If you’re searching for a career coach in Chicago, you’re probably looking for someone with real insight into the specific crossroads you’re facing — a job search after college, a shift into a new industry, a promotion that isn’t coming, or a career that no longer fits who you’ve become.

You wouldn’t be alone. Thousands of people turn to a career coach each year for help navigating one of the most consequential parts of adult life — the work that fills most of our waking hours and shapes so much of our identity along the way.

Here’s an overview of the career coaching services I offer, how the process works, and my background.

A Familiar Starting Point

A client I’ll call Ryan came to me a few years into a career that looked good on paper. Solid title, decent pay, a resume that read like a success story. But he described feeling like a passenger in his own career — showing up, performing, and going home without any real sense of direction or forward motion. He wasn’t in crisis. He was just stuck, and tired of being stuck.

That’s a more common starting point than most people expect. Career coaching isn’t only for people between jobs or fresh out of school — a lot of it is for people who are technically doing fine and still know something needs to change.

Chicago Career Coaching

The career coaching I offer is designed to motivate and support you toward real, sustained change. Acting as a bridge between where you are and what’s possible, I bring guidance, honest feedback, and the kind of accountability that keeps momentum from stalling out. Together, we work on:

Results-Oriented Career Coaching

When you work with me, I want to understand what actually makes you tick — your interests, your values, the parts of your work that energize you and the parts that quietly drain you. That’s not a formality. It’s the foundation everything else gets built on.

I care about this work. I’ll be direct: I often get more invested in a client’s career growth than some clients expect me to be. That’s intentional. I don’t disengage from a goal just because progress gets slow — but the pace of the work still depends on you. This is a partnership, and I’ll match the effort you’re willing to put in.

With Ryan, that meant weeks of unpacking what “success” had actually meant to him versus what he’d inherited from other people’s expectations. Once that became clear, the practical steps — networking differently, reframing his resume around what he wanted next instead of what he’d already done — started to make sense instead of feeling like more items on a to-do list.

Areas I Can Help With

Career coaching covers a lot of ground. Here’s where clients most often see the biggest shifts:

Career transitions. Whether you’re changing industries entirely, moving from individual contributor to management, or leaving a role that no longer reflects who you are, transitions are where the mental roadblocks tend to show up loudest. We work through both the practical steps and the identity questions that come with real change.

Confidence and professional identity. A lot of career stagnation isn’t a skills problem — it’s a confidence problem. If you’ve started to doubt your own judgment or feel like an impostor in rooms you’ve earned a place in, that’s core to the work, not separate from it.

Interview skills. Beyond rehearsing answers, this means learning to tell your own story clearly and confidently — framing your experience in a way that actually lands with the person across the table.

Leadership and executive decision-making. For clients stepping into management or navigating higher-stakes decisions, we work on the judgment calls, communication style, and presence that leadership actually requires.

Salary negotiation. Many capable professionals undervalue themselves in these conversations. We prepare for negotiation as its own skill, not something you improvise under pressure.

Work-life balance and boundary setting. Career growth that costs you everything else isn’t really growth. We work on the boundaries that let you build a career without losing the rest of your life to it.

Values-Based Career Coaching

Part of how I approach this work might sound a little different from a typical career coach, so let me explain.

Over years of doing this work, I’ve come to believe that lasting career satisfaction rarely comes from chasing a title or a salary number alone. It comes from work that actually aligns with what you value — your natural strengths, what genuinely engages you, and the kind of contribution that feels meaningful to you specifically, not to your resume.

That’s the core of what I’d call values-based career coaching: helping you get honest about what you actually want your work to reflect, rather than defaulting to what looks impressive from the outside. This isn’t about religion or spirituality — it’s a mind-and-values approach to career decisions, echoing some of the identity work found in the writing of Carl Jung, the Swiss psychiatrist whose work on individuation still shapes how a lot of modern coaching and therapy think about identity and growth.

For Ryan, this meant recognizing that a lot of his “stuckness” wasn’t really about his job at all — it was about a values mismatch he’d never named out loud. Once that became clear, the career decisions that followed got a lot easier to make.

My Background in Career Coaching & Counseling

My background in career coaching draws from both the corporate world and my ongoing work as an educator. If you work with me, you’re drawing on 20+ years of experience across leadership, marketing, sales, and management.

I write regularly on career-related topics, both on this site and on national platforms including Psych Central and Psychology Today.

If we’re a good fit, you’re working with someone who wants to challenge your thinking, not just validate it. You can read more on my full background page.

Related Coaching Services

Career coaching often overlaps with other areas of growth. Depending on what you’re working through, you might also find these useful:

How Sessions Work

Career coaching sessions are available in person or through SimplePractice, a secure, HIPAA-compliant video platform. Many clients choose virtual sessions simply because it’s more convenient and avoids the friction of commuting during a busy workweek.

Sessions can be scheduled during the day or evening, depending on both of our availability. If I’m not able to take you on due to scheduling, I’m glad to refer you to another qualified professional.

For details on rates, visit the fees page — pricing is straightforward with no surprises.

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