Make your high-stakes decision with clarity and confidence.

When you’re making a consequential decision, you have a lot to consider. Find the best path forward with an objective, smart, supportive coach to guide you.
  • I’m almost ready to make an offer to buy a business, but want to make sure I’m not overlooking something.
  • I’m considering whether to step away from my successful startup to take something less stressful.
  • Should I take this promotion, even though I think I’ll hate it?
  • Will I be bored and unhappy if I retire?

When you’re making a high-stakes professional decision, the pro-con list can get unwieldy and ambiguous.

Friends and family can help, but they don’t always have the skills or perspective to be unbiased, candid, direct, and useful.  And there are reputational risks for talking this out with professional contacts.

I can help you pinpoint the key issues at stake, for you and others.  Together, we’ll make a plan to resolve your doubts so you can take confident action.

Meet your Instructor, Sherry Mason

I’m a warm and rigorous coach with nearly twenty years of experience coaching smart people.  Most people don’t learn the step-by-step process for aligning work with their values and goals.  I’ve thought about that for years, and I love sharing what I know.  The exercises I’ve developed and the tools, templates and frameworks I’ve created have helped hundreds of clients feel more confident about their career decisions. 

When smart people like what they do, we’re all better off.  Solving interesting problems with colleagues who value you will make you happy and effective — at work and outside of it.  I want you to flourish.  

One-on-one coaching is a special relationship.  I strive to earn the trust of my accomplished clients by reading broadly and deeply, and offering logical, empathetic, and candid feedback.  I’ll always respect you and support your wisdom, potential, and growth.  

Package Details

Who is this for?
Busy professionals making consequential career decisons.
Key Components:
  • Articulate your top priorities
  • Identify other key stakeholders
  • Evaluate your options
  • Clarify blindspots and doubts
  • Make a clear plan of action

What's Included

  • Warm and rigorous coach
  • Objective and candid feedback
  • Insightful, pointed questions to get at the heart of the matter
  • Strategic, creative sounding board

Free Strategy Call

Let's talk about your situation.

Schedule a 30 minute call to see whether working together makes sense. 

Key Benefits

Impartial observer

An outside perspective helps set aside preconceptions and limiting beliefs.

Thorough review

Surface ambiguity, blindspots, and inner conflict to make a clearer decision

Insight & support

You have great options. I'll help you see all of them.

Want to learn more about how our coaching can help you?

You'll act with confidence when you are crystal clear about priorities, values, consequences, and next steps. An expert coach can get you there faster, with warmth and rigor.

Other Available Coaching Services

Foundations Coaching Package

Who is this for?
Foundational early career strategy for ambitious professionals.

Application Audit Package

Who is this for?
Professionals who've identified a specific opportunity, and seek expert review of their application to make it excellent.

Milestone Coaching Package

Who is this for?
Professionals with 8-12 years of work experience seeking greater alignment and fulfillment in their career.

Perspective Coaching Package

Who is this for?
Executive-level clients with 15+ years of experience and a track record of success ready for a new chapter of growth and impact.

Grad School / Fellowship Application Support

Who is this for?
Applicants to highly selective law schools, business schools, fellowships, or competitive programs.

Take the First Step in Your Career Journey.

Enroll Now or Book a Free Strategy Call!

Book a Free Strategy Call