The Challenge of Leaving a Long-Term Job to Start Something New

Summary:

Leaving a company that’s been your professional home for years, or decades, is a major shift that can feel both thrilling and perilous. In this article, the authors outline six challenges that often come up when making this transition. They offer advice for how to overcome these six challenges and share strategies to ensure that your new job or career is just as successful as the last one.

Retiring from a job you’ve been at for most of your career is bittersweet — relishing a chapter successfully concluded, while grappling with the transition into a new phase of life.

But leaving a job you’ve been at for years or decades in order to start your own venture or go to another company? That’s a different emotional and practical experience altogether.

It may well be the right move for your life and career, but your transition may nonetheless feel ambiguous and unresolved; you may even grapple with feelings of disloyalty. Through Dorie’s research for her career transition guide Reinventing You, and Natalie’s personal experience of leaving a 16-year career in academia, we’ve discovered there are six key challenges to be aware of as you contemplate a shift out of a company where you’ve spent most of your professional life.

Ruminating and Second-Guessing

The first challenge you’ll likely encounter is getting yourself out of the “should I stay or go?” loop. Many professionals spend years debating whether or not to leave their longtime companies, only leaving when they reach a level of unhappiness or dissatisfaction they find intolerable.

Instead, identify small ways to test the premise you’d like to explore (“Would I enjoy being a professional photographer?”) and experiment with getting your nascent side hustle off the ground (“Will people actually pay me for my work?”). By piloting your next move when stakes are low, you’ll be more open to learning, iterating and making that leap with both courage and proof instead of getting stymied by perfectionist impulses.

For instance, Natalie inadvertently prototyped her current company, Figure 8 Thinking, after giving a TEDx talk in 2014. In her talk, she discussed how the most innovative companies have designed improvisational systems and ways of working and described the future of work as jazz. This led to a succession of invitations from companies who hired her to do deeper dives on the topic. At the time, she viewed Figure 8 Thinking as a side hustle — a repository for short consulting and speaking engagements, adjacent to her full-time work. But it provided data about what the market needed, what she was good at delivering, and what she enjoyed doing — and her side gig eventually became her full-time profession.

Feeling Guilty

You’ve built trust and rapport with your colleagues over time centered around a core premise: They can count on you. And now you’re leaving, perhaps in the middle of long-term projects where your contribution may be significant.

It’s natural for many professionals to feel a sense of guilt about saying goodbye to their team. If you’d only been at the company for a few years, few people would be surprised that you’re moving on: that’s what people do these days. But if you put in enough time at an organization, people — consciously or unconsciously — come to see you as a ”lifer.”

In the midst of the banal challenges of transition that you expected — porting over your 401(k), signing HR paperwork, wrapping up project details — you may face a wave of challenging emotions, ranging from a concern that you’re abandoning your coworkers to fear of how you’ll look to them, from hypocritical (“He said he’d always be here for us”) to treasonous (“How could she leave us for a competitor?”).

Being Afraid of Losing Status

Another frequent issue when leaving your longtime organizational home is leaving behind the professional recognition — and ego validation — that came with your position.

When Natalie contemplated leaving her longtime academic career for entrepreneurship, she realized that a large part of her hesitation was tied to her identity as a professor — a status she’d worked hard to attain. Meanwhile, nascent entrepreneurs (or newer employees at a company) often have few markers of recognition to separate them from the pack, which may feel like a step backward. Recognizing your ego reflex — and choosing to let it go — can help enable you to explore new territory for reinvention.

Needing to Adapt

Another concern that’s worth noting is around your ability to adapt to new ways of doing things, or unrecognized habits or blind spots that suddenly become apparent.

For example, if you’ve worked in a large corporate environment for a long period of time, you may have come to depend on a scaffolding of resources and budgets to get things done. If you’re moving on to join a smaller non-profit or to start your own business, then the ability to become multi-hyphenate and creatively resourceful will be essential.

Alternatively, if you’re transitioning to a much larger organization with lots of layers, give yourself the time to observe, learn the culture, and build relationships with key players (both laterally and vertically) in order to not inadvertently step on toes. Becoming aware of your “habits of mind” will enable you to adjust more quickly and avoid unforced errors in your new position.

Managing the Perceptions of Your New Colleagues

It’s also important to recognize that — whether fair or not — your new colleagues may view you, or your skills, as outdated or narrow. To mitigate that risk, think through behaviors you’ll want to emphasize (your willingness to learn new technology or systems) or avoid (constantly referencing your “glory days”).

Dorie once knew an executive whose colleagues played a game where they’d count the number of times in a meeting that he’d reference the way his old company did things. Unsurprisingly, his tenure at the new firm was short. It’s important to telegraph to others that you’re willing to learn new approaches and aren’t wedded to the past.

Balancing Opposing Emotions

Understandably, we want our professional reinvention to be clear and logical: an “up and to the right” progression. But — especially when leaving a company we’ve been at for years — it’s important to recognize that the emotional journey will probably be murkier, mixing both excitement and grief. You’re excited because of all the new learning, discovery, and adventure that lies ahead. But it’s likely you may also feel sad and fearful. What if you fail? What if it turns out that you’re not very good at your new venture? And who are you if you’re not the role you’ve performed so well for the past number of years?

Indeed, Natalie wondered if her initial side hustle engagements might be flukes, or if they only came as a result of a “halo effect” affiliation with the university. Was it possible that people would continue to hire her if she went out on her own? She went through a version of imposter syndrome, which she worked through in part by scheduling a week-long personal retreat for herself. In retrospect, that time spent alone, constructively facing her hopes and fears, was pivotal for her actual leap forward.

It’s important to acknowledge that mixed emotions are natural in this situation; as Natalie advises, the right time to shift out of your old job is when you feel 50% terrified and 50% exhilarated, because the terror will ground you and the exhilaration will keep you optimistic and buoyant.

. . .

Leaving a company that’s been your professional home for years, or decades, is a major shift that can feel both thrilling and perilous. But by recognizing these six challenges upfront, you’re better able to navigate the transition and ensure your new job or career is just as successful as the last one.

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