Socratic Coaching for All the Arenas of Your Life



~ Socrates

It is Time to Examine Your Life

We are all Philosophers.

Deep inside each human is the desire to understand. From the time that we are able to form complex thoughts, we have asked the simple, yet incisive question: “WHY?” Many of us spend a lifetime wondering “WHY?” only to find ourselves unable to satisfactorily answer this inquiry with the current tools available to us. Comfortable in our daily habits and content with the “way things are,” we risk going through life without a focused comprehension of the truth, without a full experience of joy.

W H Y ?

The wisdom captured in the writings of great philosophers, from the Stoics to the Existentialists, continues to be important today. While there have been monumental advances in the ways that humans live, human beings–and their very nature–haven’t changed much. The “answers” espoused centuries, even millennia ago, persist in their relevancy. We can still learn from our wise human ancestors.

We each seek to know the meaning of our lives.

We each wish to explore our individual “WHY?”

After decades of philosophical study and legal advocacy, Jenna Brownson, JD, offers an opportunity to those with curious and open minds to explore what it means to be human in this complex and confusing era through Socratic Coaching.

Socratic Coaching values asking questions over simply giving answers and does this through a series of Directed Dialogues that form the structure of the coaching sessions and encourage a comprehensive and deep exploration about one’s values, priorities, and objectives. These Directed Dialogues challenge assumptions while acknowledging cognitive bias. In essence, those who work with Jenna will be invited to apply rigorous honesty to their thinking to sharpen their critical thinking skills.

“Let us therefore set out wholeheartedly, leaving aside our many distractions and exert ourselves in this single purpose, before we realize too late the swift and unstoppable flight of time and are left behind. As each day arises, welcome it as the very best day of all, and make it your own possession. We must seize what flees.” ~ Seneca, Moral Letters

Now is the best time

to discover your Wisest Path

Choose Your Wisest Path

Arena Investor

Six Arena Masterclass
Refine and Sharpen Critical Thinking Skills in the Six Arenas

This is the best choice for those ready to commit to a rigorous search for individual truths in order to establish a personal life philosophy and live a fuller life.


  • Twelve 1.5-hour, weekly sessions
  • Agreed-to support by email or text
  • Invitation to join private chat group with other Masterclass attendees
Arena Explorer

Six Arena Boot Camp
Assess and Reflect to Develop Better Habits in the Six Arenas

This is the best choice for those interested in making thoughtful initial progress in all Six Arenas and begin the personal work of living a more examined life.


  • Six 1.5-hour, weekly sessions
  • Agreed-to support by either email or text
Curious Wonderer

Individual Sessions
Your Topic to be Discussed via Directed Dialogue

This is the best choice for those who want to establish a personal “life philosophy,” to examine thinking patterns, or to make a hard choice, among other topics.

$250.00 for one 1.5-hour session

$750.00 for four 1.5-hour sessions (25% savings)

Space is Limited. Secure Your Sessions and Begin on Your Wisest Path.

Socratic Coaching Credit

Single session BUY 1 Credit //// 4-pack BUY 3 Credits //// Boot Camp BUY 5 Credits //// Masterclass BUY 10 Credits



If after your coaching session(s), you conclude that your life has not been enriched by the experience, you will receive a no-hassle, 100% refund.

Invest in Yourself Today.


Because Your Remaining Time on this Planet is Precious.

After your purchase, your Coaching Sessions will be scheduled by email with jenna@wisestpath.com.
Thereafter, all sessions will be conducted in-person in Littleton, Massachusetts or via Video Conferencing or by Telephone.

Sessions Hours

Monday-Friday: 10:00-5:00
The Weekend: By Arrangement

Office Location

442 King Street, 2nd Floor Littleton, Massachusetts