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Package Description:
Eight 60-minute coaching sessions for professionals navigating a broader period of career uncertainty, transition, or stagnation. This package is for the person whose challenge isn't a single decision but a deeper question about direction, purpose, or fit. We'll start with an intake questionnaire and an opening session focused on understanding where you are and what brought you here. From there, sessions are shaped by what's most pressing or in need of further examination. But unlike a one-off conversation, the value compounds over time as we build on what's come before. Between sessions, you'll have access to me for check-ins and continued reflection. Around the midpoint, I'll send a brief recap of the key themes that have emerged so we can make sure the engagement is going where you need it to.
What you'll get from this package
Awareness of the recurring patterns, narratives, and beliefs shaping your professional decisions
Clarity on what you actually want from your career, not just what looks right on paper
Practical momentum: concrete steps you've pressure tested, not just talked about
Accountability to the commitments you've made to yourself
A mid-engagement recap capturing the themes and shifts that have emerged
Additional details
Coaching delivered via live sessions.
My coaching style is grounded and incisive. I listen for what's beneath what you're saying, I track patterns across sessions, and I ask questions designed to open perspective rather than lead you to a predetermined answer. I balance depth with pragmatism: we'll sit with the hard questions when that's what's needed, and we'll also make sure that reflection translates into action. I see coaching as a partnership, and I'll bring the same level of honesty and investment that I ask of you.
Sessions can be rescheduled with at least 24 hours' notice. For any communication in between sessions, I will respond within 48 hours. All sessions in a package should be completed within a timeframe that matches the intended pace of the engagement (for 8 sessions, roughly 2-3 months). If a scheduling conflict or life event comes up, we can discuss adjustments. No-shows without prior notice will be handed on a case-by-case basis.
Services included:
Skill Building
Career Planning
Personal Branding
Leadership
General Exploration
Talk to a team member
Schedule a call with a Leland team member who can help you explore your options.
Schedule a call
More packages from Jake
Custom hourly · $170/hr
Get help with Leadership, General Exploration, and .
Offered by Jake L.
Joined January 2026
5.0
Certified Career Coach for High-Performers at a Crossroads
I coach professionals who are facing meaningful career decisions: transitions, leadership challenges, or moments where the next step isn't obvious but standing still no longer works. Many of my clients are high-performers who look successful on paper yet feel stuck. They need a thinking partner who will challenge their assumptions, help them see patterns, and turn reflection into action. Before becoming a coach, I spent a decade leading digital marketing teams. I've navigated org politics, managed up, made hard calls about roles and direction, and burned out in the process. When clients describe what they're up against professionally, I'm not theorizing. I've been there. My coaching is both grounded and incisive. I listen closely, notice recurring themes, and ask questions that go beneath surface explanations. I believe in examining not only the decision in front of you, but also the beliefs and narratives that shape how you evaluate your options. That's where real clarity emerges. That said, reflection only matters if it leads somewhere. I'll also help you pressure-test your choices, map out concrete next steps, and stay accountable to the commitments you make. The balance between reflection and forward motion is where the best work takes shape. I hold my Associate Certified Coach (ACC) credential from the International Coaching Federation, and earned my Certified Professional Coach (CPC) designation through iPEC, an ICF Level 2 accredited program. I've also spent 500+ hours in the client's seat myself, across both coaching and therapy, which fundamentally shapes how I show up in this work. If you're ready to engage directly with your thinking and take ownership of what comes next, let's connect.
$1,360
8h of coaching