Annual Gathering 2019

October 10-13

The Annual Gathering offers both emerging and experienced leaders the chance to step back and reflect together on the challenges of career, relationships, family, community life and faith. For those who are married we strongly encourage you to attend as a couple.

There will be an optional Mentoring Workshop, Thursday October 10th, for those who are able to arrive by Wednesday evening. This is for all Mentors and also Telemachi who have previously attended an Annual Gathering. Limited to 30 participants on a first come basis.

A Thursday evening Welcome Dinner (beginning at 6:30pm) serves as the official beginning of our Gathering. The weekend concludes on Sunday morning with a worship and communion service (ending at approximately 11:00am). Over the three days participants will enjoy inspiring speakers, breakout sessions, small group discussions, delicious meals, engaging conversations, recreation, and relaxation. It is a time to connect, learn, and re-energize.

The conference fee is listed below (please note early bird and tiered pricing structure) and covers all food and a small portion of the program expenses. There is a nominal registration fee for the optional workshop. Participants are responsible for their own transportation and lodging arrangements.

Early Bird pricing ends August 15th. Registration will close September 26th.

Early Bird: $475
Regular Pricing: $575

Senior Mentors (50 years old +):
Early Bird: $575
Regular Pricing: $675

Join Waitlist

Mentoring Workshop (Optional)

Time:  Thursday, October 10th

9am to 2:30pm

You need to arrive at the Gasparilla the night before

Fee: $50 (includes breakfast and lunch)

Leaders: Rick Woolworth & Andy Chan

Participants: We hope as many of our senior mentor group will attend as well as Telemachi who have previously attended an Annual Gathering. We are limited to 35 participants on a first come basis.

Content: This highly interactive session will be an in-depth exploration of all aspects of mentoring. Topics to be explored include:

  • What is mentoring and how is it different from coaching, networking, being a sponsor, spiritual director, etc.?
  • Can anyone be a mentor? What qualities does the mentor have to bring to the relationship?
  • Best practices
  • The art of the question
  • Mentoring from a Christian perspective

Quotes from participants of previous Mentoring workshops:

I can’t recommend this workshop highly enough! It is both encouraging and practical – taking mentorship from an ambiguous concept and potentially intimidating activity to a concrete and actionable plan for serving a critical need.
~ Eric Osborne

We walked in skeptical and reluctant and walked out energized and equipped!
~ Annie & Kevon Saber

This was one of the highest return introductory experiences I’ve ever had. Rick took us through all aspects of mentoring conversations which included a toolkit of frameworks and probing questions to ask. I left inspired to become a more active mentor.
~ Duncan Sahner


Gordon Macdonald 
author, speaker, teacher

Jo Saxton
author, speaker, leadership coach, church planter

Jessica Kim
entrepreneur, CEO, speaker

Lee Camp
professor, producer, speaker

Bill Haslam 
former Governer of Tennessee, speaker

Crissy Haslam 
former First Lady of Tennessee, speaker, teacher

Josh Graves 
minister, author, teacher


Jill Phillips
singer, songwriter, musician, chef   

Andy Gullahorn
singer, songwriter, musician, bowler


The weekend will begin at 6:30 pm on Thursday, October 10 with a Welcome Dinner and will conclude at 11:00 am on Sunday, October 13. We strongly encourage you to arrange your travel so that you can stay through the Sunday morning service. This is a wonderful way to complete your time at Gasparilla as you share this meaningful experience with others in the Telemachus community.

Thursday, October 10

8:00-9:00 Breakfast (Workshop Participants Only)
9:00-2:30 Mentoring Workshop
2:00 Registration Opens
5:30-6:30 Senior Mentors Meeting
6:30 Welcome Dinner

Friday, October 11

7:30-8:30 Breakfast
8:45-10:15 Plenary Session I
10:15-10:45 Break
10:45-12:00 Plenary Session II
12:00-2:00 Lunch and Small Group Discussion
2:15-3:30 Breakout Sessions
3:30-6:30 Free Time
6:30-8:00 Poolside Dinner
8:00 Evening Session

Saturday, October 12

7:30-8:30 Breakfast
8:45-10:15 Plenary Session I
10:15-10:45 Break
10:45-12:00 Plenary Session II
12:00-2:00 Lunch and Small Group Discussion
2:15-3:30 Breakout Sessions
3:30-6:30 Free Time (Yoga, Beach Walk, Paddle boarding, Tennis)
7:00 Dinner at the Main Inn

Sunday, October 13

7:30-9:30 Breakfast
9:30-11:00 Worship Service and Communion

Book Your Travel

The Gasparilla Inn

Please note: you must mention the “Telemachus Room Block” in order to secure a room at our special discounted rate. The Inn books up very quickly, we highly recommend securing your room ASAP.

Our special room rate is $240 per night, single or double occupancy plus service charges and taxes. Room reservations can be made by calling The Gasparilla Inn at (877) 403-0599.

If you are planning on attending the optional workshop on Thursday, please make arrangements to arrive on Wednesday evening.

Visit The Gasparilla Inn

Airport travel info
Sarasota Airport – 1.25 hour drive
Ft. Myers Airport – 1.5 hour drive
Tampa Airport – 2 hour drive

Please join the waitlist for registration

Fill out my online form.