What I learned from every job I ever had

I’ve been working for 45 years. Every one of those jobs — and they were pretty diverse — taught me something. Often it was something I never realized I’d be learning.

I decided to look back and catalogue all those things I learned. If you know anything about my career, you can see a lot about where I ended up in these experiences. The numbers in these headings are the ages I was in while in these jobs.

Lab animal caretaker, Upper Dublin High School (16-17)

This job mostly involved feeding and cleaning up after hundreds of mice, rats, gerbils, and rabbits, along with one 8-foot boa constrictor. I was a professional shit shoveler (rodent shit, not bullshit) from a very young age. What I learned:

  • When people (and animals) are counting on you, you find a way to show up, no matter what.
  • Anything’s better when you do it with a friend. (My partner in animal caretaking was my friend Josh; we stayed friends for a very long time.)
  • There’s dignity in a job well done, no matter what the job actually is.
  • It’s good to get paid — but the government always takes its cut.
  • If you put a bunch of males together in a small space, they will be become aggressive and violent.

Camp counselor, Lake Owego Camp for Boys (17)

I taught nature and model rocketry and took care of a cabin of about 16 boys around age 12 for 8 weeks.

  • It’s a lot harder to take care of children than any 17-year old realizes.
  • Pre-adolescents are far more perverse than you could ever imagine.

Math tutor, Penn State University (17-20)

I tutored students on my own as a student, and then in a math learning center in the Abington campus of Penn State as a recent graduate.

  • Not everyone sees the world the way you do.
  • I like explaining things.
  • I could make money from knowing things other people didn’t know.

Graduate assistant/calculus instructor, MIT (20-23)

I taught a recitation section of the basic calculus class. I was fairly successful, so the institute tapped me to be the sole instructor of an off-semester calculus class (first calculus class in second semester, which included many students who’d flunked it the first time). One summer, I taught about 40 graduate students in naval engineering for a class that took 3 hours per day, five days a week; many were officers who were much older than me:

  • I love teaching; it inspired me to put a lot of effort and creativity into my work.
  • It takes far longer to prepare than to present. (Keep in mind, this was well before PowerPoint.)
  • Visual aids make a big difference.
  • When standing at a blackboard, I write downhill. (Watching the video of my teaching was an eye-opening experience.)
  • Military personnel will do everything you ask, even if it is an unreasonable amount of work, and will resent you for it.

Technical writer/project leader/technical support, Software Arts (23 – 25)

I wrote software documentation including mathematical equations for the company that created the first spreadsheet, VisiCalc, and the mathematical software product TK!Solver. Looking back, I learned an awful lot in a very short time.

  • Word processors and email are awesome tools because they make everything much faster. (This was the first time I’d ever used them.)
  • Passive voice is a nasty habit that you should strive to get rid of. (Hmm, that may have had an impact on the rest of my career.)
  • Working in an office is far more than just doing the job. (Ask my first boss how bad my first business letter was.)
  • Writers in a professional setting must consider not just what they write, but how it will appear in print. (This was my first exposure to markup language.)
  • Seeing your writing in a bound book is the most awesome feeling in the world.
  • Colleagues really appreciate somebody who understands math and can explain it well without being condescending.
  • You should treat your boss as a confidant and get her advice on everything. (That turned out to be wrong. I just got lucky that my first boss would turn out to be more of a good friend than just a boss.)
  • If you get a chance to do something you’ve never done before, grab it. (In that category: management and answering tech support calls.)
  • Your colleagues will be valuable contacts throughout your career.
  • If you dress nicer than usual at work one day, they’ll think you’re interviewing and do stuff to try to keep you working there.
  • Layoffs destroy the things that make a company special.

Documentation manager, Javelin Software (25-27)

I created the manual and managed the production and manufacturing of a financial modeling package intended to replace the spreadsheet.

  • Hiring and managing smart people is a great responsibility, but highly rewarding.
  • A really capable software team is an amazing thing to be around.
  • Sometimes people lie on their resumes; you should check stuff they say.
  • The most time consuming part of print production is checking galley proofs.
  • Graphic designers are essential partners for writers.
  • Spreadsheets are invincible.
  • Pink slime is a bonding experience.
  • If you’re doing a little moonlighting and you get divorced, your ex will tell the judge that your compensation is an amount that reflects compensation for two full-time jobs.

Director of product development, Mathsoft (27-30)

In addition to writing manuals, I ran quality assurance and tech support for a startup software company. I also ended up being a design and user experience counselor for the chief engineer; we collaborated to design elements of the interface.

  • If you can do math and write, you can get all sorts of great jobs.
  • It’s good to be one of the first people hired at a startup.
  • Engineers can’t be successful without all sorts of support from other departments.
  • When a new technology comes along for producing written material, embrace it. (In this case, it was desktop publishing.)
  • Every moment you use software, you are learning how software should work. Smart engineers value this knowledge.
  • Sometimes you have to fire people (like tech support people who yell at the customers).
  • If you have a financial decision to make and you’re not sure, hedge. (Invest half one way and half the other. Unfortunately, I learned this the hard way, when a decision I made cost me $750,000 after the company went public.)

VP, production & technology, Course Technology (30-35)

This startup company made textbooks on PC applications (spreadsheets, word processors, etc.) packaged with student versions of the software. After I got the print production part working well, I switched to the company’s newly launched CD-ROM division. That shut down after a year and half and I was laid off.

  • If you can do something faster than the competition (in this case, publish books based on new software versions), you can gain market dominance.
  • Authors get treated like royalty during the writing process, then treated like shit right afterwards.
  • Never take a job where you’re responsible for corporate IT.
  • If your job gets boring, find your own way to make it interesting; don’t expect your management to do that for you.
  • Tough, competent people make great hires.
  • Textbook publishing is an exploitive industry, because of the dog food marketing problem.
  • Getting laid off sucks, but can lead to better things if you have the right skills.

VP and cofounder, ThinkingWorks (35-36)

I helped design CD-ROM edutainment software for a startup that never got off the ground.

  • Severance pay is your opportunity to try new stuff out.
  • The VC investment isn’t really committed until the paperwork is signed.

Analyst/SVP of idea development, Forrester Research (36-56)

I was hired as the CD-ROM analyst. That didn’t last, but my analyst job did. I ended up creating a consumer research business, becoming the top TV analyst in the world, publishing three books, and editing two more.

  • If you find a job where you have to learn something new every day, seize it with both hands.
  • Be bold. Even if you’re not sure what the future is, you can still get paid to predict it.
  • A little math knowledge goes a long way in a research business.
  • People pay for clear direct writing in the form of analysis. Purge all the passive voice, weasel words, and meaningless platitudes and you’ll sound more impressive.
  • A wrong prediction timidly made incurs the same penalty as one made boldly. However, a correct prediction made boldly generates a bigger impact.
  • Do great work. The CEO will notice and you’ll have a lot more choices in the future.
  • Never burn bridges.
  • Arrogance is a dangerous temptation when you’re in the public eye.
  • There’s no substitute for firsthand, primary research.
  • No matter how much research you do, the people actually doing the work out in the world know things you don’t know.
  • Writing a book is the most rewarding experience I can ever have. Giving a speech in front of a few thousand people comes close.
  • Don’t be afraid to hang around a job for a long time if it keeps challenging you.

Founder/president/chief troublemaker, WOBS LLC (56-?)

I write books and help authors.

  • It’s really easy to start a business. It’s really hard to build it.
  • Content marketing works. And blogging is not dead.
  • Writing and working with authors all day is a dream job, even when it’s a nightmare.
  • If your instincts tell you a potential client is going to be a problem, run.
  • Writing books is a lot easier to get right than promoting them.
  • If you do good work, don’t compromise on price. Instead, charge a lot and do an incredible job.
  • Analysts talk, consultants listen.

What about you?

This was an incredible exercise; thanks for taking it along with me. It makes me wonder . . .

What have you learned from your jobs along the way?

What do you expect to learn from your next job?

What have you learned that wasn’t at all what you expected to learn?

Post your own lessons in the comments; we’d love to hear about them.

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  1. Thanks for taking us along your journey, Josh. I, too, have learned a lot – too much to go into now. I’ve learned most from bad bosses and awful colleagues – the way I DON”T want to behave. I used to think that the saying “when the student is ready, the teacher appears” meant that I would be presented with a guru in flowing saffron or white robes. Instead, I have been presented with those bad bosses and colleagues and have gained so much from their negative examples.

  2. I did just jot down what I’ve learned from each of the jobs I’ve had over the last 40 years of working (ages 13 and on). What a great exercise. It did resurface one or two old regrets (should’ve taken that job at Cisco in ’93, darn!), but it really was eye-opening to reflect on all of the great and not-so-great work experiences. I think if I added what I’ve learned from significant relationships, I’d have an autobiography.

  3. Hmm…. here’s a sampling:

    Marina assistant (14)
    * People will give an astounding amount of responsibility and credibility to children

    Golf pro shop attendant (16-17)
    * Some bosses are extremely petty and threatened by their good workers
    * Rich men assume young females are there for their pleasure, and will often pay for that pleasure even if you didn’t ask

    Academic writing editor (22-28)
    * Foreign faculty and grad students will pay a bundle to not have to worry that their grammar will put their theses at risk of rejection
    * However, foreign faculty who want to fuck you will stiff you if they think they’re already entitled to everything that you are, and because they know the department chair will back them.

    Professor of Economics (29-37)
    * If your advisor wasn’t a big shot, or didn’t take a personal interest in your success, you’re doomed
    * Your (male) colleagues will automatically assume that your new ideas are wrong just because a woman couldn’t possibly have thought of something they missed
    * Your (male) colleagues will refrain from engaging your research intelligently, possibly because that would constitute beating up on a woman, but the end result will be that you will never get the feedback you need to publish
    * You will be offered non tenure track and adjunct positions to fill the positions of tenure tracked men

    And perhaps the biggest lesson?
    * It doesn’t matter what your skill set or accomplishments, without a powerful man or group of men to vouch for you, you’re dead in the water.

    Yeah. Interesting exercise. I have many of the same skill sets as you, but from an early age you were given opportunity and recognition and your career was allowed to grow with you. Looking back, that is certainly not my experience. Funny the lessons we learn.