2020 Reflections: A Look Back on my Year

A lot of us may say this was the Worst. Year. Ever. Because of COVID, so many life altering things happened. Hundreds of thousands of loved ones lost. Unemployment across the globe. Weddings postponed. Birthdays and graduations celebrated virtually. It’s been a tough year indeed.

I’m sure you’re just as sick of talking about the crummy parts of 2020 as I am. That’s why I decided to write this blog-post focusing on the high notes.

I know I’m a travel blogger and I typically provide travel related value to my audience. But I wrote this article to provide value to myself. I hope you enjoy this piece.

I’m recapping my highlights from each month in 2020 and throwing in a few of my favorite shots from those months too!

JANUARY: Took Tommy to Omaha. Not only did he meet my coworker family, but I also got to show him the place I once called home for a year of my life.

FEBRUARY: I finished paying off my $60K+ in student loan debt. I became debt free for the first time in my adult life and it felt incredible.

MARCH: Quarantine started, and no one could have predicted what the next year of our lives would look like.

I cut my own hair into bangs after 2 weeks in lockdown thanks to my newfound TikTok addiction. I concluded that I should have left those behind in the 7th grade.

I created content inside my apartment which was very “off-brand” for me. But it pushed me to be creative and I’m thankful for that.

APRIL: Tommy and I found our dream apartment in the Gold Coast neighborhood via a virtual tour. I am beyond thankful to have had our own space and a balcony for the rest of the year.

MAY: Got settled into my new apartment, in a new neighborhood. I dyed my hair pink thanks to another TikTok video. Hey, I’ve been working from home since March, may as well take advantage of that, right?

JUNE: This was a tough month. The first of my 4 grandparents, and anyone in my family for that matter, passed away. It was not COVID related, however. I flew to Virginia to celebrate his life and got to see my family in the height of the pandemic.

JULY: Drove to Door County, Wisconsin with my best blogger friend and our boys. We picked lavender at a farm on Washington Island and watched the sun set over Lake Michigan. (I wrote about this trip HERE)

This made me appreciate my own back yard. International trips are amazing but who knew I’d love a short road trip just as much!

AUGUST: I took a trip I never knew I wanted to Glacier, Yellowstone and Grand Teton National Park. I met two new Insta-friends IRL too!

I felt so inspired there. For the first time in 3 years, my blog/Instagram started to gain traffic after this trip. (I wrote about this trip HERE)

I also road tripped through Michigan with my 2 sisters. We had not taken a sisters-only trip since 2015 and we were way overdue.

SEPTEMBER: My love turned 30 and I helped him celebrate with our closest friend circle. I hosted the first get-together at my new apartment and it felt like home.

I enjoyed spending time in Chicago and counted my blessings for living in this great city.

OCTOBER: My 2 sisters, 3 cousins and I got together for a girl cousins weekend in Chicago. It was the first time in a long time that we were all together in one place. We were missing one cousin from that side of the family but hoping we can do this again in the future!

I also chased every Fall color around the city until my feet hurt. This season was by far my favorite for content creation since I began my blog. I felt in my element!

NOVEMBER: I turned 31. People always told me their 30’s were the best years of their life. Well I spent my first year of my 30’s at home for 75% of my time.

I had a lot of alone time at home and started thinking about how I want to live my life differently. I’m still in the process of assessing things, seeing where my passions are and what my next steps are. I know I’ll get there eventually and it’ll be worth it when I do.

p.s.: the people of the world aren’t lying when they say everything starts to hurt in your 30’s. Lol.

DECEMBER: Unsure of what to do for the Holidays, Tommy and I booked a two-week trip to the southwest US to celebrate Christmas. We are excited to bring in the new year together and welcome a fresh start in 2021.

On a more blog-specific note, I wanted to acknowledge some accomplishments of my mine that are related to this part of my life.

My fellow bloggers can relate when I say that blogging is a full time job. Trying to run a successful business on top of my main full time job is not easy.

It’s hard not to compare yourself to other bloggers who seem to be growing, earning, progressing more than you. But it’s also important to focus on ones own journey. I’m incredibly proud of these accomplishments this year.

  • I stopped making excuses about using Pinterest and took a course in February to motivate me to get into it.
  • I set a goal to publish 1 blog post per month this year. I reached this goal and even published 2 in some months!
  • After not growing on Instagram AT ALL between February and June, I grew my audience by 7,000 followers in the second half of 2020.
  • My engagement rate went from 3% to 7% when I started to be more thoughtful about my content. I also invested in better equipment which helped me up my photography game. (You can read about my equipment HERE)
  • I created dozens of reels, IGTV’s and TikTok videos that offer advice/tips/tutorials to other content creators. I firmly believe that you get out of this community what you put into it. It’s not a “take-all” environment. You must give back in return!
  • I collaborated with 3 hotel brands during a year when my travels were less than a third of what they usually are.
  • I started asking to be paid for what I thought I deserved for collaborations. I increased my collaboration revenue by 20% vs. the year prior.
  • I stopped making excuses (again) and stopped being afraid of diving into SEO. I took another online course (from the same blogger whose Pinterest course I took) and I doubled my average monthly blog traffic from 2020 by the end of December.
  • Lastly, and most importantly, I feel like I finally created a community!

Even though my follower count has consistently increased over the last 3 years, I never felt like people gave a crap about what I was posting. I was convinced that my followers were only here because I followed them back, because they hadn’t gotten around to unfollowing me or because they were bots.

I’m moving into 2021 with a positive outlook and more motivation than ever. I’m excited to share even more creative content, tips and tutorials.

I want to partner with some of my dream brands and when I do, I’ll share with you how you can get there too. Because remember, we all get out of this what we put into it! 😊



  1. January 20, 2021 / 1:12 pm

    Love the reflection of the last year! Loved visiting so many places with you!

    • ontheroadwithjen
      January 20, 2021 / 1:23 pm

      Yes! We made some great memories in 2020!

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