I’m a planner, always have been. I always like to know the things I’m trying to accomplish and be able to plan my time and resources to hit the mark. As part of that process, I find it helpful to look back at the previous year and see if I can spot some areas that worked really well and should be done again, or find some course corrections that might make me even better in the coming year. For no reason at all, last year I shared my findings in a post and it was one of the most popular of the year. In that spirit, I share my findings for 2024 for your reading pleasure!
The number one question I ask to start this process is: “Are you living on purpose?” and instead giving a gut feel response, I look at the data points I have to answer the question. Very often the answer is sobering and I have big changes to make. This year my purpose was far more internal than it ever has been, and while a part of me feels like maybe I didn’t achieve enough, it’s
Le't’s see what the numbers say this year:
In 2023, I scheduled 1,120 meetings hit my calendar and I kept 99.7% of them. I recognized a problem in reviewing those meetings and how exceedingly unproductive the vast majority of them were. In 2024 I cut my total number of meetings by 49%, scheduled 576 meetings, and kept 99.1% of them. My mantra for the year was “If it isn’t a hell yes, it’s a hell no.”
I wanted to be more intentional in giving my time to important things this year and I made an effort to say “no” far more than I said “yes.” It paid off. My year was just as impactful in hitting my goals, and most importantly I was freed up to invest in time with myself and my family during a difficult year of grief and recovery.
I was largely able to accomplish this by delegating some of those meetings that I would have been in to others on my team. The inability of some team members to take those meetings and handle them appropriately in my stead prompted me to really ask who was on my team, and why. I exited several them from my business and my life, and it has become a key hiring criteria for me now: “Can I trust that this person can stand in for me when I’m not available?” If the answer is “no,” then the answer is “no.’
I spent a ton of time working on myself this year.
I engaged a grief therapist and met with him every 2 weeks for an hour. I attended some personal retreats that were far outside of my comfort zone. I spent difficult time with my children as they navigated their own grief trying to model how we deal with the loss of those we love.
I recognize the value of investing in yourself, I always have. When I was younger it was about learning so that I could one day be earning. This is now shifting to a model of using the earning so that I’m not burning, but able to be returning.
I have another retreat on the books. I’m taking my wife to Champagne for 10 days. My 2 year old values time getting ice cream, going to the park, and eating breakfast so we are doing that 100 times this year. My other two kids have one-on-one trips with me and with their mom scheduled, too.
In 2024, I continued to cut my overnight travel night, from 172 in 2022, to 113 in 2023, and to 101 in 2024. Travel for work continued to be a thing last year, I just didn’t partake as much and tried to be very intentional on putting the time into things that took me away from home.
I was in Napa with some fellow investors for conference on startup investing. I made good contacts, caught up with old friends and made some new investments because of what I learned and changed my theses on some topics, as well.
I was at a Family Office event on Amelia Island in December and learned a good deal about how FOs are structuring new investments today in the fallout of returns from multi-family, storage and other assets that have been mainstays of portfolios for the last 10 years.
All of my work was work-from home in 2024, and while I loved it, I don’t think it sent the right message to my team, so in January of this year I returned to the office every day. I’m already amazed by how much more productive I am, and I’m already one of the most productive people I know.
My piloting time was abysmal in 2024, not even hitting 50 hours of time as Pilot in Command. This is nowhere near enough of to justify the cost of the plane and the privilege of owning it.
I flew to Austin, on to Napa, back through Vegas on one trip, and then did another trip to Austin and back. I hired a new safety pilot to be with me and he was a trooper. We developed a friendship and I was able to mentor him through a couple of challenges in his life.
Healthwise, I invested a ton of time and treasure to addressing the physical conditions that keep me from feeling good and living optimally. I did the Executive Program at Mayo, identified some challenges, and started a conservative medication protocol. I’ll go back again this year and address some dietary issues. I started the year at 182 pounds and finished at 190, that’s not where I want to be but I consider holding the line a win for last year.
I produced a new workbook called, What I Want You to Know, a compendium of 200+ questions for you to answer for your loved ones for them to have after you have gone. I presented this to 7 groups and received mad good feedback on how much it affected people and their teams. I coached 7 CEOs in the curriculum I’ve developed for my book, A CEO Only Does Three Things. I mapped out the basics of a video course which I hope to deploy this year. I also wrote three monographs to come alongside the book and focus on topics of specific interest to CEOs. They will publish in 2025.
I managed one portfolio company from failing to cashflow break even. I advised 2 companies on both the buy AND the sell side this year, very interesting deals. I sold 3 major commercial real estate positions last year, funneled the cash largely into the public market, but reserved enough to make 18 investments, far down from the 100+ I made in 2023, and the 60+ I made in 2024. I wrote bigger checks and made bets on companies that I thought were truly innovative and would make a difference in the world and in our bank accounts. I placed several million dollars in high-coupon debt on the books with people, I know, like and trust.
I dealt with the aftermath of hurricane and subsequent weather events for most of Q4 and we are still digging out and dealing with insurance companies. The whole process is an embarrassment for an economy as sophisticated as ours and the behavior of some of these insurers and the total mids they employ is laughable. We sustained easily over $1.5m worth of damage and have collected less than $200k in benefit so far.
I was invited to speak again at MIT and a Family Office conference and will continue to take these as they become available. I spoke for a group of real estate investors in Orlando, and had several smaller online speaking engagements.
I was the Professor for a Day for our local University’s business school and chaperoned a group of students to New York City and the NYSE for their first trips to the City and my first time on the trading floor!
I read 49 books (far below my average of 100), listened to about 200 or so podcasts, wrote a kinda weekly newsletter, attended 2 masterminds.
I entered into a protracted legal fight with my local city government and the officials (both elected and appointed). The level of cowardice, grandstanding and ineptitude is not something I was prepared for. It’s the kind of thing where it constantly looks (and sometimes feels) like you’re losing, but I know things they don’t know and the win is guaranteed. There will be way more on this in 2025.
I made sure to host as many family dinners as we could throughout the year on Sunday evenings. We invited my in-laws and my mother’s boyfriend to be together, watch some sports, and just have some time to fellowship with one another. My older two are teenagers and they suck but even watching them suck is part of the privilege of being their dad.
I’m a busy person and I respect the time of busy people. I’m an intentional person and I respect when others live their lives that way, too. This exercise brings me back to lots of lessons and the way I spent the year feels to me like a B.
“Behind mountains are more mountains.”
—Haitian Proverb
Did I get it all done? No, there were things that I missed that I would have like to have experienced.
I turned 50 last year and wanted to do 5 amazing things to celebrate my entry in the third phase of my life. I did one of them, tried on some others but couldn’t do them all because I wanted to stay closer to home and adjust my focus for the year.
I didn’t intentionally spend time with friends as much as I wanted to. I have some really good friends that I never see, and only communicate with through text messaging. I should have made that more of a priority throughout the year.
Sheya and I had zero time together this year, living largely as roommates as the toddler and the teens wore us out. We’ve made a new commitment to remember to enjoy each other this year, and have started out well already.
“The Universe doesn’t want you to try harder. It wants you to breathe.”
These are data points. The point in looking at them is to ask are they trends, do they point to something larger? The story this data tells me is about a man who was treading water, doing his best to stay afloat and keep his family afloat while fighting the good fight on causes he believed in. Did he always get it right? Hell no, but he learned to listen to himself last year and that’s more of a victory than he expected.
I want a deepening this year. I want less clutter and more empowered people to ornament my life. I want to mentor more, love more, and find grace and acceptance for others. For me, to balance this against an ability to achieve that is higher than most people I know, is a challenge. But it’s the one I seek in 2025.
Be well and have a great 2025!
I love watching you evolve and your willingness to share the journey.