Compared to other Audiobooks I've listened to, this one is an engaging listen, and teaches good lessons about both team management and owning problems that is practical.
[1] https://www.amazon.com.au/Extreme-Ownership-Jocko-Willink/dp... and https://www.audible.com.au/pd/Extreme-Ownership-Audiobook/B0...
Have you started to train yourself as a lead / manager? A couple of resources I've found useful in the switch have been Manager Tools [0] (book, site, and podcast) as well as The Manager's Path [1].
While his shtick can be a bit thick at times, I enjoyed Extreme Ownership by Willink [2], if only because it codified a lot of thoughts I've had for a long time. I've worked with a lot of military and defence so the stories and life views he teaches through didn't throw me, but I know it does for some people so YMMV.
I have found that the Manager's Tools suggestion that the single best thing you can do is have weekly one-on-ones with your team to be true. It can be tough, especially if you still have a lot of your IC responsibilities alongside your new team lead roles, but it is truly remarkable how much more insight you can get into what your team is thinking from holding these sessions. This is they crystal ball you are looking for. And remember, the weeklies are about your team members, not about you (refer to manager tools).
[0] https://www.manager-tools.com/products/effective-manager-boo...
[1] https://www.amazon.ca/Managers-Path-Leaders-Navigating-Growt...
[2] https://www.amazon.ca/Extreme-Ownership-U-S-Navy-SEALs/dp/12...
Leaders Eat Last by Simon Sinek -> https://www.amazon.com/Leaders-Eat-Last-Together-Others/dp/B...
These things come with experience over time, but the fact that you've made it far enough to ask the right questions in the right place to ask them is 90% of the journey.
I realize this sounds cliche, but I can't stress enough that health comes first. I would make the following a priority if you feel you're not taking as good care of yourself as you should:
Eat reasonably healthy (just avoiding junk food is enough, no need to go overboard)
Get enough sleep (and eliminate whatever habits get in the way of that) - Without enough sleep, your mind will in subtle ways try to put the least amount of effort toward doing things. This is especially dangerous if you are trying to counteract those effects with things like caffeine or stronger stimulants.
Don't do anything stupid to harm your body. Contrary to popular belief, you are not a Zerg mutant with infinite bodily regeneration capabilities. It will catch up to you sooner than you think it will.
It's quite hard to improve one's mental habits when not in the best shape (but if you fucked up early on like I did, it's never too late to make things better).
Assuming you're already doing all that, I'll speak specifically to your post:
1. Don't burn yourself out, especially for a job you don't enjoy.
Not a mental model per se, but more of a disclaimer that I highly advise against pursuing such efforts unless you feel the company is a good fit for you. I've personally found that being successful at a company depends as much on the company as it does you. All the talk about culture fit applies here (though I personally hate the terminology). Sometimes you can adapt to environments that are challenging, but sometimes that can be a case of learning bad and toxic habits. And sometimes, no matter how much better you think you perform, it won't improve your job security. So you have to first understand whether you're really happy in that environment. Don't burn yourself out to try to get ahead of the technical debt curve just to try to earn some job security in an environment that you don't feel at home with in the first place.
2. Document what you're going to do, and why, before you start doing it.
This doesn't mean you can't amend the plan when you see a reason to, but your technical changes should be driven by your written plan, and nothing else. If you don't do this, the complexities of the technical systems you're touching will bleed into the mental model you've set for yourself with what you're trying to build. You'll exert subconscious effort to try to maintain some grounding, but inevitably you'll slip at some point and end up doing too much or too little changes. Then you may exert significantly more effort trying to explain to your peers or boss why you spent extra time building something that has no apparent need, especially these days with the plague that is Scrum (fragile, not agile).
You don't necessarily have to do this for all of your work, but deviating from this procedure should be the exception and not the rule.
3. Avoid band-aid workarounds
Always fix the root cause! Always! Okay, there are times when this is not possible. Sometimes, the root cause is part of a piece of legacy software that can't be modified easily or at all. Sometimes the problem is with a closed-source library, an API, or data feed from external partners. It's okay to do workarounds in those cases, but you should be extra vigilant for the pros and cons of doing it. Make sure the business, not just your Scrum Lord, is getting a real benefit from seeing it done. In any case, when doing a workaround, it's wise to include detailed documentation in the appropriate places as to why that workaround exists, or it will contribute to the pain, suffering, and burnout of future members of your team. While this can happen to companies of any stage or size, the real danger zone here IMO lies with companies in the Series B range, as hacky throwaway code could be done with no consequence before then, and is even somehow encouraged by some as a best practice for early stage companies.
The other major exception to this is emergencies, involving downtime, prevention of downtime, or other significant operational incidents. However, meeting the deadline for your Scrum sprint is not an emergency. If your boss can't be convinced to understand this, your choices are to do a better job of convincing, invite them to convince you otherwise (they may succeed!), or to find another place to work. If something is time-critical for business reasons, it's your product manager's job to inform you of that.
If your job feels threatened even slightly by the concept of missing sprints, then you must make it a priority to resolve that, because even the presence of that feeling is itself a good reason for the job to be at stake, as it's indicative of critical communication problems with your immediate team. And it most likely isn't your fault but rather just a failure of the team as a whole (though you have the most power to do something about it regardless of the root cause). It is a growing pain that can be solved, as long as you're not working with assholes.
There is one time where this no-bandaid rule must be broken when you are short on time, but you should work to avoid having ever happen in the first place. If the business you work for (via CEO, PM, whoever) is mandating a hard deadline for a given feature, then you probably should err on the side of getting it done ASAP. If you are in this situation, don't panic. See if you can work it out with your team to spend time after the release to ensure that technical debt is manageable and things are working reasonably smoothly after some code polish. You can prevent some of these scenarios in the future by having a maintainable codebase, and you get a maintainable codebase by reducing technical debt, and you minimize technical debt by not implementing band-aid solutions to appease Scrum Lords. To put it simply: Business deadlines are real, but Scrum deadlines can amount to a hoax. Refer to this article to see Scrum actually addressing this problem: https://www.scrum.org/resources/commitment-vs-forecast
Another thread/post regarding technical debt: https://news.ycombinator.com/item?id=19850629
4. Maintain Good Relations and Build Influence
Building influence will make it easier to succeed in virtually all tasks, big or small. I can't recommend quick wisdom on this one, but could point you to a few good books (or audiobooks if you prefer). Takes years to learn this. I personally prefer to allow time to digest and sleep on the knowledge gained from books, though others (notably Bill Gates) swear by the method of binge reading.
https://www.amazon.com/Influence-Psychology-Persuasion-Rober...
https://www.amazon.com/48-Laws-Power-Robert-Greene/dp/014028...
https://www.amazon.com/Principles-Life-Work-Ray-Dalio-ebook/...
https://www.amazon.com/Extreme-Ownership-U-S-Navy-SEALs-eboo...
I decided to spend a good chunk of time writing this as I start a new job which I really hope to be successful at, and I want to reinforce and review what I think will lead toward that goal. But I hope this is found to be useful to others too.
If you want to get such experience without sourcing and paying a coach, read Jocko's Extreme Ownership: https://www.amazon.com/Extreme-Ownership-U-S-Navy-SEALs/dp/1...
Marc Andreessen called this out as the book he gifts most often, which IMO is a strong positive signal.
I personally found the book a bit difficult, but I think that's a flaw in me more than the book. The person I received it from is someone who lives it much more fully with staggeringly impressive results.
My personal favourite is called /Winning Through Intimidation/ , I think it is much more relevant to our capitalistic and legalistic society than military memoirs or the ancients, as much as I enjoy them. https://www.amazon.com/Winning-through-Intimidation-Victor-B... . It is not prescriptive because it is a bit dated and specific to real estate, but the core ideas are rock solid.
This alone is why 90% of people will not choose to work at a startup. You will work long hours, for crap pay, and you'll be waiting in line if there is an exit.
The odds of there being an exit worth anything to anyone other than a founder are small enough to not even worth considering.
If you are a founder you're gambling on your chances. There are ways to mitigate the risk but there's no sure thing.
Don't start a startup if you do not have the financial security to basically lose everything you put in.
Don't start a startup if you have family that depends on your income. You could choose to eat ramen and sleep on the floor of a college dorm room. Your kids (and CPS) might not appreciate it.
I agree the motivation is very important. I disagree that you cannot find the same motivation in a more stable organization (or can't motivate yourself). I recently finished reading, Extreme Ownership [0], and I bring that with me to work. People need to be responsible for outcomes: that's not unique to startups. You can also find that motivation internally and share it with your colleagues as you go.
[0] https://www.amazon.ca/Extreme-Ownership-U-S-Navy-SEALs-ebook...
https://www.amazon.com/Extreme-Ownership-U-S-Navy-SEALs/dp/1...
https://www.amazon.ca/Extreme-Ownership-U-S-Navy-SEALs/dp/12...
I recommend the read to anyone working within teams of people.
The recently published a book: Extreme Ownership[0]
He gave long interviews to Tim Ferriss[1] and Joe Rogan[2]
[0] http://www.amazon.com/Extreme-Ownership-U-S-Navy-SEALs-ebook... [1] http://fourhourworkweek.com/2015/09/25/jocko-willink/ [2] http://podcasts.joerogan.net/podcasts/jocko-willink
The biggest (and most difficult) aspect is learning to listen with both your ears and eyes. Learn body language as it is the truth.