1. Reality-check Questions (strip Away illusion)#

1.1 If Tanner’s role goes external, what is my actual upside for staying?

  • Nothing top of mind concrete
  • Opportunity to mentor new engineer
  • Increased scope while other engineer gets onboarded

1.2 If I were hired today into this team as it will look in 6 months, would I still accept the offer?

  • Most likely yes since I like the premise of the company
  • I also did not know how talented the people were when I started working here

1.3 Am I being evaluated on outcomes I can reasonably control?

  • This feels like a no right now but could possibly change with increased scope, they say you have to do the next role before you are hired into it

2. Control Vs Exposure Questions (this Is big)#

2.1 How much downside risk am I personally absorbing if leadership makes bad decisions?

  • Increased stress
  • Burnout above 50% likely if bad decisions are made. Or increased likelihood that I would burn out
  • No reputation damage unless I fail to rise to the increased scope

2.2 What protections do I have right now if this goes badly?

  • I do not have great protection
  • My manager is leaving for paternity leave ~12 weeks
  • My skip level leaves for paternity leave in a slightly overlapping ~12 week period
  • The person who usually assumes manager responsibility is moving to a new team

2.3 Who benefits the most if I step up informally?

  • The organization
  • Me with the contingency that I get promoted eventually
  • Less than 50% change in coming weeks. More than 50% change at next performance cycle at the end of next year.

3. The Promotion-specific Questions (no Ego Answers allowed)#

3.1 Do I want Tanner’s role, or do I want not to feel left behind?

  • I am not sure in my heart of hearts that I do
  • It gives me flexibility to move laterally into manager
  • It gives me credibility when applying to other companies since it shows progression and has a senior title
  • On paper, I should try for it
  • It is also a terminal rile

3.2 If I don’t get Tanner’s role, will I feel resentful staying?

  • I am not sure if resentful is the correct word, but I would question why I am being asked to do more without receiving any benefit.
  • It would feel like I am doing a favor to others and the company for me to say at that point

3.3 Am I willing to do the job before the title and maybe never get the title?

  • I feel like I could be considered qualified for the role in some capacity today.
  • I do not think that by getting the role, I would be satisfied once I am meeting expectations

3.4 If an external hire gets it, what does that say about how the company values internal trust?

  • That would sit poorly with me considering I have to go through the interview process as well
  • Partially it would feel like a gift if I got it but I would also not appreciate that there would be some margin of error based on merit I have accumulated while working here so far if I did poorly in the interview

4. The Ethical Questions#

These won’t go away with more seniority.

4.1 Is my discomfort with gambling something I can compartmentalize long-term—or does it erode me?

  • Potentially
  • It is sports
  • It really only impacts me when I consider on call responsibility
  • I feel like I could assess any company with some degree of morality. I do not know how much I would love working at McDonalds because they contribute to obesity. But how much do they actually vs the person that chooses to continually consume.

4.2 On-call: if nothing changes, how many more years can I do this without resentment spilling into my life?

  • It is infrequent that people are paged. For the most part it is not consistent
  • Of the two shifts I have done, I have been paged twice
  • Problem is that while the team is reconstructed, I will have to pick up an increased amount of shifts

4.3 Would I advise someone I care about to take this job, knowing what I know?

  • It is a great place to learn
  • It would depend on what they value and are looking for

5. The Quitting Question#

5.1 If I quit in 90 days, what would I regret not trying first?

  • Pretty much my consistent problem. I hit roadblocks with where I spend my nights and weekends. I have ideas but I get paralysis
  • I run out of energy with my job.
  • I lack direction

5.2 If I quit tomorrow, what problem am I actually solving?

  • Increased energy
  • Stress goes away temporarily until it comes from a different external factor
  • I sleep better
  • I have more control over my time

5.3 If I stay 6–12 months, what might I lose that I can’t get back?

  • My curiosity and effort I put into working outside of work
  • I try to experiment, if I invest more time into my career then my time has to come from somewhere else

6. Identity Questions (quiet But decisive)#

6.1 Am I trying to be “the reliable one” at the expense of being fulfilled?

  • Probably
  • I do not understand what fulfillment means to me as part of my career or at this company

6.2 If I zoom out 5 years, does this role move me closer or further from who I want to be?

  • I want to run my own business and make my own decisions
  • I want control over my time
  • I want to be present with my partner and with my children
  • I am not sure what my career will look like then
  • Hard to say if this is moving me closer. It pays the bills so I can buy and pay for quality experiences and things
  • I can experiment with ideas at work, I can see how an efficient company is structured and runs but outside of that I struggle

6.3 Am I staying because I’m choosing this—or because I’m afraid to choose something else?

  • Partial fear
  • I do not have a safety net if I just walk away
  • I do not know how I would explain quitting to my family

Final Grounding Question (the One That Matters most)#

If nothing improves—no promotion, no clarity, same on-call, weaker team—how long can I stay and still like who I’m becoming?

  • It is February now. Based off the changes, they will most likely last at minimum for the next two months. I get my stock and bonus in the middle of March. I have mentally kept March as a date where I would consider what is next. People leaving have sped that timeline up in my head. I get married in September. I go on a honeymoon in October. I get more stock at the end of the year. March has been my date in my head if I could start something that generates a sustainable income stream. It wouldn’t even have to replace my full income. Just a piece of it. I need confidence to make the leap. If I look for a job at a new company, I could find somewhere that I am more aligned with but that takes effort and the timeline is non deterministic. The effort that I would spend looking for a new job is effort that I would rather put into starting something myself.

Diagnosis#

You are stuck between three identities:

  1. Reliable high performer
  2. Future independent builder
  3. Ethical, present partner/husband

Your current role forces you to prioritize #1 at the expense of #2 and #3.

And you feel that trade-off acutely.