This post is a review of my 2021 goals and a public sharing of 2022 goals.

Why bother with this exercise? The Bill Gates quote sums it up:

“Most people overestimate what they can do in one year and underestimate what they can do in ten years.”

In other words, we’re capable of great things. They just take longer than we think.

The best way to stay on that 10-year road? Break it down into years. Then break those years into months, months to weeks, weeks to days…

Then as Elena Verna has said, days into hours:

“It isn’t about balance, it’s about prioritization. Becoming a parent makes you optimize every minute of your day. You become superhuman in prioritization. You have to prioritize on a weekly, daily, even hourly basis.”

My process for annual planning takes two weeks, in small increments. What it looks like:

1. Review last year’s plan. I review my notes on Roam and Twitter. These are organized into six buckets: Long-term projects, Career, Relationships, Health, Finances, and Leisure. For each bucket, I think about: (1) What went well (2) What could be improved.

2. Review the year. I review the year. This is an informal stroll down memory lane, done sporadically throughout the month. So many of life’s most brilliant moments are disguised in the ordinary day-to-day. In the aggregate, they paint a textured canvas of your life.

Most of this exploration is pure nostalgia. There’s little actionable that comes from it, but it’s a terrific emotional capstone to the year. How I do it:

  • Review photos on my phone
  • Review Google photos
  • Review Swarm check-ins
  • Review Instagram feed and Stories
  • Review my calendar

3. Plan the next year. I review notes about (1) my long-term goals and (2) my Perfect Tuesday. These are my North Star metrics as I plan what I want to accomplish in the new year; if it doesn’t ladder up then the goal should be cut.

Sticking to the same six buckets, I’ll write out goals for each one. This year, I’m borrowing Calvin Russer’s OKR process (objective and key results)[efn_note]I’ve gone full tech bruh, obvi[/efn_note]. More on that below.

Lastly, I keep two ideas in the back of my mind:

“Plans are worthless, but planning is everything.” – Dwight D. Eisenhower

And…

“Goals are for losers. That’s literally true most of the time. For example, if your goal is to lose ten pounds, you will spend every moment until you reach the goal—if you reach it at all—feeling as if you were short of your goal. In other words, goal-oriented people exist in a state of nearly continuous failure that they hope will be temporary. That feeling wears on you. In time, it becomes heavy and uncomfortable. It might even drive you out of the game.” – Scott Adams 

Goal setting is reflecting on who you want to be and what you want your life to look like. Your plan measures your progress against this aspiration. 

The plan will evolve.

You’re not beholden to it. You are not your plan. Your progress is not an evaluation of yourself or a reflection of your self-worth.

Okay, let’s dive in

2021 Annual Review

At the top of my notes, I summarized my goals for 2021: I accomplished 5 out of 6:

2021 Goals

  • We moved to Dublin, Ireland
  • I delivered an online course my first consulting gig
  • I started a new role
  • We invested +20% over this target goal
  • I published 12 articles this year (including this one)

“Distribution” was a miss. The goal was to build consistency in publishing across two channels: email and Twitter.

Next, I’ll dive into each bucket.

Long-term projects

What is this?

This bucket sums up my “side projects” to build an audience and reach Money and Business system goals. It’s in desperate need of renaming.

What went well

Completed my first online course as a consultant. CEO of Byte-by-byte Sam Gavis-Hughson and I built our first iteration of the Career Developer Program, a course to help software engineers manage their careers.

Working with Sam shaped how I think about course creation, course experimentation, and online education as a whole.

My major takeaway: it’s not the money, it’s knowing you can get the money. Creating the infrastructure to generate additional income is the win – getting paid atop of it was just the sweetener.

Writing and publishing articles/the newsletter. Big surprise during the review: I hit the goal of publishing 12 blog posts and 14 newsletters (including this one). I thought I whiffed hard here. With some stability and process improvements, I’m excited about what I can get done in 2022.

Technical site clean-up. I hired a freelancer to help me clean up my site: fixing permalinks, setting up redirects, and page speed optimization. I’m glad I hired this out versus spending 15 hours doing it myself.

What can I improve?

Focus on blog and newsletter growth. My site traffic peaked about 2 years ago and has declined since.

Blog Tracking

The Connection also stopped growing.

There are a few factors but the main ones are (1) inactivity and (2) lack of measurement, and therefore, management.

Fix my publishing processes. Two years ago, these processes were well documented and I handed them off to a VA to help me publish on time. Then I stopped publishing and the processes changed. I need to re-examine the processes, re-document, and find new VA’s to work with.

Twitter consistency. This year was an improvement over last, but I’m still inconsistent. I’ll go a few weeks of engaging every day, then I’ll get busy and forget about it. It still doesn’t feel “natural” to me but I want to continue investing in this channel.

Career

What went well

Reforge launched 10 cohorts simultaneously. When I first joined Reforge, we asked: could we simultaneously lead 2 cohorts? We agreed two was doable, but three would probably break everything.

This year, we launched 10 cohorts in a single session.

My takeaway: be more audacious.

Seamless transition to a new job. After four years I left Reforge. “It was like watching a masterclass in finding a new job,” Amy said.

Started a new job at Noom. In many ways, Noom is exactly as billed: a mission I’m passionate about, with a strong education component, lots of users, and still feels like a startup. It’s an environment where I can make low-cost mistakes, perfect for fast learning.

What can I improve?

Play to my strengths more. I struggled with navigating a larger company size and not having a deep analytical skillset. I spent the first 6 months shoring up these weaknesses and have not played to my strengths, like creating content or developing relationships.

Create time for deep work again. At some point during the 2020 lockdown, my work gears got stuck in “go fast to go fast” mode. With no childcare and no socializing, every day was a sprint. I stopped doing deep work, and focused on replying to Slacks, emails, and comments as fast as possible.

When normal life returned, I never recalibrated.

A lot of PM work is slowing down, mulling over problems, and scoping problems. I need to “remember” how to do that again.

Relationships

What is this?

I divide Relationships into two buckets: (1) family and (2) personal and professional relationships.

What went well?

My family. This starts with my relationship with Amy. It’s hard to take credit for this because we don’t “work” on our relationship. It’s incredible luck that we found one another.

What I love most is her audacity. A common pattern you see is people starting to accept smaller versions of their dreams (I put myself firmly in this category). Amy pushes us to think bigger and bolder about our future as a family: what we’ll do, experience, and create together.

My takeaway: ask yourself every day, “are we on the same team?” If the answer is no, start fixing it or start getting out.

We’ve never codified them, but Amy and I have always been aligned on our principles (the details are up for debate). A few, in no particular order:

  • Never be disrespectful
  • Tell people you love them
  • Assume good intent
  • Judge others by their Love Language
  • Be a parent, not a friend

Being a dad. With parenting, so much of the narrative revolves around what I call “expected frustrations:” tantrums, sleepless nights, goddamnit please eat the food I put in front of you.

No one talks about the unexpected delights kids bring to an otherwise mundane day, like teaching Oliver to read his first words, helping Annabel put on her shoes, or watching them play together.

What can I improve?

Document more. Via video, photos, and the written word. For example, I used to cut a video every day, and write emails to the kids to read someday. I stopped during lockdown.

Socialize more. Meeting new people and organizing get-togethers used to be some of my favorite things. This slipped since having kids, moving to the suburbs, and the pandemic.

Health

What is this?

Health is the combination of nutrition, fitness, and sleep.

What went well?

Awareness of my metabolic health. In other words, I’m noticing the effect of food on my energy. I feel exhausted after meals. I nap after breakfast and lunch.

One tweak that’s helped: eating an extra-large (1,400 calories) breakfast, skipping lunch, then eating a late dinner.

Working with a trainer again. This was the big reason I hit PRs on the squat (300lbs), bench (225lbs), and deadlift (300lbs). Squat and deadlift I could have done more but I ran out of weights.

Restarted training martial arts. One of the first things I did after moving to Dublin was restarting BJJ and striking classes.

Tracking my sleep. I’ve been using the Withings Sleep Tracker Mat to track sleep and build better routines. Now I track this on the Withings app. Here’s a typical week:

Sleep Tracking

What can I improve? 

Stricter tracking. The stricter my tracking — with calories, workouts, and sleep — the more success I have. I have good baseline habits (except for sleep). To get to the next level, however, I need to track daily.

Increase the intensity. I love working with a trainer because I’m awful at pushing myself. I’m happy to quit at 8 reps when a workout calls for 10. I do the same thing when rolling (sparring in BJJ); my mind quits. As a baseline, this is “fine”. But to reach the next level, I need to increase my training intensity.

Personal finances

What is this? 

I used to focus on tracking my net worth, but this has evolved. Today, it’s my progress towards my money and business system goals.

What went well?

Having “enough.” Before the move to Ireland, Amy took a work break. We moved, got set up (daycare, furniture, rebought everything), and continued saving. We never felt a pinch on our finances. Life continued as normal. We have enough. How reassuring.

What can I improve?

Understanding of taxes for expats. How taxes work here is still nebulous to me and I need baseline proficiency this year.

Maintain a 20% savings rate. First, this funds an emergency fund: 6 months of expenses. After that, it should automatically invest in the market.

Avoid new consulting jobs. These sporadically fall into my lap and I’m always tempted to say yes. Instead, I need to decline so I can focus on long-term projects.

Leisure

What is this?

If I don’t actively plan my downtime, I’m guilty of filling it with work or random YouTube surfing (don’t mind the former, loathe the latter).

But I have no interest in picking up a hobby for the sake of it, either. Brewing beer or learning the guitar holds no appeal. I much prefer going to BJJ class and working on projects.

What went well?

Started a regular online poker game. I hosted a weekly online poker game for my friends. A bunch of them told me it was the only thing they had to look forward to during lockdown.

Made the most of the summer. In Albany, every nice summer day was spent in the pool. An absolute highlight this year: seeing how much Oliver and Annabel loved swimming.

Restarted movies and books. I mostly stopped watching television shows. Television leads me to binge-watching. This leads to shitty sleep, which leads to shitty days. Instead, I started watching a movie on the weekend and reading books a night. Reading again is a joy.

What can I improve? 

Leisure time with others. This falls under “relationships” as well. I want to re-start regular get-togethers: monthly drinks, poker games, and board game nights.

Being deliberate with leisure time. On average I spend 100 minutes a week on YouTube, watching clips of The Sopranos, Justified, or Letterkenny. I don’t know why. I want to divert aimless leisure to intentional leisure, e.g. time with others, movies, and books.

2022 Planning

For Q1 2022 I’m focused on Long-term projects, Career, and Relationships. For 2022 planning I’ve broken these down into OKRs: a high-level objective and key results. I’ll also share 2-3 actions I’m taking to drive the key result.

Long-term projects

Objective: Build an audience in 2022 > create online products in 2023 > generate 51% of my income comes as a creator in 2024.

KR: Improve publishing consistency by automating/delegating 75% of the publishing process.

  • How: Update and record all publishing processes (written and video)
  • How: Build out these processes into a central database (e.g. Notion)
  • How: Hire a freelancer I can delete these processes to

KR: Grow blog traffic from 800 sessions/wk to 1,600 sessions/wk

  • How: Publish an SEO-informed blog post or newsletter 2x per month
  • How: Automate sharing of every post on Twitter, LinkedIn, Facebook
  • How: Update & refresh 1 top-performing blog post per month

KR: Grow newsletter subscribers from 1,000 subscribers to 1,500 subscribers

  • How: Create and test one lead magnet

KR: Grow Twitter from 400 followers to 1000 followers

  • How: Publish on Twitter daily
  • How: Retweet with comment daily

To measure key results and keep me accountable, I’ll track results across this dashboard and share them monthly on Twitter.

Dashboard

Career

Objective: (1) Strengthen my application of behavioral and user psychology in growth/product (2) reach a baseline data analysis skill level in 2022 –> Found or join an early-stage education-focused company in 2024

  • KR: Ship 12 experiments in Q1
  • KR: Define and apply one behavioral or user psych principle in every experiment
  • KR: Spend 2 hours on data analysis per week and get feedback from one data scientist

Relationships

Objective: (1) Build relationships with others in the Irish/European technology scene and (2) Build relationships with people living in my apartment community.

These feel daunting considering the state of Covid-19. However, I’m inspired by Brianne Kimmel (founder at Worklife Ventures). Brianne built her network when she was at ZenDesk by throwing dinners and events. I also think that the fact this is so hard right now is exactly what makes it valuable.

  • KR: Host one 10+ person tech meetup in Q1
  • KR: Host 2 poker games and 2 board game nights in Q1

Health

Objective: (1) Weightlift 3x per week, focusing on bodybuilding workouts (high intensity, low weight, high reps) and (2) Go to class 3x per week (BJJ 2x, striking 1x)

Not using PRs or bodyweight as the key result is new to me. I’m also not interested in competing or ramping up training specifically to reach the next belt, either. So focusing on the number of workouts per week plus visually tracking progress seem like the right key results (but open to feedback)

  • KR: Visual indicators of muscle growth in Q1

Personal finances

Objective: Make progress against Money and Business system targets

For someone who meticulously tracks their finances, that’s admittedly ambiguous. I’ve noticed two trends over the years:

First, jumps in net worth no longer make me happier or improve my quality of life. We have good habits and we have guardrails to mind lifestyle creep. Most importantly, we have enough.

Second, optimizing my spending to eke out another point on my savings rate is a weak input to reach my targets. Higher leverage inputs are building an audience for my blog and advancing in my career.

  • KR: Maintain 20-25% savings rate

Leisure

Objective: (1) Have regular in-person social time with friends & family and (2) Travel Europe

As mentioned, my hobbies are writing and training. What fills my cup is validation from online strangers, coffee shops, and working on my submissions. What doesn’t: nature, video games, brewing beer.

With that said, I am excited to host small events get-togethers and take advantage of our time in Europe by traveling. Much of this depends on the state of Covid-19 in 2022.

  • KR: Host 2 poker games and 2 board game nights in Q1
  • KR: Travel: Barcelona, Portugal, Amsterdam, Edinburgh (in 2022)

Fun stuff and notable mentions

  • Standout book. The Ballad of Songbirds and Snakes by Suzanne Collins. This is a prequel to the Hunger Games series. It’s not a perfect book, but personally worth flagging for a few reasons: First, I love YA fiction. Second, I thought it was much better written than the original trilogy. I’m inspired by the fact that a bestselling author is still improving on her craft. Third, this was my gateway drug back into reading regularly and I’m grateful for that.
  • Standout movie. The Half of It (Netflix). A quirky indie coming-of-age story about a smart young woman who writes love letters on behalf of her friend then falls in love with the recipient of those letters. Handles issues of race and sexual orientation effortlessly, both are critical to the plot without slamming you over the head. Loved this movie.
  • Standout purchase. A used Boosted Board (electric longboard).

If you’ve read this far, thanks so much. This was a long one 🙂

I hope 2022 is your best year yet. Let me know how I can help make that happen.

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