What to Do with Disappointment

At some point, everyone faces disappointment.

In general, I find that the word does not convey enough because it is often used to describe events we don’t want, but that ultimately do not cause much harm to our lives. It can be in at a sports team’s defeat, another person’s harmful behavior, or a cancelled music festival. Things we get over, fairly soon.

Yet, what about the type of disappointment that sticks, traps you, and permeates almost all parts of your life? That’s what I want to talk about.

What might be crushing to one person, might be easily and quickly forgotten by someone else, and that needs to be said from the outset.

Either way, disappointment can be the thing that ultimately gets you to where you want to be.

That is something that I find to be key about the experience.


That deep, existential disappointment can stem from shattered expectations in many different areas of life. It can be in your personal relationship desires, career or educational pursuits, current events, your goals in your chosen art or sport, and many other causes.

I have faced many of these, but the key disappointment in my life has been in my professional aspirations and pursuits, specifically, my dreams of being a fighter pilot. I don’t want to just tell you about my path, but I have to give you a sense of where I am coming from if I am to present a recommendation for whatever your situation might be.

Some people simply identify with their careers more than others, and some professions lend themselves more to this than others.

Have you ever seen someone incorporate their position as an insurance claims adjuster, into a marriage or a child’s gender reveal announcement? Maybe, but I doubt it. It’s much more likely that you have seen this from a family in law enforcement, healthcare, the military, firefighting, or the arts.

It tends to be those in the service industries that identify so strongly with what they do. When you have to give so much of yourself to your profession, it’s only natural that it becomes a part of your normal existence and sense of self.

Being a fighter pilot is just one of those things that just has an automatic “wow” factor for most people. I wanted that. It is a dream that originated from my inner child, a youthful sense of adventure, imagination, courage, service, making a difference, and competitiveness. It was my attempt at “being somebody.” My attempt at crafting myself into the type of person I wanted to be and dreamt of one day being.

In chasing this dream however, I manifested my own professional nightmare. I found the exact thing I hoped to avoid by entering the military. A non-stimulating desk job with no glitz, glam, or sexiness. No moments of thrill or beauty. No, just boring emails, phone calls, presentation slides, and staff meetings. No challenge, no competition, no immediate sense that I needed to push myself to get better, and nothing desirable on the horizon to even push for. Oh, and the alternative to this job was desertion and jail. I did however, get to “support” the people (pilots) doing what I wished I could. I was just close enough for fate to taunt me. I had earned my spot in the Air Force, but it was ripped away by what I saw as medical standards that were strict to the point of irrationality. Essentially, they were factors beyond my control. All I could control is how I responded to them. At first, it was not in the most healthy or useful way, but in time, I came around to dealing with this in what I believe is the best way possible.

I’m glad to say that the youthful sense I just mentioned is still alive. My inner child continues to dream, of other things now, because of what I did with my disappointment.


People encounter obstacles on the way to their aspirations. A setback, a diversion, or something else. These can often be overcome, and your target remains the same as you collect yourself, learn, grow, and push forward to your goal. Rarely is a door simply slammed closed in front of you, then welded shut, then sealed with concrete. Closed forever. That’s what happened to me when I lost the position I earned as a military aviator due to medical assessments, before I even got to start. Did I know I still could do it? Yes. Do I still know this? Yes. In fact, I have done it in a recreational sense. Yet nothing can be done when you are trying to navigate a system that doesn’t take the individual into account, just diagnoses.

What did I have to do?

There was absolutely ZERO immediate answer as to what I should orient myself towards instead.

I found myself stuck, as though what was lost could never be replaced. Imagine going to law school, and after earning your degree, you arrive at your chosen law firm only to find that you can’t be the one prosecuting or defending in court. No litigation, and no trial. However, since you even applied, you are hired, and now you can’t quit until 4 years from now. You’ve been reassigned to sorting mail in the back room. I hope you can make the best of the art and science of letter and package handling. Hey, you still get to support the lawyers!

Military service is something always worth doing, and this is not an indictment of that pursuit. It was simply a an expression of frustration arising from the desire to serve, but knowing you are serving in a way that is far from optimal because your duty does not align with your skillset, personality, or interests.

I tried everything. I investigated every possible avenue to do something SIMILAR. I checked into the medical regulations of every other aviation position in all the military branches. I tried to get into the Navy as a submarine officer.

It was gone, and never coming back.

No, the story does not end with me somehow finding a way to become a military pilot. This is a message of hope and never giving up on the life you want, but sometimes there simply isn’t anything else you can do, no avenue within which you can continue to fight. It’s not your fault if that’s the case.

Despite that, the following statement is true, both of my disappointment, and yours.

It does not matter whether it is in your professional or personal life. Your career goals, personal development goals, or your relationship goals.

This is the truth:

It is not a denial, it is a delay.


So what to do with disappointment? Give in to it, just for a moment. Dig into it. Let it hurt…bad. Figure out the source of the pain. Why did whatever transpired, affect you so much?

You need to know this.

Don’t ignore it. Don’t just get over it…yet. There might be something useful to be gained within.

What did you want? Why? What don’t you want something else?

Once you find out, distill it into it’s core essence. Then, search for a way to manifest it in a new way.

Deconstruct.

Then reconstruct.

Why did I want to be a fighter pilot? Was it because I wanted thrill, excitement, and beauty? Yes, but I can get those through recreational activities. Was it because I just wanted to serve? No, I could still serve in other ways.

Why did it still hurt, even years after the fact? Why did it tear me apart? Why does it still sometimes?

I figured it out, and like many deep realizations, it was amorphous, indistinct, and hard to capture or define. The exact “why” is still something I continually craft, but I drafted one sentence to capture the totality of why I wanted to be a fighter pilot.

“I want a job that is respected, exciting, and requires me to master a specific skill set or body of knowledge, and in applying them, I am able enact positive, tangible, and noticeable changes in my community or in my environment.”

So, I want something with recognition. I want something with a specific job function. I want something that offers a challenge, and requires me to be at my best. I want something that makes a difference and something where I can see the results of my efforts.

I lost that. The job I was given instead of my dream was far, far away from this ideal. It hurt, and I didn’t know why at first. Once I identified what I wanted, I had a road in front of me, with vindication at the end.

Would being a fighter pilot satisfy these? Yes. Is it the only thing that will? Not at all.

I might not fly, but I can still “fly.” I can still do that thing that calls to me, it will just be manifested in a different activity. I already know from experience that I have already found ways to make it happen. I’ve found a new career path, even temporarily in the military, that fulfills this drive that I have identified.

“Starting with Why” is important, especially in aligning your life with your values, but that is not the essence of what I am talking about here.

Do your best to create a single statement that encapsulates what you desire, and what you feel you lost in the event that led to your disappointment. Ensure that, whatever it might be you desire, is specific, but not so specific that you limit it. Ensure that a path to acquire it can be found. Also make sure you are willing to do what it takes to find it, before you commit.

Then, get after it….again.

ACCEPT that you might never actually feel alright about what happened. You don’t have to. You can still move on. You can still find that which will bring you the satisfaction, fulfillment, and passion. You can still find love.

Career goals are easier to define. I understand that if your disappointment is a different type of heartbreak, it might not be as simple, but I fully believe it can be done. This is my system for any disappointment now.

Do not give up on the SPIRIT that will not die. Do not settle, and relegate your innate dreams to the realm of all that could have been. The fight alone, and the defiance and struggle against settling, is better than the peace you might attain from doing it will ever be.

Did I get just as much pay, respectability, and promotability as a non-flying officer in a military organization dedicated to flight? No I did not, but I still pretty close.

Superficially, my life was great. Great pay, respect, benefits, and leadership opportunity were all there, I won’t deny it. Yet inside, I wasn’t happy. So, it’s on to a new career now. Move on to a new thing, that is, in some sense, the “same” thing…at least at it’s core.

If it isn’t right, it isn’t right.

Sure, you might be able to “make the most of it.” In fact, you should. Whatever your situation is, you might see new possibilities you wouldn’t have had otherwise. Make the most of those, but if you are disappointed, get to figuring out why.

If you settle for what is given to you rather than what you choose, you might be happy for awhile, but the day will come when you won’t be if you’re not in a place you belong. It will only take one poignant reminder. It might come unexpectedly, from something you see, hear, or even remember. Then you will realize, and if you don’t suppress the feeling but you have the courage to acknowledge it, you will be given an unshakeable sense of wrongness. As I said before, deny it no longer. Do something with that.


I can’t offer you anything that will take away the ache. It’s clichĂ©, but time is the best at doing that. Sometimes it’s not enough though, so take action.

What I can offer you, is this one method you can use to start moving again towards what it was you wanted in the first place. If time isn’t the best, change certainly is.

Try it out. Get to thinking and feeling, and get to writing. Putting your internal thoughts to words in an external medium is the best for defining and understanding it. If you don’t have a better answer for what to do with your disappointment, what do you have to lose?

-Alex