When work feels… "sticky"

You are accomplished. You are capable. But lately, things feel heavy. Maybe you’re navigating a transition, or maybe you’re just in a quiet season of wondering, "Is this it?"

  • The Disconnect

    Your career looks okay (maybe great!) on paper, but you aren't sure if your old goals fit the current you.

  • The Fog

    You’re at a crossroads—trying to decide between pushing for the next promotion, pivoting your career, or just trying to survive the week.

  • The Burnout

    You know your current pace isn’t sustainable, but you don’t see a way to slow down without dropping the ball.

Our Philosophy

You cannot out-plan burnout. And you cannot earn your rest by working harder.

I often tell a story about my own burnout journey. I thought if I just changed jobs—found a better title, a new contract—everything would feel easier. But the grass wasn't greener, because the gardener hadn’t changed. 

My coaching practice is a container for that change. We stop looking for the "right" answer and start looking at your compass. 

  • We make space: To name what actually matters to you right now (not five years ago). 

  • We tend the roots: We look at your boundaries, your capacity, and your "quiet signals." 

  • We build structure: Because sustainable growth requires a trellis, not just sunshine.

An iterative, interactive process, tailored to exactly what you need. You will work with Boss Insights founder Whitney Kippes one-on-one to dig into root challenges, leverage your existing strengths, and test new strategies with built-in accountability.

The Offerings

Choose the path that best fits your goals (and budget).

The Rapid Reset
(3 Weeks)

Perfect for an acute decision (stay or go?), a sudden crisis of confidence, or a specific negotiation that has you paralyzed.

Duration: Weekly sessions over 3 weeks

The Container:

  • 3 x 1:1 coaching sessions (50 mins via Google Meet)
  • Initial "values & vision" assessment (to align goals with what matters)
  • Wrap-up strategy plan for moving forward independently

Investment: $600 (or 2 payments of $320)

The Calibration Series
(90 Days)

For the boss needing to check their compass. When you feel at a crossroads—a new role, a scary decision, or a specific burnout trigger—we use this time to find your footing.

Duration: Biweekly sessions over 3 months

The Container:

  • 6 x 1:1 biweekly coaching sessions (50 mins via Google Meet)
  • "Compass Check" exercises to untangle sticky thoughts and burnout triggers
  • Email access for "gut checks" between sessions
  • Mid-point review to adjust trajectory as needed

Investment: $1,200 (or 3 payments of $450)

The Transformation
(6 Months)

For the professional ready to change the way they work entirely. This is for deep behavioral change. We move beyond the immediate fires and look at how to build a career (or a consultancy) that fits your actual life.

Duration: 6 Months (Most Popular)

Includes:

  • 12 x 1:1 coaching sessions (50 mins biweekly, via Google Meet)
  • Deep-dive leadership style assessment & ecosystem audit
  • Unlimited asynchronous support (Voxer or Email) for real-time navigation
  • Resource Library: Access to relevant Boss Insights worksheets & tools
  • Bonus: Access to the Bosscraft Consultant Network (if applicable)

Investment: $2,400 (or 4 payments of $675)

Executive & Organizational Partnership

For teams that need to stabilize, navigate intense pivots, or retain high-potential talent.

If your organization is feeling the squeeze—ambitious goals but limited resources—I partner with leadership teams to rebuild systems that sustain the people doing the work.

Customized Program:
  • Engagement and support to encourage sustainable growth and professional development
  • Ad-hoc crisis support, including priority scheduling
  • Triad intake and conclusion meetings with you, your manager, and/or HR to harmonize goals (optional)
  • Confidential quarterly progress reports
  • Full suite of assessments and tools

Investment: Custom / Retainer-based

What's Always Included

We know that investing in yourself or your team is important (and a big step!). That's why we've packed in so much value.

P.S. Our aim is that everyone who needs coaching can get access to support in some form. Email support @ bidboss . org to request information on sliding scale rates.

  • Confidentiality: A safe space governed by professional ethical standards in line with the International Coaching Federation.

  • Flexibility: Virtual sessions that fit your work, personal, and travel schedule, including evening sessions and accomodations for time zones.

  • Tangible Tools: We don't just talk; we use frameworks, visual aids, and exercises (like the Effectuation Exercise or Ideal Week tools).

  • Someone In Your Corner: We listen to hear you, not fix you. If your goals shift, so do ours. We will challenge you when you need it and champion you when you don't.

Is Whitney the right coach for you?

This isn't just about feeling better. It's about leading better from wherever you are right now.

My clients are entry-level, managers, VPs, freelancers, and everything in between. They are high-performers who are ready to stop winging it.

We might be a good fit if:
  • You are ready to admit that you can't "hustle" your way to clarity.
  • You want a partner who weighs equally the "boss stuff" (strategy, stakeholders, targets) and the human stuff (fears, values, rest).
  • You are willing to believe that your finite capacity is not a flaw.

Client Stories

Whitney is very good at shedding new light on something I may have already closed the door on mentally, and encouraging me to think longer and harder about things.

My supervisor immediately noticed my growth and confidence and my enhanced performance. It influenced my personal life in feeling more empowered and leaning more into my values that define me as a being - outside of my work.

I feel more confident saying no to opportunities that don't clearly align with my values or ambitions.

FAQ

  • I don’t know if I have time for this.

    Coaching isn’t another task on your to-do list. It is the container that helps everything else make sense. By taking this pause, you reclaim the energy you’re currently losing to second-guessing and spinning your wheels.

  • Can I get my employer to pay for this?

    Absolutely. Many of our clients are sponsored by their organizations as part of their professional development or leadership training budgets. Companies want to retain high-performers, and executive coaching is a proven way to do that. If you need help making the ask, let me know during our consultation—I can provide you with a "Business Case" template to share with your manager or HR department that outlines the ROI for the organization.

  • How is this different from therapy?

    Therapy often looks backward to heal. Coaching looks forward to build. While we make plenty of safe space for emotion, our work is anchored in strategy—where are you going, and how do we support you to get there?

  • What if I don't have a specific 'crisis'?

    You don’t need to be burned out to benefit. You just need a curiosity about what is possible if things felt lighter. You don't have to wait until you are empty to refill the tank.

  • Do you offer payment plans?

    Yes. I know that investing in yourself is a big commitment. For private-pay clients (those not sponsored by a company), all packages can be broken down into monthly installments. If needed, we also offer sliding scale pricing for those who qualify. Inquire by emailing support @ bidboss . org.

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