This Wasn’t Part of “The Plan”

How to approach a career pivot or pause

Two years ago, quitting a job seemed scary and taboo, it wasn’t something that many people wanted to talk about. Over the last year and a half, many people have been participating in “The Great Resignation” — voluntarily leaving jobs — in addition to many other significant changes. Although it’s becoming increasingly common, it is still tough to embark on a new career path. It’s something people talk about in hindsight, once they’ve “made it”, not when they’ve just jumped into the deep end.

But when we quit our jobs in late 2019 and discovered that we were not alone in the experience, we decided to write about it. As two people from different industries, with different drivers for career change, we wish we read these words leading up to our decisions. We offer a mix of practical considerations and moral support to help you to step outside of your comfort zone in the interest of making meaningful personal change.

Should I stay or should I go?

Maybe your current job is comfortable. Despite the fact that you’re contributing positively to a workplace and there aren’t any obvious reasons to leave, it doesn’t mean you can’t want more for your career. It’s also worth mentioning — showing up and going on autopilot is sometimes exactly the work-life balance that you need, but this article is for those feeling the itch for change.

To start, imagine where you want to be in 3, 5, or even 10 years. Not just your job title, but what industry? Solving what problems? Will you lead a team? Where will you live? What do you need time for outside your paid job?

Write your “needs” down in one list, then write down the needs of your current employer in another list. Now compare. A good fit would have a lot of overlap in terms of working on interesting problems, responsibilities, and enabling the life you want outside of work [1]. If you have a supportive work environment, it may be possible to work toward a better fit by asking for new daily tasks, new responsibilities, or a lateral shift. If you already know that your current work environment can’t possibly get you where you want to go, then consider an option that’s scary in the short term: leaving.

Deciding if and when to act.

Leaving your job for a career pivot, or even a pause from working, is both exciting and daunting. You want to, but should you actually do it? When? How? What next? Here are three things you can do to help with your decision-making process.

Ask real people about their career paths. People you know personally are more likely to open up about their big turning points than high-profile public figures. It’s just as important to hear about the bad times and the hard times, as it is to hear about the eventual rewards of such a decision. When someone starts over — regardless of the career stage, discipline, or sector — there is a wealth of practical and emotional outcomes to learn from. It never hurts to reach out to your network and ask for advice.

Calculate the risk. As Loran Scholars, we were privileged to be supported both financially and emotionally as we pursued meaningful growth opportunities. These are two important factors when considering any major change, especially one such as leaving your job. What is your risk tolerance in terms of financial stability, societal pressure, and professional goals? Do you want or need to have your next job waiting in the wings soon after leaving, or are you being deliberate about taking a pause from working in order to re-energize and refocus on what your next step will be? How will you plan for the move, both practically and emotionally?

Consider the opportunity cost. Assess what opportunities you’re missing out on if you don’t make a change. Dream big about what you stand to lose, and consider the risks and rewards involved in going for it. If a change is not the right answer, consider your needs in terms of mentorship, a certain industry, a role, a team, a lifestyle, a problem, or anything you value. You are the person that needs to show up for the job every day and if it’s not a culture where you thrive, this prevents you from getting the most out of the opportunity.

Navigating the winding road after you have made the decision.

Once you’ve decided the specifics of your career pivot or pause it can feel lonely and unsettling. Here are three things we wish we understood when beginning our journeys:

No one’s career path is a straight line. Linear career paths are increasingly rare, despite what conference bios or LinkedIn profiles might say in order to sell a person’s qualifications. Sure, some professions are more flexible than others, but no one wrote out a fifty-year plan at age 18 and followed it until retirement. Admitting that “this wasn’t part of the plan”, at some point in your career, is normal.

Overcoming career momentum takes strength. It’s not easy to climb “The Ladder” but there is comfort in a predictable career path because it is what other people expect. Every promotion gives you momentum, which can make it hard to change course. If you have overachiever tendencies (ahem, *raises hand*), it can be really hard to leave a prestigious career on the table to pursue something less certain. We’re here to argue that it’s even more ambitious to steer away from the shiny rewards and head down an unconventional road.

Doubts and fears are normal. You are resilient. It’s normal to get questions from coworkers, friends, and family. Even if the questions are coming from a place of love, they can still provoke shame, fear, and disappointment. Your decision could be scary for those who cannot relate because they may have a different definition of success. Know that it’s normal to feel uncomfortable. Reassure yourself by remembering your initial motivation for taking the risk, and reach out to people in your network who have made a career pivot themselves.

Your cheering squad is here!

Our goal here is to challenge traditional assumptions about success, progression, opportunity, and risk. We wish there had been a cheering squad during our career transitions to validate our personal risk in pursuit of new challenges — to remind us that we deserve to grow and that we are resilient. We wish we had known earlier how to navigate the tension between the practical and the emotional aspects of the decision-making process. Through our experiences you can see that while leaving your job can be scary and unsettling, it can also be meaningful. Leaving a job may be necessary for you to continue on your own journey of professional growth or allow you to contribute more fully with your skills and talents.

Two years after our big moves, we can’t imagine it any other way. Alison has gained experience in freelance consulting, operations, and running a business that just wasn’t in the realm of options at her previous workplace. Marin has gained experience scaling a start-up and building a global network of purpose-driven partners. The time we spent working at our previous jobs was valuable, but everyone grows and changes. Sometimes that means your career needs to move in a different direction too. We hope that this article helps to validate and support you if you’re at a similar crossroads in your life.

[1] This exercise was based on a workshop that Alison attended by Johnathan and Melissa Nightingale, the talented duo behind Raw Signal Group management training. If you found it useful, consider subscribing to their newsletter about leadership.

Author Bios

Alison Lee is a 2009 Redknee Loran Scholar and has held Product and Operations roles at several startups related to security and privacy, manufacturing, consumer goods, and most recently, infrastructure. She is currently the Strategic Operations Lead at Citylitics Inc.

Marin MacLeod is a 2009 Young Fund Loran Scholar and the Executive Director of the Reach Alliance, a partnership between the University of Toronto’s Munk School of Global Affairs & Public Policy and the Mastercard Center for Inclusive Growth.