Writing & publishing this post on the 23rd day of the new year already means I let myself down. Time to step it up!

If a man knows not which port he sails, no wind is favorable.


When I had my old site I would write up very specific goals and objectives, and while I brought over my net worth updates I did not bring over those types of posts for some reason. Despite zero traffic, and no outside accountability I’d like to start that back up again for no one but myself.

I don’t do “resolutions” because resolutions are often vague promises to one’s self that no one keeps because they don’t build out a plan to get there. For example, “lose weight” is way different than “work out 3x a week” or “do not drink X amount of nights.” I know that it may seem like I am splitting hairs, but to me, there is a world of difference. Truthfully it is probably why people fail with their resolutions.

My process is fairly simple, first, I choose an overarching theme for the year. It usually has to do with a quote, idea or feeling I recently heard or felt. For me, the quote above from Seneca really hit home. For the past 18months or so, I have felt lost – financially and professionally. The only thing that has kept me grounded is family. As such, this year, 2023, is about figuring out which port I am going to be sailing to for the next part of my life.

The second step is categorizing my life into bite-sized chunks for me to apply my goals and objectives for the upcoming year.

My current categories are:

  1. Professional Career & Law Practice
  2. Investments
  3. Real Estate
  4. Personal Life & Family
  5. Personal Finance

My 2023 Goals and Objectives

Professional Career / Law Practice

This is where I have been the most “lost.” This year is going to be a massive year for my professional life. I have been with the same financial planning firm for 16 years, but there are changes happening. The two partners are slowing down and plan on retiring in the middle of next year. This leaves me at a crossroads for the first time in a decade and a half! Despite throwing my hat into the ring I don’t think I am part of the succession plan with regard to ownership.

Over many conversations (and drinks) The Wife and I came up with the following plan:

  1. Understand the ins and outs of a standing offer to join a law firm and head up their Trust and Estates practice.
  2. With that information, I plan on approaching the partners to have a discussion about my current compensation package.
  3. After everything is on the table make a decision.

It feels weak to say, “let’s just wait to say where I land.” I have three actionable items that would help my family and I regardless of where I land:

The first is that I need to read more about the ongoings of my chosen area of planning and the law. I am sure it happens to all professionals, but you get so busy putting out fires and preparing projects/documents I have completely failed to keep on even the simplest of trade magazines. I want to set a side, and calendar 15 to 30mins a week to just read.

The second item that has fallen off is networking. With two young kids and 2 full time jobs it has been hard for me to simply network. That is unacceptable. My goal is to get back into my networking group of which I was once on the board!

The last item is to schedule one hour a week to work on my businesses rather in the businesses. That means working, again, calendaring time to work on getting myself more productive, more efficient or even building future clients.

Notwithstanding, when I know a little bit more about my future I may want to revisit this section.

Investing Goals

Qualified / Retirement Accounts – To say this account has been frustrating would be an understatement. The account is lower than it was 18 months or so ago despite 18 months of contributions! I know at 41 that is a good thing, but for someone who checks it monthly, it is super annoying. My goal for these accounts is to do nothing. I know this may seem like a non-goal, but doing nothing is often harder than doing something.

Non-Qualified Investment Account – My dividend growth portfolio funded by naked puts is easily my favorite financial asset. It is my hope that one day I can turn off dividend reinvestments and have another stream of income. My goal for this year is to make another jump in my daily naked put goal. In 2022 I went from a goal of $30/day to $40/day, in 2023 it is my hope that I can go from $50/day to $65/day. In addition, I would like to use 70 to 80% of all cleared cash to buy dividend etfs this year. Once my assigned shares are paid back I am going to use the rest of the proceeds of these transactions to pay back some long term variable debt (HELOC outlined below).

Real Estate

Currently, I rent out my old home. I am constantly looking at zillow and other sites for opportunities but with current interest rates and the unknowns with my main job I can’t imagine any acquisitions occurring in 2023. As alluded to above I would like to attack some long term debt with some of my trading profits.

Personal Life

Family Life

I am happily married with a 12-year-old and 8 year old. Regardless of any of the above categories spending time with them is the most important thing to me. Any decisions I make in the above categories always puts them first. I am acutely aware that they are getting older, and spending as much as time as I can with them is important.

For my family I have two main goals, both have to do with travel

First, I would like to help my wife plan our family trip although she does 99.99% of the work. Thus far this year, I have been negative on the idea of a large trip as I am trying to figure out my job but as I write this that seems short sighted.

The second is that I would like to plan a trip for my 15-year anniversary without kids. Obviously this takes more planning, but after the first one is booked I will start on number 2.


In addition, I am obviously a better father and husband if I am healthy/healthier. Here I have three goals:

  1. It is so damn easy – I need to get to bed earlier. On nights where I am just BSing around the house I am to be in bed by 12am at the latest.
  2. I’d like to drink a bit less, and the easiest way to do that is to slow down mid-week drinks. So those weeknights that I am not out I am going to limit myself to one drink (if anyone) with lots of ice. Whether it is good or bad, I have found that it is the act/ritual of the drink that is a driver, so I figure if I just load up the glass with ice I’ll be sipping for a lot longer. This paragraph may sound absolutely crazy for those that don’t drink but I know this 1% change could have a dramatic affect on my health.
  3. I have to figure out a workout routine/schedule that works for me. Growing up I always lifted weights, but that eventually turned into crossfit then peloton then running outside/gym workouts. Nonetheless, I have zero routine and I hate it. I think a set amount of runs mixed in with WODs will do just fine, I just need to create more of a schedule (2x – 3x a week).

Personal Finance

I have been disconnected for quite some time with my personal finances focusing on working, earning and investing and hoping everything else takes care of itself. This is the opposite of my view years and years ago and I’d like to shift a little bit back towards that way. So I have a few actionable items to help.

  1. Audit all my reoccurring monthly services. I have zero clue what is going out on a monthly basis for services. I have always found it easier to have that stuff optimized so it can be ignored. Sooner, rather than later, I will create a post to keep myself accountable.
  2. Audit all my monthly debt repayment. I loved/love 0% financing but I am at the point where I have no clue what is going out anymore and that is terrifying. It may be better use to pay off some of that debt (even at 0%) to get my monthly payment back and then reapply it somewhere else. Again, a post is needed.
  3. Audit all my automatic savings transfers. Currently, I have a ton of money going to a ton of different accounts. I need to get a handle on these transfers to determine if there is a more efficient strategy (especially taking into account the previous two audits).

These three items, when compounded, will not only make me feel better, but will save me cash month over month, year over year.