Bookie Podcast

Sunday Scaries & Self-Doubt


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I started writing this post on January 2nd as I'm mentally preparing to return to work. 

It's a short week, my calendar is still fairly light on meetings, and I know everyone else is also gingerly getting back into the swing of things.

And yet here I am, watching the sunset at 4 PM, nursing this anxious pit in my stomach brought on by the prospect of needing to be any sort of productive tomorrow. 

Sunday Scaries are often a sign of a well-deserved break. During my time off, I took another Christmas day trip to Vegas with my parents, I spent time reading & writing, and even cooked a New Year's Eve feast for my friends

I'm dreading returning to work because a part of me just wishes I had more time to do more of these things. 

But today's symptoms feel especially acute. I think there’s something else going on here.

Why am I dreading doing a job I supposedly really really enjoy? Why does it feel especially bad tonight? And is there anything I can do about it? 

I have some thoughts messily bullet-pointed in my Notes app. And while I know I'm not going to finish this exercise tonight those ideas feel worthwhile to start unpacking now.

Why am I dreading work?

I decided to use the "Three Why's Framework" to diagnose my Sunday Scaries because, well, a PM problem requires PM framework 😂. 

It's not rocket science, it just involves asking yourself "Why?" 3 times so you don't immediately jump to the first conclusion. 

Anyways, here's roughly how the exercise went down:

* I’m dreading needing to go to work tomorrow.

* Why am I dreading work? There are emails I need to send, memos I need to write, and presentations I need to start preparing for. There are all these tasks that I have no motivation to do.

* Why aren't you motivated? I'm doing all this to convince a team to work with us. And I worry that all of this isn't going to be enough to convince them.

* Why does that scare you? I hate being reminded that I might not be as good at my job as I think I am. 

Wow. Is that what it is? Self-doubt? 

If I'm not careful, I'll fall into the unproductive cycle I often encounter during a crisis of confidence:

* I worry

* I avoid doing what actually needs to get done

* I feel guilty for not getting anything done

* And the cycle repeats

I know how ridiculous this sounds. Advancing a project and stressing over my job performance feel like massive undertakings even though they're really insignificant in the grand scheme of things.

But even if our challenges aren't significant on a cosmic level, goals often represent something we value.

Maybe you want to run a marathon because you value challenging yourself. Or perhaps you want to start a business because you value autonomy. For me and this project, it's about being dependable—I value being the guy that can show up and make things happen. 

If I didn't care about my job, I wouldn't worry about the quality of my work. Indifference leaves no room for worry. 

So it's comforting to know where my anxiety comes from but "I care too much" also just feel like empty words. 

That knowledge is useless unless I can do something about it.

So I tried a few things...

Staying Present

For starters, there's still a good chunk of the weekend left. I don't want to let anxiety ruin what could be a great rest of my day. I'm going to text some friends, read a book (currently enjoying Hangry: A Startup Journey by GrubHub's founder, Mike Evans), and make dinner for my parents.

I have a lot to be grateful for now even if the primitive parts of my brain want me to anticipate some perceived threat in the future.

Worrying about tomorrow serves no real purpose other than distracting from hobbies and connecting with people I love.

So I’m writing this as a reminder for myself: to combat feelings of dread, focus on what's going well, schedule time for activities you enjoy, and stay present and engaged with them. 

Reframing discomfort

I HATE pitching to other teams even though my job often requires it. I've done it well in the past, but it’s never been something I naturally enjoy.

There are two main reasons for this:

* I just hate asking for help. I'd prefer to do everything myself, even if assistance can make the whole process less painful. This is definitely an ego thing that I need to work on

* The possibility of rejection still makes me uncomfortable. I could draft the best email, turn on the charm, and give my best sales pitch and still get rejected. It's one thing to check something off a to-do list and feel confident that you'll be rewarded, but it's another to know that you might not succeed despite your best efforts.

I told myself that I'd practice reframing discomfort this year and this feels like a good opportunity to do so

We all want certainty. We all want to be the triumphant hero of our own story. So step one is reducing my guilt around feeling anxious. That feeling is neither good nor bad, it's just my body's natural reaction to uncertainty and the possibility of a bruised ego. 

Step two is reminding myself that regardless of the outcome of these tasks, this work week, and this project, there’s something to be gained from this experience.

I'll be forced to ask for help, I'll receive feedback on my communication, and I'll practice facilitating discussions with a new group that honestly intimidates me a little bit intellectually. 

It's also not all about me! My team invested a ton of time and energy into this project. Letting my own psychological baggage stop me from putting my best foot forward would be such a disservice to their talent and effort. This is another opportunity to practice consistently showing up for the people you care about. 

I'm going to remind myself that there's a lot to gain if I can treat this discomfort as an opportunity to grow regardless of the outcome.

Making tiny steps

So I know I’ll need to write an email, draft a memo, and prepare for a presentation. Again, those tasks aren’t excruciatingly difficult—we’ve all sent emails, written memos, and given presentations before. But coming off a holiday break and weighed down by self-doubt, it feels like I might as well be climbing Everest. 

I’m not going to waste time half-assing them tonight (see Staying Present). Instead, I'll just make a list of all the first steps I need to take and schedule when I'll do them.

* I schedule time to just write the bullet points of my email

* I schedule time to actually read the docs that'll inform the memo I'm supposed to write. 

* I schedule time to actually schedule time with people I need help from. (As you can see, I really hate asking for help...)

All of this took less than a few minutes but started a process of transforming these seemingly insurmountable tasks into something more manageable. It's much-needed scaffolding to start my work day with some quick wins rather than staring indecisively at my to-do list wondering where to start. 

Sometimes all it takes is just a tiny bit of momentum for you to get into the swing of things.

Conclusion

I'm writing this last part of this post near the end of the week with the benefit of hindsight. I'm happy I took the time to evaluate what I was feeling even if it didn't transform my Sunday Scaries into some superhuman state of productivity. 

In a way, that brief episode of intense dread forced me to develop a blueprint for how I'd like to cope with self-doubt moving forward. 

So I guess that's a pretty good deal. 

To summarize:

* Anxiety's not necessarily a bad thing. It's just your body reacting to uncertainty about something you care about.

* Stay present. Don't let something you can't control in the future ruin what's happening right now

* Reframe your discomfort. Hard things are supposed to be hard. There's still valuable experience to be gained regardless of what happens.

* Take a tiny step. That'll give you more clarity and momentum to take on the bigger task. 

I'll probably slap this on a PostIt Note somewhere and re-read it whenever these feeling starts resurfacing. 

Hopefully, they're friendly reminders for you as well :)

A quick personal note: Thank you for all the kind words about these more personal posts. I’m always nervous airing dirty laundry but I’m happy folks are finding value in my writing. You kind words really keep me going! I’m hoping to grow this newsletter some more in 2023 so if you have friends and family you think would benefit, please share!

It’d really mean a lot :)

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Bookie PodcastBy Phil Ou