I've had 10+ jobs since 2008. Here's what I learned about the system.
Every time I switched, I thought: what's wrong with me? Why can't I just stay somewhere?
I’ve had 10+ jobs since 2008.
Government contractor. Nonprofit program coordinator. Communications specialist. Freelance writer. Yoga teacher. Career coach.
Every time I switched, I thought: “What’s wrong with me? Why can’t I just stay somewhere?”
Turns out, nothing was wrong with me. The system was broken (has been broken for some time).
Here’s what I mean:
The Old Promise (That Died)
Our parents’ generation was sold a story: Pick a field. Get a job. Stay for 40 years. Retire with a pension.
Accounting, marketing, teaching—it didn’t matter. The structure was the same. Stability came from staying.
But that world dissolved while we were in college
By the time I graduated in 2014, the recession had gutted that promise.
Pensions? Gone. Job security? A myth. “Loyalty” to your employer? A joke.
Companies started hiring contractors instead of employees. Benefits got slashed.
The system that promised stability if we just worked hard enough... stopped working.
But nobody updated the advice.
We were still told:
“Just find a better job”
“Network your way up”
“Be a team player”
“Work hard and you’ll be rewarded”
All of it is based on a system that no longer existed.
Why Job-Hopping Isn’t a Character Flaw
I used to think my 10+ jobs meant I was:
Flaky
Uncommitted
Bad at picking careers
Incapable of “sticking with something.”
Now I know: I was responding to a system designed for extraction, not longevity.
Get a job straight out of school (or at least an internship in the same field)
Stay in that job for 5+ years (work your way up the ladder)
(technically 2.b) Stay late at that job, ask for promotions, take continuing education for that role/industry - basically go above and beyond with no guarantee of stability or success or reciprocity
Change jobs? Retire after 20+ years at a company
The System Wants Wild Bees to Think They’re Broken
Here’s the thing about worker bees and wild bees (I’ll explain this metaphor fully in next week’s essay): 🐝
Worker bees in extractive designed hives are built for hive life.
Wild bees don’t survive in hives. They need autonomy, variety, and self-direction.
The corporate world is a toxic hive.
And if you’re a wild bee trying to survive in a hive, you’ll feel:
Constantly exhausted
Like something’s wrong with you
Trapped, but don’t know why
Creatively dead
Because you’re not BUILT for hive life.
And the system needs you to think that’s your fault.
Because if you think it’s your fault, you’ll:
Keep trying to “fix” yourself
Stay in roles that drain you
Never question the structure
Blame yourself when you inevitably burn out or leave
But if you realize you’re a wild bee? 🐝🐝 Then you stop trying to fit into hives.
You start building something that honors how you’re wired.
What I Learned from 10+ Jobs in 10+ years
Every job taught me something I now use in my business:
Government contracting: How bureaucracies work (now I help people navigate them)
Nonprofit work: How mission-driven orgs operate (now I help people exit them strategically)
Freelancing: How to price my time (now I teach this)
Communications roles: How to position a narrative (now I do this for clients)
Yoga teaching: How to integrate body wisdom (now I use cycle-based planning)
None of it was wasted. I wasn’t failing. I was learning about myself and the system.
And now I help other wild bees do the same thing:
REPURPOSE what you gained in the hive. Use it to build something that actually fits you.
You’re not broken. You’re a wild bee in a system built for worker bees. And that’s not a flaw. That’s information.
The 3-Step Process I Used to Repurpose 10+ Jobs
Here’s how I turned “job-hopping” into a STRATEGIC advantage:
Step 1: Audit What You Gained (Not What You Lost)
Most people look at job changes as LOSSES:
Lost stability
Lost benefits
Lost seniority
I reframed it as GAINS:
Gained skills in 5+ industries
Gained insight into how systems work
Gained proof I can adapt to ANYTHING
Exercise (Hive members, do this now): 🐝
List your last 3-5 jobs.
For each, write:
-1 hard skill you gained (software, process, certification)
1 soft skill you gained (communication, conflict resolution, etc.)
1 system insight (how that industry/org actually operates)
Example from my own audit:
Nonprofit job:
Hard skill = grant writing.
Soft skill = stakeholder management.
System insight = mission drift happens when funding dictates programs.
Repeat this step for all your jobs/industries you’ve been in. You now have a bank of transferable skills.
Step 2: Identify Your Pattern (Not Your “Problem”)
Look at why you left each job. Most people see: “I keep leaving. I’m the problem.”
Reframe: “What pattern do I see in what doesn’t work for me?”
For example, my pattern:
Left every job that had a rigid hierarchy
Left every job that required 40+ hours in the office
Left every job that didn’t allow creative input
I’m a wild bee. I need autonomy, flexibility, and creative control.
Your turn (Hive members): 🐝
Why did you really leave your last 3 jobs?
Not the “professional” reason. The REAL reason.
Write it down.
What pattern do you see?
Step 3: Position It as Strategic (Not Chaotic)
Here’s how I talk about my 10+ jobs now:
Old framing (apologetic): “I’ve had a lot of jobs... I know it looks bad, but I was trying to find the right fit...”
New framing (strategic): “I’ve worked across nonprofit, private, and government sectors. I’ve been every worker classification. I know how the system works—and I teach people how to repurpose their experience to build what actually fits them.”
One sounds like a liability. One sounds like EXPERTISE.
Your turn (hive members): 🐝
Rewrite your “job-hopping” as:
Cross-industry experience
Versatility
Systems knowledge
Proof you can adapt
This is how you turn 10 jobs into a SUPERPOWER!