职业转型六问：用 JTBD 框架找到下一步

👋 Hey there, I’m Lenny. Each week, I share deeply researched product, growth, and career advice. For more: Lenny’s Jobs | Lenny’s Podcast | Lennybot | How I AI | Become an AI-Native Builder and my other favorite AI/PM courses

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Building on last week’s very exciting launch of Lenny’s Jobs (that’s a lot of likes!), I’m thrilled to bring you a companion post that will help you clarify what job to look for in the first place.

Cliff Maxwell teamed up with the legend Bobby Moesta (co-creator of the Jobs to Be Done framework and a two-time guest on Lenny’s Podcast) to build Vocation, a career navigation platform that helps professionals figure out their next step. Cliff’s own career has spanned building CPUs, education research, product management, venture capital, and serving as Chief of Staff to the late Clayton Christensen. Based on insights from over 1,000 interviews with professionals changing jobs and hundreds of one-on-one coaching clients, this hands-on guide will help you take a step back and connect with what you truly want from your work—and life.

Let’s get into it.

It’s a disorienting time to work in tech right now. For some, the rise of AI is a thrilling adventure, but for others, it’s a source of existential dread. No matter how you’re feeling, change is coming. The World Economic Forum reports that by 2030, 39% of today’s skills will change or become obsolete, and more than 90 million jobs will be displaced even as 170 million new jobs will be created.

Every generation of workers in tech has lived through recessions, layoffs, and technological change, but AI’s impact on work will be fundamentally different. It won’t just require new skills. It is redrawing the boundaries between roles and changing the day-to-day responsibilities inside them. Work may feel unstable now, but this will likely be the most stable it feels for a long time.

With this much uncertainty on the horizon, it is imperative that you develop the ability to navigate change. As your responsibilities shift and new opportunities emerge, the durable career advantage will come from knowing what kinds of problems, people, and environments bring out your best work—and having a repeatable process for identifying your next step even when the ultimate destination is unclear.

For the past year I have been building career navigation infrastructure with Bobby Moesta, one of the creators of the Jobs to Be Done framework and a two-time guest on Lenny’s Podcast. Bobby brings a product-oriented lens to career change: you are the customer, and the right next career move is the product you are looking to purchase.

Through more than 1,000 in-depth interviews with professionals changing jobs (some by choice, some by necessity)—and hundreds more people we have coached since—we identified what helps people make a successful job transition, and built a process to support them.

This is not a laundry list of LinkedIn hacks, resume tips, or ideas for how to automate your recruiting efforts. This is a step-by-step formula for designing a system that allows you to understand yourself, your context, and your best next steps when you’re in a state of change.

In this post, I’ll help you answer six fundamental questions that will instill confidence and focus anytime you are navigating a transition at work. Each question comes with exercises and tools to help you build understanding.

• What kind of career progress do I want?
• What career quest am I on?
• Which work brings out my best?
• What possible moves should I explore?
• Which tradeoffs am I willing to make?
• Can I get what I need without leaving?

Once you know your answers, you’ll be equipped to find your bearings now and every time the labor market throws you a curveball.

1. What kind of career progress do I want?

About a year ago, we coached an individual who, after spending several years at a startup that was running out of funding, assumed his next step was another early role in a venture-backed company.

After evaluating his core motivations and reflecting on his growing desire for impact, he found an opportunity to lead the entrepreneurship center at a local university, a job that he previously would have avoided and that none of his peers would have recommended. When he met with the administration, they effectively hired him on the spot, telling him, “You are exactly who we were looking for.” He’s now crushing it in his new role.

This story demonstrates the difference between career “progress” and “progression,” a distinction that is critical to understand when you are at a transition point in your career.

Progression is the philosophy that underpins most people’s mental model of careers. You start as an IC, get promoted, and up and up you go on the imaginary career ladder. This mindset will become increasingly less relevant as AI continues its march through knowledge work. Job boundaries and job titles will continue to blur, new job titles will emerge, and companies will struggle to neatly map job descriptions and career pathways into their org chart or KPIs.

Progress, on the other hand, is contextual and dynamic. It is ultimately a question of what your professional Job to Be Done is, and allows you to chart your own course rather than follow a single, narrow path of progression. Depending on your context, progress may be about autonomy and flexibility, preparing for the future, respect and recognition, or simply collecting a paycheck during a time of instability. It can look like a more traditional step up, but it may also look like a lateral move or even like a step back from the perspective of others—while it solves the most important problem in your life and gives you space and time to move forward later on.

A focus on progress is an active commitment to putting yourself in environments that will bring out your best. It helps you stand out amid the army of applicants all reaching for the same rung on the career ladder. Progress gives you the freedom to see your career in chapters and create space to be emergent rather than assuming you have to write one linear story all at once. To do this, you have to define the progress you’re seeking right now.

A 10-minute progress exercise

Take a blank page (or, if you’d like a live template, we made one for you here) and complete the sentence: I want to leave or change my current situation because…

Write down every friction or negative force you’re experiencing right now, or that you last experienced at work. We call these pushes. Do not polish the language. “My manager changes priorities every three days, and it’s getting exhausting” is more useful than “I want better leadership.” Unpack each one of these, and ask yourself “why” until you get to the root cause.

Then complete this sentence: I want my next chapter to give me…

List the desired outcomes you wish were true right now. We call these pulls. Again, make them concrete. “Control over when I do focused work” is more useful than “flexibility.”

Now circle the two or three pushes and two or three pulls that carry the most emotional weight. When you see the forces together, you can start to assemble what progress means for you, not for anyone else. For example, two people may both feel overburdened by new management, but one wants to join a more supportive team while the other is seeking more autonomy to work alone. Your unique combination of pushes and pulls forms the basis for your career quest, or the core motivation guiding your desire for change.

Below is an example of how this might look for someone seeking a new role:

2. What career quest am I on?