Find Your Next Pursuit

Finding work that’s aligned, meaningful, and satisfying requires three things: 

  • a crisp vision, so you can recognize and describe what fits and what would just give you the same frustrations in a new wrapper.
  • a map of your options, and the obstacles you’ll need to be ready to overcome along the way.
  • people who can guide, champion, and support you on the journey. 

This program moves you through three distinct and structured missions designed to deliver insight, build conviction, and guide your outreach efforts for the next chapter of your life. 

Get expert guidance tailored to your situation. Curated frameworks and resources. And a warm, candid, and rigorous thought partner.  

Enroll Now: $3600
Book a Free Strategy Call

Feeling Uncertain About What’s Next?

You’re used to being the person with the plan. You’re great at executing through hard work and brainpower. That can make the ambiguity that comes when it’s time to change direction very unsettling.  

“The through line I tracked to move through life has sort of disappeared.”    

“I want to be intentional in my choices. I don’t want to look down and it’s been five years.” 

“I’d like to structure my spiral a bit more productively.” 

“I’m having a high achiever midlife crisis. There’s no more cookies, no more gold stars. I’m just here doing the work.” 

“I’m missing something, or I don’t have the skill right now to figure this out.” 

You don’t need to do this alone. 

With expert guidance, you’ll:

  • Identify and articulate your personal "north star" -- the activities, culture, and purpose that bring out your best.
  • Reconnect to your energy, optimism, and drive.
  • Build a curated short list of real paths worth pursuing.
  • Tap into your network without dread, insincerity, or overwhelm.
  • Develop a clear way of describing your superpowers, gifts, and goals that is authentic and grounded in conviction.
  • Evaluate tradeoffs, skill gaps, and potential challenges to reduce risk and make confident choices.

Key Components:

Mission One: Find Your North Star. Stop scrolling helplessly around LinkedIn, going around in circles in your mind, or wondering vaguely whether you’d enjoy something completely different. We conquer ambiguity with two concrete exercises: 

  • a work biography where we mine your past to uncover motivators, strengths, and resources unique to you.   
  • a values exercise designed to vision your future around the priorities you choose for this next chapter.

This phase concludes with a Mission Brief, articulating the work that lights you up. 

Mission Two: Map The Possible Paths Forward. Smart thinkers recognize risk — and that can keep you paralyzed in cycles of indecision, overanalysis, or the magical hope that someone else will make the decision for you. We break this pattern with design thinking: 

  • first we generate multiple ideas;
  • then we evaluate and select a handful of the best for future research.

This results in a Quest Menu, to help you evaluate your possibilities in light of your values and the person you want to become.  

Mission Three:  Recruit Your Support Team. Other people can facilitate or hinder your access to opportunities. We conquer fear of reaching out by getting crystal clear about the four ways your network can help you and building a Personalized Networking Plan.

What's Included

  • A values card deck, shipped in the mail, for identifying and articulating the values that will guide your next chapter. 
  • A Mission Brief Document: Upon completion of the first mission, you’ll get a 4-5 page synthesis, detailing your superpowers, the work activities you love most and excel at, the culture of the environments where you do your best work, and the red flags or frustrations that you’ll want to avoid or treat with caution. 
  • A Quest Menu: Upon completion of the second mission, you’ll get a 5-6 page document naming real possibilities to research, and the tradeoffs, benefits, and connections to your values and your professional identity to date. 
  • A Personalized Networking Plan: The third mission will give you the tools, clarity, and even some scripts to strengthen and tap into your professional network, without being creepy, inauthentic, or entitled.
  • Structured homework assignments and reflection exercises, designed to move you from overwhelm and paralysis to clear, energized, and ready.
  • Momentum and confidence from taking directed, specific action around clear missions, instead of worrying, drifting, scrolling, or vague networking calls.
  • Curated library of resources, templates, videos, podcasts and books.

This Program Will Give You

  • Relief from self-doubt, over-thinking, and paralysis
  • A clear framework for decision-making
  • Optimism and energy
  • Strategic and tactical guidance from a career expert
  • Feeling in control of your work trajectory
  • The ability to convey genuine confidence, conviction, and authenticity in career conversations

Avoid These Reputational Risks

You’ve built a strong professional reputation, and you know that your network is the most powerful tool you’ve got for making a career pivot. 

But you’re also aware that your credibility is your most valuable asset, and you recognize that networking without a game plan can hurt more than it helps. 

Here are two common risks that I see high achievers facing when they reach out to a warm network. 

  • Go out to your network too early, and your indecision will come through loud and clear.  You’ll have a series of pleasant, unstructured conversations that don’t lead anywhere — and at worst, can give the impression that you’re a little bit of a mess. Your contacts will say, “Keep me posted if I can be useful,” and you’ll both leave wondering whether the time spent was worthwhile.  People don’t spend their reputational capital on someone they can’t describe. 
  • Alternatively, early conversations can lead to offers and opportunities that arrive before you have the criteria to evaluate them. Sometimes your advocates and former colleagues get so eager to help that they start delivering introductions and referrals to you like a golden retriever dropping slobbery sticks at your feet.  Suddenly you’ll find yourself with an opportunity that’s not right and a person who means well you don’t want to disappoint. 

We solve for both of these problems by getting you ready for confident, structured, clearly framed conversations that burnish your reputation rather than risking it. 

Enroll Now: $3600
Book a Free Strategy Call

Meet your Coach, Sherry Mason

I believe that when smart people like what they do, we’re all better off.

I’ve spent the last 20+ years exploring the elements of professional satisfaction, beyond external achievement, money, and prestige. I read dozens of books each year within fields like behavioral economics, productivity, psychology, negotiation, and career growth. Clients appreciate that it’s a huge shortcut to meet with someone who’s done all that reading, rather than hunting for key frameworks or tools by reading four books yourself.

My coaching approach is rigorous, systematic, and grounded in research. It’s also personalized to your values and priorities. These will change over the course of your life and career, so it’s not unusual to outgrow a role you used to love, or to feel yourself called in a new direction.

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.

  • 20 years experience coaching high-achievers
  • Trained in Navigating Transitions; Motivational Interviewing; Financial Counseling and Career Development; Mental Health First Aid; Intergroup Dialogue Facilitator
  • Former Dean of Students: University of Maine School of Law

I Bet You Have Lots Of Questions.

What Happens In A Coaching Session?

Career coaching sessions are a little bit like therapy, and a little bit like a personal training session.  Expect a combination of questions, conversation, and instruction/evaluation.  Your coach will have a plan for the session, but we’ll always adjust the agenda in response to your most pressing needs in the moment.  Sessions are used to clarify priorities, discuss and problem-solve around obstacles and insights that emerged from the homework or reflections between sessions, and set your next steps.  

It depends.  Some of it depends on you, and some of it depends on the role you seek.  It’s useful to consider this a 6-12 month process for someone in a full-time job, because capacity for networking, follow-up, and research will ebb and flow.  

This program doesn’t end with a job. Instead, it gives you all the ingredients you’ll need either to get one, or to job craft your current role to better fit you. 

The skills, mindset, and frameworks you build through this process will guide your intuition and inform your career decisions beyond your next role. 

Sometimes clients seek to extend our coaching relationship, either for ongoing strategic support in a new or existing role, or to maintain confidence and accountability as they implement their career action plan.  I offer alumni pricing for ongoing coaching support after the program is over – and stay in touch informally with former clients for years.

Maybe, and maybe not.  Career clarity, action planning, networking strategy, and interview preparation support don’t have regional variations, and we’ve had happy clients in Europe and Asia.  Materials review and application support, on the other hand, may benefit from regional expertise.  Let’s discuss on a strategy call.  

Clients can choose to schedule 50-minute, 75-minute, or 90-minute sessions, depending on what works best for their situation. We work together in these sessions to move through the three specific missions in the program. 

Mission 1 usually takes 2-4 hours of synchronous coaching time to complete.  Mission 2 usually takes 1.5-3 hours of synchronous time to complete. Mission 3 usually takes 2-3 hours of synchronous coaching time to complete. 

I might not be!  There are a number of skilled career coaches out there.  It’s important to find the right fit.  I encourage you to talk to other career coaches, and I’m happy to share names of colleagues I hold in high regard.  A strategy call conversation will give you an abbreviated feeling for how I work and whether you feel a productive rapport.  I also encourage you to read my blog, subscribe to my newsletter, or connect with me on LinkedIn to decide whether my approach resonates with you.

My background and temperament have prepared me to support high achievers as they encounter the professional and personal challenges of mid-career and beyond.  I am particularly interested in the struggle to balance growth, identity, achievement, security, and meaningful commitments beyond work with a rewarding career and high expectations for oneself. 

Yes. If after two sessions together, you decide that coaching isn’t right for you, I refund your money in full. You can keep the values cards. I don’t want you to spend your time or money on something that isn’t fruitful.

I devote a portion of my time to pro bono and discount rate services, so that career support can be financially accessible to more people.  Clients who pay my regular prices permit me to offer this support.  If you seek reduced-rate services, or can contribute to underwrite services for someone else, please email me to discuss.

  • Your Mission Brief is a 4-6 page document built from our coaching sessions. It captures your superpowers and the work activities you love doing, the characteristics and culture of organizations where you’ll do your best work, and red flags to watch for that may indicate frustrations or poor fits.
  • Your Quest Menu is a 3-5 page document that identifies a short list of possibilities to pursue, and the ways in which each possibility might align with your goals and values. It gives you a way of identifying which questions you need answered, and turns vague aspirations into a research project you can tap your network to pursue with rigor and intention. 
  • Your Outreach Plan is a set of tools and worksheets that helps you identify who you’ll talk to, what you’ll be talking about, and how you’ll frame your story. You’ll always be clear about what you need from your network, and what activities you’ll be undertaking to keep the project moving.  

 

I’m an experienced career coach, and I love to help clients put themselves forward with confidence. But Your Next Pursuit is not about the application process, and we don’t specifically work on documents or interview answers in the program. 

At the end of the Your Next Pursuit program, if you want specific support with application materials or interview preparation, I am available for as-needed or ongoing coaching. 

It’s not unusual for people to consider “job crafting” in addition to leaving for a new role, industry, or organization.  Job crafting is the process of making adjustments to your current role to give you more growth, less stress, or otherwise better alignment to your values. 

Staying doesn’t mean complacency. Clients articulate “being intentional in my choices,” as one of the benefits of coaching, whether they move to a new role or choose to stay and renegotiate their relationship with their existing responsibilities. 

 

Treat Your Career With Rigor, Intellect, and Intention.

Enroll Now or Book a Free Strategy Call!

Enroll Now: $3600
Book a Free Strategy Call