My 2020 Retrospective (& 2021 Action Plan)


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A one-hour exercise to help you celebrate your biggest wins, identify your biggest opportunities, and dominate the new year.

Where does one begin when writing about 2020? Coronavirus, the election, masks, racism, riots, Bitcoin ⏤ the options are endless. But I don’t want to talk about any of that stuff. (I’ll leave that to thousands of other blogs.)

I want to talk about what’s controllable.

And this personal retrospective serves as a way to keep that organized and action-oriented. Plus, it’s more helpful for you.

I started this exercise with my 2019 personal retrospective and I want to carry on the tradition since it served as a springboard into the new year.

Hopefully mine can encourage you to do the same.

What’s a retrospective?

A retrospective is when you look back on past events to identify what worked…and what didn’t work. A retrospective helps you celebrate your wins and identify your weaknesses. It helps you learn from the past and correct for the future.

How to do your own personal retrospective

To do a personal retrospective, you simply pick a particular project or time period and ask yourself the following questions:

  • QUESTION 1: What’s working? (“What did I do right? What am I proud of?”)
  • QUESTION 2: What’s not working? (“What could be improved? What are my biggest opportunities for growth?”)
  • QUESTION 3: How can I fix what’s not working for a better result? (“What specific things can I focus on next time?”)

Then you spend 15-30 minutes writing about each.

My 2020 Retrospective

QUESTION 1: What’s working? (“What did I do right? What am I proud of?”)


One thing I pride myself on is my internal locus of control. No matter what’s going on externally, I do my best to remain calm internally.

Which is fun to think, until it truly gets put to the test. Surprise⏤this year was that test.

After being born and raised in Kentucky for the last 26 years, I moved to NYC in August to live with my girlfriend Mal (and cat, Karl) while she attends law school in the city. Not to mention, in the middle of a pandemic.

Our first day in the city.

It’s by-far the most “adult” thing I’ve done. And I’d be lying if I said I was excited about the idea when Mal first brought it up to me.

But after hours of contemplation, I realized there was really only one thing holding me back from moving: fear.

  • I was scared of leaving my friends and family.
  • I was scared of living in a big city, nonetheless the biggest in the U.S.
  • I was scared of the expensive cost of living.
  • I was scared of the unknown because I couldn’t control it.

That security I felt from staying home was addicting. But it was also holding me back from a once-in-a-lifetime opportunity: to live in New York City with a girl I love.

And the question I kept asking myself was, “why not?”

So I moved. And after six months of living in the city, my internal locus of control feels stronger than ever.

Funny enough, I’m writing this at my parents’ house in Kentucky while I’m home for the holidays and I’m noticing… I actually miss New York.

Words I wouldn’t even think about uttering just a year ago.


  • It made me a better speaker. It’s forced me to collect my thoughts, speak slowly, and be concise when explaining ideas (instead of my normal word vomit filled with “um” and “like”).
  • It made me a better listener. There’s a weird “dance” to guiding conversations, but it becomes much easier when you shut your mouth and be genuinely curious.
  • It made me more self-aware. I’m constantly spouting things people should try to improve their lives, so I feel like a hypocrite if I’m not taking my own advice. It’s forced me to be my own role model and live up to what I preach.
  • It allowed me to connect with awesome people. The sole reason you should start a podcast is so you can have an excuse to chat with your role models for an hour and propose it as “content.”

==> Click here to subscribe: The More Than Fitness Podcast.


I made roughly the same amount of money in 2019 as I did in 2020. A touch less in 2020, if I’m being completely transparent.

But my total number of hours worked were probably cut in a third and total transactions made were down 41%. So, less work for about the same money. I’m cool with that, and I think it was a direct result of thinking more and doing less.

2020 was filled with deep reflection, planning, and strategizing on what direction I want to pursue in 2021. I’ve figured it out (for now), but I’d be lying if I said it didn’t make me anxious during the process.

I think one reason why is because I follow many ambitious and successful people. I text some of them regularly. As a by-product, I see them winning, even in a crazy year like 2020. My problem is that I can get sucked into admiring other people’s “amazing” lives, but forget to keep building my own.

The other problem is that I love learning new shit, which was the catalyst for finding direction for 2021, so that’s good. But information is only as good as the action you take after learning it.

And my lack of action⏤especially in these last few passive weeks of holidays⏤was producing a non-specific background hum of anxiety for me.

So, my point, is that 2021 will be getting back to my roots: doing the work. Checking the boxes. Day in and day out.

For me, 2021 = The Year of Intentional Action.

VV Pointless

via @visualizevalue

QUESTION 2: What’s not working? (“What could be improved? What are my biggest opportunities for growth?”)

I wanted to categorize this section between business, relationships, and health.


Leading up to 2020, a lot of my work could be described as “messy action.” I barely had a plan and I was shooting from the hip, hoping to hit something.

Like I mentioned earlier, 2020 was for recalibrating and reflecting on what was important to me. Then, to design a plan around my ideal daily schedule, how much money I want to make, and the type of work I want do.

In 2021, it’s time for me to execute. I’ve already noticed a subtle inverse correlation between my productivity going up and my anxiety going down.


  • Being present: I’ve noticed when I don’t get my work done on time, my relationship suffers. I’m thinking about work instead of giving my girlfriend the full attention she deserves. The end result is me feeling guilty about not finishing my work AND upsetting Mal.
  • Spending time with friends: Since I’ve been in KY for the holidays, I’ve shared some drinks and laughs with my best buds. It showed me how much I miss it and how important it is to keep that in-person connection. Damn you, COVID.
  • Connecting with smart people: I want to actively reach out and be helpful to people I look up to. Not only to build genuine relationships, but to make a bigger impact.


I’ve put fitness on the back burner for the last two years due to other priorities. In 2021, I’d like to be more structured and re-gain that spark of pushing myself physically.

When my fitness and health suffers, everything suffers.

DB Row

QUESTION 3: How can I fix what’s not working for a better result? (“What specific things can I focus on next time?”)


  • 5 hours of deep work per day, using a scoreboard. “Deep work” is 100% focused work without distractions. My scoreboard will be a sticky note on my laptop that resets each day.
  • Setting 90-day macro goals and 30-day milestones. This will push me to work towards deadlines and track progress more effectively.
  • Scheduling my tomorrow, today, based on priority. Before I end my day, I’ll schedule out my next day through time blocking what’s most important.
VV Manifest

I’ll use the Daily Manifest by Visualize Value for this.


  • Get my work done on time so I can be fully present after hours. Stop dicking around and be a professional.
  • Reach out to friends every two weeks. Ideally, this would be an in-person meetup.
  • Have a “connection” day once per week. I’ll reach out to followers, random check-ins with coaching clients, comment on friends’ posts, and send thoughtful messages to people I look up to.


  • Buy/Create a 4x/week workout plan. Probably an upper/lower split.
  • Train different energy systems. Low intensity, moderate intensity, and high intensity cardio, 1x per week.
  • Don’t eat like an asshole. More meat and veggies, less bullshit and drinking.

Write your own Personal Retrospective

OK, now you have an example of mine ⏤ it’s your turn.

Give yourself some time to think, reflect, and write. It should take roughly an hour, but you owe it to yourself⏤both past and future you⏤to take this seriously.

What went well? What could you improve to make 2021 as meaningful as you could possibly make it?

And the biggest question: what are you going to do about it?


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    This was freaking fire ? as always!

    • Matt McLeod

      Late reply, but thank you brother 🙂


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