Some musical artists are exactly the same album after album, year after year and even decade after decade.  This more or less describes the majority of the music industry.  The quintessential example of this is AC/DC. Their singles from 1975 to 2015 all sound about exactly the same.  Sometimes artists have a progression in stylization, but that progression is usually all apart of the same genre.   A pop artist usually makes pop music throughout their entire career and adopts to the trends in popular culture.  A good example of this is Madonna’s career.  Very different sounding music sonically, but it’s all radio friendly dance pop tunes.  Then there is the true artist.  These creatives can’t help but explore significantly different flavors and styles within their medium.  These musical artists aren’t very popular with the mainstream audiences because the mass market and the business interests that underwrite the music industry likes consistency.  

One of my favorite musical artists is this more creative type.  His name is Jon Anderson and his main gig throughout the majority of his career was as the lead singer of YES.  When he discusses his solo career, one that spans New Age, Dance, Latin, Irish, Symphonic, and other releases, he describes himself as a “Musical Gypsy”.   I’ve been thinking about this lately as I talk to more and more people who make major career changes multiple times throughout their careers.   To me, they are “Career Gypsys”.  They go where they can fit in and hang around for a little while until the next adventure calls them.  

Thinking about it more deeply I realized that there really are at least two models.  There is the Career Gypsy and the Industry Gypsy.  For descriptive purposes I have an example of each.   For the Career Gypsy my example is a friend of mine.  She went to school and got a bachelors.   Then she promptly became a stay at home mom, to construction officer supervisor, to arts and crafts retailer, to certified mental health professional (with Masters level credential) and her most recent career journey is real estate.  There is little in the way of aligned skills to these positions.   The model of the Industry Gypsy is someone who jumps industries but with basically the same job.  I can use myself as an example of this.     I did all manner of high tech outreach jobs from software sales, to consumer electronics sales, to industrial product sales, to business outreach for a government program (which is way more technical than you would think).  I look at what i’ve done as a bit more like Madonna, or some other artist who continually reinvents their own style, but which just has variants on the same theme.  In my case it was all about selling technical products but I could have just as easily used the example of an engineer in manufacturing and goes into civil engineering.  

Today’s article is not about the Industry Gypsy nor is it about the person who just landed in a different career than they started in.  Some people get formal education in one subject like special education, and wind up in financial services for thirty years.  I have one friend who got a masters in aerospace engineering and spent the rest of his life coding software for vertical market applications.   This article’s focus is on the Career Gypsy.  The person who jumps from field to field. I’m talking about someone who enters a completely different career multiple times in their life.  They would go from medical office administration to law enforcement to owning a local coffee shop.  (FYI, you get one guess where i’m writing this article)

On the face of it, this sort of behavior doesn’t make much sense.  Our system is set up so you get born, go to school and learn the basics, go to college and learn some advanced specialized skill,.  Then you are supposed to get a job using that skill for the majority of your life.  Many people do this.  Every teacher who retires after 30 years with the state is a perfect example.  I said many people, but many does not equal the majority.  The majority of people will have to make a career change but those changes are more aligned to the model of the Industry Gypsy.  A transition from human resources to workforce development isn’t unheard of.  Teacher to Salesperson, or vice versa is also a pretty standard change.  But  what could possibly cause a teacher to go back to school to become a lawyer only to give that up after a decade and become a fisherman,  to finally decide that they want to run a B&B?


The first cause is boredom or burnout.   Boredom can come from any industry where you find the whole thing tedious.  Think lawyer to fisherman or any other desk job to something where 99% of your time is spent outdoors.  This makes perfect sense if your bored of cubicles, process and  regular days.  There are many industries where operations are built around cycles and standardized activities and over time this can get tedious for the personality who has a tendency to want to experience new things.  

You could see the same people, day after day and it can become highly tedious.  When I say the same people, I don’t necessarily mean the same office mates.  Your job can be to help some at-risk population but maybe the population really can’t be helped.  As an example, you could be a lawyer and deal with serial repeat offenders again and again.  What about the social worker who’s caring for an indigent population? Process, repeat, process, repeat.  I could see where an inspector, auditor, or accountant could fall into that trap.  Even industrial maintenance folks can get sick of working on the same systems that all wear down the same way year after year.  

Burnout is something that’s just as prevalent a cause, maybe more so, but different than boredom.  There are many industries where the industry is structured so that everything is pushed to the max in an effort to increase short term performance and results with little regard to long term longevity of the system.  In this regard it’s the polar opposite of an environment that creates extreme career tedium.  

The most interesting example to me is the video game industry when you are working with what’s known as an AAA publisher.  The video game industry is allot like the rest of the world where the industry is being bifurcated into two different types of products.  You have the AAA type games, these are the very high end.  They are big budget affairs that are created by large corporations.  You also have the low end, the independents where game creators scratch by hoping to earn a living.  In the high end the business is still, mostly, run like many information businesses who follows the production best practices developed over the industrial age.  There is deadlines, metrics, and intense pressure to deliver products by unrealistic timelines.  This creates ‘crunch’ where game creators will spend months putting in 18 hour days and sleeping under their desks to get the job done.  Going through it once or twice isn’t really a big deal.  When you look at workers living through a crunch cycle for six months of every year or every other year and it’s easy to see why people who spent their entire lives dreaming of making video games for a living all of a sudden dream of a job where they are spending most of their time working in the woods for a logging company.  Maybe then they can make a game out of how many trees they can get to float down the river for their new employer.    It’s obviously not just video game crunch time that can cause the burnout effect.  Even when limited to 40 hours, there are jobs that include stuff you deal with in that shorter work time can create burnout.   Jobs like the investigative social worker for abuse cases or the emergency room nurse have high levels of burnout.   You see too much of the negative of humanity and anything about that industry will draw you back into those difficult emotions. You would just have to get as far away as you can, inspiring a career gypsy lifestyle.  

Sometimes the cause of the career change is simply that there is no more jobs.  Going back to the Industrial Engineer, what happens if manufacturing goes away in the speciality that they were an engineer in? What if you were a local travel agent before  Maybe you are a big box retail manager in the age of Amazon? You could be a high paid fuel logistics expert for a large chain of gas stations and automation comes your way.  Yes, in these cases there is a possibility that you could compete for other like jobs, but the total number of options is shrinking or going away, it may necessitate a move to something completely different.  There are volumes written about the growth of artificial intelligence and automation and how it has accelerated this destruction of jobs.  Tech disruption is great for investment returns and productivity gains but not for paying your monthly mortgage.  

Another cause of falling into the cycle of a career gypsy could be health or life changes.  It’s hard to stay employed as an executive consultant when your a single mom of three kids because of an unexpected divorce.  It’s really hard to be a traveling sales rep if all of a sudden your the primary caregiver of a parent with early onset alzheimer’s.  It’s difficult to remain warehouse manager if you develop a bad back.  Life changes with all of these scenarios make the movement to a completely different career easier than trying to stick with your existing career choice.  

Another reason why people would change is that they have nothing ‘sticking’ them.   If you were smart enough to get some sort of gatekeeper credential, say a license to practice medicine, or a license to be a special education teacher, or maybe a CPA, then the credential generally means there is going to be more jobs than there are people to fill them.  This causes the inverse effect of the the life change which encourages change.  If you don’t have anything holding you down to a specific career other than your experience it’s simply easier to change when you get bored, burnout, or a life change happens to you.    

If someone has a tendency to want to explore new things or get away from old things and any combination of these events happens to them throughout their life, it’s easy to see how a career gypsy can be created.  

Pro’s and Con’s

Much of my work includes a slant that talks about the friction points between work and life.  I vent, I complain, and I rally against the injustices of our modern world where working professionals are continually squeezed by a huge volume of factors into either having a flat or shrinking quality of life.   There are some of my observations where I am undecided about the nature of the point I’m trying to explore.  This is one of those second types of articles.  The question is: would you be better or worse if you continually jumped careers?  Their are clearly pro’s and con’s to sticking to a single career vs. jumping through careers over the course of your life. There also are some major benefits to being a career gypsy.

The first benefit of being a career gypsy that comes to my mind is the satiation of an innately inquisitive nature. For me, this is just a fancy way of saying I am the kind of guy who loves to learn new and different things. I know I’m not alone in this as I have met others who continually strive to better understand the world. These are the kind of people who read non-fiction books and who watch documentaries that may not include a great white shark attacking a plastic raft that looks like a seal.   There’s always the possibility that this pollination across industries will help you see the broadest and largest view of the world’s existence.   Unfortunately this understanding comes with a catch-22. Even if you are the president of the United States the odds of being able to effect change at this high level are next to zero.

The second benefit has to do with real career sampling. Let’s be honest here.  The way the school system has evolved we don’t have anything even remotely close to what would be a true comprehensive career exposure process.   Job shadowing a production supervisor at an autoplant for a couple of days is nothing like working in manufacturing for a year or two.  If you’re a Career Gypsy and you have the opportunity to work in one or more manufacturing environments for six months to a few years, then you really understand that industry in a way that no classroom or short term job shadowing would ever be able to communicate.

The natural progression of the benefit of career sampling is that you may actually find something you love and stick with it for a very long time.  You could spend a couple of years in the military, then a couple of years in manufacturing, and then try something like education and you have found the thing you want to do for the rest of your life.  The more jumps you make the greater the probability that this could happen. The real problem is you don’t know if you’re jumping because you’re in a negative spiral or because you just haven’t found your thing yet.   I have a cousin who is about ready to retire and never found his thing.  Author, Karate Teacher, and Physical Therapist have all been on his resume.  My great aunts tell me he’s ‘still trying to find himself’.  I figure if your eligible for Social Security, then what ever you were trying to find is gone for good.  

I have talked at length about the idea of the Purple Squirrel. The purple squirrel is that job candidate who has the absolute best mix of skills and background for ever more unique opportunities in the workforce. These opportunities are unique, of course, because of the continual folding in of multiple positions into a single individual contributor job.  For example imagine somebody whos being hired by a real estate school that needs to teach, administer the office and also  represent some industrial real estate sites that the company still represents as part of the corporate real estate division.  At that point a career Gypsy who has a K-12 teaching certification and experience,  who has managed a large law office, who worked in economic development and who became a realtor for a few years would be the perfect fit.  They get the benefit of being able to demand a livable wage. I’m not talkin political livable wage, i’m talking a good quality of life in relation to the cost of living where they are located.  Somebody who had experience in only one of those fields would be overlooked unless there was no other option and then the company would try and get them for cheap.

Another benefit is that you really don’t have much to lose when jumping as generations had in the past. There’s too much of a squeeze on limiting existing costs to the company.  Beyond a couple of years, sticking around for the long-haul doesn’t get you extended vacation or greater contributions to your retirement plan and vacation/time bank.  Those benefits existed when companies wanted and valued people who remained for their entire careers through good and bad times.  Today wall street would penalize those organizations.

Those are the pros, but like any kind of change in anything, there are some negatives associated with having a life of work that includes many jumps from career to career. The first con of being a career gypsy is the the grass is greener effect.   When things are tough in your current industry, it’s easy to be susceptible into thinking that a different career with its associated differences in lifestyle is much better than the one you’re currently living.  My favorite example of this was a class I had taught where I had one student who is in the class because they were trying to get out of real estate into a different career and one student who is in the class because they were trying to get into real estate from a different career.  Both were ebullient about their opportunities in their new industry.  The reality was probably that real-estate was going to be just as tough as anything else they could do, in some cases even tougher. It was the perspective that was different between these two students not the reality of a real estate career.   I don’t have any hard numbers to back this up, just anecdotal evidence, but I think being a career gypsy slows down later in your career for this same reason.  Part of this can be explained by some people having found the thing they really like and were meant for after a few jumps over their first couple of decades in the workforce.  I think the greater reality is that sooner or later we learn to keep your eyes out for the ‘gotchas’ in any industry as we have experienced enough to know that every industry has benefits and negatives.   At that point the grass isn’t greener after the jump and so we might as well stay where we’re at.

Another major negative of being a Career Gypsy is the transaction cost.  Think about the two students from earlier.  From a purely monetary and time perspective, it makes sense to keep one in the real estate industry and the other in whatever industry they are in.  That would probably be what would have happened if individuals weren’t responsible for their own retraining.   You would only train for new entrants needed for growth or workforce attrition, not career transition.  Since we are responsible for our own training, and there is a hugely effective government education complex including a guaranteed student loan industry, transitions are accelerated.

The final and biggest con has to do with retirement. Different companies have different matches and different vesting for the 401K.  When you leave you take your money with you and can transition it to cash with a small penalty.  Retirement only works well with life long consistency and generous employer contribution.  I know one profitable manufacturer that only matches one percent and only after two years on the job.   Imagine jumping into that.  

One element of being a career Gypsy that includes both pros and cons is the idea of opportunity for advancement. In one way by jumping around you potentially could slot yourself into a unique position that may not have direct reports but potentially has a ton of oversight.   This would be the benefit of the Purple Squirrel effect.   The negative, or flip side of this, is that by jumping around it’s sort of like diving in and out of different investments. You don’t stick around long enough for the long-term gains to take effect.  Sometimes the promotion or growth happens just because you stuck around and there was nobody else in line to do it or they didn’t have the time for the right kind of search. I know several individuals who are in positions of power because they 1) stuck around and 2) the opportunity opened up and they had the time invested.

So let’s wrap this up. The question we have to ask ourselves is: Are you a career gypsy?  If so, do you like the pro’s of it more than the con’s of it?  Do you dislike it enough to change?   If you like the pros of it and don’t mind learning things then it seems playing Financial Defense is the way to go. The lower your income needs the greater opportunity and flexibility you have with your transitions.   It’s easy to go from a job that pays $20K a year, to one that pays $60K a year to one that pays $40K a year if you have no bills and only need about 12 to 15 thousand a year to live and are aggressive about managing your own retirement.  My advice is to have fun, discover new things and reset your career often.  

If you are a career gypsy and really do want to change into something stagnant for the rest of your working life, the only real way out  that I can see is the stickiness of the gatekeeper credential.  Become the RN, then you will always find jobs that require the registered nurse certification.  This could be office management in a medical practice, medical device sales, or school nurse.  You may not always have the same job but you will always have similar jobs in the same career field.  You could get a project manager certification like a PMP and you’ll always find work as a project manager.   You could be a project manager on a large it installation or you could be a project manager on a major construction project. A project manager is a project manager.  The problem with this approach to getting out of jumping careers is the aforementioned cost of transition, I.e.  retraining. It is an especially onerous cost if you are in the middle of your career and have things like a mortgage and kids who need braces.  If you don’t do this then the thing that made you a Career Gypsy in the first place will probably keep you in that lifestyle.

We can’t forget that part of this equation is based on personality.  You may not have an option one way or another.  You may be hardwired with a career wanderlust that keeps you going from place to place, or you may only feel comfortable in a 8-5 office setting doing the same thing over and over.  You may have made bad early education choices that force it.    The undulations of employers are creating more opportunities for people to at least think about jumping careers.  I won’t make the judgement here that it’s overall a good thing or a bad thing.  I think it’s just, simply a thing.  For many, it’s a trend that’s going to continue growing for the foreseeable future.  

I started off by saying there are some articles where I vent and bemoan the challenges between work and life.  There are some I write where the best advice I can offer is self awareness.  This is one of those.  The advice is the same here as it was with the financial offense vs. defense article.  First figure out if your a Career Gypsy or not.  Secondly, decide if you want to continue or change and then enact the best practices.  You may have to struggle with going back to school to get a gatekeeper credential.  You may have to lower your expectations on quality of life for the inevitable changes that are going to happen.  Like many things in life, if you prepare well for what you want, your life will be easier.   That’s true no matter what career you currently or will ever have.  


A note to my readers:

Today’s content creators such as myself work in a volunteer economy(donations).  This only is successful when there is a large subscriber base.  We (all the direct content creators) are doing our best to build traffic (and hopefully patrons) to help offset the hundreds of hours we put into these works for you, our readers.  Our success starts and ends with you!  It can only happen when you subscribe and repost, retweet, etc. and encourage others to do the same.  The links are below.  Even if you can’t become a patron at patreon, I do hope you will subscribe and share and help build our audience.  There is good stuff here, I hope you feel it’s worth letting the world know about it.   Thanks!   


Read the Blog:

With hundreds of published articles, Peluso Presents is your weekly source for commentary, ideas and insight in navigating the collision between work and life.

Listen  to the Podcast:

For those who are on the go, every episode of the Peluso Presents podcast includes a reading of a highlighted post as well as other great entertaining information.  Available wherever you get your podcast fix from!  Subscribe and please don’t forget to review it on iTunes!




Join  the Conversation:

Get reminders of articles, Tweet AT me, and occasionally see some other great tweets by Mike!

Share  your input: Peluso AT

For those who still like to communicate old school!

And most importantly:

Support the Effort (Please):

If you like what you are reading and hearing, then please be one of the first to help support this effort.  100% of Patreon donations will go to enhancing our offerings in all of the formats that we currently provide content in!

Posted by Mike Peluso

Mike Peluso writes about the collision between between the business / professional world and life. He also writes about the journey involved with the Peluso Presents efforts including the Blog, Books, and Podcast so that others may benefit from his efforts. From Mike: I spend hundreds of hours working on these articles every year with no compensation other than support I get through donations. You can support with a tip and by Subscribing to the Podcast (and writing a review on iTunes would be really appreciated as well!) One time tips:

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s