Living the Dream!

Mike Peluso
7 min readDec 16, 2019


I was having a conversation recently with a generally upbeat and friendly professional colleague. Unfortunately he was having a tough day, week or month. This isn’t all that surprising because the world of the professional is generally saturated with tasks relating to problem solving, and some problems can be harder to solve or even impossible. If your job is to deal with these types of challenges, some which may have no solutions, then, almost by default, there can be a ton of stress that goes along with the job. The tell that my colleague was struggling with something in their job came when I asked ‘how’s it going?’ in a ritualized greeting. I got the response ‘living the dream, just livin’ the dream’. I always took that as sarcasm but just to make sure I double checked with the urban dictionary. I was right, it’s mostly used as sarcasm but I was surprised that it is also regularly used as a positive affectation about one’s preferred job. Either way, considering the tone of voice my friend used in this instance, i’m pretty sure it’s use was the sarcastic former vs. the more positive latter usage. Its funny how sometimes the littlest things can get me thinking… this was one of them. The phrase ‘living the dream’ rolled around in my head. I couldn’t help myself from thinking, What is the dream? What is the goal of the dream, at least professionally? Why are we using it sarcastically?

What is the Dream?

I would argue, and have often, that the dream as it relates to the careers of professionals includes a stable and engaging job with a high quality compensation package. Starting with compensation, it is not just about take home pay. Yes, in an ideal world pay should be enough to meet an average quality of life, but total compensation should also provide the expected benefits that we are enculturated to expect out of a ‘good job’. Today that means retirement and medical as well as paid personal time off (PTO). But it goes just beyond the base needs that are provided by employers. Living the dream professionally should also include working on a good team with good management. The job should be highly engaging for the professional and include reasonable challenges and good rewards. This is the professional and career component of the top part of Maslow’s hierarchy. The pinnacle of the pyramid is the spot that self-actualization needs occupy. I think most would agree that any position that meets this description would be a ‘dream job’. Going back to the ‘living the dream’ statement, saying it in a way that’s drenched in sarcasm when talking about your job is sort of like saying ‘I love my Ferrari, when sitting in an 1980’s K car.

I had a moment of dissonance because I was under the impression that my friend had something that approximates a dream job, at least according to the rough template I just outlined for what constituted a ‘dream job’. My confusion got me contemplating his situation. It was clear he was unhappy, but was it just a aberration or was it really the job I wondered?

I know that it is a very well paid job for the industry but the position is limited in its ability to affect change directly. There is also very restricted resources available to get the job done. The limits on being able to affect the situation and resource availability have to do with the systems bureaucracy. There are hugely complex initiatives that don’t have clear support from real decision makers. Unfortunately the ability of any of this macro-situation to change is limited / nonexistent because of the laws that govern what he does, laws that literally stem from an act of congress as well as federal and state bureaucracies. This caused me to reassess my initial impression of the job of one that is desirable and empowered as it appears on the surface to one that is tough and filled with many no-win situations. He has a job that’s really about managing chaos. When I came to this conclusion, I realized the real surprise shouldn’t be that he was unhappy this particular time, but that he is generally so upbeat. That’s one of the things that made me think he had a great job.

How To Really Live the Dream

I like this person, which is not surprising. People who have positive attitudes the majority of the time are generally likable. I also consider him a friend and I want him to have a great life that includes a great career, something aligned to the work situation that I described earlier. I wondered, How to do that? Neither I nor my friend have high levels of control over his work environment even if that’s the outward perception. That being said he has control if he stays or goes. There are of course pros and cons to either staying or leaving.

For example I realized I never heard a remotely successful entrepreneur say they were ‘living the dream’ sarcastically. I have only heard it from people who were experiencing the stress of the modern employment environment. Successful entrepreneurs who left the rat race to walk their own career path are typically happier than people who work for others. So going out on your own could actually be ‘living the dream’ for real without out sarcasm. Shouldn’t you try and live the dream? There is a ton of risk. There are lots of mis-steps unseasoned entrepreneurs make and even then there is a huge component of luck with successful private ventures. Remember what I said earlier when I described a dream job, the first word I used was stable. Rarely are the words ‘stable’ and ‘my new business’ used together.

Are there other ways to do it via a regular job? I guess it boils down to job and personality alignment. A radio talk show host for a consummate extravert or a researcher on a well-funded multi-decade long research project are definitely in situations where ‘living the dream’ is a high probability. I say this assuming the work environment is congenial and stable which can be as rare as a high alignment to skills, interests, and job responsibilities. This connection of alignment to personality means that ‘living the dream’ is different for everyone. My buddy mostly likes, and was aligned to his job, at least I thought he was. I’m not sure if that has permanently changed or if he just entered into a period where the unending and unfixable problems got to be a bit more than he could handle while keeping his generally positive attitude. Sadly, in his environment it’s impossible to empower him to actually do the things that he’s tasked with, but that would be one way his job would be a real dream permanently.

Sometimes ‘living the dream’ is more about what the job brings than the mechanics of the job itself. I cite myself as an example. My dream isn’t really about my day job. In my case it’s about security, another thing I’ve discussed often. I personally can’t ‘live the dream’ until everything is paid off and I have enough investments to generate enough revenue to not have to work for the rest of my life. By my estimate that’s 3 to 5 million dollars for a sustainable middle class lifestyle. I guess I won’t be living the dream any time in the near future but I don’t intend to give up trying.

There are other conversations to be had about better aligning people to jobs or modifying the work environment to remove some of the things that make people frustrated. Those can become very deep conversations more about the availability of opportunities and macroeconomics more than a focus on people and it pulls us away from the real point I wanted to make. My main takeaway is this: If you are discussing your job, being sarcastic about the unpleasant nature of it once in a while is ok, being sarcastic every day is really bad. It means there is a systemic problem in your professional life that needs to be addressed. If you are continuously unhappy, stressed, and finding yourself starting to adopt sarcasm as a coping mechanism, then maybe it’s time to reconsider that part of your life. I mostly discussed work but realistically the problem could be anywhere. It could be finances, housing, even your various personal relationships. Ultimately, no matter the root cause of the issue, this is a sign that something’s got to change. Since everyone is different and every situation is different, then it follows that every change that needs to be made is going to be a little different. I know one thing. If you figure out what needs to be changed and you make that change, there is one way to know you’re on the right track. I figure you know you’re heading in the right direction if you never have the urge to sarcastically answer ‘Livin’ the dream’ when someone asks you how’s it going?

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Mike Peluso

Mike Peluso writes is about the collision between the professional world and life. Read more at or listen to the Peluso Presents Podcast