A Roaring Goodbye to Our 20s

by | Sep 13, 2018 | life, life changes | 0 comments

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I’ve always seen meaning and had so much appreciation for things like milestone events such as birthdays, celebrations, and holidays. It’s in those moments where I want to just stop time and soak it all in, because I know I’ll never get those moments back. It’s sort of how I felt about my 20s and turning 30 in general. 

The last milestone birthdays I really consider to have had have been 16, 21 and 30. Being one of the oldest of my friends, I have usually celebrated my birthdays before everyone else. It’s exciting, but also a little nerve wracking because I feel like there’s more pressure and expectations involved. Anyways, looking back on when I turned 16 and 21, they unfortunately weren’t the best birthdays. On my 16th birthday, I visited my friend in the hospital who had overdosed on drugs the day prior. On my 21st birthday, I was forced to rush girls for my sorority all day long and would have had to be a hefty fine to get out of it (not ideal when you’re poor AF). These were really not the way I would have liked to spend these monumental birthdays, but c’est la vie.

So, when it came time to decide what I wanted to do for year 30, I knew I wanted to celebrate in a way I hadn’t been able to for the last few big birthdays. And with Adam and I both turning 30 in the same week (we are 15 hours apart!), I knew that we couldn’t not have a party to celebrate! I wanted to make it a party where we could bring our closest friends together and so it gave me a reason to look forward to turning 30. (Also, real talk, why is it nowadays if you want to have a party, you have to plan it yourself? Sigh, adulthood.) When I began thinking of the possibilities for our celebration, I toyed with a bunch of ideas but finally landed on a ‘20s theme – a goodbye to the 20s, if you will.

A Roaring 20s Party Pinterest Pin

I wanted a cool spot to rent out that had prohibition vibes and I also wanted to ensure all the decorations nodded to the ‘20s era. I started reaching out to restaurants and bars around the city of Chicago and to be quite honest, had extreme sticker shock when I got the numbers back. Rentals and/or food and beverage minimums were upwards of nearly $3K! I love my birthday, but not that much. I did more Googling and landed on Peerspace. In the simplest terms, Peerspace is like AirBnB, but for event space. It’s pretty awesome because you can search in the area you want and find a bunch of venues you may not normally would have come across. And that’s exactly what happened with the venue for our party, @North Bar.

Turns out, @North Bar is in a less traffic area of the city so the owner relies on people renting it out or hosting things like comedy shows. I found the bar on Peerspace and coordinated via the Peerspace Messages with the owner of the bar to see if I could come see the space before booking. I also did this with another venue, which didn’t end up fitting our needs. Upon entering the bar, I knew it would be perfect for our ‘20s party needs (plus, it was a lot cheaper than the other venues). The great thing about booking a venue on Peerspace too is that you’re able to bring in food and decorations and make the space truly your own, which really appealed me. The booking process reminded me actually a lot of AirBnB and I paid for everything upfront. In the days leading up to the party, I coordinated with the owner, Jim, on music and what to display on the TVs in the bar (old black and white TV shows and movies!). He also okayed me to come in a few hours early to set up all the decorations.

I truly believe a good party touches on all the little details. With the help of my two friends, we got @North Bar to transform to the ‘20s. I had ordered gold metallic balloons and the standard “3” and “0” gold balloons, gold streamers for a makeshift photo booth background, photo booth props and put together some cute little signage in gold frames to place on the bar.

A "Kissing Your 20's Goodbye" sign

Having props and signs are a great way to add flair to your themed 20’s party.

Gold balloons and gold streamers create a fun photobooth

Photo booth black and gold props

Cute little 20s props for the makeshift photo booth!

Even better, everyone dressed up for the theme! Mostly everyone I talked to believe it or not purchased their attire on Amazon. I personally rented my dress from Rent the Runway (can’t say enough good things about the company) and purchased my headband from Amazon. I was honestly super impressed by the quality of the headband!

Kelly & Adam pose for a picture at their 30th birthday party

Ladies dressed up for the roaring 20s party

Kelly and her friend pose at the photo booth with some props

Taking advantage of the photo booth props!

Male guests pose for a picture at the 20s themed birthday party

Themed parties are even better when the guys dress up!

Kelly's female guests pose for a picture at the photo booth

We drank, we danced, we sang (karaoke, duh). What a night! What themed parties are your favorite? 

Pink lipstick stain


Welcome to Lipstick & Ink®, your home for everything career and wellness inspired. I’m Kelly, a Chicago-based career coach, writer, speaker, and events host.

Whether we’re working together on your career aspirations, refreshing your professional documents, or keeping your mental health in check, I encourage you to own your power and make your mark.




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