Welcome to Fail Files 👋

Failure. We all hate it. It’s a messy, uncomfortable truth… That can ultimately lead to progress. You can learn so much from failing—sometimes more than from winning. So let’s reframe it together.

Failure isn’t always pretty, and sometimes it’s harmful. But it’s often in those very moments that we learn the most. Even when the failure feels off-track or unjust, there’s usually something we can take away from it.

Failure is essential for growth, even foundational to success.

Each week, Fail Files breaks down a failure that matters. Whether it’s a personal mistake, a systemic collapse, or a business flop, we’ll dig into the lessons that can help us rethink what’s next.

Ready to explore failure and where it can take us? Let’s go!

This week, I wanna talk about some ways I messed up last week at work and how I’m ensuring they don’t happen again.

🤷🏽‍♀️ W T F H A P P E N E D ?

Last month our new boss started at work and naturally, everyone gets a little nervous when a new boss starts. It also doesn’t help that right now, we’re recruiting for a new incubator program while also marketing one of our biggest events of the year. There’s a lot going on.

Our team switched from Asana to Jira, changing systems while also executing tasks. We were STRESSED, to say the least.

Do you know what happens when you’re stressed? You make mistakes.

Here are some I made:

1. I sent an email on the wrong day to 10K+ people. (yes you read that correctly)

2. I sent the same email to the same groups more than once. (I forgot to use the “don’t send to” feature to exclude people who were on more than one email list)

3. I missed some easy edits on the website that I should’ve noticed.

4. I made a formatting mistake on our website.

🧠 L E T ’ S A N A L Y Z E

Why did this happen?

• Making easy mistakes is a sign that we need to slow down — Unless you are ACTUALLY saving lives… there is always time to slow down and double-check something. Last week, I was trying so hard to meet deadlines that I missed simple updates webpages that needed to be made and simple formatting errors that took two seconds to fix. Even when I’m stressed, I need to learn to take a breath.

• Anxiety causes us to think we need to work fast instead of putting a system in place — Out of anxiety, I end up rushing things like sending emails when a deadline is coming fast. If you work in email marketing, you know how many things you need to check before you send an email: links, images, subject lines, preview text, send lists, design, etc. In this example, I clicked the wrong date on Hubspot and sent it the day after. Simply because I was rushing. Instead, I should have a checklist in place so that even if I need to work fast, I can ensure I’m not missing crucial steps.

• A new boss might make us feel like we don’t want to ask stupid questions because, well, we don’t want to look stupid — I missed that “don’t send to” step because I was too afraid to ask my boss about our segmented lists for this email campaign. I was (again) working too fast and forgetting my process to ensure contacts don’t receive emails intended for different lists. It’s such a simple, easy fix that I’ve done a MILLION times before. If I had just asked her, I would’ve been reminded that I knew how to do this, done it and been over with it.

✅ A C T I O N I T E M S

Here’s how I’m moving forward:

• Workflows: if I know there’s a process I repeat often (like publishing a landing page), I should make my life easier by creating a proper workflow for this process. This allows me to cite which stakeholders are involved, where and when, and what tasks need to be completed at what time. This way, no one misses a step in the process, and we have a straightforward and streamlined plan to follow. It’s also a great way to check in with my boss and determine if something is missing. With a proper workflow in place, I could avoid missing small mistakes on our website because I’ll have a step in my workflow to double check, but also to have stakeholders QA a page before I publish.

• Checklists: For something solo, like sending an email, I can easily create a checklist so I’m not missing anything before sending one out. This could include simple things like ensuring I’m associating an email with the right campaign and more complicated stuff like determining “don’t send to” lists BEFORE I even start writing the email. A checklist is so simple and will also show my boss that I’m organized and committed to not making the same mistake twice.

• FAQs: I’ve started keeping a running list of questions I find myself asking or wondering about often. The next time one comes up, when I get an answer, I write it down on a page in Notion so I don’t need to keep asking. This helps me a) not be afraid to ask because I know that once I do ask, I’ll never have to ask again, and b) takes away a lot of anxiety because, in future, I know I have a trusty database of answers to essential questions, so I won’t be bugging anyone or coming off airheaded for not knowing something. It helps me feel equipped to move forward, like I’m not alone.

Thanks for reading our 39th issue. 🚀

Remember: failure isn’t the end; it’s a moment to pause, reflect, and evolve. Every breakdown carries the potential for breakthrough, and every failure is an opportunity for growth.

So, what did you learn from today’s failure? How will you use it to move forward, shift your perspective, or take action?

Let me know—your insights are part of the bigger picture. Until next time, keep exploring, keep learning, and keep evolving.

And most importantly, DON’T be afraid of failure, babe; welcome it.

Have a great week,

Shiv 💁🏽‍♀️