Our first annual Millennial Planners Retreat was a huge success; its success was the result of significant preparation and some smart planning.

The experience was so influential that we decided to share some of our time together with the rest of the Millennial Planners community in hopes that we can inspire you to do something similar one day.

For the first time ever all four of our group members were in the same region of the country, and we took full advantage of our close proximity. We should disclose that the idea of a retreat was adopted from an idea we took from Michael Kitces - you can learn more here. We took the idea and ran with it.

Designing the Retreat

First, we knew we needed to separate ourselves from the hustle and bustle of the big city of San Francisco. Fortunately for us, being located in the Bay Area we were able to find an Airbnb available in the nearby beach town of Half Moon Bay - besides the idea for a retreat in the first place, that was our first good decision.

From there we needed to craft one full day that would tackle everything we could want from a "Retreat."

Early Morning - Private Time

Our group is largely comprised of morning people so we knew that private quiet time was essential for the early morning hours - this time was spent with walks and jogs along the beach, reading, and for some, study time for the CFP® examination. This time was very important to the success of the day, as it allowed us to clear our minds and prepare for the conversations that followed.

After private morning hours, a solid breakfast brought us to the dining room table for some light conversation, along with our first round of (strong) coffee.

Late Morning - First Group Sessions

Besides the great idea to hold the Retreat in a beautiful beach town in Northern California, the next best idea was the breakout sessions we held - this served to be the bread and butter of the entire experience.

There were a couple tricky parts to designing the group sessions, the most important of which being: "What are we going to talk about?"

Luckily, we have some thoughtful guys and decided to let each member have their own time slot that they were in charge of leading. Since our personal attention spans are only so large, everyone was given around one hour on their session topic. The topics themselves were completely up the individual in charge and they were free to run it however they wanted. We used a Google Doc to share what each of us were planning on talking about in our group session - this helped everyone get a sense of what the topics were ahead of time and also prevented any overlap in topics.

After breakfast, we were ready to jump into the meat and potatoes. Joe volunteered to get the sessions started.

Joe's Session

The first session focused on the qualitative side of financial planning. Specifically, the use of stories, analogies, and the ability to communicate complex ideas in simple terms. The conclusion we reached was that mastering this requires deliberate engagement with others in conversation. One has to step outside their comfort zone and practice, having as many conversations early on as possible. A potential way to begin might be with family members or close friends. Author Edward Hess writes the following:

We develop efficient and effective learning skills through practice, practice, and more practice. Learning well is not done carelessly. Learnings skills are improved through intentional practice with contemporaneous feedback that focuses on improving specific weaknesses. We have to learn “how” to learn.

Is it possible to become an expert in conversation at a young age? Not if one remains in his or her comfort zone. Only through deliberate practice can one expedite what otherwise only comes with experience. However, what can be viewed as an obstacle can often also be turned into an opportunity. As Reid Hoffman writes in The Start-up of You, “You may not see inexperience as an asset to highlight, but the flip side of inexperience tends to be energy, enthusiasm, and a willingness to work and hustle in order to learn.” Overall, we reasoned that a millennial that harnesses the strengths of youthfulness, such as technology skills and an eagerness to learn, and who also regularly engages others in conversation to practice communication will find themselves with an abundance of possibilities sooner rather than later.

Regan's Session

The second session consisted of imagining our group and individual circumstances one, five, and ten years in the future. We then went around and each discussed what we had brainstormed. Thinking outside the box was encouraged. Lastly, we reflected on our past and answered the question, "what was the one big experience that changed the framework from which we view the future?" This last question in particular was very interesting because all four of us have significantly different backgrounds, which have affected the way we view our career. One of the potential mistakes to be wary of when forming a study groups is collaborating with people that are too similar.

Within Millennial Planners, some of us went to very large schools and some of us went to very small schools, some of us are very extroverted and some of us are introverted, some of us grew up in a very rural setting and some of us grew up in a more urban setting. Point being, a difference of opinion is a good thing when brainstorming. Overall, this session was very reflective and got us all thinking deeply.

Lunch and Beach Therapy

Just like exercise, thinking requires a periodic break. A few of us grabbed some groceries and we had lunch. Then we headed down to the water to enjoy the weather and view. This refreshed us so we were ready to go for the two remaining afternoon sessions.

Early Afternoon - Final Group Sessions

Bryan's Session

“Don't underestimate how much you like going to work. It should be worth giving up part of your salary to stay there.” - Anonymous Millennial Planner

After taking a break to eat lunch and walk down to the beach, everyone filled up on caffeine to resume the afternoon sessions.

The first afternoon session focused on work satisfaction and what it takes to build an environment that everyone can succeed in. A few minutes into the session, one of our group members said something profound and is quoted above. Since we spend a majority of our waking hours either at work or thinking about work, we should not only like it, but we should also know why we like it.

As our careers and aspirations continue to grow, the ultimate goal for some of us will be to create a workplace that could attract the best talent, keep everyone happy, and produce the best work for our future clients. Our group was a lot of fun to have these conversations with, as we all come from different backgrounds and continue to work in different office environments.

Since the financial planning industry is so young, we fully grasp that our opportunities as young professionals are different than the careers of some of our friends. For instance, in this industry, a 30-person financial planning firm is considered to be "huge." On the other side of the spectrum, several of our friends and colleagues work at 2-person shops that operate more like "start-ups." No matter which path a young planner should choose, there is room for all personality types and the potential upside is tremendous.

Luke's Session

The fourth and final session consisted of brainstorming on how to field challenging questions from clients. Several common scenarios were presented and as a group we walked through how best to approach the client’s concerns. As with all the sessions, certain takeaways from one were applicable to the others. This was true for this session in particular.

The majority of the block was spent thinking on how to blend the technical details with an empathetic message. We concluded that in challenging rather than trying to convince someone or change their mind, it is usually preferable to walk them through it with examples or stories. In the book Mindwise, Nicholas Epley writes, “Arguably, your brain’s greatest skill is its ability to think about the minds of others in order to understand them better.” One has to put themselves in the other person’s shoes so to speak. Overall, it was session with a high degree of collaboration, and we talked through several answers together.

Evening Fun - Drinks, Dinner, and A Few More Drinks

After a long day of discussion and thinking, we had a few drinks and went to a local restaurant for dinner. As Tim Ferriss notes, “alternating periods of activity and rest is necessary to survive, let alone thrive. Capacity, interest, and mental endurance all wax and wane. Plan accordingly.” While the sessions were certainly productive, the evening was candid and fun.

After a few beers and some wine, we had dinner and saw what Half Moon Bay had to offer. This was a nice way to wind down the day, while also having a bit of fun at a bar or two after dinner.

Reflection

Each of the four sessions were very reflective. Rather than trying to cram too much into one day, we tried to have a deliberate and focused day. As Phil Race, psychologist, professor and learning specialist said: "The act of reflecting is one that causes us to make sense of what we’ve learned, why we learned it, and how that particular increment of learning took place. Moreover, reflection is about linking one increment of learning to the wider perspective of learning – heading towards seeing the bigger picture."

We live in a world where there is always an emphasis to do more. However, one of the reasons we decided to meet for this weekend in Half Moon Bay was to be a bit more secluded to help with deep reflective thought.

One for the Books

From left to right: Joe, Luke, Bryan, Regan

Our group, Millennial Planners, has been in existence for over one year. After numerous phone calls, group video chats, and regular messaging over several mediums, we decided it was time to get together in person. While technology has drastically improved communication capabilities, there are some things that can only be accomplished in person. In addition, it was fun to relax and have a few drinks with friends within the industry. Not only was the retreat valuable from a professional point of view, it was also valuable for our friendships with each other.

Ultimately, our group members have a deep trust with one another to the point where we would gladly appoint another member to be our own financial advisor. While there are plenty of textbooks and discussions about the quantitative side of this business, it is the qualitative side and similar personal circumstances that keeps it all together.

Our similar life stages brought us together over a common bond, but the empathy, trust, and core values that we share will hold our group together for many years to come.

MP