Knowing When to Call it Quits: The Power of Letting Go and Moving On

Fifty years ago, staying with the same company for your entire career was the dream. Start from the bottom, enjoy a few promotions along the way, and rely on stability over all else. 

Ambition was still around, sure, but most people would recommend against including a job on your resume if you were there for less than two years. Job hopping was considered a red flag, a sign of employer dissatisfaction. “There must be something wrong with them,” they’d think. 

Not anymore. 

Millennials (of which I am one) notoriously keep their eyes open for new opportunities. Only half of them even expect to be in their current position a year from now.

In my , a music industry executive who has worked at basically every record company you’ve ever heard of, we discussed never staying in the same place for very long. 

Benny works from a single principle: 

“Once you’ve maximized what you can give or what you can get—move on.”

That sounds great from an employee perspective. But what about the CEOs and entrepreneurs desperately trying to retain their best people? There are ways around that too. Let’s talk about it.

A shifting mindset

Let’s go back 50 years to the 1970s, a time of bell bottoms, disco music, and a sense of steady job security. 

At the start of the decade, the world was buzzing with optimism, and employees felt confident in a job market that offered opportunities for long-lasting, stable careers. 

But a severe oil crisis and soaring inflation led to plummeting profits and once-healthy manufacturing sectors riddled with uncertainty. As companies scrambled to cut costs and stay afloat, they discovered that they could outsource and offshore jobs to countries with lower labor costs. 

Seemingly overnight, workers saw their once rock-solid careers vanish, replaced by a growing sense of insecurity. The idea of holding onto a position instead of using it as a springboard was widespread. 

But it wouldn’t last. By the 1990s, as Millenials entered the workforce, perceived job stability in the United States and Canada started normalizing. 

This improving sense of job security led ambitious young employees to start not only hopping jobs but entire industries and sectors. You weren’t tied to a single skill, and the idea of lifelong learning took hold.

The influence of tech

Today, people are more concerned than ever about staying on the cutting edge of technology. Because every industry is constantly adapting and innovating, the fear of being left behind—coupled with the rapid change in the tech landscape—has significantly influenced workers' career paths. 

You can’t be tethered to a single company for decades and remain relevant, competitive, and employable. 

Job loyalty vs. career loyalty

It’s created an interesting dichotomy between job and career loyalty. You used to be loyal if you stayed at the same company; now you are if you stay in the same industry. 

Software developers, aerospace engineers, or executive chefs. All three can show loyalty by staying in their respective sector but aren’t expected to be in the same role for long. 

Gig economies

While the gig economy has undoubtedly been a boon for those seeking flexibility and diverse career experiences, it has also left many workers with little choice but to hop from role to role in search of stability. 

This constant hustle can significantly impact transportation, hospitality, and creative workers.

For some, holding onto a traditional full-time job with benefits and long-term security is almost impossible. 

As companies adopt new business models centered around freelancers, contractors, and part-time employees to reduce overhead costs and increase flexibility, workers traverse a series of short-term roles. 

While this offers the opportunity to gain diverse experiences and develop a broad skill set, it often comes at the cost of stability and peace of mind.

Embracing instability

That might sound scary, but there are ways to turn it into a positive. For savvy workers, hopping from role to role can become a strategic career move—using short-term positions and projects as launching pads to propel their upward career trajectory. 

Embracing instability involves a proactive, adaptable mindset, relishing the chance to gain new skills, expand your network, and diversify your experiences.

Don’t fight it; dig in

As Benny put it, "Become a student of the game." When entering a new role or project, take the initiative to learn as much as possible about your new surroundings—not just the specifics of your position but also the industry, the competition, and emerging trends. 

Absorbing this knowledge and staying ahead of the curve allows you to offer unique, invaluable insights that set you apart from others.

Diversify your arsenal

Seek out mentors and connections wherever you go. Building relationships with thought leaders, innovative colleagues, and experienced professionals at each pitstop in your career journey enriches your professional network and opens doors to new opportunities.

Instead of limiting yourself to a specific niche, broaden your horizons by exploring different aspects of your field and learning complementary skills. This versatility makes you more adaptable and widens your career move possibilities.

Invest in yourself

More than anything else, I see each opportunity as a chance for personal and professional growth. 

Invest in yourself by continuously expanding your skillset through on-the-job experiences, online courses, or certifications. Observe and analyze how your industry is evolving and capitalize on those insights to ensure you are always one step ahead.

Build a personal brand

I know, “personal brand” is a buzzword that causes a few wrinkled noses. But I don’t mean buying Instagram followers. 

Use your unique experiences and expertise to craft a compelling narrative highlighting your adaptability, creativity, and value. Share your story within your industry’s community to assert your presence, gain recognition, and find new opportunities.

Networking is still one of the best ways to get ahead, even if it’s done a little differently these days. 

Lessons from the other side

It’s not just ambitious young professionals reading this newsletter, though. We need to talk about it from the other perspective; how to prevent the loss of top talent and avoid constantly trying to recruit replacements. 

The art of retaining skilled team members is no longer about preventing them from leaving. Instead, it is about creating a corporate culture that fosters career growth, promoting an environment where employees feel empowered to learn, grow, and succeed. 

Building development strategies

By establishing a reputation as a company that nurtures talent, the organization becomes an attractive destination for skilled professionals, thus creating a self-sustaining cycle of high-quality recruitment and retention.

To build this reputation, you have to invest in employees' personal and professional development. Provide resources and opportunities for your team members to hone their skills, explore their passions, and continuously evolve within their chosen fields. 

Adapt and innovate

No one chases a job at the stuffy 100-year firm with brown walls and cubicles (even if it is as stable as it gets). 

Encourage employees to think creatively, take risks, and embrace diverse perspectives. By doing so, you create a stimulating work environment and empower your team members to push their boundaries and unlock their full potential. 

This approach can lead to groundbreaking ideas and solutions that drive personal success and company growth.

The work-life balance equation

Nearly two-thirds of American workers would choose a better work-life balance over better pay. Only 15% would definitely chase the better paycheck. 

Let that sink in for a second. You can’t just offer money anymore. 

Remote work, flexible schedules, and robust time off policies are changing how the average worker expects to be treated. 

If you allow your team enough time outside the office to pursue their passion, they may not be so quick to look for something new.

Remove the ceiling (glass or otherwise)

If you’ve skimmed along to this point—stop. This is the most important part of the whole newsletter.

Vital to retaining and attracting top talent is ensuring that all employees, regardless of gender, race, sexuality, or background, have equal opportunities for advancement and success within the company. 

The ability to rise through the ranks without encountering insurmountable barriers makes your organization more attractive to a diverse talent pool. It leads to a more inclusive, engaged, and productive workforce.

That doesn’t mean just interviewing all candidates. It means putting systems and procedures in place to protect their candidacy. Even you—yes, you, who are reading this thinking, “I have no biases”—need to have checks in place to ensure you’re providing fair opportunity. 

Things like:

Bias-free hiring and promotion: Adopt blind recruitment and establish fair promotion criteria to eliminate potential evaluation biases.

Mentorship and sponsorship programs: Establish mentorship and sponsorship initiatives that actively promote career development for employees from diverse backgrounds.

Diversity and inclusion training: Regularly provide diversity and inclusion training to all employees, emphasizing the importance of an inclusive work environment and equal opportunities for advancement.

Inclusive performance review: Incorporate 360-degree feedback in performance reviews, ensuring that employees receive feedback from multiple perspectives, helping to minimize potential biases in evaluations.

Transparent career pathways: Communicate clear and transparent career paths for all roles within the company, allowing employees to understand the requirements and expectations for advancement, regardless of their background.

It also means getting out of the way if you’re the one blocking advancement. You should be hoping to make yourself redundant by growing employees who can do everything you can—but better.

Final thoughts

Maybe 50 years from now, these ideas will have completely flipped once again. Maybe a 40-year career with one company will once again be the goal that everyone strives for. 

But right now, if you put your employees in a holding pattern, you will lose them. Worse, no one will be waiting to replace them.  

If you want to hear more from Benny on this subject, or the others we touched on in our hour-long talk, head over to the Success Story YouTube page. He had some remarkable insight into deconstructing masculinity and fatherhood, something I might want to touch on in a future newsletter (once I fully grasp it myself). 

Otherwise, that’s all I have for now. Talk again next week!

If you enjoyed this article, I’d love to hear from you.

Also published here.