A lot happens over the course of a year and think there is value in not only writing your goals down, but also reviewing them to hold yourself accountable…even if it is just to yourself since no one reads this blog.

I wrote my 2023 Goals and Objectives Post late on January 23, 2023 and as is my usual course of action I broke my life into various bite sized sections, however, my overarching goal was,

…this year, 2023, is about figuring out which port I am going to be sailing to for the next part of my life.

It may have taken until December, but the next professional chapter of my life has been decided. I don’t know if the chapter will 3 years, 10 years or 15 years, but at least I have removed some of the uncertainty…and for that I am grateful.

The bite sized chunks are:

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

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.

This took almost 365 days, but I now have my answer. I have also let the law side of my world know I am going to try and slow down. I give myself an A+ for accomplishing the biggest thing that was weighing on me.

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.

Success. I did absolutely nothing which includes not overacting. As to be expected the 401(k) came roaring back.

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).

Partial Success. I jumped from $50 to $55 and absolutely crushed it. In addition, I used almost all excess towards either ETFs or individual holdings. It took almost the entire year but I was able to clear out 66% of my assigned shares so I never got to a place where I would use excess for debt. I think this will change in 2024!

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.

Failure. Interest rates jacked up and all cash flow was simply sustaining the debt. Again, this is going to change early in 2024.

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.

Partial Success. We did travel as a family to Jamaica, and without the kids to the Keys. Both trips were amazing, but I did not put the work in like I wanted to.


  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).

Complete and utter fucking failure. No easier way to put it. I was not in bed earlier, I did not drink less and I certainly did not work out more.

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)

Partial Success. I don’t think I went as deep on the audit as I should have. I just didn’t, I need to go for bigger wins in 2024. Notwithstanding, I did pay off a lot of the 0% debt that was hampering cash flow. In addition, I tracked my automatic savings, although I didn’t do much with the information.


While I haven’t prepared my final net worth update, I think the successes and partial successes absolutely outweighed the failures when it comes to my finances. However, and it is a big however, my health absolutely suffered this year. This will have to change in 2024.