No. 16 - GRIEVING THE POSSIBILITY

GRIEVING THE POSSIBILITY

July 23, 2025 • Issue No. 16

Last issue, I was definitely having a procrastination problem. You can imagine my confusion when I wrote the email, took my own advice, and was still having trouble starting and finishing projects. It turns out there was something else standing in the way: grief.

I’ve heard grief compared to the ocean, the way it ebbs, flows, and overwhelms. But when I feel overwhelmed by the waves at the beach I get out of the water. When you’ve lost something or someone it’s not as simple as standing up and walking to dry land.

Grief is not a typical work topic, but it impacts our workday: especially if your job is to sit behind a desk tapping away on a laptop, especially if your mind is the thing that helps you do your work. You’re working just fine until your mind sees fit to wander and then you’re swirling back into sadness. It feels impossible to get anything done. Also impossible? Bringing your sparkle to work with you if you’re compartmentalizing or masking how you really feel.

Grief is not just a funeral feeling. I’ve felt grief after a romantic breakup, the end of a friendship, during family member illness, a colleague leaving or moving, a heartbreaking news story, missing out on an opportunity, or when I’ve worked really hard at something and it’s gone awry. Sometimes I’m directly or indirectly impacted, sometimes I’m mourning an aspiration like my dream job or promotion. Grief is defined as “deep sorrow” and death is not the only thing that draws it into our lives.

[This is not medical advice. I’m not a therapist. As an executive coach I focus on career performance, but you can’t get any work done if you don’t tend to your heart. 💔]

🎙️ Record It 🎙️

You can use a voice memo, your notes app, or a journal for this. When those fantasies (or memories) float into your mind, give them a different place to live. Don’t fight them, let them flow out the same way they flowed in.

• I imagined that we’d go get ice cream this summer, I’m sad we won’t be able to.

• I thought I’d be writing this email from my new office, it feels unfair to still be at my regular desk.

• AAAAAAAH! I! CAN’T! BELIEVE! THIS! IS! HAPPENING!

🛟 Ask For Help 🛟

You need someone (*ahem* a human person) to talk to like a friend, relative, or a therapist. Sometimes you’ll need to call them in the moment when grief strikes. Other times, you can ask them if they have time to talk later. Often, just knowing that you have a space to talk about it in the near-future is enough to help you reclaim your focus for a few hours. If this is a community loss and you’re not the only person affected, offer help to someone else who’s impacted.

• Hey Jasmine, I’m feeling really down today. Was wondering if we chat for sec? What time is your lunch?

• Hi Aunty! I’ve been thinking of you since Mom’s surgery. Can I give you a call this evening?

• Hello Dr. J, I know we have a session scheduled for Tuesday, but I was wondering if we could check-in briefly tomorrow.

⏳ Take A Break ⏳

Sometimes it feels like too much because it is too much. If this is the case, consider what a break might look like. If you have the flexibility to step back from your responsibilities and go on an Eat, Pray, Love-style journey, I support it! But this suggestion is not all or nothing. In fact, running away from deep sorrow may work for some people, while for others there’s no place their grief won’t follow. When and how you can, set aside time to feel your feelings without trying to shoo them away.

• I’m going to go home early today to eat ice cream, watch sad movies, and cry until my eyeballs fall out.

• I’m going to spend my weekend re-reading all of our letters and looking at our pictures, so I can say goodbye.

• I’m going to use the PTO I have saved up to finally take the trip I planned in 2020. Life is short. 

At the root of each of these suggestions is the idea that grief needs somewhere to go. Grief is an uninvited house guest that doesn’t take nicely to being ignored. If she’s going to pull up a seat to the dinner table anyway, you may as well gussy up a place setting. In my experience, she’s going to keep showing up until you’ve found a way to make peace with saying goodbye.

If you’re in a season of grief right now, please know that my heart goes out to you. It’s terribly difficult but I imagine you’re trying your best, and that is good enough.

💎 Sometimes grief comes to work with you. 💎 

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