How to scope tasks that you have not done before

That is certainly a miserable feeling and all jobs can have busy patches at one point or another. One thing that worries me is that they are working on weekends needlessly with no context whatsoever. That can happen even as we start to pick up new roles, but with the whole team doing it, it suggests they're really scared about the macroeconomic effects present in the current economy and may be overcompensating which isn't good and impacting their physical health which certainly isn't good. For you, you should have the option to handle employment as you see fit. If the current team isn't your cup of tea, consider making your own team. If you're going to be working the long hours, you might as well make more money doing something you love.

This definitely seems like a challenging situation.

In summary, if I'm understanding correctly:

• Your manager and teammates are working on the weekends, implicitly giving you an expectation of doing the same
• You're underestimating tasks, further adding to the pressure of working weekends to meet the "deadline" you set for yourself

The second one is an easier one to solve, but the first one is really adding to the pressure of working weekends; so let's start with that one.

To me, it seems like you'd really need your manager's support to not feel that pressure. You could just start not working the weekend, and that is totally a valid option. At that point, you can wait to see if your manager brings it up and if it starts to create other challenges.

But for now, I'll assume the goal is to get your manager to explicitly say to you: "Please do not work weekends."

In this case, you'll want to have another conversation with your manager. Here's how to approach it:

1. Establish mutual respect and purpose
   For more info on this, see my article here, but the general idea is you want to start off by getting on the same page with your manager about your common goals. You both want to see the company and team succeed. You appreciate all that your manager has done for you and you notice how much he cares about the team. You feel the same way about wanting to be on a great team with a good culture. Afterward, you can get into the main topic. Doing this creates safety in the conversation, makes your manager feel good, and gets him or her to want to help.
2. Make it about your mutual purpose, not your personal passions.
   You could start the conversation off by asking something like, "With that said, I wanted to talk to you about some of the expectations I have been feeling lately and the impact I feel it could have on our goals as a team. Would that be okay?"
   
   Afterward, you can explain how the specific actions that have been making you feel pressured (like everyone working weekends), which is leading to a feeling of burnout on your end. You're worried that this may impact your ability to productively contribute impact toward our goals over time. You could also mention the impact on your mental health. And then ask, "What are your thoughts?" or "I'd really like to hear your opinion on this."

This is actually the exact 3-step approach in the article here: https://careercutler.substack.com/i/113691080/step-approach-to-success

Here it is copied and pasted in:

1. State what you have noticed from a factual perspective

2. Describe the impact on the mutual purpose

3. Ask their thoughts

   1. “What are your thoughts?”

   2. “I’d really like to hear your opinion on this.”

   3. “Please let me know if you see it differently”

After you ask their thoughts, the hope is that they would be receptive. However, that might not be the case. They may say something like you previously mentioned of, "We should be lucky to even have a job in this economy." If they do, here's a sample of how you could keep pushing at it:

"Yeah, I get that. The economy is really tough right now. However, I can't help but feel like this will hurt us in the long run. I'd really like to talk through a solution with you."

Alternatively, if it seems like your manager won't budge, you should probably start looking for new positions--or just don't work weekends and see what happens. Your company isn't paying you for working on weekends so you really shouldn't be.

Lastly, since this is already pretty long, on estimates, check my LinkedIn explainer here: https://www.linkedin.com/posts/jordancutler1_softwareengineering-activity-7051234920660099072-cwyg?utm_source=share&utm_medium=member_desktop