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2020 Annual Review

25 min
Essays  ✺  Reflection

It’s been one helluva year and I am grateful beyond words that I made it through in good health, great company, and a deeper sense of who I am. I am happy to say that many of my 2019 hobbies became what my job is in 2020. That is a privilege that not many can say. 

2020 is a year I will never forget. I never knew Bill Murray could encapsulate so much of how I felt this past year from the movie Groundhog Day. What seemed impossible became possible. Curveballs hit. It truly tested the agility muscle of every human. It shook our grounds and forced us to look even longer in the mirror to ask ourselves what really mattered. 

This year made me question what was normal even more than usual, so much that I am convinced seeking normalcy is naive. It is such a subjective term that I caution myself from using it.


This is my second time doing an annual review. My first time sharing it publicly. It has honestly been one of the most rewarding exercises of my life. Here are some of the benefits I gained from the process:

  1. Re-alignment of my values while mining the previous year’s struggles for insights. 

  2. Clarity on my intentions and what I care about all while forming more clear creative constraints.

  3. Awareness of themes and patterns that happened during events while allowing myself to celebrate the highlights.

This self-indulgent exercise affords me to feel a greater sense of grounding and a deeper meaning for the projects I’m inspired and motivated to pursue. They feel more connected to my underlying values that drive my creative spirit. In addition, this is a chance to reflect on struggles experienced in 2020 (along with most of humanity) to glean lessons to carry with me into the future.

Before we dive in here’s an overview of what will be covered:

  1. Achievements I am most proud of

  2. A look back at 2020 goals

  3. Things I wanted to do less of in 2020

  4. Five things I am most grateful for

  5. A look at some peak and trough events

  6. 10 Lessons from 2020

  7. Things I want to do more of

  8. My three words for 2021

  9. Some miscellaneous highlights from courses and best buys

  10. Shoutouts to people who impacted and inspired my year

Now let’s jump in!

Achievements I am most proud of:

A look back at 2020 goals

365 days of Journaling 

I journaled everyday mostly in my physical notebook but also on my phone, laptop, or post-it-notes. This means that every day I wrote this past year. This was and still is a non-negotiable in my life. This year I am wanting to implement a better system of reviewing my journal entries and integrating them into my public writing.

The most fun exercise from journaling was freehand writing a tabula rasa (a blank slate) during the mornings. How does it work?  At night, I envision myself being a podcast guest and ask my future self a question that has been itching at the skull that I don’t have a clear answer to. Then in the morning, I write. 

Some of my favorite daily questions that I started to ask myself each day were:

Grade: A+

156 workout sessions

3, 1-hour workouts each week, can be a walk outside or yoga inside if needed.  

I probably did this. I didn’t set up a system to track these. I’m really not sure. In the first quarter of the year, I was consistent in going to the gym three times a week, but after that closed it took me some time to readjust. My most active month of the year was July through September when I started biking and running. Overall, it was quite cyclical. A learning from this is that I need to prioritize some form of fitness to help with my mental health no matter the form. 

Grade: A-

104 home-cooked meals

2 per week that are NOT breakfast foods.


I set this goal with the intent as I had been working late nights in 2019 and eating out more than I ever had before. I definitely had many more home-cooked meals considering I haven’t been to a restaurant since the summer. However, much of my time quarantined at home, I didn’t contribute as I could have to cook dinner. I tend to stick to the same boring grocery list and prep the same meals. There’s an opportunity here to improve. 

Grade: B+

52 meaningful conversations

With existing family or friends via in-person or Facetime

Jacuzzi time is the best time.

Jacuzzi time is the best time.

I needed a better system to track these. This was something that I wanted more of in 2020. Given I lived with my family for 4 months during the pandemic, many meaningful conversations were baked into those meals and dog walks together.

Grade: A- 

26 intentionally uncomfortable situations

Meetups with strangers every other week: join an improv group, Dutch-speaking club, new workout class, dating, attend a networking event or conference, interview a complete stranger.

I set these to be every other week to force myself to do something out of the ordinary. In Jesse Itzler’s course, he called these Kevin’s Rule trips. They are a routine for not always being in a routine. They are to force you to stay out of a rut. 

Here’s the Zoom Wedding Reception. This was the Dance party I got to DJ. It was a hoot!

Here’s the Zoom Wedding Reception. This was the Dance party I got to DJ. It was a hoot!

When the world went virtual I still found ways to incorporate this by meeting strangers: Lunchclub meetups, online community events for Compound, Writer’s Bloc, and Ness Labs, Twitter DMs that led to offline conversations, and a Zoom wedding facilitation. I also got to try to put myself out there in numerous online course sessions through the Write of Passage, altMBA, Performative Speaking, and the Part-time Youtuber Academy. 

Grade: A

12 monthly reviews

Record 5- 10 minute video to myself so I can easily create a video at the end of the year for myself to document what happened. 

I ended up doing a monthly review for the second half of the year starting in June. I shared a quarterly review as well in letter 28 from the summer. The trigger for this was that I joined an accountability group with questions to ask myself about what I loved, learned, and lacked. There was so much friction for me to review the month that even writing it out was hard enough. I still am quite fond of starting a vlog to capture expressions and see my past self talk about life. Recency bias inevitably comes into effect.

Grade: C

6 trips

Travel to 2 familiar places (Netherlands and NYC) and 4 unfamiliar new places (Australia, Colorado, Atlanta, Boston). 


For work reasons, I did get to travel to New York for a quick weekend trip. That was great fun to be there while the city still was like the city. In March, before lockdown, I am beyond grateful to have also had a friend reunion for colleagues in Atlanta. I was heartbroken when I canceled my trip to the Netherlands in April. I thought I was postponing it to June. Little did my naive self know… 

Grade: N/A

2 running races

10K in April and a half marathon in September.

In April on the day the race was supposed to be, I ran the 10K. 


When I set this goal of completing races, I realized what I was really attempting to do was to shift my identity to one as a runner. I ran every day during the month of August for my monthly habit. This culminated in running 100 Kilometers = 62 miles. The following month my training for the half-marathon pushed me to do my longest run of 8 miles and 100 miles in total in September. This running fell off the bandwagon in October after I weakened my left ankle and rolled it a couple of times. For my health, I quit training for the virtual half marathon I intended to run in November. 

I never thought I could ever enjoy running. It did, and I am proud. I wrote more about it here

Grade: A+

1 successfully chartered Toastmasters club in Chicago

Monthly speeches given after the charter starts realistically in February. 

I took on many new client projects in February and this fell onto the backburner and I prioritized the Chicago office learning committee interviews and newsletter write ups instead. I was hoping there would be synergy with meeting leaders in the office that could provide buy-in to join the club. I needed 25 people to sign up and could only find about 10 willing to truly commit. 

Grade: N/A

1 book published 

Be a Learn-it-all through New Degree Press— will have a daily writing habit. 

This was an unfinished project I started in 2018. This large project is what served its function for me in finding my passion for writing. The book pivoted into me writing my newsletter. I feel a need to get more reps in as a writer, to find my audience, and what exactly I enjoy writing about. 

Grade: N/A

1 bi-annual review in June

To assess the progress of these goals and change if needed. 

I ended up doing a quarterly review at the end of the summer and realized I needed to recalibrate my goals. This was instrumental in helping me realize I could still pursue my writing goals and led me to my 100 days of writing Ship It project along with my running goal. 

Grade: C

Things I wanted to do less of in 2020:

My first St. Patrick’s Day in Chicago seeing the green river Circa 2019 that I was miserably hungover for days after.

My first St. Patrick’s Day in Chicago seeing the green river Circa 2019 that I was miserably hungover for days after.

Binge drinking. Post-graduate life had me escaping reality most weekends to go be hungover. I loved the social aspect of it, but I replaced this with other meaningful ways to find a connection while sober. I can happily say that I did not blackout from excessive drinking once in 2020. Also, during the 5 months of strict quarantining, I can count on two hands how many nights I drank liquor, beer, or wine. This past August I moved further north in Chicago to the quaint neighborhood of Lincoln Park away from Old Town which is a dominant drinking culture area. December 2020 had many social Christmas events, and to prove I do not have a dependency, I am pursuing a dry January this month. 

Doubt my ability. At KF being a junior level talent, it was so easy to never speak up or try to be heard. Now working at startups, I feel like I have a voice and that it is heard. Silencing this voice of self-doubt is something I am still working on. 

Eating out more than 3 times a week. Covid worked in my favor here. I cook a meal almost every day. Nothing all too fancy and while I was living at home mostly my mom or dad or sister made dinner. I want to get more creative with the foods that I eat. 

Drinking caffeine.  I have a tendency to be an extremist. For middle school Jen, when I was a daredevil, this meant going on every single roller coaster at Cedar Pointe. Similarly, with caffeine, it can get out of hand for me. I get excited and then I start to feel palpitations. After Thanksgiving, being surrounded by family who drink tea and coffee every day, I gave into my environment and started to as well. It was too much. I decided to go cold turkey and quit fully in December. It was awful headaches and rough sleep for about a week but I feel so much better now. I would rather have internal energy drive my motivations than something I consume. I don’t like addictions. I have replaced this drink with having an alternate drink in the morning of herbal tea with mint or lemon. 

Five Things I am most grateful for:


  1. Learning: Believing in the human ability to learn has given me so much faith in the universe and God. It pulled me out of dark paths my mind gravitated towards. Reading books, journaling, discussions with peers, walking with a podcast, and taking online courses are a few of my favorite ways to learn. I shared a tweet thread on this here.

  2. Trying new things: I faceplanted many times trying to get up on water skis without a tip connector that I had as a child. I swam a mile across Walloon Lake in Michigan with my dad. This was the first time without a life jacket on. I loved learning new board games, road biking rolling hills, how to be more strategic with marketing, and learning how to build an online course curriculum.

  3. Time with family: For the first time in the past decade since middle school, I was physically in real life with my parents and siblings for their birthdays in May and September. 

  4. Zoom: Not only did it spike my stock portfolio, but it also gave me confidence at my old job to upskill and facilitate during sessions I would normally never say a word during as the project manager. Zoom also allowed me to stay connected with family and friends around the world, and make such fabulously curious-minded new friends as well from online courses and writing communities.

  5. Twitter: It is one of the best places to make friends (regardless of a pandemic or not). I learned the power of sending a direct message and keeping the conversations going offline. This blossomed into fruitful friendships, where life would be much more lonely without.

A look at some peak and trough events that happened


Korn Ferry successes in Quarter 1:

Meet Jellybean

Meet Jellybean

Caring for pets. While walking with my dad, I spotted 3 bunnies abandoned by their mother. We welcomed them into our home and offered shelter for a few weeks in April. My parent’s two golden doodles and three cats were also monumental in helping to ground me in the present moment. They are a constant reminder that I don’t need to be so future-focused.

Playing piano. Every evening for at least half an hour (sometimes two hours) in March and April I played the piano. To be honest, I didn’t get all too good and nothing I’d hold my breath over. It didn’t matter to me though. It was the way I rewarded myself for making it through another Groundhog day. It just felt right. No questions asked.

Sailing across Lake Huron in July. I was very hesitant to go on this race in the first place because typically sailors aren’t the most Covid-friendly lifestyle folks. Despite my reservations, we all came out without the virus and had a great 42-hour sail. We didn’t place all too well, but it was a great escape. I shared more about why sailors sail here.


Speaking at the virtual graduation of altMBA in August in front of 240+ people across the world. Seth Godin was in the Zoom Room. My hands were oh so sweaty. Who knew virtual graduation could be so fun yet nerve-wracking? Each of the eleven cohorts presented a farewell gift and I got the honor to recite a part of my classmate’s poem. It was lovely. These classmates I met led to a small book club that I now am fortunate to be a part of. This book club began in September and I am grateful to be surrounded by other Godin fans.


Created a personalized Roam Research system. After taking Nat Eliason’s Effortless Output course. I am happy to say as for my Roam system I am still exploring but of all the systems I’ve used to capture ideas – notebooks, journals, sticky notes, Apple notes, Evernote, OneNote, Notion – writing in Roam has been most enjoyable. It feels great to me even though the lack of structure is daunting. It has forced me to build my own system since there is not an implicit way of using it.
My escape through novelty. I began running and actually enjoying it. This was a surprising development. I learned new board games thanks to my roommates and enjoyed some old goodies- Linkee, Scattergories, Catan, Monopoly, Spoons. I also sought some discomfort with covid-friendly dates. 

Starting my own business. This started out just doing a favor for a friend of a friend for a Zoom wedding. I started to do some freelance writing. Then the idea of helping to build courses was planted and I joined the startup scene. In October, I officially signed to do business as my own name as an independent consultant in the state of Illinois. This same month I became a content manager for Astutely Media where I create and produce the podcast series Subject Matter. I am also the course manager at Vitalize Talent building the first cohort to launch on January 18th in the coming weeks.

Meet Minty

Meet Minty

Successful plant mom. Huzzah! I kept my plants alive. In July my mom bought me my lucky bamboo and a mint plant. They have been thriving. I killed an orchid back in 2019 and was afraid ever since.


Being laid off. On April 23rd which I after spiraled into a whirling pit of victim mentality. I wrote more about my reflections from this happening here.

My farewell poem I crafted within my remaining 12 hours in corporate America

My farewell poem I crafted within my remaining 12 hours in corporate America

Driving an 18-year-old Jeep. This legacy my grandpa left to my family. Almost driving off the snowy road in January. The migraine after my car accident being rear-ended in July. It sounded like it’d blow up in August. The starter dying in December. All these hiccups have forced me to become a more patient person and realize what is in my control.


Solopreneurship. It can be lonely. Figuring out legal contracts, accounting, and negotiating stresses. I didn’t exactly know what I was signing up for, but I knew that this was something that would eventually happen with having two entrepreneurial parents.

Rolling my ankle in October. I tend to push myself too much physically and then completely cut off my fitness. I want a more regular balance. 

Internet skepticism. I was scammed out of heaps of money over the phone in October. There are scars there now that shake me awake out of my naivete of some of the people that exist in the world. 

10 Lessons from 2020

  1. Planning instead of plans. As Dwight D. Eisenhower said, “Plans are worthless, but planning is everything.” Plans are stagnant, so instead opt for planning. I could have never seen the two job opportunities I landed come my way. I never sent cover letters or felt like I had to be a different version of myself. These were both friends that I met at a Summit and in a breakout room of an online class who then became clients. 

  2. Intentionality with learning. This is why I love courses so much. You get thrown into the deep end with the support of so many things you never had an inkling to exist. There is a map presented to you with what you’ve learned, where you need to unlearn, and the shifts in your mindset to get you to the light at the end. A couple of big ones for me this past year were from being merely a podcast listener to producing a podcast. 

  3. Dividends. By living at my childhood home for four months, and saving money I historically would have to spend on train transport, groceries, and social events. Despite this, I financially felt like the least productive person in my life without an inflow of cash. A sad sack you might say. My stock portfolio felt otherwise and had a mind of its own that excelled past my expectations. In essence, I was making money while I slept. Because I canceled trips, I reinvested that budget amount into the market instead. 

  4. Trust in yourself to manifest your desires. Much of my life today was manifested in my journal last year. I wrote that I missed being surrounded by creative people in the fall of 2019. Every day now I have the opportunity to connect and be inspired. Through this, I’ve found that daily journaling is more than nice-to-have. It is a must. It is part of who I am now so I do not feel a need to set a metric for it. I’ve convinced many people on Twitter and friends to start journaling by sharing my practice more. 


5. Focus on what is in your control. I think I slept more at the end of April than I ever had in my whole life. I didn’t have a sense of purpose as a large piece of my identity was torn away from me without a job. Later I discovered this is what depression is like where it swallows you whole. I was such a victim after losing my job and canceling my travel plans. I thought the world was against me. 

I’ve learned since that mood follows action. If you’ve got 8 + hours of sleep, force yourself to get going. Ruts build on themselves but so do actions. You don’t need to feel good to get going. You get going and then you feel good. This is why I started using this little accountability tracker to partner with me as a tool to see what I was actually moving the needle on.

6. Don’t dither on answers that aren’t there.  I wrote myself a letter at the end of 2019 as if I were writing a friend’s advice. This was something Brad Stulberg recommended I do on his community call. This exercise is also called Solomon’s Paradox. I integrated a SWOT analysis of my job at Korn Ferry after being there for six months. I felt like I didn’t have a compass of where exactly I was going. I felt like my potential was under-indexed, but it was hard to come to terms with. That 15-minute call with the head of HR on my calendar was one of the bigger blindsides I ever received. I felt like I was the chosen one and I didn’t know why. There weren’t any answers and I hated it. 

Since, I have realized that sometimes there aren’t answers and you just need to focus on what you do know. For me, that was running month-long experiments and trying to figure out more of who I am and what lights me up.

7. Rewrite your story. My loss of a corporate job was a great way to pull the carpet out from under me. It forced me to really ask myself what I wanted to spend my time doing and who I was. I feel empowered to have ownership over my time, the freedom to explore my curiosities, and the choice of who I want to work with. I have found more of my voice. Through advocating for myself, without there being a ladder in a formal sense, at these startups has been energizing. It feels like I am being paid to be a rigorous student. This is a dream come true. 

8. Systems shape who you are and shift your identity.  I know I’ve read it again and again in James Clear’s Atomic Habits book that your actions will shape you into who you are, but it actually happened this year. I am in shock. I identify myself as a writer. A creator. I began systemizing my writing process and my creative process this year. Much of this system has been taking many MANY walks outside. Spending copious amounts of notes in my personal knowledge management system called my second brain.

My favorite place to think thoughts in Oz Park.

My favorite place to think thoughts in Oz Park.

9. True connection can be cultivated in Zoom. I think I counted myself having cried on Zoom at least 4 times this year with a room of people you think I’d call strangers since I hadn’t met them in real life before. This emotion was a breakthrough to me that yes it is lonely to not have physical contact, but also technology is miraculous. Much that you don’t think can be felt across a screen actually can.

10. Discovering the world of online writing. Write of Passage is a game-changer. It opened my eyes to the possibilities of online writing. It took me three times of the course to finally feel like I was living out what is taught. Many of my most proud accomplishments stemmed from the tools I learned in this course of starting my newsletter and writing online. For altMBA, I stepped up my game to maximize this tool and created a personal challenge to ship an article for 100 days. The closet writer Jen in 2019 could not fathom this as being possible. I believe in this to my core and I am excited to see what other magic can happen as I continue to write online. 

Many of the numbers from last year I didn’t hit. I am going to recalibrate much of my future goals below after the first quarter with more clarity. I think there is still power to have a number to show how important that priority is. Intentions are too foggy, so I tried my best to quantify below. Much of what follows here is the curriculum for my life. I don’t want to set it to be too strict since as I learned in lesson #1 above, I want to focus on planning instead of plans. This affords me the opportunity to intentionally leave room for serendipity. 

Things I want to do more of:

IMG_2482 2.jpg

Cadence calls with loved ones. Family and friends need to be baked into my calendar and make time for them. 

Prioritization of channels. Have a feeling of joy from missing out on things. This means for me that I will stop allowing YouTube to take up space in my brain. If I want to become a YouTuber that means I need to consume it but I just really don’t want to take the time right now. Maybe in the future. I still love watching videos but for now, I am intentionally going to focus on my craft of writing. 


Send snail mail. I absolutely love writing letters to my future self so this year I want to write and send more to others. I have been writing daily gratitudes in my journal for almost 2 years now and I feel that I have become Why the rule of only sending for big events? I want to send more just because. 

Strength training and fun with fitness. Not having workout classes doesn’t mean that I can’t plan for fun workouts. I am going to take a physical mobility test to see where my underactive muscles are. Some other ways to have fun in my fitness are to get back in the pool, bike more, dance for no reason, and stretch every day. My upper body strength has shriveled up and because I want to eventually be able to go rock climbing, I am setting these as follows: 

Cooking new foods. Follow recipes and swap favorites with friends.

Diversify my music choice. For the past few years, I have had the same exact artists to be my favorites. There is nothing wrong with that but there is much to still explore here. 

Intentionally explore history. Just because I continually failed history in school doesn’t mean I will be bad at it for the rest of my life. I began to study history on my own terms on topics varying from – New Amsterdam turning into New York City, Audrey Hepburn’s biography, WWII, the Industrial Revolution.

Explore bitcoin. My investing portfolio performed quite unexpectedly well this past year and I’d like to diversify even further in cryptocurrency. 


Allow Chicago to feel more gezellig (homey). I have been living here for a year and a half on and off and still feel like I don’t know so much. I am Investing in a biking lifestyle. I bought a Divvy bike membership for the city bikes. I want to get lost around the city more often. I have a car and 2 able working legs but I don’t explore the city enough. When I lived in Amsterdam I intentionally got lost often while biking around and it was the best way to find my way. 

Intentional rabbit holes. Much of what I consume I feel pressured to make it productive. this intent is to give me permission to explore my curiosity and not make it feel like work. Reserve Saturday or Sunday mornings to shamelessly allow me to explore what piqued my curiosity without intention.  

Words for 2021

  1. Play

  2. Intentionality

  3. Experimentation

These words serve as benchmarks for how I want to live in 2021 and provide guidance to my future self. I am thinking of them as pillars that hold up the house that is my life. 

To help me make future decisions I will ask if it aligns with my three words, whether my future self would regret not doing it or if it would be a story worth sharing to add to my life resume? These questions can help me move through my future with more certainty and grounding.

Some miscellaneous highlights

Shoutouts to people who impacted and inspired my year

These are just to list a handful. If I missed you, know that you matter as well. Thank you for making this year the best one of my life. I appreciate you all. I am beyond grateful to call myself a dyslexic reader, writer, creator, and lover of life.

Here’s to a bright future ahead full of learning for the rest of our lives.

If you’d like to stay up to date on my learning journey, you can join along below:


My 2022 Annual Review

My 2022 Annual Review

My 12 Hour Walk

My 12 Hour Walk

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