Meet Your Coach, Sherry Mason.

About Sherry

I have been coaching smart people since 2005. I believe in rigor and am comfortable with high expectations.

I do this work because I love it. I read career development books for fun. I listen to podcasts about work culture, decision making, and life satisfaction. Having me on your team gives you access to expert knowledge that will save you time and make your journey easier.

Our work together will stretch you and energize you. I serve clients by being observant, kind, candid, supportive, and practical. With warmth and humor, I will help you build confidence in your professional possibilities and present your best self to the world.

How I Can Help You

Career Clarity:

You can’t get what you want until you know what it is.

I’ll help you take vague feelings and turn them into specific goals.

Find Opportunities:

Identify roles, orgs, and pathways to get what you want from work.

Conduct targeted research to reduce risks and increase success.

Confident Applications:

Know how to package and present yourself to win opportunities.

Highlight your strengths without being braggy or inauthentic.

Support and Accountability:

We make progress on goals when we make time and space for them.

I’ll keep you from stalling, wasting time, or getting stuck.

My Approach

I believe that when smart people are flourishing at work, we’re all better off. Happy people are more productive, more creative, and more connected. I want you solving problems that matter, alongside colleagues who value you, with enough time, money, and energy to pursue goals outside of work, too.

Some fundamental principles I bring to my work as a coach:

I respect you, and the decisions you are making. Finding work that aligns with your goals and values doesn’t just happen. It deserves intelligent focus, and requires space and attention.
I trust you. You know more than I do about the circumstances of your life. My job is to offer options, perspectives, and challenges, but you’ll always be the expert on what’s best for you.
This isn’t about me. I won’t save the day. I’ll do my best to make it easier, and to help you make progress, but the execution and implementation is up to you.
I support your growth. I want to see you succeed, and will bring my full attention, focus, and curiosity to your challenges.

A coach is different than a friend, a mentor, or a family member. My job is to balance supporting you with encouraging your growth. A coach offers candor, challenge, and a different perspective on your interpretations or assumptions.

I bring frameworks, systems, and processes that have worked for hundreds of clients facing career decisions. Together, we’ll apply these tools to your situation to help you find the best way forward.

Background, Certifications, and Affiliations

My academic and professional journey has been both diverse and rewarding, providing a strong foundation for my career coaching practice. Here’s a snapshot of my credentials:

B.A., Yale University: Geology & Geophysics
J.D., University of Maine School of Law: Summa cum laude, Recipient of the faculty achievement award (1st in class)
10 years as Career Coach / Pre-Law Advisor: Bowdoin College & Tufts University
Former Dean of Students: University of Maine School of Law
Law School Admissions & Financial Aid Expert
Accredited Financial Counselor: Designation earned in 2018
Racial Equity Institute Phase 1 & Phase 2 Training
National Coalition Building Institute Train-the-Trainer Certification: Earned in 2022
Intergroup Dialogue Facilitator: Certification earned in 2015
Motivational Interviewing Training: Completed in 2022
Trained & Experienced Public Speaker

I've spent much of my career advising and supporting people who care about justice -- lawyers, law students, and people who work in public service -- and I have spent 18 years in higher education. This gives me a specialized understanding of the hiring processes, challenges, and opportunities in the legal field, higher education, and federal agencies.

Learn With Me

I'm always reading and thinking about work, play, and strategies that help clients flourish. I share the best via email.

Subscribe to get inspiration and resources.

Client Success Stories

I’ve had the privilege of working with professionals across various industries, helping them achieve career breakthroughs and discover new opportunities. My clients’ success is a testament to the power of personalized coaching and a commitment to continuous growth.

What's a Daymark, Anyway?

A daymark is a tower or buoy that helps boaters find their way. I come from a family who loves the ocean. Both of my grandfathers served in the Navy. My father made his living as a sailmaker. Spending time on boats, responding to the invisible powers of wind and current, has made me attentive, practical, and brave. The nautical charts pictured on this website belonged to my grandparents. They defied the expectations of the snooty New York society in which they were raised, and chose to settle in Maine. These charts remind me of their adventurous spirit, capable seamanship, and determination to fill their lives with worthwhile experiences.

Find Your Way to Career Success.

I invite you to explore the resources here and take the first step toward a more fulfilling career. You deserve to flourish at work. I’d love to help.