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Not Another Holiday Checklist!

December 21, 2022

2022, or as I like to refer to it, “the year of three two's,” is finally coming to a close. Families across the world are getting together to celebrate the holidays, which means that the final scramble to finish shopping and wrap presents is officially underway. For me, this time of the year is my favorite “to slow down to speed up.” One way I do so is by taking some personal time to check in with my wife and myself on our life compass and reevaluate how our finances are underwriting that journey.
Over the years, I have refined and reduced this process using Occam's Razor. It has transformed from over-the-top complicated, with charts and graphs that quantified satisfaction levels using a multi-factor scoring methodology (not kidding, unfortunately), to a very simple framework. The dream scenario is that it is so simple that anyone in high school and above can apply it, and yet meaningful enough that the wisest and experienced can find it useful.

The process is a relatively simple exercise that includes six steps but is valuable as it can uncover incorrect assumptions, biases even, that can act as a blindspot in our vision. In fact, the reason I am sharing this is that I incorrectly assumed that most people have a framework like this of their own. When talking to a few friends, I found that I was sharing this framework with them for the first time, which means that it might bring value to you, or someone you get to visit with over the holiday season. Here it is…

1. Write out what you value and how you prioritize them: Understanding what is most important to you is the critical foundation for the rest of this exercise. Here is what I recommend as a prompt: what are the three most important values to you right now? How do you prioritize those values with the time, money, energy, and talent that you have? For me, I can say that being healthy, having a thriving family, and having a career that I am passionate about are three values that are top of my list. How am I prioritizing my time, money, energy, and talent in those three areas? What would the optimal balance between them look like? How does that compare to my wife's list? These are all questions to ask during this phase of the process. Again, write all of this down. Saying it in your head is simple; writing out your values and prioritizing them, however, can be a much more complicated, illuminating, and refreshing process than you might imagine it to be. Pro tip: I highly recommend that you and your significant other do this separately, and then after you are both done, share what you wrote down. It's a great way to learn about each other's perspectives and ensure that both of you are being considered before any further steps are taken.

Pro tip: I highly recommend that you and your significant other do this separately, and then after you are both done, share what you wrote down. It’s a great way to learn about each other’s perspectives and ensure that both of you are being considered before any further steps are taken.

2. Set goals and track them: In business, the best leaders have key results and indicators of performance that act as a scorecard for how well they are tracking their targets. In life, the same is true about the best leaders of their personal lives. Now that you have built out your value and priority framework, how will you measure the success of those things? What is the outcome you are seeking to achieve? Using myself as an example again, the questions I need to answer are what a successful outcome for my health, family, and career look like in 2023? Be specific and create goals that are somewhere between audacious and realistic that you can measure. For example, I want to get rid of the three big processed foods that I eat from my diet (chips, chips, and chips), visit four national parks this year with my family, etc.

3. Build your roadmap: Goals are nothing without a map to get there. If someone else had to convince you that your goals are attainable, how would they do so? What hypothesis and evidence would they need to present that you can get there? Use the SWOT analysis framework (strengths, weaknesses, opportunities, threats) to help guide you in this stage.

4. Identify your team: When looking at your roadmap, what areas do you feel are kind of blurry and lack clarity? Where do you feel like you could use a second opinion or additional support? Where can you delegate to free up additional time to accomplish something that only you can accomplish for yourself? Now is the time to write out your roster of talent to recruit alongside you. For me, I would like to hire a personal trainer this year as I have been in a rut doing the same workout routines. I’d also like to find a specific charity for a specific cause I would like to donate. For others, it might be to seek a dietician, a therapist, or a business coach. Almost every successful and happy person I know is a firm believer in delegating to subject matter experts in areas that are not their core competencies. In finance, your roster of subject matter experts is typically going to be your financial advisor (build wealth), estate planner (protect your legacy), and accountant (do it efficiently). Having your roadmap will make the best use of your time with your team member(s).

5. Follow your compass: Having a map is great, but life does not go to plan. I know this very well as I grieved the unexpected loss of a close friend this year. We can plan all we want and have a roadmap to get there, but sometimes life has other plans. It’s key to remember not to hold these plans tightly (which is why I like to keep it simple) but to take a flexible approach to how you might become where you want to go. Do not create a plan that has so many rules baked in that if you violate them, the whole thing crumbles. Add some cushion for the unknown that allows you to become stronger during moments of uncertainty. That is the entire premise of the book Antifragileby Nassim Taleb.

6. Celebrate your wins: A friend of mine wrote a thoughtful response to me the other day. It was compassionate and brutal in that after he thanked me for the impact I have had on his success, he finished with “give yourself some credit.” I’ll be honest; I do not take inventory of my wins as often as I should and can do a much better job of this. However, when I visit my roadmap for the year, I quickly remember how much effort was put into achieving my personal goals with precision and clarity. Further, I can help others acknowledge their wins by expressing gratitude and articulating my perspective of how amazing they are and why I am so fortunate to have them in my life.

Once this is done the first time, you can keep a running document that compiles all prior year’s planning. The key is to not look at that document until after you have created this year’s version. The reason I believe that is important is that you want to see the authentic contrast between the years. Peeking at prior entries can contaminate thoughts and shift how you respond to these prompts.

What Does This Mean to Me?

My hope is that this is a useful framework or reference point on how someone could go about planning for their personal growth in the new year. It can be something that is implemented yourself or used as a reference point during a conversation about living a purposeful life with a loved one during the holidays. In the words of James Clear in his excellent book Atomic Habits, “every action you take is a vote for the type of person you wish to become.” Keep voting for that person through the framework you outlined above, and eventually, the compound effects may take you to places you could never have dreamed of!