In the prior post, we chatted about the unpleasantness of viewing work as not fair. From blaming one’s boss to resenting how one’s career has turned out, complaining that work isn’t fair isn’t fun for the complainer nor for the audience. But what if it isn’t just work that’s your problem. What if it’s bigger? What if, in your mind, life isn’t fair?

pointers“Life isn’t fair” – an interesting and debilitating dysfunction indeed. As I was noodling on this dysfunction while agonizing at the gym (amazing what pops into your head when you can feel your heart stopping on the treadmill), it hit me that this dysfunction differs by generation. How you perceive life is very much tied to both the stage of life you are in as well as the generation and culture in which you grew up. To that end, my apologies to our Eastern friends. As I take on this dysfunction, because of my own experiences growing up in the United States, I will be looking through the lenses of the Western world and the generations that are commonly present in U.S. workplaces today: the “Baby Boomer” generation, “Gen X,” and the “Millennial” generation.  For context, consider the following population chart outlining the differing sizes of each generation (source:



If you would classify yourself as a “Baby Boomer” (born between 1946 – 1964), your version of “life’s not fair” has its own particular flavor – “Cherry Garcia” might best sum it up given its reference to The Grateful Dead. The largest generation in terms of population, your generation grew up in a post-World War II era in which large families and traditional values were the norm. Having rebelled against those values in the late 1960’s as the “Woodstock generation,” your generation in many ways reclaimed and redefined many traditional values. As a generation, Boomers are particularly characterized by the values of hard work, loyalty, belonging, winning and prestige. Here is your quiz that, through your eyes, you may deem life today as not fair:

  1. I resent that my profession is changing
  2. I resent that after all of my hard work and sacrifice over the years, my employer has / may let me go
  3. I resent that my loyalty and dedication means nothing to my employer – shouldn’t that count for something?
  4. I resent that my retirement savings is not where I think it should be. Like real estate, I’ve always been told that investing was a “sure thing”
  5. I resent that I put in so many hours over my career and didn’t spend more time with my family
  6. I resent that my family doesn’t appreciate the sacrifices I’ve made

If those statements resonate with you, here’s your mini-prescription:

Rx3Redefine loyalty – Loyalty no longer means a mutual commitment by both parties to stick around – both personally and professionally (yes, I did say personally. Divorce rates among Boomers are encountering an unhealthy spike post-retirement). That’s an old-school definition of loyalty – just stick around. Today, loyalty means committing to mutually meet each other’s needs every day. Simply showing up won’t keep you employed or married. Bring your “A” game each and every time you get out of bed.

Redefine winning – Traditionally, winning was easy to define for Boomers: a big title and a bigger house. The prevalence of trophy homes among the Boomer generation is unparalleled by any generation prior or since. Today, your job is to redefine what success means to you. Create your own scorecard, not what others have suggested defines success. Titles get yanked and houses suck resources. What really matters to you?


If you would classify yourself as a “Gen X” (born between 1965 – 1981), like the Boomer generation, your version of “life’s not fair” has its own particular flavor – “rocky road” would best represent this generation given some of the societal challenges this generation faced. The smallest generation in terms of population, your generation enjoyed some of the highest divorce AND abortion rates in U.S. history as you were youngsters. Also referred to as the “latchkey kid” generation because of your parent’s propensity to leave you home alone, your generation is characterized by the values of independence, freedom, cynicism / mistrust of authority, giving back and work / life balance. If you are a Gen X-er, here is the “life isn’t fair” quiz just for you:

  1. I resent the expectations of loyalty and sacrifice that is placed on me by my boss and work
  2. I resent the special treatment that Millennials get at work. No one did any of that for me
  3. I resent Boomers at work. They are slowing down my career path and are refusing to change or retire
  4. I resent the expectations that my parents continue to place on me. Where were they when I needed them?
  5. I resent the demands and expectations my kids place on me. They need to understand that my life is not all about meeting their needs
  6. I resent the expectations my spouse has for me. I’m my own person with my own needs, goals and wants

If those statements resonate with you, here’s your mini-prescription:

Rx3Decide what you are committed to – One of the most admirable traits of Gen X-ers is their ability to commit to things bigger than themselves. Consider what it is that you truly want to commit to: your career, your marriage, your family, etc… and choose. The key to overcoming “life isn’t fair” for a Gen X-er is to know that you can choose to opt in to the things in life that matter to you. Make the choice, define who you are or want to be and stick to it. Don’t let “should’s” and “supposed to’s” weigh you down.

Compromise on needs – Clarifying what you expect from others (your boss, spouse, parents, children, etc…) AND have that conversation. Having a clarifying conversation can cure what ails a Gen X-er. Get clear on what you expect or need and be open to what others need and expect. “Redefining the rules on your terms” is music to an X-er’s ears. Just remember, don’t punish others simply because they have expectations of you. It’s not their fault that your expectations and needs are different.


If you would classify yourself as a “Millennial” (born between 1982 – 2004), like the generations prior, your version of “life’s not fair” has its own particular flavor – “rainbow sherbet” would best represent your generation given the sunny perspective your parents attempted to paint for you. The children of the Boomer generation, your generation is robust in size and has grown up with technology and information like no other prior generation. Also referred to as the “Echo Boomer” generation, your generation has been significantly colored by the values of your parents. The architecting that your parents put in place resulted in such phenomenons as: overscheduling and “play dates,” “helicopter parenting” and a sharp rise in anxiety and mood medications prescribed for you as children. In a nutshell, failure was not an option – neither to experience or to feel. That being said, your generation has risen above material things and is often characterized by the values of meaning, giving back, work / life balance, loyalty, immediate feedback and flexibility. If you are a Millennial, here is the “life isn’t fair” quiz just for you:

  1. I resent the lack of structure, the lack of clear expectations and the poor organization at work
  2. I resent the lack of feedback I get at work. I resent how disinterested my boss seems as it relates to me and my career
  3. I resent the way Gen X-ers treat me at work. What did I ever do to them?
  4. I resent the expectation that work is supposed to be my life. I don’t want to “pay my dues” like my parents did. Look what it got them
  5. I resent that others aren’t giving me the opportunities that I know I’m ready for
  6. I resent the pressure others place on me to “grow up.” I’ll marry and start a family at my own pace

If those statements resonate with you, here’s your mini-prescription:

Rx3Fail early and often – Your generation has a sparkle in their eye like no other. Knowing you are good, valued and special will serve you well as life progresses. However, as a generation, failure is an unfamiliar concept. As a result of the architecting of your parents, most Millennials don’t encounter failure until their early 20’s resulting in what some researchers have coined a “quarter-life crisis.” Your best strategy is to take as many risks as you can and fail early and often. With the experience of failure under your belt and surviving to tell the tale, you’ll proceed through life confident feeling as though you are “enough” regardless of the challenges life throws your way.

Get comfortable clarifying expectations – Like the Gen X generation, your ability to clearly articulate what you expect and need is critical to your short and long-term happiness. However, unlike the Gen X generation, you may need to be willing to compromise more frequently re: the expectations of others. Play the game and work and adjust… or not. If you decide that you prefer the flexibility and work / life balance that working as an outside contractor provides, then what are you waiting for? Go for it! And if you fail, you can check off the first prescription. No one said you have to play by other’s rules. Just don’t expect them to change for you.

Summing it up

Whether you are a Boomer, X-er or a Millennial, viewing life as “unfair” isn’t gonna get you very far. Work on your respective prescription and you’ll suddenly see yourself authoring life rather than turning up your nose at what it has offered you.