You Coach You: How to Overcome Challenges and Take Control of Your Career: Summary & Key Insights

The idea of the 'Squiggly Career' began from our own lived experiences. Neither of us has had a straightforward, orderly career — we’ve zig-zagged between roles, industries, and ambitions. And what we realized was that this pattern wasn’t a sign of failure or indecision; it was the new normal. The world of work has shifted away from the ladder model — the linear climb up a single hierarchy — to something more unpredictable and fluid. In this world, people change jobs more often, explore different skills, and rarely fit into one-label definitions.

This shift requires a new mindset. Instead of asking 'What’s my next promotion?', we ask 'What am I learning? Where can I grow? Who can I connect with?'. The squiggly model encourages exploration over expectation, and adaptability over certainty. It also means success looks different: progress isn’t measured by titles, but by purpose, autonomy, and learning.

However, such freedom can create fear. In the absence of a clear roadmap, self-doubt can creep in. Many of us feel stuck because we assume others have it all figured out. That’s why self-coaching is so essential. A squiggly career rewards those who know how to reflect, reset, and reorient — those who are comfortable asking, 'What do I need next?', instead of 'What should I do next?'.

We encourage you to embrace the squiggle rather than fight it. The unpredictability of modern work isn’t a problem to solve — it’s an opportunity to shape a career full of variety, creativity, and fulfillment.

The foundation of *You Coach You* is the self-coaching mindset — a way of thinking that turns challenge into learning and uncertainty into clarity. In our experience, successful self-coaches have three essential traits: curiosity, reflection, and action.

Curiosity is where self-coaching begins. When faced with frustration or doubt, many people default to judgment — 'I’m not good enough' or 'I don’t know what to do'. A self-coaching mindset replaces judgment with questions: 'What might I learn from this?', 'Who could help me?', or 'What else could be true?'. By asking instead of assuming, you open new possibilities.

Reflection then helps transform those questions into insight. In our programs, we often ask people to pause and notice their patterns — when do they feel energized, bored, confident, or frustrated? The goal isn’t perfection but awareness. Once you see your patterns, you can start to choose rather than simply react.

Finally, self-coaching only becomes powerful when reflection leads to action. This doesn’t mean huge leaps every time — often it’s a small experiment or conversation that starts momentum. We call this the 'try-learn-repeat' loop: try something new, learn from what happens, then try again based on those insights.

By practicing curiosity, reflection, and action every day, you turn coaching into a lifelong skill. The more you do it, the more resilient and resourceful you become.