🗞️ Issue #49: September Scaries and the 3 things that are blocking you from success

If you have Post-Holiday Depression or End of Year Career Blues then this newsletter is for you

Sep 03, 2024

👋 Hola friends! I’m Kax and welcome to my newsletter where I write about enjoying a career in Product Management, becoming your favorite version of a Product Leader, building a Startup, and all the human mess in between.

In this issue, I’m sharing

September Scaries or why it’s difficult to come back to work after holiday
Top 3 Things That Are Making It Difficult For You To Make Change Happen
And how getting to know yourself better can help you face your fears

01 Do you have the September Scaries?

It’s September! How did the -ber months get here so fast?

If you’re reading this from the western hemisphere, +/- a few thousand kilometers, you’re probably coming back from your summer break.

And I’m going to assume some of you are feeling one of the things below:

Dread and Trepidation — For me, September is the Monday of the year. Imagine coming back from a few weeks of doing something new, exciting, or relaxing. And then you come back to… reality! To meetings that could have been emails. To emails that should have been meetings. To stakeholders you never seem to get off your back. So you start counting down the days until your next vacation.
Pressure and Stress — The 2nd half of the year brings with it a few milestones.
1. Personal development conversations and the question: did you achieve your goals? (more riveting than Harry Potter and the Goblet of Fire!)
2. Promotion season and the panic of: did I manage to become strategic, proactive, and a better communicator in the last few months?
3. Followed by the scrambling to make as much progress as you can, and hoping it’s enough.
Existential Crisis — After having experienced a few weeks full of fun and excitement, coming back to the same old context, environment, and even gossip can be a huge downer.

Sometimes these feelings inspired rebellion, “I have to make a change!”

Awesome! But when faced with the work that needed to be done — intimidation and procrastination put their powers together and just said “Nope! You’re not ready!”.

And before you know it, it’s 2025. Rinse and repeat.

In the months leading up to my burnout, I was feeling all three at the same time.

When I returned from my summer break in 2023, I dreaded going back to work to face everything I left behind before vacation. The nth wave of a reorg, a huge-ass organization-wide-re-platformization project, the uncertain future of my role, and all the feelings of my team.

After just a few weeks of being back, I was already up to my ears in stress and pressure.

My goals as a Product Leader felt impossible to achieve. It felt like no matter what I did, I couldn’t make any progress. Never mind my personal goals that I thought I had to set aside just to make space in my brain.

By October, I was asking myself “What am I doing with my life?”.

I didn’t feel like myself anymore.

The thought of “making a change” crossed my mind several times but there was always a reason not to:

I was too tired. And the mere thought of having to start all over again was exhausting already.
I’m not a quitter. Making a change felt like giving up. And giving up felt like I was just not good enough.
I don’t even know what change I’m looking for. Something needed to change. That’s for sure. What? I had no idea. And I also had zero energy to figure it out.

So I pressed on. I wanted different results but I kept doing the same thing over and over again. I went to meetings. I had 1:1s with my team. I defined and implemented new strategies. I aligned and negotiated with stakeholders.

I fought the same battles with the same weapons as usual.

At some point, there seemed to be progress — at least on the operational side. Parts of the giant ass project have been unblocked. Some of the people in my team were finally feeling more secure with the never-ending waves of changes. And I found my voice again.

And I got rewarded and recognized for a job well done.

But the dread, the pressure, and the existential crisis never went away. There was a niggling voice at the back of my head that never stopped asking for change.

The progress that I was seeing, while it was real, was not what I needed.

And we all know what happened after that - I burned out.

Unfortunately, my story is not unique.

I’m working on the same problem with some of my coaching clients. And my friends and I talk about this a lot over a bottle of wine (or two) on Friday nights.

And if you can relate, let me share the same message I had for my clients and friends. A message that took a burnout and everything that came with it for me to learn:

YOU’RE NOT STUCK

02 Top 3 Things That Are Making It Difficult For You To Make Change Happen

Or the 3 things that contributed to my burnout and why it took me so long to change my situation.

A. Your plate is TOO full.

You’re probably constantly putting out fires. You’re still on the 3rd item in your to-do list and 30 more things were added to your list 3 seconds ago. And we’re just talking about work. There’s also laundry, dentist, and 500 other personal errands waiting to get done.

This doesn’t get said enough: whenever you prioritize something, something else gets deprioritized — whether you do it consciously or not.

“I don’t have enough time,” is a common response when the thought of doing something for yourself crosses your mind. And often what gets deprioritized is… YOU.

And YOU need time to think sit down and think. You need it so you can be strategic about your product and your team. Why would it be any different when it comes to YOUR needs?

If Beyoncé can do it, I can do it too!

Absolutely! You can also run 5 businesses, put out an album, do a world tour, and raise a kid, while still being fit!

But Beyoncé is also probably not filling out endless spreadsheets for the annual budget, doing her laundry, and commuting 20 minutes by metro to get to her yoga class. She has a team for those.

You should probably be doing the same to win some time back to think and be strategic.

As in:

Deprioritize - Remove things from your to-do list that do not have impact. Consistently! Say NO with conviction and without fear. And do it consciously and proactively. Otherwise, you’ll always feel like you’re running late on everything else.
Delegate - Some of the things that are on your plate probably don’t need to be done by you. You can share tasks with your team (and help them learn new skills along the way). Outsource. Get help!
Discuss Expectations - Negotiate your commitment with your stakeholders. Not everything needed to be done yesterday. Have open communication with people so you can adjust what can fit within your limits.

B. Misdirected need for control

Do you spend an inordinate amount of time:

Being frustrated because there’s somebody in your team who is just so toxic they’re making you want to pull your hair out. You give them feedback. But no change. Then you escalate to your manager. Nothing happens. So you fixate on them, keep expecting them to do the things you think they should, and when they don’t you complain. You escalate. And get frustrated. Then you do it all over again.
Being worried about how other people perceive you. Does your manager think you’re good? Does your manager’s manager? How do your stakeholders feel about you? So you’re constantly trying to police your interactions with them and always going the extra mile to make them “happy”.
Being exasperated that the executive team just shared a new strategy alongside the news of another reorg (only 6 months after the last one!). So you scream internally and you keep giving feedback for why you think this doesn’t make sense. Only nobody’s listening. And you’re not feeling heard and ultimately incapable - because surely if you’re good at your job, they’d listen to you… right?

You’re trying to control people’s behavior, perception, and decisions. Or at least you want to.

But you can’t. No matter how hard you try.

Humans are wonderful like that. Free will and all.

You can influence with objectivity, data, and with trust. The stronger the relationship is with the people you want to influence, the more likely you’ll get your ideal outcome. But it’s still only a possibility.

But while you can’t control their behavior, perception, and decisions — you can control yours.

The sooner you realize and focus on what you can control, the sooner you can shift your attention and effort to where you can have a real impact. And that includes your well-being and growth.

C. Your definition of success is not clear.

When it comes to your product - When your definition of success is unclear, you run after outputs. The number of features you deliver. The number of workshops you do with your team or your stakeholders. It becomes harder to prioritize what will have an impact because you’re not clear what is impact.

When it comes to your career - When your definition of success is unclear, you fill your time with what feels productive. You compare yourself to other people’s progress and titles and feel envy. You chase after titles and not get them. OR get them but you repeat the cycle of frustration all over again. And you constantly feel that you’re not ready — because what are you getting ready for?

When your definition of success is clear, a few things happen:

Your priorities become obvious
You become laser-focused on what matters vs using other people’s validation or progress as a proxy metric
There’s a stronger sense of fulfillment with what you do. Because what you’ve achieved is aligned with the things that you value.

03 Getting to know yourself is your best bet

It all seems so simple but even these 3 things can feel difficult to unblock. And mostly it’s because:

Your fears and self-limiting are making it hard to take a leap of faith
You haven’t taken the time to get to know yourself and the things that are important to you.

When you know who you are and what’s your story - What are your values? What are you good at? What comes easy? What do you care about? What is important for you? What do you not like? What challenges have you gone through unscathed? How did you solve them before? And many more…

Your awareness of your strengths can help you overcome your self-limiting beliefs.

Your awareness of what you deserve can help motivate you to overcome your fear of the unknown.

Your acknowledgment of your story and everything you’ve achieved can help build resilience towards the challenges that you might face.

TL;DR

Change doesn’t start from “just doing things”.

Change starts from within.

It starts from knowing who we are and what we stand for so we can create a narrative that comes from a place that believes deserve good things.

It starts from acknowledging the things that we are afraid of, even if it hurts so that we might figure out how to address them — or even better, realize that we already know how to address them.

And when this work is done, the actions that we need to do, and the behaviors we need to build can come through.

🙋🏻‍♀️ If you want change but don’t know where or how to start, I’d love to work with you. Let’s have a call to discuss how I might be able to help you figure things out.

B. 5 Things That I Loved This Week

👩🏻‍💻 Hi I’m Kax! And I offer support through 1:1 coaching. I typically work with experienced Product Managers, aspiring Product Leaders, and Women in Tech to help them address the challenges they face in their day-to-day. My goal is to help them achieve their operational and career goals while still enjoying their work and without compromising their well-being.

Here are some topics that I usually work on with my clients:

Creating a sustainable job search system and strategy to help them attract the right opportunities
Effectively leading a transformation in their team or wider organization
Navigating their day-to-day challenges to battle their overwhelm and positively impact their well-being
Creating their personal operating system to successfully deliver impactful products and get the reward and recognition that they deserve
Identifying and pursuing their next best steps that are fully aligned with their ambitions, preferences, and values.

If you’re interested, you can learn more about working with me.

Or book a discovery call :)

And If you reached the end of this issue, I’d love to read your thoughts, feelings, and violent reactions in the comments. 🫶

💙
Kax

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