👋 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
P.S. Get a full free year of Cursor, Notion, Replit, Lovable, Wispr Flow, Linear, ElevenLabs, Factory, PostHog, Granola, Brain.fm, Waking Up, and more, by becoming an Insider subscriber (while supplies last). Learn more.
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.
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.
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:
When you are seriously considering a job change, or when change is forced upon you, it’s easy to label and hold onto your most immediate feeling, whether that’s burnout, the excitement of something new, frustration, or disrespect. But underlying these emotions, less-obvious and subconscious factors are working together in a unique combination to animate your core motivation for change. This is your career quest.
Your quest for progress should inform every aspect of your job search, but most people skip this diagnosis and go directly to job boards, answer the recruiter’s call, or ask their network about job openings. They are halfway out the door before deciding what they even need this move to accomplish.
For example, I once coached an individual who was frustrated by the lack of leadership opportunities in his product role at a large tech company. When he was recruited to lead and grow the analytics function at a nearby startup, he felt excited and flattered to finally have the opportunity to grow a team.
But as we explored other pushes and pulls acting on him, a more nuanced story emerged. Despite the lack of leadership opportunities, he fundamentally liked his job. He was also in the middle of renovating his home, he wanted to be able to spend more time with his two young kids, and he wasn’t all that excited about leaving product for analytics.
The new role solved his most immediate and apparent problem, but it wouldn’t offer him the progress he needed both personally and professionally.
In our work with professionals looking to make a change, we have identified four common quests for progress that emerge again and again.
These quests are not mutually exclusive; you can be on multiple quests simultaneously, though one usually dominates. Even if you have been laid off and the immediate goal is “I need a job,” reflecting on these quests can help you decide which opportunities deserve your attention, and which you can avoid.
You have hit a wall you cannot fix from where you stand. Something about the manager, culture, leadership, or environment has made it hard to succeed or remain healthy. The dominant feeling is escape, and the desire to get out is usually quick, not something you stew on for months at a time.
Common pushes:
Feeling disrespected or not trusted to do great work
Working for a manager who is wearing you down
Losing trust or respect in leadership and/or your peers
Not seeing a place to grow in your current organization
Common pulls:
The pulls are often vague: a fresh start, a healthier environment, or simply “anywhere but here.”
When someone is looking to get out, they often accept the first available escape but run the risk of landing in the same conditions at a different company.
Work has swallowed too much of your life, even if you still enjoy the work itself.
This quest often follows a change outside work: a new child, caregiving responsibilities, a health issue, or a shift in what you want your life to look like. It can also emerge when a previously manageable role becomes chaotic, or when the way your manager or company leadership is running things no longer works for you.
Common pushes:
Feeling worn down by management
Work is dominating your life and you’re starting to make sacrifices
Unpredictable demands, or feeling challenged beyond your ability
Little control over your schedule or priorities
A workload that no longer feels sustainable
Common pulls:
More time to spend with others
A job location that fits better into your personal life
An employer who properly values your experience and credentials
A scope of responsibility you can sustain
Your job has drifted away from what you do best, what you value, or what you originally agreed to do. You may still be performing well. In some cases, that is part of the problem: you have become useful for work that does not fit you, and you don’t feel respected.
Common pushes:
Being underused or miscast
Watching your responsibilities move away from your strengths
A growing gap between your values and the company’s
Feeling unchallenged or bored
Not seeing a clear place to grow inside the organization
Common pulls:
Work that uses your full capabilities
Greater alignment with your values
Recognition that matches your contribution
A role built around the things you do unusually well
You have completed something meaningful, mastered the role, or reached a point where the work no longer stretches you. Alternatively, you’ve hit a personal milestone (baby, move, etc.) and want a change. You are not necessarily unhappy. You are simply ready to be challenged and get the support you need to grow.
Common pushes:
Hitting a personal or professional milestone
Feeling unchallenged or bored
Not seeing a clear place to grow
Needing to provide more support for family or loved ones
Common pulls:
Feeling like a job is a clear step forward
Joining a tight-knit team you can count on
Developing new skills as part of a stepping stone to something else
Finish this sentence: More than anything, I need my next move to…
Get me away from a situation I can no longer tolerate.
Give me control over my time, workload, or life again.
Let me do work that fits my strengths and values.
Give me a new challenge or chapter.
How you finish the sentence will not capture every part of your situation, but it will usually reveal which quest you may be on—and also help you label what you don’t need right now.
Most professionals know their skills better than they know the conditions that allow them to do their best work. You take on responsibilities, become known for certain outcomes, develop valuable skills, but are often too busy doing the job to understand the circumstances you need to be successful and feel fulfilled.
Then a shiny title or compensation increase appears, and you accept a role that actually makes you miserable—an outcome common to ICs-turned-managers who realize too late how much they hate management.
You need to figure out what you need before you switch jobs (or are compelled to switch), not figure it out by switching. This is what building your energy profile is all about: it provides a blueprint for evaluating new opportunities, along with a starting point for questions you can ask a hiring manager or peer as you explore open roles.
To get started, grab some Post-it notes or spin up a Miro board, and make a simple timeline of roles you’ve held and the title, company, and duration for each role (including your current role if employed). If you want a pre-built template, we’ve got one here. The steps below will show you how to fill this out, and I’ve included an example of the beginnings of my own energy profile:
Pull up the past month of your work calendar and list what you actually did, hour by hour.
Do not use the language of your job description. Describe the activity:
Collaborative planning meeting
Individual research
Customer call
Writing a strategy document
To help you through this, you can integrate your calendar with an AI agent of your choice (via a simple connection or MCP) and use this simple prompt:
“For the past month, make a list of core meetings and time blocks on my calendar and ask me 1-2 questions about each to uncover what I actually did during those blocks of time. For example, if you see a ‘team meeting,’ ask me br…
