Everyone seems to be reassessing their “relationship with work” these days.  It’s about time.  Getting a job has always been freighted with so much meaning.  I run into many younger people who expect every job to be a peak experience.  There seem to be many jobs that nobody wants to do right now.  It is easy to forget that sometimes a simple job can teach something of value. Much of what I know about the world, I learned from each one of my 33 paying jobs.  Easy for me, but what advice would I give someone just starting out with work?

My two kids are in college.  They also work. 

They are not “working their way through college.” That is largely an outdated fable.  My wife and I, at the peak of our earning power are basically spending a solid chunk of what would be our retirement savings instead covering their college experience.   Ostensibly they are going to college “to get good jobs” though I’m careful to tread lightly on this idea.  To those two concepts in quotations, I say this; as a society we carry a lot of unhelpful baggage about work and why we work.

One is a bike mechanic on campus.  He also “interns” doing free research work for a professor—watching hours of game camera footage of deer corpses, taking notes on the scavenging animals.  Both jobs interest him while providing perspective into what he doesn’t want to “spend the rest of his life” doing.  This summer, the other is office managing at the dance studio where she studied through childhood.  At college she gives campus tours where her boosterism sometimes conflicts with her actual experience as a student.  Both jobs provide her an adult view into institutions she still mostly views through the idealistic eyes of youth. I can observe that for our kids, earning money represents a dose of freedom and self-respect.  It teaches them responsibility and provides experience navigating other people and the ways of the world.  

Besides being insufficient for today’s college tuition, neither earns wages that come close to paying their monthly rent, which isn’t really the point of work for them…yet.

Each opines as I did once (and occasionally still do at age 53) about the perfect job, or ideal career.  They agonize over employment choices looming ahead.   They worry over making enough money.  They also worry about their skills, their fortitude and most fundamentally, they worry about their value (Full stop there).  Yes, I mean self-worth, which is woven indelibly into work, perhaps more so for some than others.  I’ve certainly known people who are competent, if dispassionate, about their work which allows them enough to do what they want with their free time and to not think for a second about their job till they show up at their station again.  Contrary to all the hype about employee engagement, Instagram postings about the perfect side hustle, articles about bosses, perks, benefits, and compensation or “the best places to work” the world needs a lot of people who just do their jobs well, or well enough. Some would consider that a “healthy” relationship with your job.   I don’t think that is where either of my kids are headed.

They worry as did my wife and I did about choosing that first “real” job poorly and getting stuck in a profession they dislike for the rest of their lives.  They worry about being compromised through work.  Because of a lifelong condition, my son is very concerned about finding a job with good employer-attached health coverage (until someday when the U.S. provides universal care).  Health care was something that didn’t occur to me until I had kids, so I sought quite different jobs then.  My kids each look at the home they grew up in and wonder aloud if they could ever afford it or one like it here.  Honest answer:  probably not for 20 years for more and then, only if they find “good work,” some other place first.   We live in a place where working 98% of jobs in the area wouldn’t pay enough to afford to live in our neighborhood.

Such contemplations can be oppressive.  They also set unrealistic expectations about most of the work they will likely do throughout a lifetime.

In anxiety about working, they would not be alone.  Evidently there are a lot of adults of all ages re-thinking their relationship to work these days.  Since COVID, over 4 million people are quitting jobs each month with roughly 47 million quitting a job in 2021 according to CNBC.  Fox Business has called it a “reshuffling” while Bloomberg cites a survey from HR firm Mercer that says 1/3 of current workers are considering quitting in the next 12 months in spite of what the same article refers to as a looming “economic hurricane.”

Oh, and between the weather, and the rapidly changing climate, reservoirs running dry, the Supreme Court looking supremely partisan, Congress gridlocked, gun violence making the news every day, black lives matter, blue lives matter, politics being more hostile than it has been in over 50 years, with some people pumping themselves up for an un-civil war, a pandemic, pandemic backlash, an actual war near where the last two World Wars were fought, and well, the cost of… everything, young adults can be cut some slack trying to reconcile all of that with what they may want from their future, or if there is a future worth planning.  Of course, all that too will pass, but pass into what is the question? 

Maybe all those “externals” just shouldn’t be factored into an employment decision.

The thing is, I’ve had over 30 “paying” jobs so far in my 53 years, and I’ve enjoyed just about every one of them at the time.  Though I needed money, the choice of any specific job was rarely made because of the wage itself.  Very few of those jobs did I think then would turn into a career, although a couple did, if you count 5-10 years in a profession to constitute a “career.”  A few jobs were for a month or two, one for a week.  Some jobs were overlapping; most were instructive in one way or another, and each of them I can embrace as part of my life’s journey, my ongoing education. 

As an exercise, I listed my lifetime of jobs, listed place and duration, and wrote something important that I learned from that job that I take with me now:

  1. Paper Route delivering The Columbian – Vancouver, WA.  There is a different world behind every door.  Deliver no matter the weather.  Even people in a big home sometimes cannot afford $5.50 that week and will hide when you knock to collect (6th-11th grades)
  2. Chores for my Grandparents – Marrowstone Island, WA.  People can be fascinating to talk with, and you can love them even if you don’t agree with them.  It takes 8 hours to mow all the lawn in 3rd gear.  I love sawing, chopping and stacking wood.  Taking care of 20 acres with an orchard, over 1000 rhododendrons, and outbuildings is a one way for workaholics to “retire.” (4 summers)
  3. Free Lance Photographer, The Columbian – Vancouver, WA.  Take enough photos of houses for the classified section and they will give an actual assignment – like when the homebuilders association built house in one day for charity.  I learned a lot watching!  (one summer)
  4. Leadership Camp Counselor, Camp Cispus — Randle, WA.  People tend to support what they help to create.  Don’t make important life decisions when sleep deprived in a temporary social bubble. The CCC was one of America’s best ideas that we left behind.  (three summers)
  5. Fruit Picker, Firestone Orchards – Fruit Valley Rd, WA.  Riding a bike to work is more fun than riding back.  Peach fuzz itches.  Somebody harvests everything you see in the store. (one summer)
  6. Rental Dock Attendant, Vancouver Lake Marina – WA. Windsurfing is harder than it looks; the wind blows everyone south, and this provides a job for someone.  Now, I prefer not to smell or hear a gas motor when I’m on the lake. (half a summer)
  7. Grocery Night Stocker, Safeway — Hayden Island, OR.  People steal cigarette cartons for drugs.  People rummage through dumpsters for food.  Even prostitutes go grocery shopping.  Taking “lunch” at 4 a.m. is harder than just working.  I love a store with perfectly faced shelves, mopped floors before anyone comes in.  Best work advice when I thought I should work on my day off because the store was short-staffed, “the sooner you learn this place will run just fine whether you are here or not, the better off you will be.” (one summer)
  8. Grocery Checker, Safeway – Hayden Island, OR.  People go to school to be checkers!  Before scan codes, it was good to know what everything cost—memorization mattered.  Most people cannot run a register, look up prices or codes and bag groceries while carrying on a friendly conversation.  I could. Now they say you can’t really multitask.  (one summer)
  9. Residential Assistant (RA), Whitman College – Walla Walla, WA.  I loved our building built in 1912.  Being of service and mentoring people is very important to me.  Nearly everyone has some condition or character flaw, but with kindness and support, most rise above themselves.  (three years)
  10. House Sitter, David Stevens—Mill Creek, OR.  Fire a contractor for a professor on vacation while house sitting and you will have a friend for life.  (one summer)
  11. Residence Hall Manager, Whitman College – Walla Walla, WA.  I love taking people on overnight rafting trips.  I’m too proud to just hang around my college, read, play and talk with students for free room & board and $600/month forever.  Be kind to the cooks, janitors and secretaries. (two years)
  12. Fruit Picker, Dean and Irene Phillips Family Orchards — Clifton and Hotchkiss, CO.  I dreamed of moving to a small town in the West, entering “the real world” with a pickup truck and a dog, getting to know people outside of academe, dating the waitress at the breakfast diner and writing about all of it.  Instead, I found the Utah desert and San Juan Mountains with my Subaru, listened to a lot of John Prine and fell in love with the Western Slope of Colorado where I eventually met my wife while I was waiting on her table in another small town. (one special summer and fall)
  13. Waiter, Western Belle Lodge – Lake City, CO.  Spend a winter in an isolated town of 300 residents as a waiter, and you will get to know just about everyone and more than you want to know about most of them. (one winter/spring)
  14. Snow Shoveler, Hinsdale County School District – Lake City, CO.  Someone had to do it, but it was weird being “the help” for teachers who I considered my peers. (two winters)
  15. Odd Jobs for Charlie Carlyle – Lake City, CO.  I can fix broken pipes, do every phase of construction for a small project, operate equipment, jack up and put a foundation under a 100-year-old building.  I can roof a house by myself.   I can figure out just about anything.  Tools are an investment.  If you are honest, show up, and tell people when you will be back if you go away, you can take a week off a month and a month off a year and there will always be work when you return. (two years)
  16. Waiter, The Lake City Café — Lake City, CO.  I love working a room.  People who own a café can make a living off a seasonal business if they work their butts off.  Diners don’t understand tipping. (one summer)
  17. Lumberyard worker, Blue Spruce Building Materials – Lake City, CO.  Learned quickly that I prefer making things to selling things. (one week)
  18. Night Manager and Barista, Kaladi Brothers Coffee – Anchorage, AK.  I can rock a 4-gang La Marzocco espresso machine making drinks for customers faster than the register can keep up.  Living with extended family is a great way to extend your 20s.  When employers don’t understand the value of their employees, employees find ways to compensate themselves. (one year)
  19. House Sitter — Eagle River, AK.    You can install an invisible fence, but unless you train a Malamute to fear it, it will run right past the fence and get hit by a car 8 miles away.   When dogs get killed, relationships end. (two weeks)
  20. Firewood Seller (self-employed) – Minturn, CO.  A face-cord of firewood fits in the back of a Subaru Loyale.  Delivered up three stories of stairs is worth $75.  (one summer/fall)
  21. Snowmaker, Vail Resorts – Beaver Creek, CO.  Learned to snowmobile at night at a ski area.  Learned I have no interest in working for a large, bureaucratic company that doesn’t care that I exist.  (two months)
  22. Framing Carpenter, Signature Homes – Cordillera, CO.  Working outside can be glorious.  Giving shape to something that didn’t exist before is thrilling.  I can’t work for people I don’t respect.  I love the smell of wood.  Every bunk delivered had the name of some mill in my home state.  (five years)
  23. Trustee, Mayor Pro Tempore and Mayor – Eagle CO.  Public service provided the graduate degree I never got.  Facilitating a meeting or public hearing well is an acquired skill.  This role eventually clarified that someone must fight for their community.  Only counts because “pay” was $250/month stipend. (ten years)
  24. Assistant Superintendent, Beck Building Company – Vail, CO.  Taking a pay cut for a better opportunity can be worth it. I am just as happy being mentored by someone I respect as mentoring myself.  Managing a 10,000 sf custom home build for 2 years is a huge puzzle.  Don’t treat the masons, laborers, or any contractor differently than the architect or owner.  (three years)
  25. Superintendent, Beck Building Company – Vail, CO.  After building over $60M of projects for other people, I finally gained enough knowledge and confidence to fulfill a life goal of building my own home.  The title “superintendent” doesn’t get the respect that it should outside of a construction context. (four years)
  26. Project Manager, Beck Building Company – Vail, CO.   I don’t think I ever want a job working for rich people again.  I felt trapped in construction as a career and hoped that PM was a title that translated across professions–managing people, schedules, budgets, clients and contracts.  I struggle with a full day of desk work, but construction management was the closest I got to being trained as a professional.  (two years)
  27. County Commissioner – Eagle County, CO.  People elect you for their reasons, not for your reasons.  Respect is currency. (five years)
  28. Town Manager, Town of Eagle – Eagle, CO.  Falling in love with your dream job is a recipe for personal disaster.  Working for a board can suck.  I cannot make myself “small enough” for some people.  Evidently, I am also not so good at hiding when I don’t respect people and their actions. (33 months)
  29. Consultant, 5th Judicial District – Eagle, Lake, Summit and Clear Creek Counties, CO.  Workplace assessment, and staff interviews is fascinating, but a difficult way to earn a living. (one month)
  30. Landscaper, Ceres Home Care – Gypsum, CO.  Better than sitting on the couch.  (one month)
  31. Raft Guide, Sage Outdoor Adventures—Dotsero, CO.  Some bucket list jobs should be age appropriate to 20-year-olds.  Though I have had better days with bigger water or better weather, act as though every trip is the best day ever for the client.  (one summer)
  32. Project Foreman/Lead Carpenter, Habitat for Humanity – Gypsum, CO.  Even having “purpose” isn’t enough if you are not fully engaged and working closer to your full potential or earning enough.  Working “bags-on” in construction at 50 is not the same as at 30! (three months)
  33. Executive Director, NWCCOG – Silverthorne, CO.   When you get very skilled and efficient at parts of your job and hire excellent people, you can shape other parts of your job to do things you enjoy doing.  Managers should not overbook themselves in order to preserve the capacity to observe strategically and contemplate rather than just react and so that they are available.  Working from home is a privilege for which I am grateful.  (Five years and counting)

You would be forgiven if you read through that list of jobs, for thinking

1) this guy needs to edit his resume,

2) this guy sure took a long time to get a serious job, and

3) this guy is probably a work-a-holic with no work-life balance.

You would be correct in the first two, incorrect on the third.   One clear exception was my 15 years in construction (while also on the town board for a decade) and 3 years as a Town Manager, during which decades I worked stupidly long hours, had very little time off and was consumed with my work or thinking about work nearly 24 hours a day, to the detriment of my health, my family and other ambitions.  Sometimes you just need to work your ass off and push through until another opportunity presents itself.  That said, most of my jobs could be characterized as “lifestyle” jobs rather than “career” jobs.  Folks this is not a new thing, employers and the world is just catching on.

From the end of college, until I was 27, though I didn’t formalize it until I got to Lake City, I had a policy of taking a week off every month to travel or visit people, and a month off every year, usually to travel overseas.  You can take a job with you, or you can find work where you go.  This is something people seem to think was just invented.  Granted, remote work over the internet was just invented.  The first 21 jobs got me through till I got married at 27.  Before that, work provided me just enough money to do what I wanted to do, as well as the free time to wander and explore.  Suddenly at 27, I had to get “serious” about supporting a life that included a wife, rent and accumulating stuff to support our shared interests.  This was not all that different from many of my college peers except at the point that I put on carpenter bags and a wedding ring, many of them were starting or finishing graduate school and finding commensurate professional work.  When I am depressed, I look through my alumni magazine and see that I’ve spent a lifetime deliberately under-employed, perhaps stemming from a lack of confidence or self-esteem or just plain fear of failure.   When I am at my best, I give myself credit for being a very resourceful, hard-working adventurous guy who has figured out life in his own fashion, bucked some norms, and benefitted from a lot of key support from others along way including friends, family and employers. 

Speaking of the alumni magazine, one of my few regrets is in not getting a graduate degree.  The question has been a degree in what?  And did I actually need that degree to do the work I wanted in that field?  At various times, because of various compelling work experiences I’ve wanted to study to be an architect, a city planner, or construction manager, and have considered getting a degree in a Master of Fine Arts (writer), the law, public policy, or public administration among other passing ambitions.   Instead, I “work”-studied them all, with each field filling a library shelf at home as I strengthened those areas in whatever job made them interesting to me.  I am very fortunate that for the last two executive level jobs in the public sector that I was hired with work experience substituting for a graduate degree.  I don’t think I broke through that ceiling, I just crawled around and over it.

After this exercise, what advice would I have for my kids? 

Work can be a part of your journey of discovery in life.  Work does not define you or define your worth.  If you are fortunate, you fundamentally like to be occupied and engaged.  Work is an opportunity to do that.  You will likely have a lot of different jobs.  They may provide a “path” to a job you think is perfect for you.  It is common to not see that path until you look back.  You do not need to like the work that you do, but it is often easier if you find something about every job that you like, and something you can learn.   You will need to work to do things you want to do.  If you only see it as a means to an end, work can be drudgery.  If you see every task as a game or a challenge, and you find some joy in it, the time will pass much more quickly.   Even working for other people there is often (but not always) the opportunity to shape your work, or at least you always have the ability to shape how you see the work.  Don’t weigh happiness so much over competence.  There is always an opportunity for somebody who does something well.  Whatever is worth doing is worth doing well.

I can write that here, but I’ll crumple it up instead of sharing with my kids.  They have to discover their own way.  My parents were supportive and provided very little occupational advice.

I know families with generations in certain professions.  That is not us.  Maybe its something that runs in the family.  Upon his 60th birthday, which was 23 years ago, after 30 years working in public schools as a teacher or administrator, my Father said to us, “I still feel like a kid who doesn’t know what he wants to be when he grows up.”  Approaching that age myself, I couldn’t agree more.