hero cover image
The Entrepreneur vs. the Job Hopper

The Entrepreneur vs. the Job Hopper

19th Aug 2026
Sean Britton
Consultant
View Profilehero chevron
Sean Britton
emailsean@topsjobs.com
phone412-701-9007
referral linkhttps://referrals.bestinrecruiting.com/join/sbritton
Share
3 min read

A few weeks ago, I was sitting with a relatively new client that I didn’t have much history with yet. We were having an alignment meeting, and I brought along a few example resumes from candidates we had successfully placed in similar positions with another client.

 

The goal was simple: Make sure the client, my team, and I were all on the same page about what we were looking for from a skills and employment history perspective.

 

During the meeting, I presented a resume of a candidate who had worked for nine different employers over the previous two years that we placed at a different client.

 

Frequent job changes aren’t always indicative of a poor or unskilled employee, but they will almost always raise questions for the hiring manager or HR team reviewing the resume.

 

The client was surprised that we had represented this candidate for a position. On paper, the candidate appeared unreliable.

 

Could that have been true? Absolutely.

 

But without knowing the story behind the resume, I believe it is unfair to judge a book by its cover. (By the way, he’s been killing it in his new job.)

 

So, why did we decide to represent a candidate with such a jumpy job history?

 

People all over the world idolize entrepreneurship. Everyone loves hearing stories about how many times Mark Cuban, Oprah Winfrey, Barbara Corcoran, Walt Disney, and countless others failed before finally getting one idea right.

 

They didn’t have to be right every time. They only had to be right about one idea, one time.

 

So why are we so quick to judge someone who is trying to figure out what they enjoy doing and where they belong professionally?

 

Would you want to spend more than 40 hours every week working at a job you didn’t enjoy or didn’t feel you were good at?

 

I sure wouldn’t.

 

Most people begin their professional careers between the ages of 18 and 22. Full Social Security retirement age is currently 67 for most people entering the workforce today.

 

That’s a long time to spend doing something you don’t enjoy.

 

Every single person fails at something. Without failure, there is no way to determine what you’re good at. Plus, you lose the opportunity to grow, learn, and understand why something didn’t work out.

 

My Advice to Job Seekers:

Chase what you enjoy doing.

If you have a job-hopping resume, work with a recruiter who will take the time to understand your situation and help tell your story. A good recruiter can explain the context behind your employment history and help a hiring team see more than a list of dates and job titles.

We want to see you land that new job just as badly as you do!

 

My Advice to Hiring Teams:

Be open-minded.

Try to place yourself in the candidate’s reality.

Did they move? Were they working several temporary or contract positions in a row? Did something change in their personal life? Were they caring for a sick loved one? Or maybe they simply haven’t found the right culture or position yet.

There are endless reasons someone may have changed jobs several times.

 

Is that true for every candidate?

 

Of course not.

 

Sometimes frequent job changes really are a sign that someone may not be the right fit. But without taking the time to understand the “why,” you could be passing on your next lifelong employee.

Blogs and Insights

TOPS Staffing
Hiring
Career Advice
The Entrepreneur vs. the Job Hopper

Sean Britton

TOPS Staffing
Career Advice
Hiring
Job Hopping in Manufacturing | Hiring manager’s point of view

Bill Gaffney

Accounting
Industry insights
AI and ChatGPT are game changers, but not always for the better

Tom Welsch

Accounting
Hiring
Remote work remains a trend... NOPE!

Scott Suchy

Accounting
Career Advice
What I've Learned from Talking to Hundreds of Finance Professionals

Chloe Knupp

TOPS Staffing
Career Advice
Hiring
Could You Be Our Next Top Recruiter?

Garett Lange

Career Advice
Accounting
The Best Employees Aren’t Perfect. They’re Consistent.

Cody Cope

TOPS Staffing
Hiring
Light Industrial
The Hidden Cost of Being Short-Staffed in Manufacturing

Sean Britton

TOPS Staffing
Hiring
Industry insights
Skills Matter More Than Ever: Why TOPS Staffing Focuses on What You Can Do

Jen Pometo

All Brands
Industry insights
Recruiting Tips
AI is the Best Admin Assistant Recruiters & Salespeople Have Ever Had

Susan C. Dietrich

TOPS Staffing
Career Advice
Industry insights
The Future of Blue-Collar Networking Starts on LinkedIn

Tyler Sechrist

Industry insights
Recruiting Tips
AI Overtaking the Staffing World – Wait Just a Sec

Scott Suchy

AllTek Staffing
Career Advice
Industry insights
Why Accepting a Counter-Offer Might Be the Worst Holiday Gift You Take

Jeromie McBride

Proxy Legal
Hiring
Recruiting Tips
How Virtual Interviews Are Changing the Hiring Process - for Better and for Worse

Carter Breen

TOPS Staffing
Light Industrial
Hiring
The Rebirth of American Manufacturing: Creating the Career Boom of the Next Generation

Jason Kelly

All Brands
Company News
Hiring
Turning the Holiday Staffing Slowdown Into a Strategic Win

J. David Cepicka

Career Advice
Hiring
References are easy…..right?

Jordan Skwirut

TOPS Staffing
Hiring
Career Advice
How to build an “Always-On” Talent Pipeline for Your Organization

Garett Lange

eStaff Search
Career Advice
Industry insights
IT and AI: Don't get Overwhelmed, Just Keep Pace

Tom Welsch

Proxy Legal
Hiring
Career Advice
Midnight the Cat: Part 3

Jackie Cepicka

TOPS Staffing
Career Advice
Recruiting Tips
Importance of Referrals: Candidates and Recruiter

Bill Gaffney

Accounting
Hiring
Why You Should Partner with a Recruiting Firm- Not Just Use One

Career Advice
Hiring
Trust, Transparency, and the Power of Honest Conversations

Cody Cope

AllTek Staffing
Career Advice
Why Yinz Should Use All of Your Vacation Days

John Kuhel

All Brands
Career Advice
Hiring
Why You Should Take a Contact Job

Susan C. Dietrich

eStaff Search
Hiring
Industry insights
Help Desk vs. Service Desk & DevOps vs. Software Engineer: Key Differences

Tom Welsch

Company News
Hiring
Building a Great Team Culture

Career Advice
Embracing Change at Any Age

Career Advice
Industry insights
Match Your LinkedIn Profile To Your Resume

Jordan Skwirut

Career Advice
Accounting
Why Choosing to Major in Accounting is a GREAT Move

Scott Suchy

TOPS Staffing
Recruiting Tips
Listening and Understanding Skillsets

Bill Gaffney

TOPS Staffing
Light Industrial
Industry insights
5 Key Hurdles in Light Industrial Staffing and How to Tackle Them

Garett Lange

Proxy Legal
Career Advice
Hiring
A Black Cat named Midnight’s Journey to Spooky Law

Jackie Cepicka

View more industry insights and blogs here

View more industry insights and blogs here

decoration

TOPS STAFFING

Skilled light technical and assembly-level people

Contact Us

Whether you're searching for a new opportunity or looking to hire, we're here to help. Reach out and let's get started.

Get in touch
arrow top right