Top-Rated Chicago Therapist for Entrepreneurs & Business Owners

Running a business means your brain never really gets to clock out. But while stress, the pressure to perform, and the drive to achieve often come with the territory, they don’t have to run the show.

At Still Oak Counseling, I help entrepreneurs and business owners like you find confidence and ease in your personal life to match the success you experience in your career. If you’re tired of constantly grinding or feeling like an imposter, you’re not alone, and I’m here to help.

Meet your entrepreneur therapist

therapy for entrepreneurs

Elizabeth Bodett Dresser

I get it—you didn't build a business to spend your days feeling anxious and overwhelmed. My approach combines Internal Family Systems therapy with trauma-informed care to help you get to the root of your struggles, because chances are, the foundation was laid long before you started your entrepreneurial journey. Our work together can help you quiet that inner critic, set boundaries that actually stick, and lead from a place of calm confidence rather than constant stress. I work with the whole person, not just the CEO version of you.

  • Good fit for: High-achieving professionals, perfectionists, those struggling with imposter syndrome

  • Credentials: Licensed Clinical Professional Counselor, IFS Level 1 trained, EMDR trained

  • Clientele: Adults

  • Location: 30 N Michigan Ave, Suite 901, Chicago, IL 

  • Virtual therapy: Available

How it works

1. Schedule your free consultation call

We'll discuss your goals and see if we're a good fit.

2. Begin your personalized therapy journey

We'll work together to understand your patterns and gently shift how you show up.

3. Maintain your growth with ongoing support

Continue building on your progress with regular sessions tailored to your evolving needs.

Common reasons why business owners seek therapy

  • Burnout that coffee can't fix anymore: You're running on empty and wondering if this is just "the cost of success"

  • Ongoing imposter syndrome despite your success: You’ve achieved so much, but you still feel like you're one mistake away from being exposed as a fraud.

  • Decision fatigue from being "the one in charge:” Every choice lands on your desk, and the weight of constant responsibility is exhausting.

  • Perfectionism that slows everything down: You're so afraid of making the "wrong" choice that you end up stuck in analysis paralysis.

  • Relationship struggles because work always comes first: Your personal relationships are suffering because you can't seem to turn off "business mode.”

  • Anxiety that shows up as physical symptoms: Your body tells you something’s off through headaches, insomnia, or that constant knot in your stomach.

  • Feeling like you've lost yourself in the business: You started this venture to create freedom, but now you feel more trapped than ever.

How therapy can help entrepreneurs

Quiet your inner critic

That voice telling you you're not doing enough? You know the one. Therapy can help you recognize it as just one part of you, not the entirety of who you are. You'll learn to show up from a place of self-compassion instead of self-criticism, making decisions out of clarity rather than fear.

Set boundaries that actually work

Many entrepreneurs struggle with saying no because they fear missing opportunities. We'll help you identify what truly deserves your energy, and, more importantly, explore why exactly it feels so tough to set boundaries—potentially in other areas of your life as well.

Build authentic confidence

Instead of relying on external validation or constantly proving yourself, you'll develop a quiet confidence that comes from truly knowing and trusting yourself. This can look like more effective leadership, clearer communication, and generally feeling more grounded in your day-to-day life.

Process stress and trauma

The pressure of running a business can activate old survival patterns that no longer serve you. We'll help you understand how past experiences might be showing up in your current leadership style and work toward healing that actually sticks.

FAQs about therapy for business owners

  • My clients tend to be highly driven, successful, motivated individuals who feel burnt out, throw themselves into work to cope, and feel disconnected from themselves and others. 

    Here's what sets my approach apart:

    • I understand the entrepreneur mindset. I’m a business owner myself. I know you're not broken—you’re just operating from old frameworks and patterns that worked once but don't fit who you want to be now.

    • I focus on deep healing with evidence-based methods. Surface-level “fixes” don’t lead to long-term success. We’re a good fit if you’re tired of just getting by and want to dig into the deeper work.

    • I get that your time is valuable. Sessions are focused and productive, not just venting sessions that go nowhere. And while I’m eager to help you do the serious work of healing, I also bring levity to our time together when appropriate.

    Still not sure if we’re the right fit? Book a complimentary consultation here.

  • I primarily use Internal Family Systems (IFS) therapy, which helps you recognize and work with different parts of yourself, like the perfectionist, the people-pleaser, or the inner critic. Instead of fighting these parts, we help them find new roles so you can lead from your authentic Self. 

    I also weave in person-centered and trauma-informed approaches, such as EMDR. All sessions are tailored to your unique needs and goals.

  • Expect to slow down (which I know can be daunting for entrepreneurs like you) and get curious about your patterns instead of just powering through them. 

    We'll start by understanding what brought you here and get to know all of your parts—even and especially the ones you so often push away. Gaining this intimate knowledge of how your emotions show up will help us address the deeper roots of the challenges that have brought you to therapy, allowing you to develop a lasting ability to handle whatever your business—and life—throws at you with confidence and clarity.

  • Book a free consultation call to get started. During the call, we’ll briefly discuss what you’re hoping to gain from therapy and get a better feel for whether we’re the right fit for each other. If we choose to proceed, we’ll schedule your first full session and let the real work begin.

Start therapy for business owners & entrepreneurs in Chicago today