Favorite Foolish Fiascos
The disadvantage to being a boomer is that we’ve had more time than younger generations to make mistakes. The advantage, though, is that we’ve been able to learn from them … if we’re smart. Stephen Rosen has made his share … maybe a share of yours, too…and is ready to share the lessons he has learned from His Favorite Foolish Fiascos.
The front bumper of the taxi I was driving gave a little ‘love tap’ to the rear bumper of the guy ahead of me; he got out of his car, punched me in the face, and I quit driving taxis. Right career move; wrong reason.
Maybe the dumbest career blunder I ever made was getting a PhD in physics because I thought people would say I was smart. Wrong career move; wrong reason.
Getting fired as an investment banker (right career move) when I didn’t like finance (wrong reason) was another of my many foolish fiascos.
Fired. Quit. It doesn’t really matter. I changed jobs and careers often over twenty-five years, and collected here what I learned about what not to do. What I did wrong, may point the way for others to be right.
I’ve worked as a car washer, taxi driver, physics professor, management consultant, book publisher, author, and investment banker. Since I’ve had so many careers and mistakes and changes myself, I feel I’ve earned the right to speak with confidence about them. I’ve seen myself and other boomers recover from making poor career choices or bad job decisions, and learn by correcting plain errors in judgment. Somebody has to do this.
Does each of us have a lifetime allotment? Is the idea to make our mistakes quickly — to get them out of our system, over and done with — then move forward? I’ve paid those dues myself, and as a result became interested in helping other baby boomers do the same: I am now a career consultant.
So here’s my lifetime goof list. What are your own favorite foolish fiascos?
- Working at changing a job or career — only when I was unhappy.
- Waiting for opportunities to fall into my lap.
- Deferring decisions until I was fired or burned out.
- Intellectualizing about where to go and how to get there.
- Hoping to fall into something by being a generalist.
- Allowing negative prophecies and despondency (the “nocebo” effect, the negative counterpart of the placebo) to overwhelm my job choices and career decisions.
- Coming to conclusions prematurely, without reflection (“chicken little syndrome”).
- Imagining that I could read other people’s minds without supporting evidence and corroboration.
- Taking everything personally — which made me angry, guilty, or depressed.
- Believing that success in one area automatically translated to success in every area, without the need for the same effort that led to the first success.
- Assuming, without debate or doubt, that what I imagined my critics said about me was true, without bothering to determine its validity.
- Aspiring to be perfect in all things, especially when setting my work standards unattainably high.
- Comparing myself to others who are more accomplished, and accepting a negative and discouraging contrast.
- Worrying about what I couldn’t change — instead of coping with what I can.
- Responding “Yes, but …” to every positive thought, intention, or bit of good advice.Deciding I must earn the same money, or maintain the same level of status, responsibility, or prestige in my next career or job — instead of pursuing what I enjoy doing well. Believing I’d be hired to do something only because I have been formally trained.
- Getting another degree when it isn’t a requirement for work I’d really like to do.
- Keeping my feelings of dissatisfaction to myself — or dumping them on my family and friends … or on myself in angry self-criticism.
- Expecting my work-life to bring complete personal fulfillment.
- Burning my bridges behind me.
- Ruminating on what I should have done in the past, instead of focusing exclusively on what I can do in the future (“shudda, wudda, cudda”).
- Postponing gratification in my work or my life indefinitely.
- Staying where I was for fear of failing elsewhere.
- Holding onto an irrational belief that I owe a lifestyle commitment to my current employer, my next job, or my career, or to a sizable investment in my habitual expertise (which can be a form of ‘addiction’).
Everyone makes mistakes. Even dumb mistakes. But smart people make dumb mistakes and learn from them. They remind themselves of their strengths. They re-affirm their assets without denying reality. They don’t dwell on their failures. They learn and move on. I did. You can.
During the darkest days of World War II, many boomer parents heard and sang a Johnny Mercer/Harold Arlen song: “You’ve got to ac-cen-cu-ate the pos-i-tive.e-lim-i-nate the neg-a-tive.” Let’s bring this song back.
Category: Baby Boomers, Lifestyle, Steve Rosen





These are excellent points for anyone, anytime, but especially for someone who’s thinking about reinventing a career at midlife. I’ve made some of the mistakes on your list, Stephen, especially the one about “staying where you are for fear of failing elsewhere.” I’m working on it. Thanks for the great post!
Great post! I know EXACTLY what you are talking about!
Like you, I’ve done all sorts of different jobs in my life. A couple of fiascos:
1. Giving up on the possibility of a PhD in Social Psychology and trying to work for a Masters in theology instead. Really dumb!
2. Thinking I’ve got a novel in me and taking time to try to write it.
There’ve been others. But I’ve learned from each fiasco, so perhaps they weren’t fiascos, after all, just rather expensive ways of learning life’s lessons.