Navigating a series of jobs toward a fulfilling career

Jason Mashak
4 min readJun 30, 2023
Editing IT market research reports from an old historical building in Prague

Recently I volunteered to be a mentor in a new Runecast mentorship program to help younger team members to develop their careers. It got me thinking… How do you define ‘career’? I’ve often heard young people express frustration and concern around aspects of the nebulous term. Is it something you can actually plan? People in their 20s and 30s often perceive a career as some singular path to be planned and followed.

My experiences have aligned more with the famous quote attributed to Mike Tyson: “Everyone has a plan until they get punched in the mouth.” That is, I put myself out there, willing to learn new skills wherever there were opportunities, and the decades began to reveal some trends.

My ‘Career’ (AKA a Series of Jobs)

I’ve done a lot of jobs to help support the family or myself over the years and I’ve listed some of them here (I say “some” because I keep remembering more and adding them to the list).

Note that these do not include standard ‘chores’ that I had in parallel, like mowing the fields, working on tractors, rebuilding rototiller engines, tilling the garden, maintaining farm equipment, repairing fences, cutting/splitting/stacking firewood, gathering and stacking hay bales, feeding the animals, sharpening and cleaning tools, etc.

It’s crazy now when I think about it, that most of my teachers assumed that my typically late and/or incomplete homework was because I was a slacker — and even called me an “educated underachiever” a couple of times to my face (to which I didn’t even bother trying to explain). Fortunately, I was often able to ace my exams to offset any low homework scores and somehow still graduated with honors (cum laude).

Ages 6–13

During middle school.

  • Ran sidewalk lemonade stands
  • Sold flower bulbs door-to-door
  • Sold magazine subscriptions door-to-door
  • Sold film development coupon books door-to-door
  • Provided lawn mowing services (for a cemetery and a real estate company)
  • Delivered newspapers (2 routes, 1 with each parent)

Ages 14–18

During high school.

  • Managed a western cowboy boot store (Dingo, Acme, Dan Post dealer)
  • Washed semi trucks & trailers at a truck stop
  • Worked night shift at a Shell gas station
  • Managed a pressure-washing business (2 shifts of men 2–3x my age)
  • Drove long-distance deliveries (with my ex-step-dad)

Ages 19–21

Instead of going to university right away.

  • Worked as a warehouse and loading dock guy at a rug factory
  • Owned/Operated a pressure-washing business with 2 employees (2x my age)
  • Painted house interiors

Ages 22–32

First ‘grown-up’ jobs before and during university.

  • Account Exec. for a telecommunications company (selling pagers and mobile phones)
  • Security Consultant for risk mitigation, designing and selling integrated security systems (perimeter security, CCTV, access control, fire systems)
  • Customer Retention Specialist for a security company
  • Owner/Landlord of a residential building with 4 rental flats
  • Interior house painter and handyman
  • Freelance writer and editor
  • High School English teacher and tutor
  • Full-time university student obtaining bachelor’s and master’s degrees

Ages 33–45

After migrating to Central Europe.

  • Freelance English teacher
  • Freelance marketing consultant, copywriter and editor
  • Editor of IT market research reports
  • Copywriter, focused on eCommerce, Social Media and PR
  • Voiceovers for videos
  • Senior Copywriter assisting with campaign strategies and concepts
  • Business Development Manager

Ages 45–50

Getting back into team management after many years.

  • Chief Marketing Officer (CMO)
  • Head of Marketing
  • Senior Manager, Analyst & Public Relations (I am here now)

Ages 50+

Hoping to share what I have learned.

  • Looking forward to new adventures with Runecast!
  • Maybe get back to teaching occasionally in a classroom setting
  • Maybe finally write a novel…

What All of Those Jobs Required in Common

Looking objectively at this long list of various jobs, they may not seem to have much in common. However, as the person who did them, I can say that they did in fact share some common threads — for example, they all required and helped me to gain experience with:

  • Self-confidence in providing value to VIPs
  • Persuasive communication skills
  • Understanding psychology and what motivates people
  • Patience with others and their ‘baggage’
  • Self-awareness as to what I am feeling and why
  • Empathy for personal issues that can impact professional life
  • Adaptability and being able to embrace chaos

In conclusion, three primary areas reciprocally helped each other throughout my more than four decades of work. Marketing, selling, and teaching. When selling, I was educating prospects to market a solution. When teaching, I was marketing education to sell intellectual growth. When marketing, I was educating prospects to sell a solution. Regardless what you call it, get behind something you believe in and let others know about it — sometimes it’s that simple.

Originally published 21 June on LinkedIn: https://www.linkedin.com/pulse/navigating-series-jobs-toward-fulfilling-career-jason-mashak-

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Jason Mashak

M.Ed., musician/poet, Dad to girls, Bohunk-Polack-Viking, Epicurean Stoic.