Resources

The Progress Paradox

Unstuck Monthly | February 2025

Forward progress can be messy. Let's discuss how you stay the course and focus on what matters most.

Hi, Friend!

Something fascinating happens when we push too hard for progress—we often slide backward instead of moving forward. This counterintuitive pattern has been showing up in nearly every coaching conversation I'm having lately, and it's revealing something important about how real change happens.

In this issue of my leadership and executive coaching newsletter, I’m focusing on the messier parts of making progress.

Highlights this month:

  • Sticking Points & A Deeper Look: Why meaningful progress rarely follows a straight line

  • From the Network: Stories from leaders finding breakthrough results in unexpected ways

  • Worth Exploring: A fresh take on improving your communications from expert Michael Chad Hoeppner

  • Happenings: New coaching programs designed to help you create sustainable change

  • WD-40 for Your Mind: Why working harder isn't always working

Thank you for sticking with me!

Alex

Sticking Points

The Progress Paradox

Ever been cross-country skiing? There's this moment when you're working hard to climb uphill, but your skis keep sliding backward. Push too hard, and you lose traction completely. Ease up too much, and you lose momentum. The real progress comes from finding that subtle balance point—one that often feels counterintuitive to our instincts.

(And if you're reading this from somewhere warm like I am right now in Fiji, think about paddling a kayak against the current. Pushing harder sometimes just creates more turbulence than forward progress.)

This same pattern shows up in our professional lives. We push harder toward our goals, rely more heavily on our expertise, measure everything we can think to measure... and yet something feels off. We sense we could be creating more meaningful impact, but the harder we push, the more elusive that impact becomes.

What makes this especially challenging is how reasonable our approaches seem:

  • We lean harder on our proven expertise because it's worked before

  • We create more detailed metrics because we need to show progress

  • We tighten our control because we can't risk failure

But these seemingly logical responses often become the very things that limit our growth. The expertise that got us here becomes a ceiling rather than a foundation. The metrics we're watching blind us to unexpected opportunities. And our grip on control prevents the very breakthroughs we're seeking.

The path forward isn't about pushing harder. It's about recognizing these patterns and finding different ways to create momentum.

If you're feeling this tension between effort and impact, let's explore it together.

A Deeper Look

Curious about the messy reality of creating change? These articles dive deeper into what real progress looks like:

The Transition Trap

When your expertise becomes a ceiling instead of a foundation. A fresh look at why successful people often struggle most with change.

Read more on LinkedIn

Hidden Progress

The most significant growth often happens in moments we don't think to measure. Here's where to look for evidence that you're actually moving forward, even when traditional metrics suggest otherwise.

Read more on LinkedIn

Micro-Moves, Macro-Impact

Forget "go big or go home." Here's how small, deliberate actions can trigger chain reactions of positive change.

Read more on LinkedIn

From the Network

Recent conversations with clients reveal fascinating patterns in how leaders are navigating their professional growth. The path from intention to impact rarely follows our expected trajectory.

When Simplifying Creates Space for Impact. One leader started our work together laser-focused on an ambitious plan to buy a healthcare business. But through reflection and clarity about what truly mattered, they realized the professional opportunities they needed were already within reach. This insight allowed them to channel their energy toward personal development and long-term impact rather than chasing a new venture.

The Hidden Progress in Patience. Another found themselves questioning their value when a key stakeholder seemed dismissive of their contributions. Just a month later, that same stakeholder was positioning them to lead a major organizational program. This reinforces how staying focused on creating value, rather than seeking validation, often leads to unexpected opportunities.

Small Shifts Lead to Strategic Impact. The progression from tactical to strategic mindset emerged as another common theme. As one leader described it through a bakery analogy: "I used to think I needed to be the baker, making every cake perfect. Now I realize my role is to be the bakery owner – setting vision and empowering others to deliver." 

How Clarity Cuts Through the Chaos. One client went through an extensive interview process, getting all the way to an offer, before realizing the role wasn't aligned with their goals. Rather than take a "good enough" position, they recognized that staying focused on what truly matters would lead to better outcomes.

The common thread? Creating meaningful impact often means challenging our assumptions about what progress should look like and being open to unexpected paths forward.

What resonates with you in these stories? I'd love to hear your experience.

Worth Exploring

The Self-Determination Compass Assessment

The path from intention to impact is rarely straightforward. Sometimes what looks like progress isn't, and real breakthroughs can emerge from unexpected places. The Self-Determination Compass Assessment helps you navigate this journey by measuring nine key dimensions across autonomy, competence, and relatedness—from aligning to purpose and creating value, to developing skills and building community.

I developed this assessment to help my clients gain clarity about where they are and where they want to go. The results provide a structured framework for identifying what truly matters and creating meaningful change, even when the path forward feels uncertain.

Special offer: Any newsletter subscribers to complete the assessment will receive a complimentary one-hour coaching session to explore their results and map their path forward.

Take the assessment here.

Don't Say Um: How to Communicate Effectively to Live a Better Life

When navigating complex change, our ability to communicate with clarity becomes crucial. My former professor and colleague Michael Chad Hoeppner—I was his TA at Columbia Business School—has just released a new book that includes practical exercises and insights to show how precise communication can help cut through chaos and uncertainty to drive real impact. He's already been featured on Good Morning America. Check it out!

Find "Don't Say Um" on Amazon and other bookstores.

Happenings

Spring/Summer Coaching Program (aka Autumn/Winter Coaching for my southern hemisphere community)

The path from intention to impact isn't always straightforward. Sometimes the biggest breakthroughs come from unexpected places, and real progress often looks different than we imagine. That's why now—when you have the space to explore, experiment, and build new approaches—is the perfect time to begin.

I have a limited number of six-month coaching programs starting this Spring, designed to help you navigate complexity while creating meaningful change.

My comprehensive six-month program includes:

  • Twelve 60-minute coaching sessions

  • Self-Determination Compass Assessment and debrief (bonus 13th session)

  • Email and chat support between sessions

  • Custom resources and tools based on your needs

  • Structured check-ins to ensure you're creating sustainable impact

By September, while others are struggling with post-summer transitions and year-end pressure, you'll have:

  • Clear direction and momentum on your key initiatives

  • Tested strategies for navigating complexity

  • Strong foundations for driving meaningful change

  • Confidence in your path forward

Only three spots available for programs starting March/April.

Email me or schedule a free consultation call.

WD-40 for Your Mind

When work is tough or unsatisfying, we process our experiences through humor and look for inspiration wherever we can find it. 

Like WD-40 unsticks door hinges, may this and future quips help unstick our brains.

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When Working Harder Isn't Working

Just as pushing harder against the current creates more turbulence than progress, sometimes the most powerful shifts come from questioning inherited wisdom. Take "hard work always pays off"—a maxim many of us built our entire professional identities around.

But what if the goal isn't to work harder, but to work with more intention? What if real progress comes not from pushing through, but from pausing to ask: Is this effort creating meaningful impact, or just more work?

Next time we feel caught in the cycle of "more, faster, better," remember: We get to define what progress looks like. Our autonomy lies not in how hard we work, but in choosing where to direct our energy for maximum impact.

You've survived another month. What's next for you?

Great conversations start with shared insights. My coaching practice, like this newsletter, thrives on connections – if you know someone who's navigating their own sticking points, I'd love for you to share this with them.

Lead with the bold version of yourself.

Knowledge and skills are such a waste on those who have no integrity. Sign up for my monthly article about breaking bad patterns, building strategic thinking, and taking on real leadership challenges.

Free newsletter. Unsubscribe anytime.

© 2026 Executive Coaching with Alex Pearlman. All rights reserved.

Lead with the bold version of yourself.

Knowledge and skills are such a waste on those who have no integrity. Sign up for my monthly article about breaking bad patterns, building strategic thinking, and taking on real leadership challenges.

Free newsletter. Unsubscribe anytime.

© 2026 Executive Coaching with Alex Pearlman. All rights reserved.

Lead with the bold version of yourself.

Knowledge and skills are such a waste on those who have no integrity. Sign up for my monthly article about breaking bad patterns, building strategic thinking, and taking on real leadership challenges.

Free newsletter. Unsubscribe anytime.

© 2026 Executive Coaching with Alex Pearlman. All rights reserved.