Your career ladder is actually an escalator

Either the system is working with you or against you.

Steve, the CEO of Tripadvisor, had gathered the company's top executives. As the newcomer—having joined just months earlier—I listened intently as he outlined “the most important initiative in Tripadvisor's history.”

For nearly a decade, travelers had to leave Tripadvisor to check hotel prices and complete bookings. This approach made sense when Tripadvisor operated as a subsidiary of Expedia (most of those travelers ended up at Expedia). Now, as an independent public company, we were embarking on a new strategy.

Steve explained how challenging it would be to transition a $700M-per-year business to a new model. It would require tight coordination across the entire company. He was putting a single person in charge of the initiative—someone everyone in the room would need to collaborate with closely and occasionally defer to.

Then, he pointed at me.

I was caught off guard. As the newest member of the team, I questioned whether I had the influence or credibility to guide executives who had been with the company for years.

That unexpected vote of confidence set the stage for my career at Tripadvisor. In the years that followed, I led a series of critical initiatives, each expanding my responsibilities and cementing my role within the organization's leadership.

My success at Tripadvisor was not mine alone—it was the product of diligent work, but also the support of a stellar manager, the good fortune to be surrounded by exceptional teammates, the opportunity to work on important projects, and a little dose of luck.

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Most people think about their career as a ladder—one they climb rung-by-rung, entirely on their own. A better metaphor is to think of your career as an "escalator." Factors outside your own efforts can help carry you toward your goals—or work against you.

Career development feels much easier when you're working with the system. An escalator helps carry you up, making each step a little easier. On the other hand, career development is much more difficult when outside factors add friction.

Imagine walking up an escalator going in the wrong direction. Each step forward is thwarted because the system is working against you. An extraordinary amount of effort is necessary to make progress. You can still reach the top despite adverse circumstances, but the journey will be unnecessarily challenging.

Is your escalator heading in the right direction?

When I ask this, people sometimes struggle to evaluate whether their situation is helping or hindering their career. Ironically, this is especially true when things are going well. It's human nature: we tend to give ourselves credit when things are going well and focus on external obstacles when things are tough.

Accurately assessing your situation is critical. I've coached people who were too eager to leave good companies because they were impatient to level up, only to find they'd traded a pretty good situation for a much tougher and riskier new role.

I've also coached PMs who spent years doing good work that went unrecognized or unrewarded—due to internal politics or external factors like a hyper-competitive market or lack of funding. In either case, making the right career decision requires evaluating your talents and how they match your situation.

Signs your escalator is going up

Business is thriving

As the saying goes, a rising tide floats all boats. It’s much easier to “level up” when your company is growing, and new opportunities are naturally emerging. You’ll benefit not just from that environment, but also the halo effect that successful companies create.

You got that promotion you wanted (or even one you didn't)

Does it feel like you’re playing on easy mode—especially compared to past roles? Frequent advancement is a clear sign you’re in an environment that accentuates and appreciates your skills.

You love the people around you (especially your boss)

Relationships are key to both your day-to-day happiness and your long-term career progress. A strong rapport with your manager will make your work more enjoyable and more rewarding. You'll be able to have candid conversations, give & receive effective feedback, and trust that you, your boss, and your team are working toward the same goals.

You get the recognition you deserve (and then some)

Do you feel recognized and appreciated when you do good work? Recognition can take the form of good performance reviews, praise from your boss and others, positive feedback, opportunities to work on challenging and sought-after projects, or even a simple "thank you." Well-deserved recognition is a clear sign that you're in an environment that values your talents and efforts.

You feel a sense of "flow" at work

The theory of flow, popularized by psychologist Mihály Csíkszentmihályi, describes a mental state of deep immersion characterized by energized focus, full involvement, and enjoyment. Flow occurs when we're completely absorbed in what we're doing, leading to a loss of sense of time and self-consciousness.

People experience a sense of “flow” when their skill perfectly matches the challenge

This state is typically achieved when your skill level perfectly matches the challenge of the task, creating a harmonious balance between the demands of the activity and your ability to perform it. Flow is often associated with peak performance and personal fulfillment and is considered a key component in both personal and professional development.

Do you often feel a sense of flow? If so, you're likely in a role tailor-made for your strengths and talents. Want to learn more about flow? Watch Mihaly's TED Talk, "Flow, the secret of happiness" or read his book "Flow, The Psychology of Optimal Experience."

Signs your escalator is going down 📉

No sense of flow

Do you often feel bored or overly stressed? Do days seem to last forever? That’s a signal you're either under-challenged or overwhelmed… tough conditions for doing your best work.

The promotion you want seems out of reach

Two things can happen here: 1) you feel you deserve a promotion, but still haven't received it or 2) you're unable to understand what is needed to rise to the next level. As a first step, it's helpful to work with your manager to make your career aspirations clear and set expectations for what it will take to get that promotion. If you've given it your best shot and still can't see that promotion on the horizon, it may be time to look elsewhere.

The relationship with your manager feels strained

It's extremely difficult to make career progress without a good manager relationship. Signs that the relationship is strained include:

1. a lack of feedback

2. little recognition for good work

3. no "benefit of the doubt”

4. criticism that feels unfair or unwarranted.

Open, honest communication is necessary to improve this relationship. Ideally, you should be able to express your concerns, seek candid feedback, and provide feedback to your manager about what is and isn't working for you. However, if these efforts fail and the relationship remains strained, seek out a role where you can have a strong, honest, and mutually beneficial relationship with your manager.

Feeling stuck? Try this first.

It’s natural to feel stuck at work—even great jobs have challenging moments. But, there’s an important difference between temporary frustrations and an environment that is working against you. Let’s look at some steps you can take to better understand your situation.

Measure headwinds and tailwinds

Start by taking stock of the headwinds (negative factors) and tailwinds (positive factors) that you're facing. Here’s a quick checklist to run through:

1. Is your company growing or struggling?

2. Do you have a good relationship with your manager?

3. Do you often feel a sense of flow at work?

4. Do you feel recognized for good work?

5. Do you feel supported when your work falls short?

6. Do you get clear and actionable feedback?

7. Are you working on impactful projects?

8. Does advancement come easily or does it feel impossibly hard?

This can help you appreciate the good things about your current role and recognize challenges that you may be able to overcome.

Gather feedback

Feedback is the single most important element in getting ahead. Without it, you’re flying blind. In the Product Competency Toolkit, I recommend as simple exercise you can do with your manager:

Before your next 1-on-1 with your manager, spend a few minutes rating yourself “On Track”, “Over Performing”, or “Needs Focus” on each of the competencies. Ask your manager to do the same. Next time you and your manager meet, go through each of the competencies noting where you and your manager see eye-to-eye and where you differ.

This structured approach creates clarity that casual conversations rarely provide. The gaps between your self-assessment and your manager's view offer the most valuable insights.

Take it further by creating a promotion plan that explicitly defines: 1) the specific behaviors your manager wants to see, and 2) the measurable goals that demonstrate readiness for advancement. Check in on this plan monthly. Remember, you can't hit a target you can't see.

Give it your best shot

After you and your manager have agreed on a plan, it's in your hands to put in the effort and show them what you can do. When you've delivered on your commitments, initiate a candid discussion with your manager: "Here's what we agreed I would accomplish, and I believe I've done that. Do you agree?"

Ideally, both you and your manager will recognize your progress, creating the perfect segue to discuss your next career step.

If your manager doesn't recognize your progress, ask for specific feedback. But also ask yourself a crucial question: are you fighting unnecessary headwinds? Sometimes the most strategic move is to find an environment with stronger tailwinds — one where your skills and contributions create more value, both for the company and for your career.

Is it time to move on?

If you've acted on all the feedback you've been given, honestly believe that you've achieved the goals that were set out for you, yet still haven't gotten the recognition you're seeking, take a step back.

Ask yourself: Am I in the right environment to foster my career growth?

There can be many reasons why your career has stalled. Perhaps your manager has different expectations—expectations they may not have clearly articulated to you. There may be factors outside your manager's control. The past few years have been challenging. Many companies have held back on promotions as part of layoffs, hiring freezes, and restructuring.

Your career development may be out of your hands. In fact, it may be outside your manager's hands as well. The system may be working against you, and you may not be able to change that. Coming to that conclusion can feel daunting, but it's not necessarily a bad thing.

That situation has happened to all of us—remember, even Steve Jobs and Sam Altman once got fired. The fact that you're recognizing the situation means that you can deal with it. You can focus your energy where it matters. You can change your circumstances and set your career up for success.

A new role, even a lateral move, can give you a fresh start, renewed energy, and a better opportunity to make an impact & move ahead.

Careers rarely follow a linear path—everyone has launching pads and setbacks. If your escalator is moving against you, hop off and find a better path.

"The obstacle in the path becomes the path. Never forget, within every obstacle is an opportunity to improve our condition." – Ryan Holiday, The Obstacle is the Way