New Year’s Reflection: What the f*ck happened to 2019?

It’s New Year’s 2019! How is it already 2020?! Did 2019 even happen? What did I even do?! It’s December 30th as I write this, and I honestly can’t get over the fact that 2019 is done. I feel like I didn’t actually DO anything that would require 365 days. DID THINGS EVEN HAPPEN?

But then I look at my calendar, and things happened. I did a lot. According to my calendar (yes, I literally looked back through my calendar and Clo Bare because that’s HOW hazy 2019 is to me), I powered through this year, one task, project, relationship or goal right after the other.  

2019 Highlights





  • Launched the first Chicago Boss Babe Brunch
  • Wrote about dating anxiety and worked through it
  • Got dumped
  • Developed some new friendships
  • Started getting super into the financial independence community
  • Got promoted




  • Started investing in real estate
  • Focused on self-care and socializing
  • New roommate moved in


  • Decided to take a break from Clo Bare to enjoy the summer
  • Planned a trip with my boyfriend at the time to Mexico
  • Went to Mexico


  • Continued Clo Bare break
  • Went to Traverse City with friends
  • Created Chicago Boss Babe website
  • Wrote a crap ton to prepare for life after the break and set myself up for success with pre-planned content
  • Saw Lizzo in concert



  • Wrote a book
  • Graduated therapy
  • Tried dating but decided to give up for a few months… or year, and instead focus on myself


  • Sold my car
  • Went to Germany, France, Switzerland
  • Took a couple weeks off of Clo Bare to travel and enjoy the holidays

Look at me now bitch! Lots of travel, lots of projects, and lots of fun!

Accomplishments and Shit in 2019

  • I read 56 books. 
  • Started a casual networking group for career-passionate women in Chicago with one of my best friends.
  • Migrated this beast of a blog over to WordPress from Weebly.
  • Got promoted less than a year into my new job.
  • Had two pretty healthy and overall pretty lovely short term relationships that consumed about 9 months of my year.
  • Made three international trips and visited five countries.
  • Published 34 blog posts, more than doubled my traffic to Clo Bare, got published in a few new places and wrote a book.
  • Hosted my own workshops for the FIRST time ever. 

And that’s just some of the major ticket things I did in 2019. Because I’m an Enneagram Type 3, aka the Achiever, it’s really friggin’ easy for me to list out all the things I DID or accomplished.


What about emotional and personal growth in 2019?

You know what’s harder for me to do? Figure out how I feel about 2019 and identify how I’ve grown on an emotional level rather than a tangible accomplishments and project based level.

That shit is hard. And it’s a daunting task. Which is why I’ve been avoiding writing this post because I know it will make me use my thinking cells, which after the holidays and international travel, are very limited in quantities. 

But I think it’s important to reflect so that I can identify where I want to grow for next year.

So. I’m going to use “The Art of Simple”’s wonderful New Year’s Eve Reflection Questions to get me started.

20 Questions for New Year’s Eve 2019

1. What was the single best thing that happened this past year?

I went to Italy for two weeks– something I’ve been dreaming of doing for the last four years. I had to take unpaid leave from work, but it was so worth it and I’m really freaking proud that I was able to save up enough money to do that and to do it stress free while covering all my at-home costs over the course of those two week, like rent and loans.

2. What was the single most challenging thing that happened?

Mid-year I received some news that altered my world for a bit. It’s not my news to share, but it was something that affected me and I had to do some work on accepting that it wasn’t my responsibility and it wasn’t something I had any control over.

Getting the news and realizing how I processed it made me realize that I had a LOT of work to do on fear of abandonment as well as my need for control. I’ve been working hard on addressing both those things and while I haven’t conquered either fully, I’m doing a hell of a lot better.

3. What was an unexpected joy this past year?

I got to see my soulmate, cup-filling, joy giving, war buddy, best friend not once but TWICE this year. That was fucking phenomenal and our relationship this year has become even closer. We live halfway across the world from each other, so seeing her twice this year filled me up like the best kind of soul food. Makes me happy just thinking about it.

…I’d say “slow-growth” because it wasn’t the constant lightning strikes of growth that 2018 was. Instead, it was this slow and steady stabilizing force that reinforced all the growing I did last year. Like a slow cooker. Last year I did all the chopping and ingredient searching, and pureeing– this year, I let that shit marinate and now I’ve got a pretty delicious stew of being. 

Clo Bare

4. What was an unexpected obstacle?

Dating after trauma was definitely an obstacle. Not so much unexpected but unexpected in how it challenged me even though I worked through so much of the trauma with a therapist in 2018. I didn’t expect dating anxiety to take over in both my relationships this year, but I worked through it and because of it, I now trust myself now more than I EVER have before. And that fucking rocks. It feels like a super power.

5. Pick three words to describe this past year.

2018 was such a whirlwind. I had ups and downs in the most extreme ways– broke off my long term relationship, moved in with a lady off of Craigslist, got a new job in a new industry, started my journey to get debt free, did EMDR therapy, and tested the dating waters (horribly)– IT WAS INSANE but filled with massive amounts of growth.

This year doesn’t seem nearly as nuts in comparison and the one word that rings true for this year is STABLE. It was a year of stabilizing after the maelstrom of 2018.

Besides that I’d probably say, growth and affirming. Confidence seems like too weak of a word– I’m generally a pretty confident person BUT affirming is something that means so much more to me.

I found affirmation in myself this year– affirming my own decisions and my own feelings. This year just felt like one giant affirmation of who I am, what I want, and even more than that– being so cool with both of those things. I feel affirmed to the core and that’s… Mm. Fucking decadent.

And growth– if I could add another word and hyphenate that I’d say “slow-growth” because it wasn’t the constant lightning strikes of growth that 2018 was. Instead, it was this slow and steady stabilizing force that reinforced all the growing and learning I did last year. Like a slow cooker. Last year I did all the chopping and ingredient searching, and pureeing– this year, I let that shit marinate and now I’ve got a pretty delicious stew of being. 

6. Pick three words your partner or close friend would use to describe your year.

I of course picked the same Irish Soulmate of mine I mentioned in question 3. I thought she’d say growth, learning and affirming. And when I asked her she said.. “Growth, accepting yourself, finding your voice (through writing and also speaking up for yourself when things felt off in relationships). Instead of growth how about… transformational.”

7. Pick three words your partner or close friend would use to describe their year.

Stretching, growth, and freeing.

8. What were the best books you read this year?

  1. We are Never Meeting in Real Life by Samantha Irby
  2. My Sister the Serial Killer by Oyinbraith Waite
  3. Make Trouble by Cecile Richards
  4. We Should All Be Feminists by Chimamanda Adichie
  5. Calypso by David Sedaris
  6. Heads of the Colored People by Nafissa Thompson-Spires
  7. Power of Vulnerability by Brene Brown
  8. We Were Feminists Once by Andi Zeisler
  9. Convenience Store Woman by Sayaka Murata
  10. Feminasty by Erin Gibson

9. Who were your most valuable relationships with?

OH SO MANY. I’m going to use code names and only going to share three because this post would be too long. 

1. Irish Soulmate:

The woman I got to see twice this year has continued time and time again to be one of the most important people in my life even though I don’t physically see her all that often due to living on different continents. She is who I think of when I try to be more loving towards people who annoy me because when I come to her with woes she ALWAYS comes love first. There’s no patronizing. There’s no “Oh yeah– what I did is WAY worse”. No disappointments. No judgments. Just unconditional love and support in the most authentic way ever. I strive to be that way with all my friends– but Irish Soulmate has MASTERED this craft and I am forever grateful to have her in my life and so glad China brought us together.

2. Boss Bae

Boss Bae and I have really strengthened our friendship this year and beautiful things have happened because of it. Together we started a networking group that’s caught the attention of more than 90 women in the Chicagoland area and talking to her always inspires me to be the boss woman I want to be. It’s nice finding a partner in crime who not only challenges me to do more and do better career wise, but supports you through the hard situations life throws your way. We’ve been through a lot in the short time that we’ve been friends, and I’m happy to have her as one of my closest friends. She and I are each other’s cheerleaders and that’s evolved to being cheerleaders for all the women in our networking group.

That kind of friendship? The kind where you get shit done, support each other all the way, and have absolute honesty as the foundation?

Fucking magical. 

3. Captain Danger

Captain Danger (he picked his own code name) inspired “Why I Don’t Date Nice Guys” as well as “What Dating Deal Breakers Really Mean”. He and I talk about relationships a lot and he’s really good at giving me loving, but no bullshit advice. A few of my favorites:

  1. “I don’t think you’d still be dating this guy if you hadn’t dated all the tools you’ve dated before.”
  2. “You’ve done enough for this person already– stop giving and give him the opportunity to give. If he doesn’t, you know you were the only one keeping the relationship alive.”
  3. “When you’re wondering about someone– ask yourself, is this something I’d do to a person I supposedly loved? If the answer is “no” then you know what to do.”

It’s simple, straight to the point kind of advice that always has me knocking on my head thinking– why didn’t I see that? His candor is something I value SO much and was SUPER helpful as I navigated my way through dating again.  He’s been like a brother to me over the years and I know I can always count on him to give me an honest perspective.

10. What was your biggest personal change from January to December of this past year?

Biggest personal change… jeesh. I think the absolute biggest change I went through was learning how to trust myself.

After my last relationship, I told my therapist I struggled to know if I’m thinking with my trauma brain or if it’s my gut trying to tell me something (I talk more about this and give an example of what my thought patterns looked like in my post “How to Start Dating After Trauma”). When I explained this to her, she said– “Chloe, you don’t think with your trauma brain anymore. You’ve worked through more than fifty percent of your trauma if not more. That’s your gut talking when you feel that anxiety.” 

Mind. Blown.

I’ve spent the last six years believing I couldn’t trust myself because of what happened in China (for the “what happened in China post, see “Avoiding Relationships Red Flags”) and now I’m supposed to just all of a sudden trust myself?

How does one even begin to trust herself after spending so much time doubting everything? 

Well it took a lot of work to get here, but this year the switch has flipped. I know that I know what I need more than anyone else possibly could. I know that I’ve done more work on myself than MOST people have. If anyone should be wondering if they should trust themselves– it’s not me.

I know myself. And I have all the credentials to trust myself.


That’s pretty fucking badass and revolutionary for me. But I feel really fucking great about it and kind of excited to go into 2020 with this whole trusting myself thing. It’s a muscle that I need to keep growing, but it’s there and it’s getting stronger daily.

11. In what ways did you grow emotionally?

Hmm… Another great question.

My first thought is (and it’s kind of embarrassing to admit)– I didn’t drunk dial one person in 2019.


I know that’s not impressive for most people, but it was a bad habit I’d developed in college years– literally getting blitzed and calling people to affirm me in some way. Usually men I’d dated or almost dated. Seeking healing from those who’d hurt me, or at least those who I’d perceived had hurt me.

I don’t do that anymore. Didn’t even get close. To me that’s emotional growth because again it shows that I know I don’t need affirmation or closure or assurance from anyone but myself. Well at least not from dudes I used to love or like or want.

And that’s progress.

I’ve also been gentler on myself in general. Like allowing myself to feel things like anger and frustration and confusion and sadness and not feeling bad about feeling those things. I allow myself the grace to know: “Yes. What I’m feeling is valid. The pain I have is real. The experience I’m experiencing is OK and part of being human.”

That’s a massive amount of emotional progress, the simple process of allowing myself to feel and allowing it without judgement or shame.

That’s the fucking bomb.

12.  In what ways did you grow spiritually?

Hmm… I don’t consider myself spiritual so this is a hard one.

I’m not religious– borderline atheist, but mostly agnostic. This year I did lean into a sort of spirituality though, through meditation and being present. I found myself several times talking to myself or the universe in a way that would resemble someone praying–and although it was never to a specific deity, it was comforting and healing in its own way.

I’ve tried to allow some spirituality in my life, which is not something I’ve truly allowed myself when I renounced my Catholic/Christian faith back as a teenager and young adult.

It feels nice to allow possibility and hope back into my life. Even if it’s through tarot cards, deep breathing, yoga, meditation or just talking to myself. There’s a sense of calm that comes with believing in something, even if that something has no definition or religion.

I don’t know if that makes sense, but it makes sense to me. So I’m okay with it.

13. In what ways did you grow physically?

‘Scuse you, that’s personal. My hair and waistline grew? I have more muscles than I did last year? Gained some wrinkles? Oddly enough, I stayed the same height. Was really banking on a growth spurt.

14.  In what ways did you grow in your relationships with others?

I’ve focused on improving the relationships with people who bring me joy, and I also let go of some people I’ve outgrown.

I’ve recognized more and more that time is so precious– I can’t allow myself to spend time, mental energy, or otherwise on people who drain me. I just can’t. I have too much shit going on to allow for that in my life. It’s something I’m still refining but I finally let go of a friendship that had been draining me for about 8 years, and I let go of the guilt associated with letting that person down. 

I’ve also taken space from friends I’ve needed to take space from and developed friendships with people who are exactly what I need right now. I’ve learned that it’s okay that not everyone is going to be along for the ride all the time but they might hop on and off as they are able– and that’s totally cool too. 

Outside of friendships, I’m happy to say my relationship with my family has improved. I’ve had tough talks with a few members of my family, and because of it we’re closer now– we talk more, we are more able to discuss things that aren’t okay and we’re able to also enjoy and feel more comfortable around each other. 

15. What was the most enjoyable part of your work? 

I really loved learning more about Marketing this year. I love learning something new and then applying it to see if it makes a difference in what we do or not. We built a new website for our company this year, and I led the initiative and I really friggin enjoyed it even though it was difficult. 

16. What was the most challenging part of your work?

I struggle with putting on a smiling face when I don’t feel it. Sometimes in my career I have to grin and bear it, and that’s not something I’m always great at. I’ve been trying a lot harder to get that enthusiasm to know my audience and act accordingly, and it’s making my job easier. 

I also really struggled with focus this year. I’d REALLY like to improve my focus in 2020. Between running a blog, running a networking group, managing social media channels for each, dating, maintaining friendships, and planning multiple trips– life is FILLED with distractions and I let it get the best of me too often. I’d accomplish SO MUCH MORE if I could focus, and so I’ll focus on focusing in 2020. 

17. What was your single biggest time waster in your life this past year?

My phone. Social media. That feels like one in the same. Maybe dating. Jk. But really.

18. What was the best way you used your time this past year? 

HMMMMMMMMMMMMMMMM. That’s such an interesting question. OH! When I took two months off from Clo Bare, I used the second month to prepare articles so that I’d always have a month of material in advance– so I wouldn’t feel like I was rushing to get something out every week. By FAR the best use of my time.

19. What was the biggest thing you learned this past year? 

To listen to my anxiety and not let someone tell me how I feel.

I know I’ve said this a few times, but that has been the biggest growth this year for me on all levels. My anxiety isn’t my trauma brain anymore– it’s telling me that something is wrong. I’m not going to question that anymore. In 2019, I let someone tell me for the duration of the relationship how I should’ve felt.

Every time I’d present my anxieties to him, he’d tell me that everything was okay and I was just letting my anxiety get to me. And I’d believe him. I’d tell myself he was right and that I shouldn’t be feeling the way I felt. 

But the truth is– the anxiety was telling me that something was off and wrong in our relationship. I should’ve listened to that, and acted on the fact that he and I were simply not right for each other.

I also learned that if someone is on the fence about dating me– that’s my answer.

GTFO. Thank you, next. Bye.

I’ll never date someone again who is on the fence about me or doesn’t know if he wants to make it “official”.  Absolutely nothing good can come from that. I knew that deep down, but didn’t actually let myself know that, if you catch what I’m throwing.

20. Create a phrase or statement that describes this past year for you. 

I didn’t write this, but I love it, and I’m using it:

“There is nothing stronger than a broken woman who has rebuilt herself.”– Hannah Gadsby

Well that was fun and enlightening. 

I guess I did learn things this year. Still quite a few things to work on though.

New Year’s Eve 2019: Things I still Need to Work On in 2020

Boundaries & Dealing with Confrontation

I need to say what I mean. I need to work on speaking my truth in a kind way and putting down boundaries and saying “no” when I need to.

There have been several instances over the last couple of months where I’ve literally bit my tongue to keep from saying something might upset someone. But by not speaking what boundary it is I need to say, then I dishonor myself in the process and it builds resentment not only towards the person I failed to boundary myself with but also with myself for not respecting my own needs. 

I struggled a lot with this in November and December. Part of me wanted to jam pack all the things with all the people into the last two months of the year.

Dating? Let’s go.

Traveling to three countries in ten days to visit some of my best friends? Let’s do it. 

Going on ALL the social outings I’m invited to because it’s the holidays and that’s how we do it? Sign me up.

Not being sober since November? Obviously.

Oh, and while you’re at it– let’s join some professional development associations as well because you got time to volunteer, right? MHMM.

Houseguest. Don’t forget– you need a houseguest. Check!


You know the saying “If you want to get it done, ask a busy person to do it.” 

I am that. That is me. And I need to chill the fuck out, as per usual.

Honoring What I Need

January and February will be hermiting months, allowing myself to reconnect. When this stuff happens– when I feel this need to literally disappear or run off into the wilderness and stay in a cabin for a month– I know it’s because I need to reconnect with Chloe. Chloe feels like a distant memory right now, and I’m having those urges– to retreat, to move away, to rent a cabin in the UP and get the fuck out. 

But I don’t need to do those things. I don’t need to disappear.

I just need to pause. Turn off notifications. And reconnect with myself so that I can enjoy where I’m at, right now.

New Year’s Eve 2019: Goals for 2020

I have goals for 2020 but I haven’t totally finished mapping them out. In 2019, I more than doubled the number of views and visitors to my blog, and I’d like to double that again in 2020. 

I’d also like to focus on me. I know that’s generic, but in 2019 I spent 9 months focusing on two relationships, and quite frankly, I’m exhausted. There’s so much I want to do, both for myself, Clo Bare, Chicago Boss Babes and my career, so I’ve decided I’m not going to online date for now. I need some time to build myself and the life I want solo and eventually I’m sure I’ll get back out there, but for now? 

It’s me in 2020. I’m dating myself and I’m pretty fucking pumped for that.

Other goals for 2020:

  1. Spend more time moving and eating things that make me feel good and help me manage my anxiety (IE, less coffee, sugar and alcohol).
  2. Try to only schedule one to two social things a week. More than that gets overwhelming.
  3. Work on focus. Start using my phone less. 
  4. Finish writing my book.
  5. KILL it with my budgeting.
  6. Get my own apartment (no more roommates!) closer to work.

What are your goals for 2020? 

Do you have any goals for 2020? Do you do any questions like the above to get you centered for the new year? Share in the comments below.

New Year's Reflection: What the f*ck happened to 2019?
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New Year's Reflection: What the f*ck happened to 2019?
Reflect on 2019 with a list of 20 questions to do on New Year's Eve. Clo Bare works through the questions and plans goals for 2020.
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Clo Bare
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12 thoughts on “New Year’s Reflection: What the f*ck happened to 2019?”

  1. well, looks like we have a lot in common. i too went to italy for 2 weeks in 2019, got my heart broken and stomped on, started therapy, and had to look at why i like guys that don’t treat me awesome. now i’m 100% focusing on myself + career for the first time. 2020 let’s go.

    congrats on starting the networking group and leading the self-care workshops! how did it go? i’m trying to launch a few different workshops through my private practice here in dallas (mental health dietitian) — i’d be curious to hear if you have any feedback/suggestions/learning experiences!

    1. YES 2020 let’s do this!!!! I am also 2100% focusing on myself this year, and I’m super pumped about it! The workshops went awesome– would love to do some more in the future and might start offering them for free at my house or another inexpensive/free venue to get my feet wet and build my portfolio. That’s so great that you’re going to start doing them! Also so cool that you’re a mental health dietitian. My biggest pieces of advice– practice workshop with your friends if you’re nervous. They’ll give you honest feedback. Also, record yourself doing it. It feels weird but you’ll get a youtube video out of it and also get more experience just going through the workshop! Let me know how it goes– excited for you!

    1. Top 5:
      We are Never Meeting in Real Life by Samantha Irby
      My Sister the Serial Killer by Oyinbraith Waite
      Make Trouble by Cecile Richards
      We Should All Be Feminists by Chimamanda Adichie
      Calypso by David Sedaris

  2. What an inspiring post! Thank you for sharing all the details of your life over the last year. It’s really amazing being able to reflect on how much has changed in a relatively short time. I look forward to reading more posts!

  3. Wow, I feel exhausted reading all that you’ve done. Italy is on my list and I want to revisit Mexico as an adult. I went when I was 11 for a summer camp. You should feel extremely proud, especially about all the awareness you’ve gained about relationships and self care. I hope 2020 brings all your goals and desires into being.

    1. haha! That’s oddly affirming that you’re exhausted by reading it 😀 Hell yes– Italy is amazing! And thanks– the awareness is definitely my favorite part of this past year. Hope 2020 brings you all the goodness as well <3

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