Work-Related Red Flags from My 5-Year Gratitude Journal

Kate Erwin
Hack/Slash Media
Published in
4 min readJan 11, 2022
What was supposed to be The Happiness Project exposed what was making me unhappy at work

Writing in a gratitude journal every day from 2017 to 2022 was an interesting exercise. Using Gretchen Rubin’s The Happiness Project, I learned a lot about what makes me happy and now have a record of my most joyful moments from the past 5 years. Cannot recommend the practice more.

But rereading some of the entries — especially those related to work — gave me pause.

A lot changes when you’re aging from 27 to 32. For one, I went from making $40,000 pre-tax to nearly 3x that (thanks, side hustles!). Plus, the pandemic has shifted our entire global culture and made many of us (myself included) a lot less addicted to work. In short, my relationship with work is a whole lot healthier now than it was 5 or even 2 years ago.

In 2017, I was super “grateful” about things that were downright toxic. I was overworked and undervalued and didn’t have self-awareness about my damaged mindset.

In hindsight, my gratitude journal entries are 🚩 red 🚩 flag 🚩 city. Here are some of the cringiest entries.

“Today flew by cause I was super busy”

It’s “business,” not “busyness.” There are so many signs that I was obsessed with overbooking myself and valued the hustle above all else, including my own sanity.

Looking at this now, it’s a sign that I was filling my time to distract myself from my own unhappiness. I wasn’t living in the present and this was a warning sign that I missed, even while writing it down.

“Left the office on time”

Entries like this one show how often I didn’t set proper boundaries. And how grateful I was on the days I did set boundaries for myself.

I also said things like, “It was my second 10-hour day in a row!” with such pride that it makes me feel kinda sad. Now, thankfully, I value myself no matter how much or how little I work.

“Friday means freedom!”

Uh, did I feel trapped every other day? Such a hardcore cringe.

If you feel this way, make a change. I’m not saying to quit your job, but look inward and figure out why you don’t feel free every single day of the week.

“Everyone needs me”

This is, unfortunately, verbatim. I was obsessed with feeling needed. I didn’t value myself unless I had some sort of external validation.

There are lots of similar entries like, “Lots of work made me feel important.” It’s clearly a coping mechanism, but it’s painful to read.

And I had the lowest bar for workplace interactions, saying things like, “People at work were respectful and apologized for being abrasive.” Oof. It’s great to be grateful when people apologize, but the best apology is a change in behavior and I can tell you that did not happen.

“Got to work from home to avoid the blizzard and worked until 3am — almost 16 hours!”

Cringiest entry award?

There’s a lot to unpack here, so let’s dive in.

Living in Syracuse (frequent winner of an award called “The Golden Snowball”), I was honestly obsessed/terrified of snow and there are lots of entries like, “It’s delightful working somewhere people are understanding about crap weather.” In this case, there was a dangerous snowstorm with over a foot of accumulation on the roads. I was grateful that I didn’t have to risk my physical and mental wellbeing to do work I could easily be doing from the safety of home.

Working from home was a privilege that often came with working around the clock. And I was just so grateful to work at home that I’d do anything to maintain that privilege.

Also, importantly, I was excited because I got paid overtime. And I got paid overtime because I was severely underpaid.

Being More Critical (in a Good Way)

Rereading all these entries, I’m not sure I understood the assignment. From internalizing hustle culture to having the lowest bar ever, I did not value my time or energy enough.

Additionally, I was “grateful” for a lot of “opportunities” that never came to fruition: job interviews that led to rejections, projects I never finished, promotions promised and never received.

And in typical millennial fashion, I often worked for things like free snacks and gift cards and “kudos” vs. demanding fair pay.

This is to say, my biggest takeaway from 5 years of journaling is that it’s good to be critical as long as it’s productive. Journaling can help you recognize behavioral patterns that you want to change and then proactively make that shift so you’re living a life that aligns with your values.

I’m grateful for the ability to reflect on the past 5 years and know I’ll do better this year. Next time, I’ll catch the red flags instead of being grateful for them.

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Kate Erwin
Hack/Slash Media

Kate is a content marketer working at a SaaS startup. She's the Co-Founder of Hack/Slash Media, a blog that shares what startup employees are really thinking.