Let’s Talk About Disappointment

  1. You’d never know it by looking at social media

I’m not going to sugar-coat it.  My 2019 was a year filled with disappointment at work.  As I started to think about this, I realized this is a subject we need to discuss.  So, let’s talk. Honestly!

First, the context.  Social media is rife with positive, “good news” stories.  Almost exclusively so. I’ve heard this said about Facebook and have decided that, among other reasons, I just don’t want to spend my time on most forms of social media.  But I realize that the world evolves and maybe there’s a place for social media in my professional life. So, for many years now, I’ve been active on LinkedIn.  

There are benefits to be sure.  But when it comes to our perception of reality, there’s no worse place to go than your professional social media feed.  It’s filled with notifications of promotions, work anniversaries, and conferences and conventions. All the good stuff. Never mind that promotions might be rare in the life span of a single career.  Never mind that people get laid off and their work anniversaries are prematurely truncated before they can celebrate the big milestones. Never mind that in today’s cost-conscious companies, it’s almost unheard of for many in the insurance industry to attend conferences and conventions (“We can’t send everyone”, “it wouldn’t be fair”, etc.).   That is true, unless you are part of an Insurtech firm seeking investment or part of a sales team providing a service!

Against this backdrop of almost exclusively positive social news feeds, there’s the broader economic situation.  It’s booming! Fantastic! Terrific! Look at unemployment, for example, the lowest it’s been in 50 years!   And the stock market!  Up 24% in 2019 alone.   We get the feeling that anyone who is not doing well must just not be trying.  Forget the fact that about 7% of workers face underemployment.   Forget the fact that middle class incomes are flat when adjusted for inflation.  Forget the fact that workers, especially but not exclusively Millennials and younger workers have taken on a lot of debt ( trillion in aggregate student loans).  Forget the fact that regional and industrial differences come into play to counteract many of the positive developments going on in the larger economy, with some states having twice the rate of unemployment as others.  The housing market is not the only thing that’s “local” – so is the economy and our professional experience in it.

What this means is that disappointment and work struggles are real.  From job loss, to other less-than- ideal situations like dead-end jobs or demotions.  Throw in health concerns that may force us to work less or not at all. Or family and personal situations that we can’t control.  They can happen. If not now, at some point, they will happen. So how are we to deal with them?

Social media doesn’t provide a very good example.  Every now and again on LinkedIn I see a video posted about an animal that’s struggling to get itself out of a tough situation, and how it overcomes the obstacle.  The other day, a dog was featured in a deep ditch. Another dog was pulling its leash and eventually freed it. The message? Keep fighting! You can do it! A great message but not exactly much of a roadmap if the direction you’ve been heading is not where you ultimately need to go.  (Think about a manager who suggests, without specifics, how an employee can achieve a future promotion. However, after the associate exerts effort and time to develop themselves, their manager informs the associate that they are “not at the next level” and the promotion is not in fact forthcoming.  In this case, how helpful was the social media message to “keep fighting” or “keep working at it”? Or does the associate need a different roadmap and direction for what to do?)  

Through all of this, I realized that the disappointment I experienced was complex.  Sometimes it was frustration with the organization at the highest level, and sometimes it was quite specific down to a decision that involved my daily role.  After reflecting, I realized there’s more than one kind of disappointment and sat down to identify a few types shared here. Realizing that disappointment is not always easy to assign to only one category, here’s a list to get us thinking more about the kinds of disappointment we face at work.

2. Types of work disappointment 

Organizational disappointment.  High level disappointments with the organization can include the quality of leadership or constant change at the executive level leading to a lack of progress or continuity from one business cycle to the next. Organizational disappointment can emerge when business strategy is poorly articulated, communicated ineffectively, or when bad business decisions are made.  We also can experience organizational disappointment when the hierarchy or structure of the business is suboptimal or worse yet, presents obstacles to getting the work done at all.

Role disappointment.  These are directly related to your current role or position.  Role disappointment can include demotion, reduced responsibilities, loss of direct reports, or lack of training or other resources and tools to do your job.  On the flipside, what may appear to be increased responsibilities may turn into role disappointment if the responsibilities are a result of staff reductions, reorganizations, or other changes that are not rewarded with increased compensation or title.

Cultural disappointment.  This occurs when the organization, department, or team and its leaders fail to live up to their aspirational values and goals.  Perhaps they say one thing and do another. There might be clashes between you and the organization in terms of what you believe, or there are competing objectives within parts of the organization itself.  Think about how a part of an insurer (e.g., marketing) often wants to grow the insurer, at any price, while another part of the business (e.g., underwriting) seeks to reduce risks, costs, and inefficiencies.  

Career disappointment.  These are disappointments that present career path obstacles. Career disappointments might include lack of a career path or failing an exam (think actuaries, CPCU candidates, or other programs of study).  Note that role disappointments (such as ambiguities with your job duties) may bleed over into a career disappointment since it can be difficult to see how today’s job can lead to a future career.

Social disappointment.  Social disappointments can include a lack of sponsorship or difficulty identifying a mentor.  Associates face social disappointments when we have trouble fitting in with the team and therefore feel isolated.  Others face feelings of irrelevance in an organization, department, or team, sometimes linked to large organizations.  At their worst, examples of social disappointment include abuse, exploitation, or feeling “used.”

Disappointment related to Identity and passion.  These are struggles with finding out what you enjoy and excel at, and how you can pursue it.  Perhaps the organization, department, or team leaders don’t encourage you (or worse, they actively prevent you) from identifying or pursuing it.  Or perhaps there’s just a more fundamental issue of not being free to be yourself in the team, department, or organization. Political perspectives, mental health struggles, parenting challenges, and gender identity come to mind, but are by no means the only examples of “identities” or aspects of who we are that we might not feel we can share at work if the climate doesn’t accept a diverse staff and ensure everyone feels included.

Work product disappointment.  By work product, I mean deliverables.  What is it you produce on a daily basis?  Actuaries produce indications for factors from rating models.  Underwriters handle caseloads of policies. Marketing associates develop content for client email campaigns.  IT staff maintain software and hardware platforms. And project management staff plan and guide projects through various stages from initial kickoff to final implementation.  When projects are delayed, run over budget, or fall short in delivering objectives, “work product” disappointments will most definitely ensue as anyone at a large insurer with legacy IT system integration projects can attest.  And this is before we even discuss whether you like what it is that you are “producing!” Disappointment may be particularly chronic when associates generate deliverables in which they are just not interested.

Ok, so you get the point – there are at least seven types of disappointment you may experience in your career.  It’s important to be able to acknowledge and describe disappointment. But then what?


3. A Way Forward: A Proposal

A lot has been written about the disappointment from a psychological perspective.  Most of it involves reframing how we see success and failure. I encourage you to explore that material yourself, so I’ve suggested a few articles (hereand here), and won’t summarize it here.  What I’m proposing are complementary steps to address the struggles with disappointment we all will face at some point in our careers.  I believe this proposed way forward can:  

  • Reshape the organization, department, or team culture from the ground up – the steps kick-start the process by doing something right away (no need to wait for a top-down cultural transformation like an executive sponsored engagement plan)
  • Help each other – following the steps builds relationships 
  • Be especially appealing to action-oriented people – it boosts confidence by doing something

Here are the proposed steps for a way forward.

Step 1: Acknowledge the disappointment to yourself.  Sounds basic but for many of us (ok, me), recognizing and admitting our feelings isn’t always easy and seems perhaps less than professional (hint: it isn’t).  I find myself irritated or upset at a certain point of time and then realize it’s from a lingering disappointment that I’ve been struggling with for weeks. It’s helpful to be in touch with that and acknowledge disappointment.

Step 2: Share the disappointment with someone you trust.  I don’t pretend to have an answer to the social media bias towards positivity that’s out there – you’re simply unlikely to see a lot of posts about disappointing job situations or careers.  However, I do think it’s important to have honest conversations about work disappointments. We need more open dialogue to recognize that we are not alone in how we feel. To be listened to and validated.  To pull back the veil. Who should you admit it to? I’d recommend starting with a trusted colleague, friend, manager, or mentor. If your workplace feels too risky because maybe you’re worried about confiding something confidential or harmful to your career, consider speaking with someone that you trust who is outside the organization.  Examples include a former manager, former colleague, or mentor. How? Start simply. When they ask, “How are you today?” You can respond, “Well, I’m feeling disappointed, and here’s why…” It opens the door to the next step.  

Step 3: The development of a role model. Then once we have a little perspective, we need conversations about disappointment to realize that others have faced disappointment and they’ve survived (maybe even thrived!).  It’s an important starting point, a shift in which we see that if someone else faced it and are ok now, then we can be too. Our confidant’s experience serves as a role model for us.  One that will never appear in a LinkedIn post, profile, or resume. Wait a minute, you say? The disappointment my confidant experienced is not the same as what I’ve experienced? Hold on for the next step, where you may need to get creative when it comes to the path forward.  

Step 4: A path forward.  In this step you begin to forge ahead. A path forward starts with having a discussion with your confidant – what disappointment did they experience and how did they work through it?  If this isn’t applicable, because perhaps the situation is just too different to gain insight from, one idea that may be helpful is to think about how you would use disappointment to your advantage.  Let’s call it, “the interview trick.” Consider a behavioral question in which an interviewer asks you as a hypothetical interviewee, “Tell me about a time you had an obstacle and overcame it.” Presto!  You’ve got a ready-made success story to tell when it comes to your disappointment! You can answer, “Well, as a matter of fact, I did just have a situation where my project was delayed and over budget. That was very disappointing.  What I did was to speak with the key partners involved, determine what went wrong, and used that to avoid those kinds of pitfalls in the next project.” This interview trick is a way to “flip the script” and consider what we learned and gained from a disappointing experience.

Two comments about the proposed steps.  First, I don’t mean to imply that a series of 4 steps is quick or easy to follow.  In my own experience, it can take weeks or months to process disappointment. Then it may be just as long or longer to work through the rest of the steps.  Second, I recognize that step 4 doesn’t erase any emotional wounds of your disappointment. And if these steps don’t seem to help or you’ve experienced social disappointment of the abusive kind, I encourage you to seek the guidance of a trained therapist who can help you address these feelings directly.  But reframing the disappointment by flipping it is not simply useful for convincing an interviewer that you’re an insurance professional capable of growth (which you are). This technique can also give the disappointment meaning when it might seem meaningless. Furthermore, the interview trick puts the focus back on what you can control.  And having honest and open conversations about disappointment won’t just provide us with a role model for experiencing and surviving disappointment but can also operate in the reverse fashion, by providing an example for others. Even situations with the worst-case outcome such as leaving the company – perhaps because management wasn’t supportive of your need for flexible work as a parent of young children – can be flipped.   Here’s an example, where you are a hypothetical candidate interviewing with another company after leaving the previous company: “I was disappointed that I could not find a way to achieve work-life balance at my previous company, but I discovered how crucial that was for me to have in my next role. Can you [the interviewer] tell me more about flexible working arrangements at your company?”  

This year, I’m resolving to speak more openly about disappointment by following these steps. First, I’m going to acknowledge the disappointment to myself.  Next, I’m going to share that with someone whom I trust and start a conversation that may help me understand how they have faced disappointment. Finally, I’m going to flip the script to find a way to leverage the disappointment.  If the dialogue is open and honest, I hope to not just learn from others, but perhaps find that I’m helping colleagues as a role model. In the coming months, I plan to return to these pages to discuss a few stories of disappointment.  I’ll update you on how things are going as I share my disappointment with others and start down the path towards a different future.   

Now it’s your turn!  What do you think? Reach out and let me know.  Disappointment at work is inevitable. But together our conversations about disappointing experiences might just start to change the way we think about it and how we relate to one another.  It starts with each of us.


  • Michael McCrary

    Michael McCrary, Ph.D., CPCU builds personal lines pricing and underwriting predictive models for a large nationally recognized insurer that is not responsible for the content of this article. He’s had a few work-related disappointments in his journey from sociologist to banker and retailer before landing feet first in insurance. He credits Tony and the Insurance Nerds group for their infectious encouragement to complete his CPCU and continue learning more about risk management and insurance.

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About Michael McCrary

Michael McCrary, Ph.D., CPCU builds personal lines pricing and underwriting predictive models for a large nationally recognized insurer that is not responsible for the content of this article. He’s had a few work-related disappointments in his journey from sociologist to banker and retailer before landing feet first in insurance. He credits Tony and the Insurance Nerds group for their infectious encouragement to complete his CPCU and continue learning more about risk management and insurance.

2 thoughts on “Let’s Talk About Disappointment”

  1. Even when I grew up at a public housing project and literally had virtually no food in the house and an almost barren Christmas, my glass has always been half full. It’s a mindset based on perception that we largely create for ourselves with optimism, determination and perseverance. It helps to associate with people who have the same mindset, especially mentors who believe in you.

  2. Great article! I weaned myself from social media for many of the reasons you’ve cited. Hyper positivity (and negativity) can be annoying and can cause me to make snap judgments that aren’t fair. Despite what my experience tells me, it just takes one glimpse of my push notifications before I start comparing myself to the smoke and mirrors of delusion someone can craft in 140 words or less.

    This may be hard to believe after what I’ve just shared, but I’ve always considered myself to be an optimist. The problem I’ve found is when people conflate optimism with positivity. Optimism whispers, “things will improve,” while positivity tends to boast, “things are great.” Optimism is rooted in observation and self-reflection while positivity often seems to be rife with sunshine and rainbows. Knowing the difference between the two can keep us hopeful through disappointment without having to create an alternative reality.


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