Unexpected Meeting

A few months ago, I ran into a former colleague at a mall. Over coffee, we caught up on life and work. At some point, he leaned back and sighed.

“Vinay,” he said, “I don’t know what I’m doing wrong. I work hard, but every time I feel close to a breakthrough, something blocks me. Last quarter, I was promised a bigger role, but it went to someone else because of ‘visibility.’ Before that, I poured my energy into a project, and just when it was about to take off, leadership changed and the whole thing was scrapped. And honestly, sometimes the office politics makes me wonder if effort even matters. I feel like I take ten steps up and then slip all the way down.”

Introducing the Snake & Ladder Analogy

I listened quietly. He sounded drained from navigating setbacks. I asked, “Do you remember playing Snake and Ladder as a kid?”

He laughed bitterly. “Yes, but right now it feels like my career is full of snakes and no ladders.”

“That is exactly what I want you to think about,” I said. “Every dice roll is like the effort you put in, showing up, building skills, delivering results. Sometimes, the dice places you on a ladder: a mentor, a project that showcases your strengths, or a chance to learn something new. Suddenly, you move upward.

Then there are snakes: missed promotions, scrapped projects, toxic politics. They pull you down. Yet notice one thing. No snake in the game takes you back to the first square. Even when you slide, you do not lose your learning, credibility, or growth. The game is not about avoiding snakes. It is about continuing to roll the dice, because ladders will appear again. The only way to climb them is to stay in the game.”

He paused. “I have been staring at the snakes so much that I stopped noticing the ladders. I guess I need to keep rolling.”

Visual Exercise: Map Your Career

I suggested he draw a Snakes and Ladders board for his career:

  • Ladders: growth moments, successful projects, mentors, skills gained, recognition.
  • Snakes: setbacks, missed promotions, organizational changes, conflicts.

He wrote the snakes first: a project canceled after months of effort, a promotion lost because of internal politics, a client engagement that went sideways. Then he listed the ladders: leading a critical initiative, receiving positive feedback from a senior leader, learning a new skill that opened opportunities.

Patterns became clear. Many ladders were deliberate actions, volunteering for challenging projects, networking, and investing in learning. Snakes were mostly external, but some could have been managed better through preparation or seeking support. He realized that while setbacks were painful, they had not erased his skills, credibility, or experience.

Planning Next Moves
  • Create ladders: take on projects aligned with long-term goals, nurture mentoring relationships, and increase visibility strategically.
  • Manage snakes better: clarify expectations before taking on projects, step back when politics distracts, and learn from setbacks without dwelling.

By the end of our coffee, he was talking with renewed clarity. Setbacks were part of the journey, not the end. He was ready to focus on ladders, navigate snakes with awareness, and stay in the game.

ACTIVITY: “Your Own Snake & Ladder Board”

I often use this as a tool for flow coaches or anyone who wants to self-coach and reflect:

  1. Draw a simple Snake and Ladder board on paper with 30 squares.
  2. Mark 3 ladders: write down three opportunities that helped you climb in your career, such as a mentor, a key project, or a skill you picked up.
  3. Mark 3 snakes: write down three setbacks you have faced, like rejection, conflict, or a missed promotion.
  4. Reflect: Did the snakes take you back to zero, or did you come back stronger with more clarity?
  5. Action step: Write down what your next “dice roll” will be something small but consistent that you will do to keep moving forward.

This simple activity helps people realize that even though snakes exist, ladders have always outweighed them. Progress comes from continuing to roll the dice.

Why This Matters

This session reinforced the power of simple metaphors in reframing complex career challenges. It also counted toward my ICF-ACC credential, contributing to my mandatory 100 hours of coaching practice. Beyond the credential, it reminded me that coaching does not always need a formal setting. Sometimes the most impactful sessions happen in spontaneous, authentic conversations.

Key Reflections

  • Career growth is rarely linear. Recognizing ladders and snakes helps you navigate setbacks without losing perspective.
  • Reflection turns frustration into learning. Visual mapping provides clarity about what worked and what could improve.
  • Agency matters. You cannot control every factor, but you can control preparation, choices, and responses.
  • Coaching can happen anywhere. Authentic conversations guided by curiosity and listening can produce deep insight.

By the end, my colleague left with a visual map of his career, renewed perspective, and actionable steps. For me, the session reinforced why I coach. Helping someone transform frustration into clarity and motivation is profoundly rewarding. Setbacks, no matter how discouraging, are part of a broader trajectory of growth.

KEY TAKEAWAY

The game is not over until you stop rolling the dice. Sometimes, the simplest frameworks, like Snakes and Ladders, can reveal the clearest path forward.

REFLECTION PROMPT FOR YOU

Take a moment today to draw your own snakes and ladders:

  • What are your ladders?
  • Where are your snakes?
  • How can you roll the dice differently to climb higher?

If you want to get coached with me

I am currently preparing for my ICF-ACC credential and completing the mandatory 100 hours. If you want a free coaching session to reflect on your own career snakes and ladders, feel free to connect with me.