a dead end career. Due to layoffs and having to take less and less pay for the same work with more and more hours, we are so laden with money and time debt, that going back to school is not an option.

I still have hope for the future. Otherwise I would not be here following Robb and many others, trying to leverage my way into an online freedom lifestyle.

Koky September 9, 2020 - 5:13 pm

hi Robb, can you explain this question for me: “do you think the lockdown during the covid 19 pandemic was an essential measure in spite of the hardsip it brought economically? what would you have done differently and why?”


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