Leverage Maps #7: Many Jobs, One Clear Map

We teach ourselves that the key to success is picking a land, going deep, and staying consistent. But not everyone takes that path.

Some of us have resumes that look more like a map than a ladder. I’ve been:

  • A mechanic’s assistant
  • A camp counselor
  • A day trader
  • A computer science tutor
  • A pizzeria associate
  • A chess coach
  • A supply chain researcher
  • A technical writer
  • A smart contract developer
  • A UX software researcher
  • A technology consultant
  • An embedded software engineer

On paper, it looks chaotic. In practice, it’s been compounding.



What a Nonlinear Work History Actually Builds

First, context switching as a skill. You learn to quickly adapt to new systems, new people, and new rules. It's mental agility.

Second, pattern recognition across domains. You start seeing echoes between disciplines that teach you structure and not just facts:

  • How trust works in technical analysis indicators and smart contracts
  • How feedback loops drive both tutoring and embedded systems
  • How miscommunication derails kitchens and client meetings alike

Third, resourcefulness. When you’ve run machines, taught kids, dealt with unhappy pizza customers, and debugged firmware, you build an inner toolkit no job title captures.

Fourth, system clarity. You don’t just ask, “How do I get better at this?” You start asking, “Is this system working the way it should?” That’s where leverage lives: in zooming out without disconnecting.



The Myth of the Perfect Resume

A lot of people still think of career success like software architecture:

Elegant. Linear. Modular.

But careers, especially in uncertain times, are more like biological systems:

Messy. Resilient. Adaptive and layered.

Those who’ve held many roles often become systems thinkers by necessity. We learn to balance constraints, navigate dysfunction, and see leverage where others see chaos.



Nonlinear ≠ Unfocused

I used to worry that the range of my jobs made me look unfocused.

Now I realize:

  • It gave me range.
  • It taught me leverage.
  • It made me durable.

The takeaway:

If your work history doesn’t follow a straight line, that doesn’t mean you’re lost. It might mean that you’re building a broader map and finding better leverage.

Every job teaches you something different, so don’t bury the variety. Learn from it. Connect it. Use it.

Know that the messy path might be the most antifragile, resilient one.



Leverage Maps is a series about how systems shape us and how to shape them back. Follow me and Small Levers Lab for more insights.

I hope you're thriving today. If you’ve worked jobs that seem unrelated on paper but secretly shaped how you think, share one in the comments.