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Package Description:
Twelve 60-minute coaching sessions for professionals who know the work goes deeper than a single decision or transition. Maybe you started thinking about your next role and realized the real question is about your relationship to the work itself: the patterns you keep repeating, the narratives you've outgrown, or the gap between where you are and where you feel you should be. This package gives us the time and space to do that work properly. We'll begin with an intake questionnaire and a grounding first session. Over the next eleven sessions, we have room to go beyond surface-level problem solving. We can revisit earlier conversations with new perspective, let insights develop rather than rushing to act on them, and make sure the changes you've been making actually stick. You'll have access to me between sessions, and I will share written recaps at key points throughout the engagement to reflect back what's emerging. Around session five or six, we'll step back together to check in on whether the engagement is evolving in the right direction. Our vinal session is explicitly reflective: synthesizing what's shifted and what you're carrying forward.
What you'll get from this package
Deep clarity on the beliefs, patterns, and internal narratives that have been driving your career decisions
A fundamentally different relationship to how you evaluate professional choices
The ability to distinguish between what you want and what you think you're supposed to want
Sustained momentum and accountability across a meaningful stretch of time
Written recaps capturing the themes, shifts, and breakthroughs from our work together
A reflective closing session synthesizing what's changed and what you're carrying forward
Additional details
Coaching delivered via live sessions.
Over twelve sessions, my coaching becomes increasingly tailored to you. Early sessions focus on understanding your landscape and building trust. As we go deeper, I draw on everything I've observed (recurring themes, contradictions, breakthroughs) to ask sharper questions and surface what matters most. I don't follow a curriculum. Every session is responsive to where you are that day and what I'm noticing across the full arc of our work. I bring directness, curiosity, and genuine investment. I expect the same from 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 12 sessions, roughly 3-5 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
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
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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.
$1,836
12h of coaching