My 101 in 1001 List + Dinner Boat Cruise Giveaway

My love for a good list knows no end, as evidenced by my quarterly bucket lists. I’ve slowly but surely been building my list of 101 things I want to accomplish in the next 1001 days and I’m so excited to finally share it with you guys today!lake michiganMackenzie originally started the whole idea a few years ago and Jessica recently inspired me to make it a priority to finish mine. I’ve been working on it for what seems like forever now! Over the weekend I got out for a long run along the lakefront and my mind was overflowing with ideas, as it usually does (this is both a blessing and a curse), and I stopped every so often to jot down notes in my phone. Seeing how so much has changed in my personal life over the last year I had to cut out a lot of what I had originally planned to include, but I’m happy with what I’ve got and feel like the things on this list really speak to what I value in this life.

Let’s get to it!

Start date: 1/30/18
End date: 10/27/20

It’s wild to think about the year 2020, isn’t it? I broke things down into a few different sections, but some of them definitely could have gone under two categories as I’m sure you’ll notice.


  1. Go skydiving again, but this time, in Hawaii!
  2. Watch the Cubs play from the Wrigleyville Rooftops
  3. Ride the ferris wheel at Navy Pier
  4. Rollerblade along the lakefront
  5. Watch the fireworks from a boat on Lake Michigan (Be sure to enter the giveaway below!)
  6. Try an infrared sauna
  7. Visit the AIRE ancient baths
  8. Get a cryo toning facial
  9. Get a deep tissue massage
  10. Staycation in the city
  11. Take an indoor rock climbing class
  12. See a Blackhawks game at United Center
  13. Set up my hammock by the lake for an afternoon of reading (my sister and her boyfriend got me this one for my birthday and I know just the spot to hang it!)
  14. Visit the Lincoln Park Farmers Market
  15. Go hiking at Starved Rock State Park
  16. Spend an afternoon at Shedd Aquarium
  17. Have tea at the Drake (I’d also like to have tea with Drake, if anyone knows how to make that happen)
  18. Play a round of golf
  19. Take ice skating lessons
  20. Take a tennis lesson
  21. Take a cooking class (or better yet, a Drake on Cake workshop) with Joy the Baker
  22. Go horseback riding
  23. Go kayaking on the river
  24. Run in a Turkey Trot
  25. Coachella
  26. Mamby on the Beach
  27. Lollapalooza, round two
  28. Watch KU play at Allen Fieldhouse
  29. Go to Junior Council’s Snowball event
  30. Run a 10K with Tyler (my step brother!) in Chicago
  31. Take (another) outdoor trapeze class
  32. Weekend in Chicago with my little brother Camden
  33. Weekend in Chicago with my little sister Harper
  34. Weekend in Chicago with my little sister Cailley
  35. Weekend in Chicago with my (not-so-little) brother Dawson
  36. Weekend in Chicago with my sister Jordan and her boyfriend, Long


  1. Buy new carry-on luggage (preferably one with a USB charger because I am that girl who is always frantically looking for an outlet)
  2. Banff, Canada
  3. Diablo Lake (2 hours outside of Seattle)
  4. Santa Monica
  5. Yacht Week with my girlfriends
  6. Charleston
  7. West Palm Beach
  8. New York City at Christmastime
  9. Austin
  10. Rent a cabin in Colorado and spend the weekend skiing and hotΒ tubbing
  11. Celebrate baby Erin’s 30th in Colorado
  12. Spend a night in a tree house
  13. Take another trip to St. Simons Island, Georgia (Hi, Jetter πŸ‘‹πŸ»)
  14. Oak Valley Plantation in Louisiana
  15. Savannah, GA
  16. Visit the Michigan wineries
  17. Go on a wellness retreat
  18. Take a trip somewhere with just my Mom (thinking skydiving in Hawaii which might be considered cheating since it’s listed above, but I’m going with it πŸ™ƒ)
  19. Girls weekend in Chicago with my Mom


  1. Get abs (haha I wasn’t sure how else to say this), but seriously, I want to strengthen my core and as superficial as it sounds, I want to see the definition!
  2. Be able to do 10 regular push ups in a row
  3. Read 15 new books
  4. Go see a movie solo
  5. Go to the eye doctor and get a prescription for the glasses I so desperately need
  6. Find a dermatologist in Chicago I trust
  7. Find a new dentist in Chicago
  8. Continue going to therapy
  9. Find a flattering pair of white jeans I feel confident in
  10. Set a new PR for the half marathon
  11. Be able to do a handstand in yoga
  12. Be able to get into a headstand in yoga using only my core
  13. Negotiate a raise

Around my apartment:

  1. Invest in new bedding
  2. Have my apartment repainted
  3. Give my bedroom a refresh and share on the blog
  4. Same goes for my bathroom
  5. …and my living room, too!
  6. Create a breakfast nook in my apartment
  7. Create an area where I can work from home (opposed to posting up on the couch with my laptop)
  8. Organize my front hall closet
  9. Overhaul my closet and focus on buying pieces that truly represent my personal style
  10. Get a real Christmas tree

For shits and giggles (and good deeds):

  1. Throw a shot glass at the bell at Federales
  2. Start a ladies who lunch club
  3. Go skinny dipping
  4. Play blackjack at the casino
  5. Leave a 100% tip for great service
  6. Send my Grandma flowers just because
  7. Donate blood
  8. Pay for the person behind me at the coffee shop
  9. Bake cookies and hand them out around the city


  1. Rebrand my blog
  2. Host an Instagram takeover for one of my favorite brands
  3. Create a Chicago travel guide
  4. Share my round-up favorite workouts in Chicago
  5. Share my round-up of the best places to get pampered in Chicago
  6. Plan a blogger brunch
  7. Master the art of taking outfit photos (hello, awkward hands)
  8. Shoot in a swimsuit and share it on the blog
  9. Grow my total reach to XX (this is a number I’ve got written down for myself!)

For my eyes only:

There are five things on my list that are just a little too personal, but rest assured, I will be chipping away at them and who knows, I might have a change of heart about sharing in a few years. Only time will tell!

There’s so much I want to elaborate on when it comes to this list, but for the sake of time today, I’ll be sharing as I go!

To celebrate, I’m giving away a dinner for two on an Odyssey boat cruise in Chicago, Washington D.C., or Boston! This way, one of you can check off seeing the fireworks from the back of a boat out on a lake πŸ™‚ Can’t wait to hear what’s on your bucket list!

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Join The Discussion

    1. Jess Post author

      That’s what I’ve heard! I didn’t believe it at first, but someone swore up and down the photos weren’t edited and I was in awe. Can’t wait to see it for myself!

    1. Jess Post author

      You should! (and then let me know what you put on it!) It’s so nice to have a list of things you’re hoping to do/see/make happen/etc. and being able to look back on all the experiences and things you’ve accomplished always offers up some perspective πŸ™‚

  1. Sydney

    Banff is one of those places that is sitting at the top of my bucket list…. just saying… let me know when you start planning that one! πŸ˜‰


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  3. Sarah Lagen

    You have a pretty list going girlfriend, so many great travel places!! Banff is as amazing as you think it is, I hope you make it!! I really want to go back and go to Jasper, Canada! This makes me want to sit down and write out some of my dreams and goals! Great seeing you last night girlfriend!

    xo, Sarah

    1. Jess Post author

      Your trip there put it at the top of my list! So SO pretty. You should! I want to know what’s on it πŸ˜‰ Great to catch up with you!

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