Executive | BUSINESS Coaching for Entrepreneurs in West Hollywood: A Different Way to Think About It

At Oliver Drakeford Therapy in West Hollywood, much of my work involves sitting with founders, executives, and creative leaders who aren’t struggling with motivation — they’re struggling with pressure.

When people search for business or executive coaching in West Hollywood, they’re rarely looking for motivation or productivity hacks. Most entrepreneurs and executives I meet are already disciplined, driven, and capable. They’ve read the books, hired consultants, and built something real.

What they’re actually looking for is help thinking clearly under pressure and managing complicated team dynamics — without burning out, overreacting, carrying the weight of everything alone.

Business Therapy can be a very different kind of support than traditional business coaching.

What Entrepreneurs Are Really Looking for When They Search for Executive Coaching

Entrepreneurs don’t usually say, “I’m anxious.”

They say things like:

• “I can’t turn my brain off.”

• “Every decision feels heavier than it should.”

• “I’m successful, but I’m constantly tense.”

• “Work bleeds into everything — even when things are going well.”

Behind most coaching searches is not a lack of strategy, but internal overload. Decision fatigue. Responsibility pressure. A nervous system that never quite settles, even when the numbers look fine.

That’s where most coaching models miss the mark.

Why Anxiety Is Often the Hidden Bottleneck in Leadership and Executive Success

In high-performing adults, anxiety doesn’t look like panic. It looks like:

• Overthinking decisions

• Avoiding certain conversations

• Micromanaging

• Difficulty delegating

• Feeling personally responsible for outcomes that aren’t fully yours

This kind of anxiety is subtle, patterned, and often mistaken for “just part of leadership.” But anxiety has rules, and once you learn how it operates, it becomes far easier to interrupt.

Most executives don’t need to become calmer.They need to become less reactive.

Executive Performance Is a Systems Issue, Not a Motivation Issue

Entrepreneurs don’t operate in isolation. Every founder or executive is embedded in multiple systems at once:

• A business system

• A partnership or family system

• A leadership team

• An identity system built around responsibility and competence

When pressure rises, people don’t suddenly become irrational — they become predictable. They overfunction. They absorb tension. They step in too quickly. They struggle to separate thinking from feeling.

This is where Bowen Family Systems Theory becomes surprisingly practical for leadership. Concepts like differentiation, reactivity, and over-responsibility apply just as much in boardrooms as they do in families.

If you want a deeper example of how this plays out relationally, this piece on focusing on yourself in relationships translates directly to leadership and executive roles

The skill is the same: staying grounded while others are not.

Why High-Performing Entrepreneurs Still Feel Stuck

One of the most confusing experiences for entrepreneurs is feeling constrained despite external success.

This usually isn’t about capability. It’s about fusion — when identity, performance, and worth become too tightly linked. The business becomes the emotional regulator. Every decision carries personal meaning. Every setback feels destabilizing.

In systems terms, this creates chronic pressure — not because something is wrong, but because the system has no slack.

Coaching that ignores this tends to focus on output. Coaching that understands it focuses on positioning.

What to Look for Instead of Traditional Business Coaching

If you’re an entrepreneur or executive, useful coaching isn’t about answers — it’s about clarity.

Instead of asking:

• “Do you have a framework?”

• “How fast can I scale?”

More revealing questions are:

• “Can this person help me think when I’m under stress?”

• “Do I leave sessions clearer, or more activated?”

• “Do they help me separate urgency from importance?”

The most effective support helps you respond instead of react, especially when the stakes feel personal.

A West Hollywood Perspective on Entrepreneurial Support

West Hollywood attracts a particular kind of entrepreneur — creative, visible, values-driven, and often deeply invested in their work. Many are managing leadership, relationships, identity, and performance all at once.

In this context, business challenges are rarely just operational. They’re emotional and relational — even when they show up as strategic problems.

That doesn’t mean you need therapy instead of coaching. It means you need support that understands how pressure actually moves through people and systems.

If You’re an Entrepreneur Looking for Coaching in West Hollywood

I’m Oliver Drakeford, a licensed psychotherapist in West Hollywood, and much of my work involves helping high-functioning adults think more clearly under pressure — especially when anxiety, responsibility, or relational dynamics are quietly shaping decisions.

This work sits at the intersection of anxiety literacy, systems thinking, and executive functioning. It’s not about fixing you. It’s about helping you operate with more choice and less internal drag.

For some people, that looks like therapy.For others, it looks like executive support informed by psychology and systems theory.

Either way, the goal is the same: clearer thinking, steadier leadership, and a business that doesn’t require you to carry everything alone.