28 Things That Happened at 28 Years Old

28 was a good year. It was a lot – a lot of growth, but also it was a year of setbacks. I’m turning 29 and yes I am in the same position I was when I turned 28 – unsure about my career, my body. Unsure of if I would have a boyfriend or if I would finally get an apartment with a bedroom or atleast a living room. Unsure if I would have more savings than last year. Unsure of a lot of things. But with all this uncertainty, I also had a lot of proud girl boss moments at 28 years old. And since this is a time of my life where you grow and learn about yourself – who you are, I wanted to share my 28th year with you.

Travel and Adventure

1. I celebrated my 28th birthday on a road trip with friends and strangers

My birthday was on Thanksgiving, and I was born on Thanksgiving. So it was a special birthday. My friend invited me on a road trip with her, her brother and her brother’s friend. We were supposed to go to the Grand Canyon, but only made it to Denver. I hiked up a mountain and popped bubbly and I learned that sometimes we weren’t meant to make it to the destination- we were supposed to enjoy where we were. This mantra and mindset shaped a lot of me at 28 years old.

2. I visited my friend in the Bahamas and rented an Hermès Birkin Bag

Friends are so important and I was happy to go visit my friend in the Bahamas and learn about resort life and island life. I was so nervous going on vacation. Vacation feels good when you’re doing good work and need a break but I was very much trying to figure my life out and nervous to go, but I am lucky people want me to visit them and I am so glad I went. And it was even cooler to partner with a woman founded startup and rent a Birkin bag.

3. I saw Mickey Christmas at Disney World with my nephew.

This was special. I went with my sister’s family to Disney. Despite growing up in Florida, I didn’t remember going to Disney. It really was a happy and magical place.

4. I made it to two out of state weddings.

Yes, I suck at weekend adventures. For the first wedding, I went out of state to a small town outside of Ann Arbor, Michigan. Let’s just say I slept through my bus, got ready on the train and the person next to me on the train drove me to the wedding. I was 3 hours late but excited to be there. The other wedding was in Valpariso, Indiana. We also were late – about an hour. And despite the rain, the nacho food truck which my date hated, and the fact that we were all burning up for a summer time wedding, I enjoyed every minute of it. Showing up for your friends is important- no matter the distance or transportation obstacles.

5. I visited the Wisconsin Dells with my book club.

I took a road trip with friends to the Wisconsin Dells and we had the time of our lives. I forgot how fun theme parks are. I was freaking out, but managed to bungee jump and drop into the water. Like – the lifeguard almost thad to rescue me. The next day we ate the best Mac and Cheese and watched the World Cup Final as I drank $3 Long Islands. We finished the trip with a duck tour. Wisconsin Dells aren’t just for family.

6. I went to a Wisconsin Lake House for 4th of July.

Wisconsin became a second home for me over the years because my sister in law is from there. This year we said goodbye to the lake house at the annual 4th of July party. I loved that tradition and I’m sad to see it go.

Girl Boss

7. I went on a blogger trip to cover a Future of Work Conference in Kansas City.

This was huge for me. It was the first time I wrote a proposal for a PR company to fly me to another city (ok, Kansas City) and interview Hallmark and HBO execs. It was a 24 hour trip but I will forever remember martinis at the hotel lounge, waking up at 5 am to swim in the middle of America in the middle of winter outside (in a heated pool). And that the keynote speaker mentioned me in her speech about the future of work.

8. I spoke at a SheSays Mentoring night about growing your network. It was an honor to come back for the second time and talk to creatives and graphic designers about the power of your network at Power Reviews. I learned so much from attending their first mentoring session.

I also spoke at a national tour, “I make a living” with one of the best word of mouth marketers moderating, Saul Colt at Second City.

9. I went to an AmexGold Dinner at Etta Restaurant.

This dinner was one of the most amazing nights. I had an incredible meal with other bloggers and my friends and we experienced the porron- where you fill a jug with wine and tilt it to drink so everyone can share. I will say good conversation outweighs good food every time -but good food helps Etta regramed my post.

10. I judged a Chicago bartender competition for the first time.

We tried 15 different cocktails. Fifteen. And judged them based on presentation and taste. It was fun to do this with Yelp Chicago and Emmy Award Winning Journalist, Samantha Thomas as the host. Judges included: Gregory Tatavosian, A-List Startenders, Amanda Elliott, Windy City Cosmo, MJ Tam, Chicagonista and Anna Kopsky, Yelp.

11. I hosted my own show with HBO and other Chicago bloggers as guests.

I was offered an opportunity to turn my blog into a tv segment on a real production set. It was a very surreal experience doing what I have done for 10 years – interview executives, entrepreneurs, and bloggers, and more.

12. Voyage Chicago wrote a feature article about me and my blog. Voyage Chicago has spotlighted so many badass women and shared their stories so it was really an honor to be recognized.

13. I got to work with HBO on several of their show parties.

There’s a moment when you are in awe of what is happening and being at an HBO party, sitting on a bed eating chicken and waffles and talking to writers from The Onion was one of the highlights of this year. I felt like a real writer and I was excited to be part of the HBO experience. My first party was for Crashing Season 2.

I also saw The Tale and listened to a q&a with Common and the woman who wrote it and produced it, Jennifer Fox. If you haven’t seen The Tale – it was about a woman realizing she had been raped when she was younger and her mother found her diary and helped her confront her past. When the author went on tour, she did one stop with her mother. Can you imagine talking about a traumatic experience in your life with your mother and a live audience? It was raw and it was courageous and I realized that more people need to tell their story.

14. I went on a Chicago Safaris Instagrammable Road Trip.

I was invited to spend the day traveling around to Chicago’s most Instagrammable spots which included Paradise Park and the Robin Williams mural. I was so happy to catch up with Chicago bloggers like Flo from Flo’s Favorites. You can read more about our day here.


15. Your boyfriend and your best friend might not be the same person.

I realized that some guys are best friends and some guys you want to be your boyfriend. I have really good guy friends that I hang out with one on one. Some of my friends think we should date because we hangout all of the time. But just because you’re best friends with someone doesn’t mean that you should date them. Friends are hard to come by.

16. I took a road trip with a guy and he made me breakfast in the morning – a waffle with a smiley face made out of whipped cream. It was the first time a guy made me breakfast. He drove us there and I drove us back. I also went to his boss’ dinner. I felt like a grown up. And it was amazing stepping into someone else’s world. We ate Thai food. I listened to office jokes. I did my hair a different way, and I felt like I was adulting.


17. I planned and created a partnership with Chanel.

Chanel! I met the talented, Liz Monroe at a Tulle Project party and we talked about collaborating. This partnership was amazing. This was something I didn’t think would happen, but I thought of the idea and saw it to execution and it’s one of the most proudest moments of my life.

The concept was to help professionals freshen up for board meetings. I got his and hers Chanel fragrances in the Coworking space I managed. And I threw a launch party with over 150 bloggers and press. We had a photo booth with a backdrop made of fake flowers pieced together. It was overwhelming – especially when someone compared it to a Gossip Girl Party.

18. I planned and helped facilitate about 50 events. I also built a partnership with AIRE Ancient Baths (and experienced the most relaxing spa day) and with the Metropolitan Club and saw them renovate.

It felt like I lived at work but I felt like I was doing something I was good at – creating community. And that meant a lot to me. My favorite events were a Back to Basics night where we had Somrus make pumpkin spiked lattes and then made vision boards and raffled off an AIRE Ancient Baths certificate.


19. I did hot yoga for a month. And I was also a yoga model and partnered with Bottom Line Yoga.

I tried to do 30 classes in 30 days, and I think I was 1-2 classes shy in January, but it totally transformed how I felt about my body. I felt stronger and I liked moving my body in new ways. My favorite was hip hop yoga at Bare Feet Yoga with Exavior Pope. We would dip it low and pick it up and then at the end of class, would do a mini tequila shot.

The following month, I was a yoga model and partnered with Bottom Line Yoga. It was fun to work with Lauren, who owns the studio and go to sessions after work and even their nap time at The Civic Opera House. What a dream.

20. I trained for a half marathon.

I ran the Chicago Marathon last year but this year I wanted to really train and run an entire half marathon. I trained hard for a few weeks and ran 7.5 miles straight but that was it. I didn’t actually run the half marathon but I was proud that I started running again and want it to be more part of my life. PS the Nike Running app is gold. I ran 4 miles to my friends house listening to the Headspace Nike run about goal setting.


21. I started a podcast with my friend, Duan Davie II about how men and women communicate. We called it Ok Cool Podcast because we said that when we were being passive aggressive.

22. I bought patio furniture and hosted patio dinner parties.

This was by far the best investment of this year. I had so much fun getting to know other bloggers and friends by having them over and cooking with me.

23. I had a girls night.

In college, I loved grocery shopping with my roommates. One night, I went to my friend’s apartment and we spent basically the whole night in Whole Foods shopping and getting a phenomenal deal on the largest pizzas of our life. And then going home and pairing it with a fancy bottle of champagne and two chick flicks. It was fun to just be a girl and have girl talk.

24. I went to BBQ parties and we all grilled.

When you get into your later 20s, dinner parties are a thing. Some of my favorite were hosted by my friend, Sany and we all brought something to grill and played games. We had a seafood party and then a BBQ party. I also cohosted a Memorial Day Weekend BBQ with my friend, Lee.

25. I went to one of the best taco parties and had a bonfire with all of my friends. The tequila shot hut was a fave. This was that time in summer when everyone brought their new dates who would later become serious.

26. I threw a Drake on a Cake Galentine’s Day Party.

This was fabulous. I interviewed one of the most talented bakers, Windy City Dinner Fairy and we baked a Drake cake. Later that week, I had a few girlfriends come to a ramen restaurant and make Valentine’s Day cards using Drake lyrics.

27. I took a sushi making class: Sushi & Saki 101 with my friend, Lee at Benihana. We made a feast and then went to the beach. Lee won for best presentation.

28. My book club threw me an epic 29th birthday and about 30 of my friends played Never Have I Ever and sang me happy birthday. I looked around the room and was so grateful for all of the amazing people who made 28 so great.

Conclusion – What I Accomplished in my 20s

Life is really what you do with it. That’s true of 28 and every other year. How you make the most of opportunities- how you create opportunities. I have so much to learn and so much to do. I honestly can’t say what 29 will be like. I hope its a year of good health, fun nights, more challenges, and real love.

Amanda Elliott
Amanda Elliott

Amanda Elliott is a writer and speaker and a relationship builder. She believes that meeting people in person is important. After attending numerous fashion, startup, and creative events, she founded Windy City Cosmo is 2015 to help people make connections in the city as they build their businesses, start and end relationships and see and be seen. Over the past three years, the entrepreneurs she’s interviewed have become the most successful in Chicago and Windy City Cosmo won an award in 2017 for her work for female entrepreneurs.

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