The Squiggly Career

A career used to look like a ladder: choose a profession, find a company, climb through the ranks, and hope each promotion moves you closer to success. That path still exists, but it’s no longer the only one. Careers increasingly move sideways, backward, across industries, through new projects, and into opportunities that couldn’t have been predicted years in advance. The challenge isn’t creating the perfect career plan; it’s learning how to navigate when the path keeps changing.

Build Your Career Around Possibilities, Not a Perfect Plan

Trying to plan an entire career can create a false sense that there is one correct route and that every decision must move you along it. But the further into the future you try to predict, the less certain that route becomes. Industries change, technology changes, opportunities appear, and your own interests can change with them.

A more useful approach is to think in possibilities rather than one fixed destination. You can begin with four different versions of your future: the obvious possibility, the pivot possibility, the ambitious possibility, and the dream possibility.

The obvious possibility asks what happens if you keep moving in your current direction. The pivot possibility asks where your existing skills and strengths could be useful in a different role. The ambitious possibility is something you’ve considered but dismissed because an obstacle stands between you and it. The dream possibility removes those restrictions and asks what kind of work you would choose if nothing were holding you back.

You don’t have to select one future and commit to it immediately. The value comes from widening the range of possibilities you can see. Instead of asking, “What is my career supposed to become?” you can start asking, “What could it become?”

Invest More in Your Strengths Than Your Weaknesses

Career development often begins with a question about weaknesses: What are you bad at, and how can you fix it? That sounds sensible, but it can lead to spending enormous amounts of energy trying to become average at things that may never be your strongest contribution.

A better strategy is to understand what you already do particularly well and deliberately become better at it. Your strengths come from a combination of natural talent, experience, attitude, and behavior. The goal isn’t to ignore weaknesses completely. It’s to stop giving them more attention than they deserve. The authors suggest directing about 80 percent of your development toward strengths and 20 percent toward weaknesses that genuinely interfere with your performance.

Pay special attention to your “super strengths”: the qualities other people associate strongly with you and the abilities you’re exceptionally good at using. Those strengths shouldn’t remain hidden. They become more valuable when people know you possess them and when your work gives you regular opportunities to use them.

Even weaknesses can provide clues. Someone who struggles with detail may be unusually strong at seeing the big picture. Someone who dislikes routine may thrive in work that requires experimentation. Instead of asking only what needs fixing, look for what your weaknesses reveal about the environments and problems where you perform best.

Use Your Values as a Career Compass

A job can offer impressive pay, good benefits, friendly coworkers, and still feel wrong. The missing piece may have nothing to do with the visible advantages of the job. It may be that the way you spend your working life conflicts with something you deeply value.

Values influence what feels meaningful, frustrating, rewarding, or uncomfortable. They shape the kinds of decisions you respect, the environments where you feel comfortable, and the work you’re willing to devote your energy to. When you understand your values, you gain another way to judge a career opportunity besides salary or status.

Values can also create tension. Honesty, for example, can make you a valuable source of candid feedback, but honesty used without sensitivity can hurt another person. The goal isn’t simply to name your values. It’s to understand how they show up in your behavior and learn to use them constructively.

This becomes especially useful when several career possibilities look equally reasonable. Your strengths can tell you where you’re capable of succeeding. Your values help you decide which version of success is actually worth pursuing.

Make Lifelong Learning Part of Your Career Strategy

When careers were more predictable, it was easier to imagine learning as something that happened before work began. You earned a qualification, learned the requirements of a profession, and then built experience inside that field.

A squiggly career makes that separation much harder. Jobs change. Technologies reshape how work gets done. Projects require different combinations of skills. Your career is always a work in progress, which means learning has to become part of the work itself rather than a stage you eventually complete.

That changes the meaning of career security. Instead of relying entirely on the continued existence of one role, you can keep expanding the range of problems you’re able to solve. Learning can prepare you for opportunities you can’t see yet and make it easier to pivot when the opportunity in front of you is different from the one you originally expected.

You don’t need to wait for an employer to create every learning opportunity for you. Independent study, new projects, deliberate practice, curiosity, and experiences outside your normal responsibilities can all contribute to your development. The important thing is to make learning continuous enough that your skills keep moving even when your job title doesn’t.

Try the Big Ideas

1. Create four possible futures. Write down an obvious next step, a pivot that uses your existing skills differently, an ambitious possibility you’ve previously ruled out, and a dream possibility with the usual restrictions removed. You don’t need to pursue all four. The exercise is meant to reveal options that a single career plan might hide.
2. Find your super strengths. Write down three things you believe you do especially well, then ask a few people who know your work what they think you’re unusually good at. Compare the answers and look for patterns. Choose one strength you can use more visibly or develop more deliberately over the next few weeks.
3. Define what matters at work. Identify three to five values that matter most to you, then look at your current work through that lens. Notice where your job supports those values and where it creates friction. The goal isn’t to make an immediate career change, but to understand more clearly what you need from future opportunities.
4. Give learning a permanent place in your schedule. Choose one skill or area of knowledge that could expand your future options and decide how you’ll develop it consistently. It might involve a course, a project, regular practice, reading, or learning from someone with experience you want to gain. Treat it as part of your career rather than something you’ll get to when everything else is finished.

Key Takeaways

A squiggly career becomes easier to navigate when you stop expecting the future to follow one perfect plan. Explore several possibilities, build on the strengths that make you valuable, use your values to decide which opportunities deserve your attention, and keep learning so your options continue to expand. Career uncertainty doesn’t have to leave you directionless; you can create direction by knowing what you’re good at, what matters to you, what you might pursue next, and what you need to keep learning along the way.