5 Strategies for Reinventing Your Career in Uncertain Times

During times of uncertainty, we tend to hunker down and cling to the status quo. A kind of myopia kicks in, and we focus on our most urgent decisions: how to keep our families safe and healthy, how to keep our bosses happy, or, if we’ve lost a job, how to find a new one as quickly as possible. When we’re overwhelmed, it can be hard to find the time, motivation, and mental energy to think about longer-term questions.

But despite the challenges that extended periods of uncertainty present, those periods also offer unparalleled opportunities for strategic planning. Total control and predictability are always an illusion — and when circumstance strips that illusion away, it can open our minds to the wide variety of paths we could take. On the basis of our experience as consultants and leadership coaches, we’ve developed five strategies that can help anyone leverage the power of uncertainty to reinvent their career strategy.

1. Explore a range of options — including the unthinkable.

Anything can happen in uncertain times. The breadth of possible outcomes can be overwhelming, and even when we understand them intellectually, we often avoid confronting our worst-case scenarios. But explicitly considering the most unimaginable of outcomes can actually make them less intimidating, enabling you to think through your options more clearly and to plan more effectively.

One of us, Dorie, worked with an organization that was drafting budgets detailing what it would do if the pandemic led to revenue declines of 5%, 10%, or 20% for the year. Dorie urged it to craft a scenario in which 50% of revenue evaporated. Thankfully, that financial apocalypse didn’t come to pass. But knowing what it would do in that case meant that the organization was prepared no matter what, giving it a far greater shot at success than peer organizations that avoided even considering such a possibility.

Similarly, if you’re looking for work, consider planning not just for the most likely scenarios but also for one in which you’re unemployed for twice as long as you expect, or in which your spouse also loses his or her job. Although such possibilities can be difficult to think about, figuring out exactly how you would handle them — and setting triggers for action, such as “If I haven’t landed a job by February, I’ll move to a cheaper apartment or rent out the spare bedroom” — can help ensure that you don’t find yourself in a more dire position later on, such as having to sell your home or move in with relatives.

2. Imagine your best possible future.

Of course, strategic planning isn’t just about imagining the worst possible outcomes. Equally important is considering ideas and opportunities that might never have occurred to you before. Challenge the assumptions you are making about yourself — things like “I’ve never tried that type of work before, so I wouldn’t be a good candidate” and “I’m just not cut out for management.” Think about different ways you could leverage your skills and fulfill your passions, both at work and in other aspects of your life. Would working a three-day week give you more time for parental care or entrepreneurial ventures? The more you’ve thought through your options, the better prepared you’ll be to act when an opportunity arises.

Although it may sound simple, imagining best-case-scenario futures is sometimes even harder than preparing for the worst. Here are some strategies to help you get started.

• For inspiration, delve into your most vivid difficult moments — challenges you faced during the pandemic, for example — and think about the skills or creative adaptations you drew on to meet them. Perhaps you struggled without the routine of a daily commute but then repurposed your commute time into a new fitness regimen. This could suggest that going forward, you should consider remote work opportunities.
• Construct a personal highlights reel to help you remember the moments when you were at your best. The patterns you discover can serve as clues. If you’ve consistently enjoyed mentoring colleagues, for instance, you might consider how to develop new skills around coaching or look for ways to make it a larger part of your professional life.
• To understand what you value, think about how you spend your free time. One of David’s clients, who had long nursed a side passion for writing, recently left her job and has now started to work on a book.
• Go beyond your past experience and current industry to explore new arenas and emerging trends. A few years ago one of David’s former colleagues noticed that interest in AI was rapidly growing. Although he lacked formal experience in the field, he applied for and soon landed a role in a new innovation unit focused on developing and implementing AI technologies.

3. Build capabilities relevant to your future self.

In normal times, it’s typical to first identify a job you’d like to have and then work to acquire the skills needed to land it. But in periods of extreme uncertainty, that can be a risky approach, because the company or even the sector you’re focused on may face unexpected disruptions. We suggest taking a “skills first” approach instead: Identify the skills you’ll need to cultivate in order to grow toward your broad personal and professional goals, and then determine which jobs might be a good fit. A colleague of ours was committed to the idea of becoming a “global leader.” To pursue that high-level goal, he determined that he had to improve his cross-cultural communication skills, regardless of the requirements of any particular job opening.

To identify and develop new skills, we recommend the following strategies:

• Find opportunities to practice new skills in your current role. Without changing his formal role at all, the colleague we just mentioned made an effort to cultivate relationships with coworkers from vastly different backgrounds to better understand their diverse experiences.
• Explore online programs and courses. Our colleague invested in several courses focused on managing across cultures, bolstering his confidence and helping him avoid rookie mistakes.
• Reach out to people you can learn from through informal mentoring or formal coaching. Your network is your best educational resource — and the people in it might also be in a position to advocate for you in the future as they become aware of your growing skill set. Our colleague asked a mentor if he could shadow her on certain calls and meetings to observe how she handled various situations, giving him valuable real-world perspective.

4. Start small.

To move past the paralysis of uncertainty, focus on what you can change in the short term. If your tasks feel intimidating, try “chunking” them into more-manageable sub-tasks. Writing a book might seem overwhelming, but drafting a high-level outline can be done in an afternoon. If you’re not sure what to prioritize, start with some “no regret” moves — actions that will be helpful regardless of changing circumstances — such as brushing up your résumé or updating your social media profile. Finally, ask yourself, “What small move could I make today that would bring me joy?” or “What could I accomplish if I gave myself a week?”

An executive we know was contemplating a career move, but after years of focusing exclusively on the day-to-day tasks of his job, he found the prospect of rebuilding his skills and network somewhat daunting. As a first, step, he decided to set up five calls every week with people in his network (university friends, previous customers, and people he knew socially) to catch up on news in their various industries and learn more about different roles and organizations. After a few months, some of those people started sending him job openings they thought would be relevant — and he eventually landed one of them.

5. Be ruthless about what you need to leave behind.

Planning for an uncertain future isn’t just about arming yourself with new skills or making new connections. It’s also about making strategic choices concerning what — and who — to abandon. Of course, it’s hard to give up things in which you’ve invested a lot of time, effort, and energy. And it’s easy to be nostalgic about the past, especially when facing uncertainty in the present. But moving forward means taking a clear-eyed view of what’s no longer serving you and giving yourself the space to pursue something new.

One of David’s colleagues had always envisioned herself in a portfolio career, one that would include serving on a corporate board. She realized she was not on track to achieve that goal because she chronically overfilled her calendar with work and volunteer obligations. Once she understood the opportunity cost of her current schedule, she began delegating more responsibilities. She created formal handover plans, developed a script for turning down requests and more assertively saying “no,” and practiced such delicate conversations. Once she had eliminated the unnecessary responsibilities that were weighing her down, she had a lot more time and headspace for exploring director opportunities.

Human beings are wired to avoid uncertainty — but no matter how hard you try, there’s no escaping it. Instead, it’s best to view uncertainty as an opportunity for growth, whether that means exploring new skills, a new job, or an entirely new career. There are no easy answers, but with the strategies described above, you’ll have the tools to deal with whatever the future might bring.