In this episode, Dave and Jamison answer these questions:

1. I work at a large remote company. We meet up once or twice a year. I don’t really know much about my engineering coworkers aside from the 5 people on my team, so the in person meet ups seem like a good place for me to get to know people from the other teams.

   I am a career switcher, and am currently a mid level IC (borderline junior) in my late 30s and a youthful appearance. At these meetups, my position and appearance (and honestly, possibly my demeanour) makes me feel like I am expected to socialize with other ICs in their 20s. Although they are nice people I find it hard to relate to them when talking about non work related topics since I am much older and in a different stage in life than all of them, (married with a mortgage and kids).

   I want to socialize with coworkers closer to my age and stage in life but most of them are team leads or manager. I feel like socializizing with them would be seen as brown nosing. I’ve also heard that once someone is a manager, it is very hard for them to befriend ICs because they are now their boss, and that they mostly befriend other managers. My previous career had little management/corporate politics type stuff, so I don’t know if this is true. Would I be hurting myself by doing this?

   Am I over thinking this? Would I be fine socializing with whomever I want? Do you have any words or advice regarding my situation? Thanks!

2. Hi Dave and Jamison,

   Before you tell me to quit my job, hear me out. I have worked in technology for about 30 years. I’ve been at the same company for the past 20 years, but I’ve changed roles many times to keep work interesting. I have enjoyed learning new technologies while working in development, architecture, system administration, management, vendor relations, and more. This has been very beneficial to my career, and I appreciate all the opportunities to grow. I’ve earned a good reputation and am well respected by my peers. I’ve proven my worth to leadership many times over by reducing expenses by many millions and creating innovative solutions to improve efficiencies. I work for corporate America in the insurance/finance industry, which is generally considered to be led by cold, heartless, power-hungry mongers, a stereotype that probably has a few exceptions but is generally not incorrect. I’ve never appreciated this industry’s business practices, but I’ve had to make a living over the years, so here I am.

   I am finally at my breaking point and am absolutely fed up with how employees, customers, and communities are treated by my industry. Because of this, I just cannot find value in my work. I’ve been beaten down over the years and am tired of being exploited by management. I no longer volunteer to take on big projects, and instead of being someone who outshines others, I have decided to settle for mediocrity. I’m planning to retire in a few years and honestly don’t have the energy or desire to search for another, potentially more meaningful, industry to work in, especially in the current job market.

   I genuinely care about many of the people I work with. Very few of them are in it to climb the corporate ladder. Most are just trying to earn enough money to pay the mortgage, feed their children, care for aging parents, and hope to have enough leftover for their own retirement.

   How do I not leave a wake of malaise for my peers when I leave but also not help feed the beast until then?

In this episode, Dave and Jamison answer these questions:

1. I am a senior software engineer at big tech and need a career change. With the rise of AI, I no longer enjoy this profession and panic everyday just waiting for a huge round of layoffs. At this point I feel like I am on some assembly line hitting enter like a monkey. Therefore I have been thinking of changing lanes and would like to get into engineering management. On the one hand I have enjoyed mentoring, strategic planning and coordinating projects across vendors and across teams, but besides that I don’t have clear evidence that this profession would fit me. In my current job there is no immediate opportunity to step up and manage a cross team project at the moment, so I am not sure how I can figure out if engineering management is the right choice for me. How do I figure this out without doing the job and how does one transition into it, probably as an external hire or transfer hire?

2. Paolo asks,

   I’ve stepped into a senior role recently. I’m no longer the primary driver on projects. I’m supposed to create space for junior developers to lead, make decisions, and own outcomes. My job is to mentor and support, not to take the wheel.

   But I’m seeing projects drag because of passivity. Sometimes the solutions are inefficient. Other times it feels like the core problem isn’t fully understood before execution starts. In a few cases, momentum just stalls, and weeks go by without real progress because no one is pushing the work forward. It’s worth mentioning that I check in multiple times to offer help yet these problems keep happening.

   I believe people grow by struggling, so I don’t want to jump in at the first sign of friction. But if a project slips or fails, that responsibility ultimately rolls up to me.

   So how do you strike the balance? How do you give someone real ownership, not just symbolic ownership, while still maintaining standards and accountability? And how do you avoid becoming either the micromanager who swoops in too quickly or the absentee leader who lets things drift?

In this episode, Dave and Jamison answer these questions:

1. How can I get our company to follow the law and stop sending SPAM without being regarded as negative?

   We’re sending out emails that don’t comply with CAN-SPAM, and I think we should comply due to the risks, but I don’t want to risk any blowback! People want the emails to look more ‘human’ sent, and putting your mailing address at the end of an email is not very human, so we’re not doing that… It’s a medium startup (500 people), but I’m close enough to the marketing work that they might know it was me! Should I send an email to our general consul? How can I raise concerns and do the right thing without being regarded as not a team player??

2. How do I stay motivated on a team that’s always sick?

   I’m on a team of 3 ICs and one manager. The other two ICs are plagued by health issues. I am trying to be empathetic, but this has been going on for the at least a year. One of them regularly takes sick days, often turning into sick weeks. The other has a long term issue and regularly does half days. This affects our ability to produce results, but we don’t have a PM and don’t really have deadlines given the nature of our work, so it’s not really noticed. I feel like we are moving a lot slower than we could be, and when we do check-ins on our goals at the end of each quarter, we maybe only hit like 50% of our goals.

   To me it’s quite obvious why we don’t hit our goals, but everyone else seems to be surprised by it. My manager can’t manage with enough rigor to produce results. I’ve brought this up to them before (our goal misses, not teammates being sick), but nothing seems to change. As the only seemingly-healthy member of the team, there’s no incentive to work more than the bare minimum. I feel like I should be taking more sick days! This is very demotivating and I feel like I’m stagnating. How would you all approach this situation? Should I also suddenly have health issues? Is this actually a blessing in disguise and I should make the most of it?

Show Notes

https://overcast.fm/+ABLmzfhZxak