How to Create a Client Retreat

Journal of Financial Planning: July 2017


Bill Harris, CFP®, is a co-founder and principal of WH Cornerstone Investments and president of the board of directors for FPA of Massachusetts. He is passionate about empowering widows with their financial future. Follow him on Twitter @whcornerstone or @billmharris.

Our firm has guided countless widows through the maze of financial challenges that arise after a loved one has passed. Regardless, we were yearning to help a larger group of people transition to the next stage of post widowhood. This year, we decided to host a retreat for widows. Retreats are about creating a deeper, more meaningful experience. Terrific energy and sharing occurs with a group of people who have shared a similar life event or mindset.

As usual, my first grandiose vision of the event was a conference with a big crowd and stadium-style seating. I was thinking a standing-room-only crowd. I imagined a stage manager prompting me with a “10 minutes to show” notice. I imagined heading toward the stage as the house lights dimmed and the music started to play.

Of course, after I met with my team, the real vision for the retreat was formed. A retreat is time consciously set aside to focus on learning and growth. It’s a deliberate act of stepping outside of the normal routine by withdrawing from the noise and pressures of everyday life.

We mapped out the purpose for the event, then the budget, location, marketing strategy, content, and agenda. The event would be intimate—limited to a small group of widows. My role changed from rock star to stagehand—inches from stardom but not the main attraction.

The Inspiration

Our idea for a retreat was born a few years prior. We had taken one of our top clients on a weekend retreat to the Berkshires, a quaint, mountainous region in Western Massachusetts. To get us in a creative and open-minded state, we started our day at the Massachusetts Museum of Contemporary Art, or MASS MoCA.

MASS MoCA’s home is an old factory on a river in a town called North Adams. North Adams is a small industrial town, once home to vital textile firms that decades ago played a key role in the regional economy of Western Massachusetts. But, the textile industry, along with other manufacturing industries, evaporated from the Massachusetts landscape. The vibrancy in the towns that hosted these factories vanished along with the industries. Years later, an infusion of the creative economy, like the conversion of this old factory to an art museum, paved the way for a revitalization.

The site we chose for this mini retreat was not by accident. Our client was in a funk, and it was time for her revitalization. Over two days of viewing art, eating great meals, and having meaningful conversations, we set goals, and mapped out life changes and a stellar financial plan.

That weekend retreat was a powerful experience. We knew we had to replicate it and make it scalable so we could touch more lives at one time. Little did we know that weekend in the Berkshires was the test run for our two-day widow’s retreat.

We branded it, “Rise Up: A Reinvention Retreat for Widows.” Our purpose was to craft a calming retreat and help these widows gain the necessary tools to write the next chapter in their lives.


With a similar revitalization theme in mind, we chose a semi-luxurious, relaxed-feel, high-end inn and spa that offered the comforts and residential feel of a private French estate. The boutique inn offered 40 overnight rooms, beautiful grounds, and session rooms that were spacious with lots of natural light and easy access to nature’s door. Ultimately, we wanted our guests to stay overnight, relax, unwind, and get ready to transition to their next stage of life.


Our budget included meeting spaces, meals, gifts, presenter fees, marketing costs (graphic designer and print materials), advertising costs (print advertisements, social media ads, press releases), and other miscellaneous items.

We set the price of attendance at $399. We offered our current clients a discount fee and offered our professional colleagues and centers of influence a discount code they could pass on to their clients and contacts. Based on what we were offering, we needed 12 attendees to break even. We also negotiated a block of hotel rooms for our guests.


Marketing the retreat was our biggest challenge. Four months prior to the event, we created an event page on our website with full details. We also leveraged the capabilities of Constant Contact for our event registration and payment collection, which are built into the Constant Contact system; it made collections go smoothly.

We sent out information in our own e-newsletter (a list of more than 1,200 names) with “save the date” teasers until the full flyer was ready. Even though we had a four-month head start, we had Thanksgiving, Christmas, and the New Year competing with the marketing of our event. We passed out flyers where appropriate (senior centers, organizations that provide home care services, bereavement groups, etc.).

We used social media advertising. In addition to paying for boosted posts and leveraged key words for search purposes, we joined various Facebook groups where we shared the information. We sent targeted emails to centers of influence with the discount code for their clients. Our speakers cross-promoted the retreat on their websites and leveraged their social media, and we were sure to tag them so we could cross pollinate via our respective social media channels.

Speakers and Topics

For our retreat, personal finance was to be just one of the workshop topics; it was not the entire focus of the weekend. We chose speakers who had written books, had TEDx credentials, and who were visible with strong reputations. Because we did not want our audience falling asleep in their seats, presenters were asked to infuse physical movement as much as possible. After we nailed down the speakers and the agenda, it was show time.

We kicked off the retreat with an opening circle (an idea we borrowed from the FPA Retreat). The opening circle allowed participants to meet each other and capture their objectives for the weekend.

Our first speaker wrote a book about women and transition. Every participant received a copy of the book. Her thesis was that transition is a choice. You can stay in the middle of it, or you can pass through, and that message became the biggest theme of the weekend. Other speakers included a TEDx presenter who is a life coach who helped attendees attract grace in their lives. We also had a nutritionist, and a yoga session led by a woman who was also recently widowed. She wove in special support poses and appropriate poetry.

We had a shaman close out the first day with a fire ceremony, which is a powerful Native American practice used to release unwanted energies and attachments from the past and make space for new intentions. It was truly a unique and fitting experience.

On day two, we began with breakfast and more presentations. The keynote presentation focused on empowering women about their money. We focused on important steps to take to ensure strong financial futures. We provided proprietary tools as well as a book to capture important information and final wishes.

We ended the retreat with a closing circle where participants shared their experiences. We had a facilitator incorporate all the tools presented over the weekend. She challenged attendees to craft a personal vision for their future.

During the weekend, we filmed the speaker presentations. We captured speaker video interviews and several attendees gave video feedback as well. All attendees filled out a feedback survey. We will use this material to promote future events.

Lessons Learned

Host a one-day event. We lost momentum on the second day (people sleeping late, leaving early, etc.). Also, details of hotel logistics (room blocks, dinners, etc.) are distractions that take away from the actual retreat experience.

Marketing an event like this is extremely challenging. A solid marketing plan with multiple channels is a must.

Charge a premium price to attract quality attendees.

Pay careful attention to the event date. Although no date is ever perfect, we chose late January. For a widow audience, the holidays are over and with Valentine’s Day approaching, it can be a lonely season. Marketing through the holidays is very challenging; people are focused on so many other things. However, attendees did stress they needed a retreat at that time of year when the days can seem the longest.

We were targeting widows in the Northeast for a January event. Many were traveling snowbirds who expressed interest but were unable to attend.

Have a cancellation policy. We had an attendee cancel two weeks out. We were not prepared for a cancellation. We had already paid for all the hotel meals and arrangements. We did a refund, but next time we’ll have a policy that allows for a raincheck or a substitution, but not a cancellation. The policy will be promoted in all event marketing material.

If you are planning to create your own client retreat, understand that running such an event is a business unto itself. If you want it to be successful, it needs all the attention and commitment that goes into any business. Even though we fell short of our breakeven number, we were able to strengthen our relationships with current clients. We’ve also begun new relationships with some of the attendees. Overall, it was a transformational experience for the attendees, as well as for us. We are looking forward to building on our experience for our next event. 

General Financial Planning Principles