2021 was a weird year for me. I ended up rebelling against a lot of what I learned and accomplished in 2020. In a way, it was me rejecting the digital-first nature of 2020 and returning to the real world where relationships were nurtured in the flesh. It was also the year I got married.

So like how I did for 2020, 2019, and 2018, it's time to answer three important questions:

  • What went well?
  • My biggest struggles?
  • What did I learn?

What Went Well


I let my career take a back seat to other interests in previous years. But after enough stalling and uncertainty, I finally made an effort to start asking for what I wanted. I'm still an engineer but have shifted some of my responsibilities to doing more sales-related work.

After taking on these new responsibilities, I successfully negotiated a 12% raise. While nothing crazy, it was substantial enough to make me realize that I have the power to effect change in my life. I'll discuss it in more detail later, but I learned the importance of knowing what you want and asking for it.

Doubling Down on Physical Relationships

Whereas 2020 was the year of building relationships online, 2021 was the year of doubling down on physical ones. After being a part of multiple online communities and countless Zoom calls from the year before, I finally got fatigued with it all. While I'm grateful for the many wonderful conversations I had online, they all felt too ephemeral.

Instead, I spent most of my free time growing existing relationships with those I didn't get to see as much last year due to the pandemic. 2021 also seemed to be the year of the wedding. And man, did I go to a lot of weddings—10 to be exact, including my own. I also went on three bachelor parties and attended many wedding showers and friendly get-togethers.

Needless to say, I spent a lot of time doubling down on my relationships with close friends and catching up with others I hadn't seen in a while. This year, I also made the ultimate commitment by marrying my wife in October. It was the best day of my life.

A perfect day.

Making Money Online

While I've been publicly writing online since 2018, this year was the first time I started to get paid for my words (not counting the paltry sums I've made from old Medium posts). I'm still not making much from freelance work ($100-200/month), but getting paid directly for your output is an incredible feeling, and I enjoy doing it.

The only downside to freelance writing is that I've commoditized one of my cherished hobbies, and it's why I haven't published as much on my blog this year. Time typically spent writing personal blog posts was used to complete random client work. I want to pursue paid and personal projects but struggle to find a balance.

Still, I look to do more freelance work in the new year. My priority is to be more selective with the type of freelance work I take on to justify the time commitment. Ideally, I'd like to get to where my freelance work brings in at least $500/month.

My Biggest Struggles

Letting the Little Things Slip

I started writing an entire blog post about this topic earlier this year but never got around to publishing it (the irony, I know). But letting little things slip was my biggest struggle this year. It's such a dangerous trap because subtle changes can quickly go unnoticed until you realize months later how far you've drifted off course.

For example, I used to consistently get up around 5:50 AM on the weekdays so that I'd have about two hours to read and write before leaving for work. But after reviewing my habit tracker for 2021, I noticed that my wake time slowly drifted later and later throughout the year. Those two hours of sacred free time gradually shrunk to about an hour and a half. While the shift was subtle, my output was affected as I wrote much less this year.

Realizing how much I'd let some things slide this year was eye-opening. I've never been too hard on myself, so it's easy to see how I let things slip. I know that I can't trust my willpower, so the best thing I can do is continue tracking the routines and habits I care about and review them consistently. It's too easy to trick yourself into thinking you're doing just fine until you see the hard data tell you otherwise.

Losing My Curiosity

I don't know what happened here, but I seemed to have lost some sense of my curiosity along the way. Topics that used to interest me enough to write about could no longer hold my attention, and I found myself spending a lot more of my free time engaging with low-quality content like social media and sports news.

I also found myself rejecting a lot of non-fiction works (self-help, business books, whatever you want to call it) that I used to love and opting for more fiction—mostly science fiction. I'd argue that some of this behavior change is a healthy response (most business books are a bunch of fluff), but it was still weird experiencing myself go through this change.

I know it's perfectly natural for your interests and tastes to evolve, but I haven't quite found my new "home," and it's bothering me. I think it's why I've become susceptible to consuming more low-value content, but it's a terrible substitute I can't allow to continue. Experimenting with my routine and trying new things will be important moving into the new year.

What I Learned

Ask for What You Want

The most important thing I learned this year is asking for what you want. If something is important to you, it's your responsibility to see it become a reality. Waiting for an opportunity to land at your feet is a fool's errand that will have you waiting for most of your life.

I understand that saying this is quite obvious, but following through has never come easy for me. What changed for me was finally realizing that most people aren't out there to see you fail. Instead, they're too busy, distracted, and worried about their own problems to have any time left over to think about what you might want. You have to decide what matters to you and be persistent about making it happen.

Life Still Happens in the Real World

2020 was a chaotic year that taught me how to adjust on the fly and meet many interesting people online. But after a year of Zoom calls and Slack messages, I was yearning for personal connection in the real world. Once the world began reopening and travel plans resumed, I found myself opting to meet people face-to-face.

I still believe that there is immense value in digital tools and social media when used in earnest, but humans are physical beings who need personal connection. Knowing how to navigate the digital world is a valuable skill that I wish to continue, but I don't want to lose sight that the best moments of my life have always occurred in the real world.

Moving into 2022

My goal for 2022 is to focus on improving three areas of my life: relationships, health, and financial stability.


2021 made me appreciate the time spent with people in person. I want to continue making an effort to double down on the most important people to me and remove myself from the relationships that no longer serve me.

I already have four weddings scheduled in the new year, so some travel plans have already been made, but I'd also like to make a few trips to visit friends that live further away. Making an effort to see people I care about will continue to be a priority.

Most importantly, I want to invest in my relationship with my wife. Now that we're married and living together, I want to make sure she gets the time and attention she deserves from me.


I fell just short of accomplishing my weightlifting goals for 2021. A combination of moving, getting married, and going on my honeymoon in the same month did not help me hit the gym consistently. Combine that with getting Covid at the tail-end of the year, and I missed enough gym time to fall short of my goals.

I'm really excited about my health goals for 2022, though, as I seek to hit the 1,000lb Club. The 1,000lb Club is when you can lift 1,000lbs between three different lifts. For me, that's 1,000lbs lifted between the squat, deadlift, and bench press.

I'm already close to achieving this goal (roughly at 900lbs currently) using the Wendler 5-3-1 program, so I'm confident that I can hit this goal by year-end. The most important thing will be avoiding any major setbacks. The most significant risk is getting injured, so I plan to dedicate more time to a stretching/yoga routine to maintain flexibility.

Creating a Portfolio of Small Bets

I'm stealing the "Portfolio of Small Bets" idea from Daniel Vassallo because his idea has had such an impact on my thinking that I've enrolled in his mid-January cohort for his Portfolio of Small Bets course.

Essentially, I want to become more robust by diversifying my skills and income streams by trying many things in tandem. I'm a firm believer that the world is changing faster than ever at the same time that it's never been easier to earn a dollar online.

I've already started down this path with my freelance writing work, but I want to prove further that I can adapt quickly and provide for my family in a world filled with uncertainty. It's hard to gauge how successful I'll be at creating a portfolio of small bets, but I'm excited about what will come of it. Expect to hear more about my journey in the new year.