What I decided to do when my dreams did not happen

I am a big fan of having dreams. A future vision of what is possible in your life. The bolder the better. In a previous post from this year I wrote about how to turn your dreams into reality.

This post is going to be different.

Last week I described the process I went through accessing where I am in life by searching for the truth in the rear-view mirror.

I mentioned that a work mentor encouraged me to take stock of my life, so I did. After some analysis, it became abundantly clear that several dreams I had for my life were over. They simply were not going to happen.

It is a sad reality that all of us will face at some point in our life.

The sun will set on some of your life dreams.

You will have dreams but some of them will not happen

Sorry to be a buzzkill, but many of your dreams will not happen.

This thought alone can be somewhat depressing and goes against what many are saying on the internet these days. I know because I read a lot of articles, blogs, and web content. Some say if you dream it you can make it happen.

It is a wildly popular life perspective probably because it is an attractive idea.

After all, who doesn’t want the opportunity to do anything they dream about in this world. Unfortunately, I don’t agree. I think the “you can do anything you want” philosophy for lack of a better term is naive.

They are selling you a bill of goods they cannot deliver. Here is an example.

I do not agree with this quote at all. Reality says otherwise.

I wanted to play in the major leagues

Case in point. As both of you know I like baseball. It is one of my favorite sports. Growing up I dreamed of playing in the major leagues.

That dream ended quickly when I joined a little league team. I was good at playing the field, but I was not a good hitter. I really struggled at the plate.

Hard to be a great baseball player if you cannot hit. Simple fact. I recognized this fact and decided to move on to other sports.

Both Oma and Opa were supportive of my decision because even they realized that I was not very good at playing baseball. Don’t be surprised if the same thing happens to you. You may suck at something you love.

The “you can do anything you want” disciples will tell you to keep trying. I disagree. Save yourself the frustration. Identify something you have the talent for and press forward becoming great at that skill.

I struck out a lot in baseball — big problem.

Evaluate your dreams after a major life event

Just so it is clear — I am not saying that you need to constantly be evaluating your dreams every step of the way. Rather I recommend that you evaluate them when the time is right.

What in the world does that mean? It means you will need to figure out how often to revisit your dreams.

One trigger point that I recommend is a major life event. When something big happens in your life like graduation, marriage, children, divorce, or death it is worth pausing to reflect on your dreams.

A few examples are below. I am providing them simply as food for thought.

  • When we decided to start a family — my dream of owning a Porsche came to a screeching halt…just kidding.
  • When I decided to leave the Army — the dream of having a government retirement check stopped.
  • When your mother and I decided to divorce — the dream of a life-long marriage ended.

Both of you are young right now, so you may want to wait until graduation before evaluating your life dreams. In fact, you may not have any big dreams yet. If you don’t, then get busy identifying your dreams of the future.

It is pleasant to see dreams come true, but fools refuse to turn from evil to attain them. Proverbs 13:19

Revisit your dreams when you hit a milestone birthday

Another good time to revisit your dreams in when you hit a milestone birthday like 16, 18, 21, 25, 30, 40, 50, etc. Both of you have milestone birthdays this year. Riley, you will turn 18. Gavin, you will turn 21.

Take some time after you are done celebrating your birthday to think about your future and your dreams. I did this year and it has been a helpful exercise.

I identified three different potential outcomes for my dreams — some will still happen, some may still happen, and some are dead. They will never happen.

Celebrate your milestone birthdays and contemplate the future.

Adjust your timeline for dreams you believe still will happen

Don’t give up on a dream if you believe it still will happen.

For example, I dreamed of retiring by my 60th birthday. Unfortunately, it is highly unlikely that this dream will happen by then.

During the divorce, I lost half of my retirement savings to your mother which put a really big dent in my retirement plan.

Do I have a new plan? I sure do, but it is not looking likely that I will get to the finish line in the next decade. No worries. I implemented the new plan several years ago and should be able to retire in my mid to late 60s.

I feel great physically these days and still have a lot to contribute at work, so I am not really all that worried. Sometimes you have to be flexible with the timeline for your dreams to come true.

Start saving early for your retirement — it is worth it.

Determine what you need for a dream that may still happen

I recommend that you don’t quit on a dream if you think it still may happen, especially if you have invested a lot of time and energy in the dream.

For example, in February I knew that my dream of becoming a Vice President where I work by my 50th birthday was not going to happen. The day came and went and I am not a VP.

I was somewhat frustrated because I have worked hard and invested a lot in my career. I have not given up on this dream. I still believe it will happen. It just has not happened yet.

I hope it will soon, and am working hard to get there. With that in mind, I identified what is still needed for me to realize this dream and crafted an updated plan for how to get there.

This graphic is a more accurate description of reality — no smooth ride.

Acknowledge when a dream is dead and move on

What do you do about dreams that end? I recommend that you acknowledge when a dream dies and move on. It is a lot easier said than done. But, it is the healthy thing to do. Don’t cling to dead dreams.

I have witnessed family members and friends who refused to let go of dreams that never are going to happen. It is not a healthy thing to do. They are waiting and waiting, and nothing is going to change.

Of course, it is sad to watch a dream die. This year a dream of mine ended. It was a painful experience, but I am glad that I was able to determine the end of the road was here so that I could move on.

Oddly enough my life has gotten much better since then. Next week I will share more about how to move on. It is an important skill to have for life.


I write a blog for my sons called Doug Keating Letter to Sons. I am sharing content from my blog here. I hope you enjoyed it. All feedback is welcome. Thanks for reading it

Originally published at www.lettertosons.com on April 16, 2018.




Leader and learner. husband and father. Novice blogger, www.lettertosons.com, Founder of All The Way Leadership! http://www.allthewayleadership.com/

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Doug Keating

Doug Keating

Leader and learner. husband and father. Novice blogger, www.lettertosons.com, Founder of All The Way Leadership! http://www.allthewayleadership.com/

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