A short tenure once may not be much of a red flag, if you have a good reason to change (for ex, work was not what you were told, not a culture fit, etc.). If you change jobs multiple times every few months, that may be a red flag. You want to not make it a pattern.

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I have seen people leave jobs within the first few months, if they received a better opportunity. Sometimes, it might just be that the interview and offer process took a long time, or the process was ongoing as you started at the new company.

When you join a new company, it will take you time to onboard and understand the systems, tech stack, etc. It takes a few months until you can start contributing significantly. \
The impression you make during the initial period will also go a long way. Starting positively and demonstrating small impact sooner will help you build credibility and trust quicker.

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You may come to know within the initial few months, if you like the job/environment or not. If not, it is better to leave sooner than later. 

Continuing to interview is your choice. I do not know how easy or difficult it might be to balance ramp up in the new role and continue interviewing. \
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The responsibility for your career and growth is with you, not the company. The decision to continue interviewing or not is for you to make. I would just suggest having clarity with the choice you make. 

If you leave, you want to ensure you do not burn bridges.

Leading the Platform Team at Taulia, part of SAP

Umang Vanjara

When you are submitting your appraisal, you will obviously share your achievements and impact.

Something else that you can add - request comments and feedback from people you have worked closely with and add quote their comments/feedback in your appraisal. Basically, you could request your own 360 feedback and share those with your appraisal.

Another suggestion would be to proactively ask your manager how he/she would consider feedback for the project where you are working with the other manager. They could also directly reach out to the other manager or may suggest how they would like to receive it.

Hope this helps.

I am late to answer and assume you have accepted the offer.

A few other considerations you may want to consider in terms of benefits (as FTE vs contractor)

- Medical, dental and vision benefits might be better
- 401k and perhaps there is matching, ESPP possibility
- There may be other perks too which may be available as FTE and not contracting.

If you can help others become better engineers, nothing like it. Would definitely suggest giving it a go.

As Elliot mentions below, if you plan to leave in less than a year, nothing from your options may vest. So, you may need to consider only the cash portion of the compensation.\
Though I am curious as to why you are thinking about leaving in 6–12 months, if you are excited in the AI parts of the product.

As a manager, I would be interested in 9 and 10.

The transition is one part but how to become a strong and effective manager is also critical.

The grass might seem greener on the other side.

The "What If" question will be one you will ponder many times in a long career.

What If you had joined an F1000 and the actual work might not have been what you expected.

What If you had joined the other company, perhaps you would have the same question - maybe I should have joined the startup.

In some of the big companies, it might be easier to get lost and the impact might not have been as visible as a startup.

These are just some counter examples and things might have been positive also, if you had joined the F1000.

As the other answers below mention, live a good life, your story is still being built and you have a long career ahead. Good Luck!

First, let me commend you on your awareness.

This is a great starting point.

As Alex and others have mentioned below, start with compiling your questions where you fumbled, find patterns, and proactively prepare some questions that may come your way.

An additional step would be to check with your peers/seniors/manager and do some prep, if possible, before the demos.

Observing what questions are being asked to other members during their demos and how they answer would provide good learning too.

Senior Manager at SAP

First, you are not alone in this.

I have seen projects overrun and miss estimates many times.

When we were doing waterfall development, releases would get delayed frequently.

When you say open-ended, there seems to be an exploratory angle. \
You are likely soliciting stakeholder feedback periodically. As they see what you deliver, requirements and deliverables might change.

In the Agile setup, with the frequent feedback cycle, I have also seen changes in scope or solutions taking longer than you expect.

The estimations are based on past predictors and/or what you believe needs to be done as per initial requirements.

When you start working on the project, you may find new information or experience unforeseen issues.

In another scenario, I have also seen some other critical issues come up and resources may need to be redirected to address them. As a result, in-flight projects might get delayed.

Communicating up your chain, as you have done, is the right step.

To meet deadlines, typical steps are:

- Reduce scope and break down the project into additional phases with stakeholder buy-in.
- Add more resources, if possible
- Add in buffers to ensure you have time to address the unexpected.

Love the simple template that Rahul has provided here and the suggestions from Alex too.

If the 1:1s feel like status reports, bring that up with the Manager too, and suggest sharing those offline or in another async format.

Remember that the 1:1 is your meeting and not your manager's. It might feel weird, but you drive the agenda.

A question that might be interesting to ask your manager that I recently learned through LinkedIn:

What is one thing you need from me that you are not getting?

Be curious. Ask your manager about their career journey and learnings (following along with the Personal life suggestion from Alex).

Here are a few things that I do

- Take periodic breaks and if possible, take a walk outside. 
- Don't have your lunch at your computer, have it in a different place. I prefer to watch TV while having lunch. 
- Shut down your computer after work. 
- Exercise - Go to a gym or find some physical activity outside. 

I agree with Rahul. Scheduling regular time for reflection is super helpful. 

On a different perspective, the practice of daily journaling can be helpful. Writing things down can be a way to let things out. 

You have not mentioned if you have other hobbies or interests. Regularly disconnecting and doing something else unrelated to work can be a good destressing option. 