Should I have worked on weekends to ramp up faster / deliver more?

Unfortunately, a lot of companies and managers equate employee performance to long hours worked, not the actual impact they've had. It seems like your team is one of those, so if WLB is important to you, I would honestly start looking for a way out. It seems like your side hustles are a big part of your life (similar to what side projects were to me before I got married and started Taro), so time flexibility (i.e. what you get with good WLB) will be valuable.

In the meantime, it does look like you'll need to work weekends to look decent comparatively with your teammates. 😢 If your company's stack has scheduling tools (send DMs/emails at certain times or even PRs), maybe you can use those to make it seem like you're constantly grinding? 🤔

This is a big reason why I tell people that a job with garbage WLB generally isn't worth it (no matter how much it pays). It robs you of your most important resource: Time. If your job sucks up 100% of your energy, you won't have that time to do side projects and other fun stuff. And when you want to leave, you won't have time to interview unless you sacrifice your PTO balance.

How did you guys handle the pressure and what are your schedules like? (Wake up @ 4AM, work on side hustle till 6-7AM, then go to sleep at night around 12AM LOL)?

At Meta and Robinhood, I was working less than 40 hours a week on average despite being a high performer. So coming home and working on side projects for 1-2 hours was very doable. This was possible because I learned how to get far more from my time using pretty much all the stuff I teach in Taro now. If you want to learn how I did that, I recommend these resources:

• "How do senior FAANG engineers manage time?"
• [Taro Top 10] Time Management And Productivity
• [Taro Top 10] Work-Life Balance

It comes down to whether you will bet on:

• The company's career model - largely driven by your manager
• Yourself - what the market will give you for your abilities

These past few years in tech should be quite sobering that betting on any one company's career model is a losing proposition in the long term. Given the dynamics you described, it sounds like a losing proposition even past their promotion cycle because it's a race to the bottom. Bake into your expectations that you'll likely chase a moving target if you do ramp up your throughput, as that will become the new norm.

Personally, I've been asked to work weekends and even over the Holidays before and I set my boundaries for situations I will vs. won't.

You'll require a fair bit of career capital to do this, which is determined by what actual impact you have during the hours you work and what your next best option to working there is.

If side projects are important to you and you're able to find contracts that pay your worth, you should allocate a certain amount of time to continue to build that. It is worth mentioning that doing contracts will build up your problem-solving competencies and will make you more effective at your day job, assuming you're working on the same class of problems.