Why Millennials Should Job Hop to Launch Their Career

John Knight
The Startup
Published in
4 min readJun 4, 2019

I have a unique educational and professional background. In my 6 years since graduating from college, I have held 8 titles at 5 companies.

As one may expect, during my last few job interviews, I have been asked why I’m looking to change jobs so soon, and my answer has been the same, “Your internal recruiter reached out and made this opportunity sound appealing.”

3 ways I have seen “job hopping” launch my career:

1. “Job Hopping” Builds Experience

I was given this career advice early on, “The wider you build the base, the taller you can build the pyramid.”

Right now, I enable sales operations through technology, focused on the Salesforce platform, but my diverse experience provides context for my work every day. Roles I have filled at various points include:

  • Sales (Pain Points, Value Propositions, Objection Handling)
  • Sales Development (Cold Calls, Emails, Website Chats)
  • Marketing (Blogging, Website, Paid Ads, Events)
  • IT Support (Computers, Networks, Servers, Email)
  • Sales/Business Operations (Coordinating and supporting all of the above)

Gary Vanerchuck emphasizes the need for empathy in business, and there is nothing as powerful for empathy as having actually been in the shoes of the roles I am supporting.

I’ve never been a full-time SDR, but I’ve made several thousand outbound calls across a couple of roles.

I’m not in sales, but I’ve closed deals.

I’m not a marketing expert, but I was AdWords certified and managed a $2500 monthly ad spend.

My IT certs have expired, but I still can collaborate with IT on a level that I would not be able to without the years I spent in IT.

Does this experience mean I know everything? Absolutely not! Instead, it gives me context to value the work SDRs, sales reps, marketers, and IT professionals do and to collaborate better across departments.

2. “Job Hopping” Builds Connections and References

One key in transitioning jobs is to remain positive and not burn any bridges unnecessarily.

The network of connections I have developed across the different roles allows me to give and receive help and recommendations that I would not have access to otherwise.

Anyone that follows me on LinkedIn will soon notice that I talk a lot with Ben Fuller, a former colleague. Ben and I joke that we talk more now than we did when we worked together.

3. “Job Hopping” allows for project-based work

Sometimes the context of particular jobs change over time and that’s ok. For example, perhaps a company has decided to implement Salesforce as a CRM to manage their sales process because they have outgrown sticky notes and spreadsheets, or they are focused on a big CRM migration from one platform to another. Once those projects wrap up, the nature of the job is likely to shift.

To quote Ben Fuller, “I’ve been a project-based admin who enjoys full-time benefits.”

Objection: Job Hopping Hurts Future Opportunities

The validity of this objection is largely dependent on a few factors.

The reason for each job transition:

The reason for making job transitions matters a lot and being able to articulate a good reason for each job transition

Example Strong Reasons for Job Changes:

  • I outgrew my company (eg a 50 person company didn’t need a full-time Salesforce Admin)
  • I received a new title with more responsibility (eg Admin to Sr Admin)
  • I received a large compensation increase (15%+)
  • My company got acquired and the job/culture changed
  • My project wrapped up

Who Initiates the Conversation

Actively looking for a new job after a short time in a current role can be viewed negatively; however, building connections with recruiters and potential hiring managers for professional advice and guidance is always a great idea and can lead to new opportunities when the time is right.

Company Mindset

I was talking recently with a connection in my field who is much closer to retirement than I am. I was surprised to learn that professionals could still job hop for large pay and title increases 20–30 years ago. The difference is that after changing employers more than once or twice, it would be virtually impossible to get hired again, so there was a level of fear around getting collectively blacklisted by employers.

I see this “blacklist” mindset evolving on two accounts. Firstly, out of necessity. Especially in technology that evolves quickly, recruiting candidates without extensive tenures in a current role is becoming a necessity.

Secondly, as younger professionals move into leadership positions, there is a collective mindset shift away from valuing traditional education and resume experience towards meritocracy (what can someone do vs what have they done).

What next?

  1. Do not be afraid to say yes when a good opportunity presents itself.

“If somebody offers you an amazing opportunity but you are not sure you can do it, say yes — then learn how to do it later!” Richard Branson

2. Keep the conversation open with your current employer about your career path.

Some will be eager to provide professional development, some need a push, and others are more focused on prebuilt guidelines (eg must be in a role for ___ months before being considered for anything else). An open conversation will quickly reveal each company’s mindset.

3. Take full advantage of the present opportunity.

There are often ways to continue to learn and gain experience in one’s current role. In general, focussing on the existing learning and experience opportunities will have a higher payout than spending time/energy constantly looking for the next role. Additionally, this focus will facilitate the next role when the time is right.

4. This post is in the context of individual contributors early in their career.

I cannot speak as directly to the effects of job hopping at management levels. My general observation though is that building leadership skills needed for management is different than building the skillsets and experiences needed as an individual contributor, so the recommendations in this post may or may not be relevant.

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John Knight
The Startup

Problem Solver | Builder | Networker | Data Lover | Learner | Volunteer | 3x Salesforce Certified | Trailhead Ranger | Chess Player | CaffeinatedCloud.com