Staying Positive

I’ll be at Automattic for 7 years this fall. That’s a long time to be writing correspondence in a remote workplace, on many teams, in many roles. In a past Automattic life, I did live chat for and trained live chat teams to be more efficient and intentional in their word choice. Once someone asked me to write about staying positive.

In honor of this post’s 4 year anniversary on an internal p2, I thought I’d repost here publicly on my blog with a few tweaks to be relatable to a larger audience. I hope this helps you. I wrote this mid-divorce and mid-cross-country-move during one of the most stressful times in my life.

An unhappy Happiness Engineer is a contradiction we’d all like to avoid, amirite?! It’s not a challenge that faces only live chat operators, but everyone some time in their lives.

Sometimes it’s not something at work — it’s something personal — and the combination of stress at home and work is enough to kill your mojo. Remember, we have a very supportive company that lets you take UNLIMITED vacation, or leave (and even sabbaticals if you’ve been here long enough). When you’re having trouble balancing things, talk to your team lead or HR.

I’m trying really hard to not make this sound like some sort of cheesy pep talk. It’s what has gotten me through a few tough times recently. Here are some simple steps to think about next time if you’re having trouble staying positive.

Identify & Address the Issue Immediately

If you’ve found your happiness balloon deflated, identify what did it – fill in the blank for this sentence:

I am having trouble staying positive today because ________.

It could be a multitude of things, but start small… start with the one thing that is bugging you the most or the one thing that pushed you over the edge, and address it. Do something about it ASAP.

I try not to let things sit. A painful tactic I use is going after the worst problem first. I know that it could be difficult, but once I’m done everything else will seem so easy comparatively.

Change your Outlook

Challenge your negative thoughts replacing each negative thought with a positive one. Start your day with something positive.

Silence vs. Good Morning!

“Oh man, the queue spiked. Cue panic.” vs. “We can totally squash this under 5 hours if we all take 28 tickets right now.”

Change your language and use happy/positive language – gladly, happy to, love that, will, available vs. negative – can’t, won’t, don’t, unavailable.

Try saying Sorry less and saying Thank you more. “Thank you for your feedback about ____” instead of “I’m sorry _____ did not work for you.”

Don’t forget to smile in real life and in text. Add smilies to your words! 🙂 😀 😉

Restore your workspace to your place of zen. If it’s not contributing to your mental health, switch out your desktop to something that makes you laugh or makes you happy, fix the lighting, remove the clutter. I have a picture of my kids on my desktop.

Give Thanks in Order to Receive It

What might be contributing to the negativity? Remember, positive attitudes are just as infectious as negative attitudes.

Practice gratitude. Even if you feel like you’re at the bottom, take a moment to compliment a customer on something they’ve worked hard on or :high-five: a coworker on a job well done.

Offer to help when someone is stuck, and the “thank you, you’re awesome!” at the end may be enough to get the positivity-snowball going. Pick them up and they may end up picking you up in return.


  • Thank you sooo much for training this morning. You were so on top of things. I appreciate knowing I can count on you. ❤
  • Thanks for taking on the review coordination. I don’t know what I’d do without you.
  • Thank you for not reaching through the computer to slap me for scheduling training on Sunday night in the middle of Memorial Day weekend.
  • You are once again my hero for automating that task. The time saved across all of support will be exponential.


  • Thank you so much for sticking with me on this. I knew you could get it.
  • Your site looks beautiful. I can see how much you care about the way it’s presented.
  • Thank you for raising your concerns in such a clear manner.

Stop Rushing and Take a Break

Think about the last time you were overwhelmed. Was it because you had too much to do? Were you hurrying to finish it all?

stop. breathe. refocus. take a break.

Eat lunch away from any screen of any kind. Audit your chaos filters and see if you really need notifications on that many platforms. Go away in Slack or put it in separate view/desktop and only respond to @ mentions. Put your phone on vibrate and check it less frequently. Plan your day better to give yourself the time to do the things you wanted to accomplish.

Speak Up When Something’s Wrong

If you’re having trouble solving something on your own, ask for help. Worries are like bug reports, you don’t know how big of a problem something is until everyone starts reporting issues.

Keep a Hug Folder

The president of the last company I worked for had a very prominent yellow folder in a sea of manilla ones on his desk that I asked him about one day. This is back in the day when people still printed things out. 😉

He handed me the happy yellow folder and said “take a look.” Upon opening it, I saw emails addressed to him with highlighted sentences.

Dean, you’re a genius!

Dean, I never thought I’d be smart enough to master this software, but it’s so intuitive and your staff are so helpful I can’t fail.

This latest update read my mind. You fixed everything that was bothering me and added things I didn’t know I couldn’t live without. Thank you!

He told me whenever he was feeling down, he opened the yellow folder to give himself a hug and remind himself of why he was doing it all.

So start tomorrow, make a screenshot of your next #hug and put it in a hug folder. You could set these as random images for your desktop or screensaver. Remind yourself why you do what you do and that you’re helping people.

Admit to Your Mistakes, Learn from Them, Then Move On

If you complete the sentence “I’m having trouble staying positive today, because this last chat/ticket was sooo difficult and I don’t think I worded it as well as I could have,” try going to transcripts to see from coworkers how you could have handled it better. Ask a buddy for some feedback about it.

Admit your mistakes to the customer if you’re leading them down the wrong trail – it makes you more human. It also helps you reset, so it’s not something you dwell on after the chat concluded.

You can even apply the “Fix it Twice” mentality to interactions going sideways. Fix it once for them in the moment, then be deliberate in an after action review to go over what went well and what didn’t. Fix it a second time to prevent the sub-optimal parts from plaguing you in the future.

Published by Andrea Lee Bishop

Andrea (pronounced On-dree-ah) leads Automattic's Support Leads and works in hiring. She's a fixer, traveler, mom, math geek, aspiring-polyglot, musician, and coffee lover.

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