Inauthenticity at work and the fast track to a midlife crisis

As a law student, lawyer, and law professor, I’ve spent a lot of time around people whose career ambitions are largely defined by others. To some extent, I have internalized some of those messages myself.

But one of the most important lessons I’ve learned is to pick and choose wisely among these markers of achievement. If you fail to do so, you may find yourself living an inauthentic life (at least the part spent at work), and your psyche may struggle with the grudging realization that you’re pursuing someone else’s definition of success. It’s an easy recipe for a midlife crisis.

This month, as thousands of people line up to accept their degrees at college and university Commencement ceremonies around the country, these thoughts deserve extra consideration.


In the popular Marc and Angel Hack Life blog, Angel Chernoff writes about the “10 Choices You Will Regret in 10 Years.” The first two screamed out at me:

  • “Wearing a mask to impress others”
  • “Letting someone else create your dreams for you”

In graduate and professional schools, I see this process occurring all the time. It’s all about pursuing a fast track to success, and that path and destination are defined by others who have a vested interest in keeping it that way.

Especially susceptible to this messaging are younger folks who have never been afforded the privilege of thinking for themselves. And the better their grades and test scores, they more likely they are to be pushed onto certain paths.

My summer of discontent

My first major lesson in career inauthenticity came as a law student. I entered law school intending to be a public interest lawyer, and I envisioned a career spent in social and political change work. However, I temporarily succumbed to the siren call of corporate law, and I accepted a “summer associate” position with a large commercial law firm in Chicago.

Summer jobs at big law firms are a mix of tryout camp and wining-and-dining. Over a roughly 10-week period, the work of a summer associate is evaluated closely for the purpose of considering that individual for a full-time associate attorney position after graduation. In return, the law firm pays the summer associate handsomely (typically, a pro-rated equivalent of a first-year attorney’s salary) and hosts a variety of social events to sell the firm as a desirable place to work.

This Chicago law firm treated me with genuine respect and gave me a variety of challenging assignments. But within a few weeks of starting my summer gig, I knew the corporate law sector was not for me. Despite good colleagues and intellectually demanding work, throughout the summer I felt like I was giving an acting performance. It just didn’t feel right.

Although I was invited to return to the firm as an associate attorney after graduation, I declined the offer. Instead, I embraced my original aspirations and, during my final year of law school, accepted a job offer from the New York City Legal Aid Society. No regrets, not even when the student loan bills started to match my monthly rent!


Of course, having and making choices doesn’t necessarily mean that we can have it all. As I suggested two years ago in a post about work-life balance, even the best of lives usually involve trade-offs. Electing to do something often forecloses doing another, at least for the time being.

That said, Big Life regrets tend to emanate more from inaction than actions, unless the latter are reckless or foolish. In her “10 Choices” blog post, Angel Chernoff warns against “(e)ndlessly waiting until tomorrow”:

The trouble is, you always think you have more time than you do.  But one day you will wake up and there won’t be any more time to work on the things you’ve always wanted to do.

Not always a choice

I understand that all of the above presumes a degree of choice in the matter.

However, sometimes that isn’t the case: Jobs that pay the bills and support families are in short supply these days, and pursuing an occupation that delivers a psychological reward beyond a decent paycheck may not be an immediate option.

If you have choices that create mere possibilities for matching passions with income, consider yourself very privileged. Countless millions of people in this world do not.


The challenges of matching dreams with paychecks are among the reasons why I’ve devoted a number of blog posts to the concept of avocation. As I wrote last year:

An avocation falls somewhere between a job and a hobby. It’s an activity that may produce some modest income, and perhaps show promise of turning into a full-time job, but which ultimately we are drawn to because it is very satisfying on a personal level. Avocations may be among the keys to individual fulfillment during tough times when jobs that deliver both a decent income and psychic rewards are in short supply.

Avocations are highly underrated as potential door openers and as satisfying ends in themselves.

If you have the gift of choices…

…make them, don’t let others make them for you. Learn from the experiences and insights of others, and then incorporate those lessons into your own world view.

It’s an ongoing process. And except for a blessed few, it involves some stumbling and bumbling along, hopefully forward more often than backward.

3 responses

  1. Excellent post! And…so very true. Thank you. I’ve been trying to change careers for several years now. After 20 years in the same Field, it is almost impossible to change to a totally new & different track. Although this “new & different track” has been a very large part of my life all of my life. In our present System they handsomely reward a proven track record and are reluctant to consider you for anything different than your proven resume’ track. Even though you may possess the gifts and talents for excellence within this new track.
    But things are the way they are…for now. Changing careers is more difficult and complex than it used to be. Even as little as 5 years ago. Regrets you ask? Yes and no. I regret having spent so long not pursuing my passion. But then….I had to live and pay the bills. I also had to have something that “connected” me to this world and made me a viable asset for the job market. I did not have much choice…if any. Now I’m in a position to do things different. I’m one of the blessed/privileged ones that Dr. Yamada spoke of. But I’m finding that it is still difficult and takes time.
    My only real ‘regret’ is that we don’t have a System that is more flexible and receptive to “new”. I feel that there is a vast untapped reservoir of Energy in this country. Human Energy. Talents, gifts, abilities that transcend the System as we know it. It’s regrettable that we have a System that does not readily or easily embrace this type of “Alternative Energy”.
    Being a Ronin type is not easy. But it’s doable. History is full of people who have made their own life…made their own choices and it has impacted their Culture for good. So much so that we still talk about them today. Maybe in the future our Capitalistic System will offer far more “choices” and tolerances than they do today. That is the day I hope for everyday.

    • Paul, thank you for sharing this with us. For a society that supposedly celebrates organizational learning and promotes the notion of switching careers over the course of a working life, it sure can be difficult to switch gears once you get beyond a certain turn of the calendar.

      Indeed, any market system should elevate choices and options much more than our current one. I teach at a university committed to maintaining its offerings to part-time graduate and professional students, many of whom are interested in making a career transition. However, the reality is that many employers are looking for the less molded younger person who can be fit into a cookie cutter.

      The lost opportunity to take advantage of talent informed by wisdom and experience is a huge one! So hopefully our system will be more welcoming to the wealth of good people like you who have so much to offer.

  2. Pingback: I can relate to this: Inauthenticity at work et al. | Bruce Jones

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