Aneesh’s Journey – Part 3: TAILOR: Shaping a Path That Fits You

Progress accelerates when you shape a path that fits you.

Editor’s Note (November 2025):

This post was originally published in June 2025 and has been updated for new readers with refined ACTIV framework language and additional context connecting Aneesh’s full coaching journey.

The restructuring at Company 1 brought confusion, instability, and tough choices. In the end, Aneesh made the difficult decision to walk away and start fresh in unfamiliar territory. Not with a fully formed plan, but with a deeper understanding of who he was and what mattered most.

In the ACCESS phase, Aneesh learned to look inward. He reconnected with his values, motivations, and deeper goals to uncover what truly mattered. During CHOOSE, he began turning those insights into action, making intentional decisions that reflected who he was and where he wanted to go.

Now, in TAILOR, the focus shifts to designing a path. A path that fits real life; its realities, needs, and priorities.

Aneesh knew he needed financial stability and full-time study wasn’t an option. Coaching had helped him clarify his values and strengths. Living those insights day to day? That was the next challenge.

That’s where the TAILOR phase began.

💬 Designing Within Constraints

In TAILOR, the emphasis is on shaping a path that aligns with both your goals and your current circumstances. It’s not about waiting for perfect conditions, it’s about making progress with what’s available now.

To keep moving forward Aneesh joined a small tech company. The company offered real-world experience and the chance to wear multiple hats. It wasn’t perfect, but it gave him space to grow while he explored a future in project management. In the evenings, he pursued a project management certification, balancing study with full-time work.

This wasn’t a linear sequence; it was a layered path. And that’s exactly what TAILOR is about: finding ways to move forward, even when the road is uneven.

TAILOR: Shaping a Path that Fits You.

🔍 What Is ACTIV?

The ACTIV Framework supports individuals, leaders, and organizations through change with clarity and purpose.

It includes five phases:

• ACCESS – Reconnect with your values, motivations, and deeper goals to uncover what truly matters.

• CHOOSE – Make intentional decisions that reflect who you are and where you want to go in your workplace transition.

• TAILOR – Shape a path that fits your unique strengths and circumstances.

• IMPLEMENT – Take action with clarity and confidence, putting your chosen path into motion.

• VALIDATE – Reflect on progress, celebrate wins, and refine the plan to stay aligned with your goals.

Every ACTIV phase builds on the last. But it all begins with ACCESS, where reflection turns into direction. Through workplace transition coaching and the ACTIV coaching framework, you gain both structure and flexibility to navigate change with clarity and purpose.

✨ Tension Signals Truth

It didn’t take long for deeper challenges to surface.

The new company’s culture was worlds away from what Aneesh valued. Office politics were pervasive. Leadership lacked transparency. Decision-making often contradicted the integrity he now knew was non-negotiable.

Coaching helped Aneesh name what he was experiencing and respond to it in a way that was intentional, not reactive.

Together, we explored:

✔️ Anxiety – What signals was it sending? And how could he respond to it with clarity instead of anger?

✔️ Workplace Politics – What could he influence? Where did he need boundaries?

✔️ When to Speak Up – He decided that not every problem required a fight. Sometimes the goal wasn’t to win—it was to stay focused on the bigger picture.

✔️ Locus of Control – By sorting what he could shape from what he couldn’t, he protected his energy and stayed aligned with his goals.

🧠 Anxiety, Integrity, and the Weight of Uncertainty

In one of our early coaching conversations, I asked Aneesh how he defined integrity. Not in abstract terms, but in the context of his own performance as an employee.

He paused for a moment, then said:

“It’s not just doing what’s expected. It’s anticipating what’s needed. It’s seeing the bigger picture and acting before anyone has asked you to.”

That definition reflected how Aneesh had always approached his work: with discipline and a genuine desire to contribute meaningfully. For him, integrity in job performance meant being proactive, dependable, and deeply aligned with the needs of the team.

But in his new role, that same commitment became a source of stress and anxiety.

The company’s leadership operated behind closed doors. Priorities shifted constantly, and transparency was lacking. Aneesh found himself in a moving-target environment, one where it was hard to know what was expected, let alone anticipate what might be needed.

That mismatch between his internal standards and the external chaos sparked a growing sense of anxiety.

In coaching, we worked to name what was happening.

We identified his anxiety triggers. The moments where his desire to do well clashed with a culture that offered no clarity. We talked about locus of control, and how much energy was being drained by trying to manage the unmanageable. We developed simple, practical techniques to help him pause, reset, and stay grounded in what he could shape.

He didn’t stop caring. He learned to care differently; more strategically and with greater compassion for himself.

🗣️ When to Speak Up—and How to Be Heard

In the early days at his new job, Aneesh found himself constantly in conflict.

“If something was wrong, I said something. Every time. I couldn’t not.”

That’s how he described it in one of our sessions; exhausted, frustrated, and unsure whether his efforts were helping or just wearing him down.

Aneesh’s strong sense of right and wrong made him a principled employee, but it was coming at a cost. He was burning energy on every battle, even when the outcome didn’t serve his long-term goals. And the more he spoke up, the more resistance he encountered.

In coaching, he had an important realization:

“I can’t fix everything. I have to start asking what’s worth it?”

That shift marked a turning point.

We began focusing on strategic discernment:

✅ What’s the actual outcome I want here?

✅ Is this issue aligned with my goals or just a distraction?

✅ Am I speaking up to improve things or just to relieve my own frustration?

From there, we worked on how to raise concerns more effectively.

We explored how to tailor communication based on the listener’s learning or communication style. Aneesh practiced adjusting his tone, framing, and timing. This was not to manipulate but to increase the odds that his input would be received with openness instead of defensiveness.

He didn’t stop speaking up. He became more intentional about how he raised concerns.

That’s the work of TAILOR: shaping not just your career path but the way you move through complicated spaces.

🧭 The Practice of Discernment:

TAILOR: Shaping a Path that Fits You

In this phase, coaching helped Aneesh refine more than just his résumé or daily schedule.

TAILOR helped him practice discernment. Knowing when to step forward, when to hold back, and how to stay grounded in the values he uncovered.

Aneesh wasn’t in the right long-term fit, but that didn’t mean the time was wasted. He was building clarity for the future.

📌 What’s Next

In our next post, we’ll enter the IMPLEMENT phase where Aneesh takes what he’s learned and begins moving forward with greater intention and confidence.

🔗 Need a Guide Through Your Own Transition?

If you’re trying to shape a path that fits your current reality without giving up your long-term goals, I offer a free 15-minute consultation. Let’s explore it together.